I’m scared of hiring my first employee, an email squabble, and more

by Alison Green on May 22, 2024

It’s five answers to five questions. Here we go…

1. Was I wrong in this email squabble?

I have a question about a little email tussel I recently ended up in. I am a contractor for a professional services agency and was working on a project for a client. Part of my work includes using a third party to upload documents to a publishing site. This was my first time working with the third party in any capacity. Last week, I sent the required documents to the contact at the service (“Pat”) and asked for an update when the content was uploaded. They did acknowledge the email and said they would send an update once it was completed.

To make a long story short, Pat helped with uploading documents from a different (but related) project, and when I asked about the original request, I was met with pushback about never receiving documents related to the project (despite the email chain being named after the project). It was so blatantly wrong and strange that I began questioning myself, but a coworker also on the email chain acknowledged that Pat seemed disorganized, so I surmised that it must not be me. I sent the documents again to Pat two more times before the weekend, and each time was either ignored or they said that they did not receive anything from me when I asked for an update.

Eventually, on Monday morning, the client mentioned that they still did not see the documents uploaded. I reached out to Pat for an update, to which they said again that they never received anything from me and to send a new email with the attachments. I did as requested and included screenshots of all the emails I had sent to Pat the previous week with a note “in case they wanted to investigate.” It felt a little petty as I was sending it, but I was annoyed.

Pat replied back, “Obviously I am getting your emails but I never got one related to (Project name). Make sure you’re sending to the right recipient.”

Once they had confirmed completion of the upload, I sent them a screenshot of my original email including the “to” line showing that it did indeed go to them and said I appreciated their help. Pat’s tune changed significantly after that, and while they didn’t apologize, they said they would look into it more and they were glad we were able to complete the project.

If it matters, I am a woman in my late 20s and from what I can tell, Pat is a man in probably his 50s. While I felt petty sending screenshots of everything, this seemed like a very strange situation (could he not go back to the original email?) and I didn’t feel like being pushed around or apologizing for something I didn’t do. My director and coworker were also cc’d on all of the communications. Would love your insight on if I handled this appropriately!

Pat’s the problem, not you.

It’s one thing to miss an email, but before chastising someone to “make sure you’re sending to the right recipient,” you’d think he’d first go back and confirm that he really didn’t get the email.

I do think it was overkill on your side to send screenshots of all the emails you’d sent Pat the previous week, rather than just the one in question. Sending just the one in question probably would have solved the whole thing and not dragged out the interaction quite as much.

But again, you weren’t the problem.

2. I’m about to hire my first employee and I’m freaking out

I set up a nonprofit organization last year which has grown beyond the point where I can keep delivering everything on my own. There are two other directors on the board but they are both employed elsewhere, so other than quarterly board meetings I do the vast majority of the work. Thanks to grant funding and trading income, the organization can afford to employ someone part-time to take over some of the core delivery so that some of my time is freed up to work on developing and growing the business, and making it sustainable for the long term.

I’ve been through the recruitment process, I’ve got a preferred candidate and a second choice, interviews are done, references contacted, offer letter and contract (we’re in the UK) are all drafted with guidance from a HR consultant … and I am absolutely terrified of actually calling the candidate and making the offer.

I think I’m paralyzed by the weight of responsibility that being someone’s manager and employer involves. I have literally never been anyone’s supervisor or manager before. I’ve had a lot of managers, good and bad, and have a fairly good idea of what kind of manager I want to be, but the terror is getting in the way.

If I don’t hire this person, or at least A person, I will not be able to sustain the company. There’s so much potential and so much demand for what we offer, and the only way to realise that is to employ someone who is not me to do some of it. So why am I so scared? And what can I do? I told the applicants I’d make a decision last week. I’ve already updated them that there’s a delay, but I really do need to finalize the hiring decision this week, not least because I need them in role asap so that I can shift my focus to a large and important project starting in mid-July (which will involve hiring more staff).

This is hard to answer without knowing exactly what you’re afraid of, but if it’s really just the weight of being someone’s boss … well, honestly, you’re going to mess it up at some point, probably multiple points, because that’s what we all do. You’re not going to be perfect. You’re going to learn on the job, and it’s sometimes going to be messy. (This pep talk sucks, sorry!) But this is how you learn to do it. As long as you commit to a few basic principles at the outset — clear communication, getting aligned on expected outcomes, a coaching mentality, a bias toward transparency, and a view of the other person as a partner rather than a peon — you’re going to be fine. The other person is going to be fine. You’ll both figure it out. Commit to talking about it if that’s not happening.

But also, consider some training on how to manage people effectively — the nitty-gritty, “what does this look like day-to-day” of management. (I have conveniently written a book about exactly that and it’s even targeted toward nonprofit managers, so here you go.)

Also! Make sure you have a clear role description and list of outcomes the person will be responsible for achieving, and a training plan (at least an organized outline) for what you’ll need to cover with them to get them acclimated and equipped to contribute. You’ll feel better if you have those things. But from there … all you can really do is jump in.

Related:
advice for new managers

3. Interviewer asked, “What would your detractors say about you?”

I’ve interviewed twice for the same agency over the span of several years. Both interviews included the same question: What would your detractors say about you?

The question has actually turned me off a bit from working for that agency. How do you advise answering a question like that?

It’s really just the old “what are your greatest weaknesses?” in disguise — or at least you can answer it that way. If you’ve had 360 feedback and you’re comfortable talking about something from that, you can do that and cite it as the source. But either way, the framing should be the same as for the “weaknesses” question — something you’re not as strong in combined with what you’ve done/are doing to work on it.

4. Should I say my coworker is the reason I’m leaving?

I am planning to jump ship from my current position due to my hostile coworker. She belittles me and tokenizes my identity on a daily basis and reacts poorly to both constructive feedback on her poor judgement for managing relationships with outside community partners and simple requests such as turning off her phone volume in a shared office space or using Teams for work-related discussion instead of text. She is also a terrible writer (a key job requirement), so I end up having to rewrite much of her work.

I am 100% leaving this position due to her conduct and I feel it’s important to tell leadership. I already discussed my coworker’s behavior with my manager and there has been little change. Leadership’s main concern is finishing the project we were hired to implement. My coworker’s and my positions are temporary, project-based positions, so it is highly unlikely this coworker would stay on. Would I look like the petty, aggrieved employee for sharing my true reasons for leaving or should I keep it neutral and say, “I found a position that’s a better fit for my career goals”?

There’s no point in getting into a lengthy dissection of your coworker’s behavior, but if your manager is the one asking, there’s no reason you can’t say, “It’s no secret that I’ve found Jane very difficult to work with.” If the person asking is higher up, you can share, “I’ve encountered a lot of difficulties working with Jane, which I’ve shared with Manager. I don’t want to rehash it at this point, but it ended up seeming like the right choice to simply move on.” I wouldn’t get into it beyond that — you’re leaving, and that gives them enough bread crumbs to follow if they care to.

One exception: If I’m understanding correctly that Jane subjected you to harassment or discrimination based on your race, religion, sexual orientation, or other protected class, you should spell that out, along with the fact that your boss didn’t act on it when you reported it (that part is crucial). They need to hear that, even if they don’t care about the rest of it.

5. How to raise your rates as a freelancer

Is there a good way to raise your freelancer rates with your existing clients? I haven’t raised my rates in a long time because of The Fear of never getting any work ever again. I am now pretty sure that I am undercharging. My instincts are all saying “only raise by a really small amount!” “Give them three months notice before the rate rises kick in!” But those are the same instincts that led me to not raise my rates for years so I am not sure I should trust them!

Also, do I need to give a reason for raising my rates? Or do I just state that they are going up? I was planning to say, “Due to rising costs, I will need to raise my rates from 1 September to xxx/hour or xxx/day.” As I am a freelancer writer, they may ask what costs. But, honestly, the price of coffee, my most important business expense, has shot up so I am telling the truth!

In general, you shouldn’t raise your rates only by a small amount out of fear; you want to raise them to a level that’s in line with the market and which means you won’t be undercharging. At the same time, freelancers also have to be realistic about clients’ budgets and what price point they’ll accept, and how willing you are to potentially lose some clients over a price hike. (Ideally, you’d be willing to lose some, since it will open up space for clients who can pay what your work is worth — but obviously that gets into what you can and can’t afford, how much risk tolerance you have, and how large of an increase we’re talking about.) It’s more art than science.

You don’t need to give a reason and I wouldn’t say it’s “due to rising costs.” You can just let people know they’re increasing and to what. Giving two to three months notice is good practice. You can also note that you haven’t raised your rates in the X years you’ve worked together.

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  1. nnn*

    Reading #3, I wonder how many people are actually aware of what their detractors say about them, because many people are too polite to criticize others in a way that it will reach the subject of their criticism.

    1. allathian*

      Indeed!

      It’s also a fact of life that nobody is universally liked. If nothing else, there are some people who dislike those who are popular with others just to be contrary.

      I know very well that I’m too outspoken for some people, but luckily I’m no longer dismayed when I realize that someone doesn’t like me much. It’s very liberating. I also realize that I’m fortunate because I can’t remember a single instance where I’ve faced unwelcome consequences (ordinary disagreement isn’t severe enough to count) for expressing my honest opinion when I’ve done so in a professional manner, at least as an adult to other adults.

    2. Alternative Person*

      It also assumes said detractors have/had something constructive to say.

      Too often I’ve seen cases of detractors complaining their target isn’t interested in getting involved in the detractor’s nonsense.

    3. Ask a Manager* Post author

      You’re taking it too literally. It’s not really asking for you to have known detractors and to relay what they’ve actually said. It’s fine to answer it as, “What do you imagine a detractor might say about you, if you had a detractor?” The expectation that you’ll interpret it that way is built into the question.

      I’m not saying it’s a good question; it’s not. If I could advise them, I’d tell them not to use it. But it doesn’t serve you well as a candidate to nitpick it like that. Listen for what they’re trying to get at and answer accordingly.

      1. Anonym*

        I hope one of them reads this!

        I would probably try to answer from the weaknesses / what I’ve done about them point of view and hope they didn’t push their odd framing. “But what of your enemies??”

        1. Charlotte Lucas*

          A big part of my job is making sure others follow certain standards and regulatory requirements. A lot of people chafe at that. (Until they need me to help them decide how to handle certain things.)

          I know for a a fact that some people would call me nitpicking and nagging. And that’s what they pay me for.

          1. Observer*

            I know for a a fact that some people would call me nitpicking and nagging. And that’s what they pay me for.

            So I think that a decent answer here would be something like “I think that some people would call me nitpicky and nagging. But I think I’m pretty good at only being that way when that’s my actual job.”

        2. MigraineMonth*

          “Well, my nemesis is always cursing me for foiling their villainous plans, but honestly that’s kind of the whole point of being a superhero, right?”

          1. Princess Sparklepony*

            Exactly! This is what I was thinking.

            Along with “What my archenemy is saying about me isn’t really my concern. My minions will take care of him.”

      2. Olive*

        Is there a good way to ask someone if they’re aware of having a professional/work-related weakness?

        1. WantonSeedStitch*

          I think asking someone what their greatest challenge has been in a particular role or field of work is a decent question. I recently asked someone in an interview, “what have you found most challenging about management, and how have you worked to overcome that challenge?” It takes it away from the framing of weakness, which I think puts people on the defensive, and makes it more about the thing being difficult, not about the person being inadequate–makes it more likely to get an honest and thoughtful answer, IMO.

        2. Trout 'Waver*

          Not really. Most people are profoundly unaware of their own shortcomings. And everyone preps the question so you’re not going to get a real answer anyway.

          1. Reebee*

            “Not really”? “Most” aren’t aware? “Everyone” preps the same?

            Cynicism is so freaking useless. Olive, yes, there are good ways to assess people’s weaknesses. I have found that it’s useful to inquire about them straightforwardly and then ask the person how they’re being, or have been, addressed.

            Also, how the person answers is crucial; “I work too hard” isn’t a weakness (I mean, it is in the sense of a healthy work-life balance, but saying so is a bit self-congratulatory). “I sometimes struggle with managing priorities, but I’ve been using x, y, and/or z methods to address that, and that seems to be working well. An example is… Etc.”

        3. Chalant AF*

          Olive: “Tell me about a time you received constructive criticism, what you did to address that, and what the outcome was.” For me it’s not so much about what the weakness is, it’s about whether and how they are willing to hear that and make changes.

          OT but If I think someone is a bigot… “tell me about a time when you were asked to do something you disagreed with, or had to take direction from someone you didn’t respect, and how you handled that.” They can’t help themselves. Hand them the rope.

        4. Irish Teacher.*

          Maybe “what areas have been suggested as areas of improvement in your previous roles?” or “from our job description, which parts of the role do you think would involve the sharpest learning curve?” or “in previous roles, which aspects of the job have proved the most challenging for you?”

      3. Alice*

        I appreciate the engagement on this topic! As someone who can be quite literal I struggled with the question. I’m in a financial monitoring role, so I know when people are upset with my decisions. What my detractors say about me is not the same as my weakness!

    4. bamcheeks*

      Yes, I’m trying to think how I’d answer that. I can give you what my critical internal voice thinks, but actual detractors? Not a clue.

      1. KaciHall*

        I’m pretty sure my internal voice is my biggest detractor (thanks imposter syndrome!) but I don’t know that it’s any more reasonable.

        2. FricketyFrack*

          Right? My brain is like, “Hey, you’re a useless piece of garbage and you mess up everything!” It’s not true, but my biggest detractor is a total a-hole. I’m not bringing up anything she says in an interview.

      2. Cyborg Llama Horde*

        Honestly, my internal critic is probably more useful — an honest, literal answer to this question would be, “I got bad comments about my customer service skills on a review six years ago because I didn’t push to close a sale with a client who would not have been satisfied with our product. I’m an engineer, not a salesperson, and I’m more interested in ensuring that clients are happy and have what they need than in landing a big client that will be gone within six frustrating months because they weren’t a good fit.”

        All of which is true, and probably led to the harshest criticism that I’ve ever gotten on a review. But it’s also only fractionally more useful to an interviewer than “I just love my work SO MUCH that I can’t stop working!”

      3. Beth*

        Yes — the word “detractors” easily derails the response. I DO know what one of my detractors once said about me — he wrote a nasty letter of “recommendation” for me in which he made certain I would not get into the program I was applying for.

        He didn’t know that I would be given his letter along with my rejected application, and would find out just how much BS he made up about my alleged failings. By the time I actually read it, I had left the organization where I had worked for him, largely because of his other ugly tricks. But at the time I asked him to write the letter, I thought he was a decent human being.

        Funny thing was, he was mostly describing himself in that letter of disrecommendation . . .

        1. rebelwithmouseyhair*

          Ah, of course my biggest detractor is my former boss! He told the guy he was selling the agency to that I was totally incompetent and unpleasant, in the hopes that they would let me go. However, during the transition, they noticed that actually I was friendly and produced good work within the deadlines, at double the productivity of my colleague who he had praised effusively.
          But I suppose you can’t say “my detractor would say I was totally incompetent and unpleasant but that’s a pack of lies”.

        2. Venus*

          After thinking about it, my biggest detractors are the people who got in trouble for not following the rules. In both cases I didn’t seek to punish them, but rather happened to be at lunch or coffee with managers commenting “They should have known better not to do X” and I pointed out that I’d told them that it was against the rules a few weeks ago, and those people got in trouble. They really didn’t like me because they thought I was out to get them, because I was clearly the source of their being punished, but I don’t think they ever knew how little I cared except that I happened to be in the right time and place to make an offhand comment to the right manager.

        3. Irish Teacher.*

          Yes, I’d find it hard to answer that question in a way that didn’t make it sound like I was really bad at my job or that didn’t sound like I was pivoting to a strength/avoiding the question while still coming up with something that actually sounded like something a detractor might say. I know, logically the last isn’t important, but for a lot of work related weaknesses, phrasing them with context in answer to this question sounds a bit like “well, I don’t actually do anything wrong, so my only detractors would be those who don’t really understand my role.”

          Like as a teacher, I tend to have a pretty laid back style in a lot of ways. My logic is that so long as students are getting their work done, aren’t doing anything that could hurt themselves or others, are treating each other and me with respect and aren’t disrupting our class or others, we can compromise on stuff like uniforms, seating, that sort of thing. I’ve occasionally had kids sitting on desks, but working and once in a discussion class, we were chucking a balloon around while discussing philosophy.

          So teachers who have more formal styles might well think I let kids away with too much or don’t enforce discipline sufficiently, but well, that question makes it hard to phrase in a way that doesn’t either imply I can’t control a class or else make it sound like “well, I understand students and make accommodations so teachers who don’t CARE like I do might not approve,” as if I was one of those “hero” typed teachers in really bad movies about teaching (no, I do not magically manage to inspire all my students). It’s really just a difference of style and priorities.

          The question about how your style might be misinterpreted would allow me to explain that a lot better.

    5. Emmy Noether*

      I know what my detractors say about me (or at least used to say? This was a while ago, but my character traits that get interpreted that way haven’t changed that much). I’m arrogant, aloof, cold, and boring.

      None of which I’d say in an interview. I’d just do what Alison advises and use whatever I prepared for a “weakness” question.

    6. Yoli*

      My team’s working style survey has a similar question that says something like, “How might your style be misperceived?” and I’ve seen responses like:
      –I ask a lot of questions in meetings and have to be mindful of not dominating the convo
      –My affect/shyness might make people think I’m unapproachable
      –I have a strong sense of urgency I want folks to experience as passion, not steamrolling/blame

      In our case, it’s about self-awareness, not a gotcha.

      1. bamcheeks*

        This would definitely get a better answer from me! I’ve been thinking about the “detractors” question and the best answer I can come up with is, “the people whose style tends to conflict with or rub up against mine are those who do/are XYZ, and if they feel the same about me I expect they’d say I’m too ABC”. This question gets to that much more quickly!

      3. BikeWalkBarb*

        This is a great question. I lead a team that has grown rapidly and works remotely (a few are in an office together once a week but all of us only at staff retreats we hold every so often). We open staff meetings with a question that’s meant to connect us with each other and build understanding and this would be a good one for that.

        What else is on that survey?

      4. nnn*

        Oh, that is an excellent question! And that kind of self-awareness makes workplaces run more smoothly!

    7. SarahKay*

      I’d use the ‘things to improve’ part of my annual appraisal to answer that question.
      Obviously this pre-supposes that (a) there’s some sort of appraisal/review system in place at your work, and (b) you believe the person giving the appraisal is actually giving intelligent, reasonable feedback, but if both of those are true then that’s probably a good solution.

    8. ecnaseener*

      Well, the question is what WOULD your detractors say, not what DO they say. So there’s no suggestion that the candidate is supposed to know what they do say.

      Once, for a cashier job, I got a version of this question except instead of “detractors” it was “enemies!”

      1. bamcheeks*

        Oh that’s easy:

        “Outwitted again!” *shakes fist* “I’ll get you next time, Bamcheeks!”

        *closing credits*

        2. TeaCoziesRUs*

          And I would have gotten away with it if it wasn’t for that stinking, lousy Bamcheeks!

        3. Princess Sparklepony*

          If it wasn’t for those darned kids I would have gotten away with it!

      2. Seven hobbits are highly effective, people*

        My enemies have little to say about me…anymore.

    9. Ginger Angel*

      My deficators say that I’m a scary women who doesn’t take no for an answer!

        1. Petty Betty*

          my verbal defecators are all constipated because they wouldn’t dare speak out of turn.

          However, those who work with me note that I do take on a lot at once, and while I can and do juggle the workload admirably, I do occasionally take on too much at once and can get overburdened when there are too many projects/events going on at the same time. It is a rarity and I do combat that by being the model of efficiency and always having lists, spreadsheets and calendars with reminders for all of my tasks and important information, but it is something that I am aware of about myself through both self-reflection and from outside observation.

          And yes, I have said this in interviews. Being candid about it isn’t a bad thing. I am active in multiple events/event planning as a volunteer, which helped land me the position I’m in now, which has an event coordination component.

    10. Bast*

      As Alison said, this is really “What is your biggest weakness” spelled out just slightly different. If you HAVE had a review where your employer/manager had given some constructive criticism, I’d use that and how you’ve improved upon that. “My previous manager stated that she felt that I did not pay great attention to detail in my emails. Since then, I have worked to make sure that I reread each email before sending, run spell check, and double check my numbers to ensure accuracy.”

    11. Rage*

      Oh, I have some detractors, and I know all too well what they would say – and none of it is true.

      Not to say I don’t have weaknesses or things I could improve upon, it’s just that my detractors don’t give a toss about wanting me to improve or succeed – they wanted me fired from my (former) position. (And they almost succeeded, too.)

      LOL I can just see it now, if I answered that question.

      “Let’s see….I respond with anger anytime someone communicates with me, I wasn’t qualified to be doing the work I was doing, I violated confidentiality, and failed to close out a project correctly.”

      Seems pretty damning. Except:
      1. The one who said I responded with anger could not name a single interaction when pressed, and continually refused to meet with me and our direct supervisor to resolve it.

      2. The same person went to my grandboss – who had been with us for maybe 6 weeks at the time – while our immediate boss was on medical leave, and attempted to get me terminated. She also re-wrote the process that I was overseeing, reducing me from managing the entire process to merely uploading the final document at the end. Since, you know, I wasn’t qualified to do the work I’d been doing for 2.5 years at that point.

      3. The one who said I violated confidentiality was the husband of the person in #1 & 2. I’m not sure how I violated confidentiality since the email I sent was to the care team for a particular client regarding that client – and he *replied all* to tell me “Rage, maybe you shouldn’t speak to our clients’ parents.” (Of course, my job couldn’t be done without communicating with parents, so…)

      4. Same dude waited until the day I left on vacation to jump over my boss’s head and report to my grand-boss that I didn’t close out a project properly. Except the project *wasn’t* complete – the parents had refused to sign off on the final report and I was waiting for direction from the funding agency. So, in the end, I had to break a couple of IT policies by logging in to our VPN using a public wifi (I was in the Atlanta airport on a layover), accessing our program, and clicking one “Complete” button. At the request of my direct supervisor, naturally.

      So…no, I, at least, would not answer with what my “detractors” would say. I would, however, give a response that included areas of growth that my current supervisor (who is a very different person with a management style more suited to my temperament) has previously indicated.

      Interestingly enough, none of them have anything to do with inappropriate interactions with coworkers, privacy violations, or failure to click a button. *major eye roll*

      Oh, the person from #1 & 2? She’s still here. Yeah. Fortunately, my current boss would drop a cinder block on her foot if she tried to mess with my career trajectory again.

    12. Raisin Walking to the Moon*

      My knee-jerk response to that question would be, “that my fatness prevents others from taking me seriously or looking up to me,” because I got that feedback from teachers and two awful bosses early in my career. And those are the only people I can genuinely refer to as “detractors.” Like, what does that even mean? I’m not a celebrity; I don’t have “detractors.”

      1. Rage*

        I had a high school teacher tell me that I had “no writing talent whatsoever and nothing you do will ever change that.” I guess I could include that too.

        1. Seven hobbits are highly effective, people*

          My second grade teacher said I’d become a juvenile delinquent due to my poor handwriting, so I guess I could bring that up! (I am now well past the age window for becoming a juvenile delinquent, and was too busy attending college full time at 17 to get around to it at the time.)

    13. Garblesnark*

      Yeah, almost all the “detractors” I’ve ever had who have told me their issue with me were people who were bullying me. Their problems with me were things like “does not perform work while currently undergoing surgery,” “does not apologize when unaware that there is a problem,” “does not follow instructions that have not been provided,” and “does not read minds well.”

      According to them, I am a deeply unprofessional chronic liar who can’t be trusted with anything. Interestingly, they kept assigning me work after coming to these conclusions.

      1. Kendra Logan*

        Yes. For me it’d be countless variations on “Responsible employees get more responsibility, while slackers are allowed to be even slacker.”

        Brings back the time I assembled a rather lengthy document, which had no official deadline. The next time I heard about it, they’re all antsy to get it finalized with some sizable changes.

        I was on another project and couldn’t take up this one again. Later my boss said I needed to prioritize better. Eventually we had the following exchange:

        Boss: You don’t have to do everything yourself. We’ve got a team.
        Me: So why was everybody so paralyzed without me on that project?
        Boss:

  2. Recovering the satellites*

    OP#2 In order to become good at something, you must first be willing to be not so good at it!

    You clearly want to be a responsible boss which already tells me that you’ll be mostly making the right decisions and course correcting where needed. That’s all anyone could ask from you. Good luck!!

    1. Scott*

      Your first sentence is exactly right. I know so many people who don’t do certain things for fear of not doing them well. It can be aggravating as a (friend, spouse, parent) seeing this behavior.

      Dave Grohl spoke about the concept and his early days of Nirvana. “Musicians should just go to a yard sale and buy an old f***ing drum set and get in their garage and just suck. And get their friends to come in and they’ll suck. And then they’ll f***ing start playing and they’ll have the best time they’ve ever had in their lives and then all of a sudden they’ll become Nirvana.”

      2. TeaCoziesRUs*

        I might have just read this to my kids… one of whom struggles with perfectionism. Thank you! Now she’ll understand when I say “Suck until you don’t!”

        I already tell her that if something is easy enough to do perfectly the first time it’s WAY too easy. It gets lots of eye rolls. :)

    2. Smithy*

      First of all – absolutely this.

      I would also add, that the one time I got a management coach through work – it was when I was a supervisor for the first time and also my father had just passed away. While I know that the coaching serviced organized by my employer did not have this in mind – I mostly used those sessions essentially for confidence therapy. Some of it certainly did touch on what it meant to be a good supervisor, but a lot of it was about how I was doing emotionally in other areas of my life.

      Anxiety around doing something new isn’t uncommon, and especially not wanting to “make mistakes” around a person’s livelihood is understandable. But when those thoughts are big enough to the point of not being helpful, finding someone to help process that can be really helpful. And possibly also throw in some good guidance around managing.

    3. Florp*

      My son had a chess club leader who said the only way to get good at chess is to lose 1000 games. The issue stops being an example of failure and starts being an opportunity to learn. We’ve revisited that idea in our family a lot.

      1. Antilles*

        Chess is a particularly interesting example, because the whole point of Elo matchmaking is that you should be playing people with relatively similar skill levels, which by definition means you’re going to lose (or draw) a LOT of games. And it’s not just at lower levels, the same applies across the entire rating spectrum, even world-class grandmasters regularly lose games since they play against other world-class players.

    4. A Simple Narwhal*

      This reminds me of the wise words from Jake the Dog: “sucking at something is the first step towards being sorta good at something”.

      And that doesn’t mean that you’ll absolutely suck at hiring, just that the only way to ever be good at it is to do it first!

    5. BatManDan*

      The book, The E-Myth Revisted, by Michael Gerber, goes a long way towards explaining the roles of Entrepreneur, Technician, and Manager.

    6. underhill*

      As someone else who struggles with this, how do you get over the awful feelings that come with screwing up something important?

      I’ve pushed through the suck to get good at hard things before, but those were often low-stakes things like learning an instrument. If I suck, oh well, nobody gets hurt, try again tomorrow. But something like managing (or being a parent, etc) is a high stakes thing that feels like you can never afford to suck at it because mistakes can have really big consequences.

  3. TheBunny*

    LW#5

    Not exactly the same, but similar…my stylist raised his rates a few months ago.

    He told me during my appointment and said the new rate was effective not next month but the one after. He’s been my stylist for 7 years so we totally chatted about the “why” behind it.

    We also chatted about a couple of his clients who he was giving a little more notice too because they seemed concerned about affording the cost.

    It was smooth and not a big deal at all.

    1. Antilles*

      I actually had the same experience yesterday. Went in for my monthly hair cut and she had a little sign posted saying as of July 1st, her new rates will be $X for a hair cut, $Y for a coloring, $Z for a treatment, etc. No big deal, no big discussion, just a simple sign posting the new rates and that was that.

      1. TheBunny*

        Yeah. I think it was something like $10 more for my color and cut. Definitely not going to leave over it.

      2. Butterfly Counter*

        I’ve had a similar thing at the dog groomer.

        I was told rates are going up $XX. I’m not particularly married to this groomer. I like them, but I also shopped around. I found that all groomers have gone up about $XX as well, so I stayed with the groomer I already know and like.

        So, OP5, if you’re staying in line with what others are charging, you might lose a couple of clients to those who haven’t upped their rates yet or who are newer and charging less based on their less experience, but you’ll largely retain most of them.

  4. Skytext*

    For LW1, when she said she sent screenshots of all the emails she sent, I don’t think she meant ALL the emails, just the ones Pat claimed he never got.

    1. Jo-Maroon*

      Agreed! I assumed she meant the (many) times she sent Pat the relevant documents.

    2. LW1*

      LW1 here! Correct – sorry for the confusing phrasing in my email. I only sent Pat the screenshots of the emails with files I had sent (3 total), not every single email we’d had. I mostly wanted to show him the time/date stamp and that the documents indeed were attached.

      1. Sheworkshardforthemoney*

        Considering that was the first time working with Pat, it was the correct course of action. You learned that Pat was known to be disorganized and brushed off your requests for updates. Instead of investigating at his end he did nothing. You now have an email chain of his behaviour for future reference which IMO is likely to happen again.

        1. Some Words*

          He did do one thing; tried to shift the blame onto LW. Important lesson right there.

      2. Artemesia*

        My concern would be that the client for whom yo9u are working blames you for the slowness of this getting done — so I would be CCing them or even doing a separate email in which you indicate having sent the material multiple times and the difficulty getting their contractor to do the job.

        and I would not dismiss the idea that there is sexism involved here.

      3. SheLooksFamiliar*

        I had my own Pat who would claim he never got my emails, which I addressed the way you did, OP. He wasn’t happy with me, but at least he stopped claiming he didn’t get them.

        However. He did start replying, ‘You forgot to attach the TPS Report’ or whatever I ‘forgot’ to attach, and copied my boss. After I showed my boss my actual emails with attachments intact – and with his support – I again replied to Pat with screenshots of my emails showing the attachment. But this time I copied a friendly Help Desk associate who knew what was up. My emails were solicitous: ‘Pat, I spoke to our Help Desk agent who asked to be copied when you don’t get my attachments, so he can investigate. Let’s get to the bottom of this problem for you!’

        I was also a younger woman dealing with an older man, but maybe he just didn’t like me personally. Whatever the reason, he finally stopped claiming I was ‘forgetting’ things.

        1. Observer*

          He did start replying, ‘You forgot to attach the TPS Report’ or whatever I ‘forgot’ to attach, and copied my boss.

          I think you handled it well. But I would also have started CC’ing your boss on the original emails with the actual attachment, after looping him in.

          I would also have actually attached the original email I sent, rather than a screen shot, but that’s just me.

          1. SheLooksFamiliar*

            I didn’t want to CC my boss on everything but I did think about it. When Pat upped the ante by CCing my boss on claims that I ‘forgot’ things, my boss was laughing: ‘Does he think I won’t ask you to show me your emails?’ He was ready to confront Pat, but I preferred to try and paint him in a corner. And I did.

            Also, the screenshots were of my Sent emails in Outlook, showing each email to Pat by date, and all with the attachment icon. It was a good visual, if nothing else.

        2. Debby*

          I concur! I have had the same thing happen, and it usually a man and I am a woman. So I’ve wondered if gender does play in it.
          Even recently I had one person insist that I was not sending the second page of a document. I double checked everything, and could not figure out why, when the document in question was scanned together with both pages. The only thing my Boss and I could figure was that the person’s printer was printing double-sided and he didn’t realize that page 2 was on the back side. I had to start scanning page 1 and page 2 as separate documents. He then was able to get both pages. LOL

      4. learnedthehardway*

        I would have just forwarded the emails with a “Please see below – as discussed, this was sent on March 15. I have reattached the files.”

        I have done this on occasion – it makes the point, and gets the files over to the person who can’t find them in their inbox. I don’t judge their organizational skills – finding things in one’s inbox can be fraught (and it’s sometimes the program’s fault, not the user). I DO, however, get a bit lit up when people claim that I haven’t sent them something, when I most definitely have done so.

        1. Grumpy Elder Millennial*

          This is what I do, too. If I need to remind someone to do something, I’ll find the e-mail where I asked them to do the thing and forward it back to them, with a “Hi Pat, any updates on this?” Since it’s a forward, rather than a reply, all the attachments should still be included.

          1. Grumpy Elder Millennial*

            To make sure I’m being clear, none of that means that the LW did anything wrong with the screenshots! It seems very likely that Pat was lying and trying to make the LW look bad for his failure to do what he was supposed to. It is 100% reasonable to expose that to decision-makers. And even if he wasn’t lying, it gives him all the information required to figure out what kind of technical problem is happening.

        2. Insert Clever Name Here*

          I forward the original email and include the original email itself as an attachment, cc’ing whoever they’re complaining to. “So strange that you didn’t get the attached email! I’ll call you shortly to confirm you’ve received this one.” Lo and behold, that call always confirms that they did receive the email. Funny how that works.

      6. RedinSC*

        Screen shots, I think, are nicer than I am. I keep forwarding the original email with all the headers below on it.

        Didn’t receive? Let me send again, and make sure to check your spam folder, sometimes things go there.

      7. Jess*

        My go to move is to go into my sent folder and forward the initial email to the recipient again so they can see the original content was error free. I would do this nay time they asked of r another email. just keep forwarding the email chain until they deal with it, not create a new email each time.

        This helps if a higher up needs to be involved at any point bc they can just scroll and see all attempts to deliver the information historically.

        Hard to make bull$hit excuses when each incident is in a direct line of an email :D

      8. RunShaker*

        I’ve had issues with some coworkers in past saying they didn’t receive my emails with attachments. My first action is to verify the email address and then forward them the prior email which has time stamp or forwarding the email that shows their response of receipt along with the attachment. That stops any argument on their side. Not doing this to be petty or mean, I’ve learned that I have to do this in general. I’ve had to ask people to resend an email to me though due to accidently deleting and couldn’t recover it.

      9. Starbuck*

        In these sorts of moments, I highly recommend just replying to your original email to bump it up, that way it’s so clear when it was sent and what was included. But somehow it feels slightly less intense than the screenshots. Were you composing new messages each time?

    3. Anax*

      Honestly, even if it was all the emails, that seems justified to me! If Pat really HADN’T gotten this email, then it seems like the most likely cause would be a technical issue – for instance, emails being quarantined by an overzealous firewall.

      If that were the case, knowing what emails were sent when would be the first step toward resolving that issue with IT. They would probably need specific dates and times to check their system logs, and being able to compare emails might help them find a common denominator which is preventing emails from arriving.

      (This might sound far-fetched, but I’ve had it happen before! I once had to send a bunch of attachments to a union attorney, and the union’s system apparently flagged me as “suspicious.” After that, any email with an attachment or a hyperlink in the body was quarantined. I think I even had one email where I had missed a space after a period (“Thanks.Next, let’s…”), and that one didn’t go through. To be fair, they had just had a VERY costly ransomware attack, so their IT had reason to be overzealous at the time.)

      I think that “oh, there must have been a technical issue” is the gracious and polite excuse here, just as it would be if someone accidentally sent a steamy text to Coworker Alice instead of Cute Date Alice.

      As such, sending the evidence needed to investigate a technical issue feels appropriate. I mean… maybe there was. Maybe something else happened which was embarrassing but not precisely incompetence on Pat’s part – like Pat’s cat stepping on the “delete” key while Pat was trying to sort through emails. Maybe Pat’s assistant was overzealous in sorting emails. There are a few possibilities, and graciousness is only going to make LW1 look better here.

      Maybe the wording was passive-aggressive – and I can’t blame LW1 if so – but we don’t have evidence either way there.

      Glad you CCed up the chain, LW1, because that feels very appropriate here! You don’t deserve to take the blame for whatever Pat had going on.

      1. bamcheeks*

        Yes, with things like this I always proceed one the “assume they’re telling the truth and there’s an unlikely tech issue”, and sending screenshots and asking them to investigate is exactly what I’d do! If they were being very unhelpful and uncooperative about it I’d also tell them I’m going to escalate to IT myself (obviously not possible if you’re outside the organisation, but there might be someone you can escalate to.)

        It definitely sounds possible to me that there was a tech issue and the emails got quarantined or directed to junk mail or something, but it’s hard to tell when Pat isn’t being helpful and willing to communicate!

        1. Slow Gin Lizz*

          There’s also an aspect of “pretend they’re telling the truth even when you are almost certain that they’re not” or “pretend you believe them even when you don’t.” For instance, at my recent ExJob, my nightmare coworker claimed she wasn’t getting the automatic emails from the system notifying her when someone filled out our webform. Which I knew to be untrue because I’d set it up for her to get the emails, I’d sent her a test email, and she confirmed she had received it. A few months later, she claimed she was not getting any of the emails but when I asked her to check if she’d gotten the most recent one she confirmed she had. So *then* I asked her, “So you got this recent one and you got the one I sent months ago, but you didn’t get all the other ones that were sent in the meantime? This is concerning, because that means there’s some technical issue I need to resolve.” I was pretending to give her the benefit of the doubt even though I knew she was lying. She never responded to that question, which is extremely telling….

          All this to say, OP, that Pat sounds unreliable at best. Is there someone at your company or his company who could help you figure out the best way to work with him going forward? I’d say keep CCing the important people on those emails so that they know you’re not the problem (you’re not!), but also have a conversation with someone who has a little more influence and can nudge Pat to actually do his job, or possibly have you work with someone else for these tasks.

          1. Grumpy Elder Millennial*

            Exactly this. Even if you’re as certain as you can possibly be that the person is lying about not receiving things, it’s a great tactic to pretend to be very concerned about the technical issue and figuring out how it needs to be escalated. Because you’re just being helpful! The other person is likely to *miraculously* figure out the problem and fix it themselves. But they will have learned that they can’t pull that nonsense with you.

            1. Slow Gin Lizz*

              My nightmare ex-coworker was forever trying to pull this nonsense and I always called her out on it. My wonderful ex-boss would too. But unfortunately nightmare person was able to somehow convince her boss that she was amazing and doing excellent work and that I was not doing excellent work (guess which one of us *was* doing excellent work? hint: not her) so I left that job for one that pays 40% more, at a place that seems to actually value people who do excellent work. Joke’s on her, I’m MUCH happier now. My only regret is that I couldn’t take my wonderful boss with me (I hope she can find an excellent new job soon!).

      2. djx*

        “Hi Pam, here is a screenshot of an email I sent that you seem to have not received. Can you please contact your IT team about this, cc’ing me – this is a apparently a serious problem.”

      3. Harper the Other One*

        My last name includes the letters C O C K (hopefully this will not get caught in moderation!) and my emails frequently get caught in spam filters. It’s more likely to happen when I send the first email in a chain than when I reply. I ALWAYS start with the assumption that my email didn’t get to the recipient… and it’s proven very handy from time to time when I CC someone I know already has me on their whitelist to say “I don’t think Fergus is getting my emails.”

      4. MCMonkeybean*

        Yes, I’ve had it happen before where for some reason I was not receiving any emails from people outside my company. I was so annoyed that one of our vendors hadn’t responded to a couple of emails I sent until we ended up figuring out the issue through someone on another team at my company who works with the same vendor.

        So if someone is claiming not to get emails, I would definitely treat it as a genuine technical issue! But if they then come back as Pat did and say “well obviously I’m getting your emails, just not the ones on X project” I would frankly be at a bit of a loss on how to respond. If all your bosses have already been copied on everything though then at least they can clearly see that Pat is the problem!

    4. GammaGirl1908*

      Not for nothing, LW1, but when I’ve been involved in email tussles like this, maybe the second email — if that late — sent about who sent what to whom?

      Is CCed to both people’s supervisors.

      That’s if it’s not sent to both whole teams, including bosses and great-grandbosses.

      You were NICER than many people would be.

      2. Sloanicota*

        I agree, once I was concerned Pat was legitimately not getting my emails for whatever reason, I would have CC-d their supervisor on my next attempt, not in a gotcha! way, just because sometimes CCs reach one of their intended targets even if I’m going to spam for someone else. And to cover my a*s.

        1. GammaGirl1908*

          Exactly. Doing so serves several purposes, most of them not even spiteful. The gotcha is only one.

      3. Seeking Second Childhood*

        Yep.

        After the third time I’d have emailed the attachments to the *customer* asking them to forward it.

        “Apparently Pat’s email system isn’t receiving my emails. It might be an overzealous spam filter, and we know your emails are received. Could you please forward this and ask Pat to add my email address to their whitelist?”

        Give Pat a socially acceptable reason excuse – in this case the customer’s & contractor’s different domain names – and your email can be sweet & helpful while still nailing Pat to a missed target date.

        DO NOT feel guilty–you might be saving Pat’s income. Third-party providers have had their service contracts canceled for behavior like this. (I’ve been the canceling customer.)

        1. Seeking Second Childhood*

          I didn’t realize until I re-read what I just wrote that I’m still salty about a translator we stopped working with almost 10 years ago.

          First it was claims that we hadn’t sent all materials or instructions to justify missed deadlines and mis-translation. Then they were unable to supply the TM (translation database) that was part of the contract.

        1. Carol the happy elf*

          I had one of those coworkers for 2 years, “Larry”, lazy and utterly incompetent but related to a senior staff member. For months, my work showed up with his name above mine, or completely ignored despite complete email chains.

          The senior staffer commented that Larry had buttonholed him at a family birthday party for an elderly grand-aunt. Seems he really got into the complaint, with wild claims and details. Even the aunt got so tired of it she told Larry, “You should just march in there on Monday and slam your folding computer (work laptop) on your boss’s desk. Then you should tell him that even though you never finished college, you’re smarter than anyone in the place. Then you say I QUIT!, and slam the door on the way out!”

          Senior staffer rolled his eyes and said, “I know my cousin, he got caught plagiarizing people’s work in college and had to leave. So show me your take on this.”

          I gave him every email for this project, every note and complaint from clients, and notes on meetings that Larry had rudely blown off.

          Then I went on a much-needed vacation for a week. When I came back, Larry had been demoted and sent to another department 45 miles away. But he left a scathing email, CCd to everyone in power:

          “Carol, I tried my best to work with you, but between your “Miss Know-it-all” attitude and your fake accent (?) I should have guessed that your next trick would be trying to get me fired by playing your little CYA card!” He also told me that if I ever needed him for a reference, he would tell them everything about the sneaky tricks I played, like coming in early and keeping evidence, and bringing the boss coffee.”

          Decades later, my head still pounds when I think about it all. (He wrote his own obituary and suggested his eulogy- and his gravestone, which says “Admired By All Whom Knew Him”)

      5. The Younger Woman*

        This is a good way to sour the relationship, and if you need to work with the person long term, a good way to make your own (work) life difficult. Yes, you may get this one thing immediately done, but as for future projects? Good luck with that.

        (Plus, if you’re somewhat mid-level, management is going to wonder how valuable you are as an employee if your people skills are such that you can’t get someone to do something without cc’ing their bosses. I imagine your name will also be memorable to the grandbosses, but not in a good way.)

        1. Slow Gin Lizz*

          I think that depends very much on the parties involved. If you are the one at fault and you are blaming the other party and CCing the bosses, then, yes, they’re not going to look too highly on that. But if you are doing everything right and for some reason the other person still claims you aren’t doing what you know you have done, CCing the bosses is a perfectly reasonable thing to do. Especially if you phrase the email in a way that suggests you are confused as to what actually happened and why the other person doesn’t seem to have the docs you sent (did they get stuck in a spam filter? or somehow got lost in cyberspace?) instead of just blaming the other person. It helps to think collaboratively instead of adversarially when dealing with work situations like these. I think OP did it the right way, and especially with the added fact that her coworker also thought that Pat seemed really disorganized, was right to stick up for herself and not let Pat continue to blame her for his own error.

        2. I Have RBF*

          Naah. If I am getting thrown under the bus, I want my superiors to know the whole thing, not just the bus driver’s side. If they are actually having a technical problem, maybe their manager can help with a solution. If they are a bit unreliable, I want all of the stakeholders to have full information.

          There are some people where I work who are so quick to blame me for their fuckups that I always CC my manager when I send them email. It keeps me from getting that run down feeling. IDGAF if they get butt hurt by having my manager CCed, they have proven that I need to cover my ass that way. They’re lucky I don’t CC my great grand boss, who is the one they always complain to when they throw me under the bus. If they whine, I can honestly say that my boss has requested a CC whenever I email them, because he has.

  5. Captain dddd-cccc-ddWdd*

    OP2 (fear of hiring their first employee) – I think the key to this is to identify whether it’s being their “manager” you are uncomfortable with. Or their “employer”. I’m a manager in a company (rather than my own company) and comfortable with that, but would have the similar sort of fear OP describes if I was employing someone to work with/for me in my own company. Why is that? – because I’d be taking on the weight of being their source of income, their financial position would depend on my company continuing to be successful. They’d likely have left another job, perhaps at a more established company, to come and work for me. And then there’s interpersonal stuff like “what if we don’t get on and it is just the 2 of us”, etc. Of course as a manager I someone else’s company these things are still true, but the company doesn’t swim or sink solely based on what I do.

    1. LW2*

      I think you might have put your finger on it. It probably is about the fact that their salary will be paid by the income I bring in. When it was just my financial position on the line, it felt less scary (though still quite scary).

      Your comment did remind me that this is a part time role and won’t be their sole source of income, which is helpful reassurance.

      1. Allonge*

        Their salary will be paid by the income you and this person will bring in. They are needed because of the business needs them, and they will be contributing to its success.

        Presumably they will also be aware that they are joining a small company, so anyone not comfortable with that will self-select out.

        I totally understand it’s scary! Change is scary. It will be just as scary leaving them in charge for a day or two when that time comes, or letting them make their own calls on some things where now you are in charge of everything. It will be scary to learn they have good ideas on how to handle things that you did not consider.

        1. Sloanicota*

          Well, the person is part time I think, so *literally* OP is likely not their sole source of funding. I have worked part time and it also clues me in that the level of the company/workload might differ from the norm. I think I would screen carefully for an employee who looks willing to take on the challenge of a new (and nervous) manager – but also do keep in mind, it’s probably not quite as dire as you’re imagining.

      2. bamcheeks*

        LW2, I would more broadly remind yourself that whilst there is always a power differential between employer and employee, this person has agency! You presumably haven’t deceived or pressured them into applying or interviewing for your job, so it’s fair to assume that they are making a positive choice, and that whatever you are offering them is a decent deal from their point of view. They know they are entering a start-up charity in a very early growth stage, and they almost certainly know that there is inevitably a bit of uncertainty associated with that. Assume that they have made a well-informed decision to accept that risk, and that they are getting something out of it. It might be the flexibility you offer, the part-time hours, the cause, the location, the opportunity to develop new skills, the possibility that the charity might grow and their might be a bigger role for them in the future, the opportunity to see the early stages of a charity close up so they can start their own in the future– whatever it is, respect that person by being fair and honest, seek reasonable levels of support for yourself from the board and any external HR consultants when necessary, keep them in the loop about the income and business sustainability to whatever degree is sensible for their role and understanding, and then assume that they can make their own decisions!

        Good luck! You’ve got this!

        1. Smithy*

          That’s such a good reminder.

          My first front facing fundraising job was with a smaller nonprofit that couldn’t pay what a larger or older organization could nor did it give my resume “name brand” recognition. I knew all of that when I took the job. But beyond being an issue I cared about, the job gave me so much more exposure and experience than I would have gotten in a more name brand place. Also because our Executive Director hated fundraising, I got assignments that in other sister organizations were taken by the ED.

          All to say that for a while this really benefitted me, my career and ambitions. And then after a few years I was ready to grow beyond what that job could offer.

    2. AlwhoisthatAl*

      And don’t forget OP that your employee is obviously competent or you wouldn’t be employing them. They do not need to have their hands held, they just need a introduction to the company, a detailed discussion of what their duties entail and a way of being able to easily talk and communicate with you. Then a couple of check-ins over the first week. Apart from that they will be fine, they are an adult and almost certainly have done this working lark before.
      We always take new people to lunch at the end of their first week just to make sure they are ok and feeling appreciated.

  6. No touchy!*

    LW5, the way the freelance tutor I get some classes from handled it was simply by informing me she would be raising her rates and opened up her reservation slots a little earlier than usual so you still had time to get some classes at the cheaper price.

  7. No touchy!*

    LW4, I’m interpreting this the same way as Alison (that she was harassing you based on a protected class) so I would definitely bring that up – perhaps not in an accusatory way (as in “I can’t believe Company allows this” – they may counter that you could have gone over the manager’s head) but more as an FYI that *this particular manager* didn’t adequately address it – it’s up to them to decide what to do afterward.

    They can’t fix an issue (and frankly I’d say the manager is the bigger issue) if they don’t know there is one. And they might not know! If everyone leaves without mentioning this then…well, there’s no way for higher ups to know unless they observe it themselves.

  8. WS*

    I wouldn’t say it’s “due to rising costs.”

    I had to raise prices with a particularly price-sensitive group of clients and this actually worked well – it opened a conversation where we could have a general complaint about everything being more expensive these days, without the grumbling being directed at me.

    1. MJ*

      Costs are rising in so many places – utilities, basic essentials like food etc. I don’t think LW 5 needs to worry about it just being about coffee. I put up my rates recently for a long-standing client, did close to what Alison suggested – said I’d need to raise my rates and noted that they’ve been the same for a number of years. In the reply the client spontaneously mentioned the cast of living, and said they completely understood the need to increase.

    2. Guava*

      Agree – I would specifically say “rising cost of living.” We are all aware that that has been a serious issue, and in most non-freelance jobs you can expect regular COL raises. No reasonable person would begrudge you that!

      1. Sloanicota*

        Ideally I think in most cases it’d be more persuasive to connect it to your own improved experience and higher level of performance, honestly. Of course everyone will understand that rising costs play a role.

    3. londonedit*

      Indeed – I think the cost of living is pretty much universally accepted as good reason for prices to go up, as long as you seem genuinely sorry about it. I’ve just had a letter from my optician saying the cost of my eyecare plan is going up by £1 a month (it’s a plan where you pay a small amount each month and then you get as many eye tests/contact lens checks as you need in the year, plus 10% off your contact lenses, which for me works out as a pretty decent saving). Even though it’s only £1, the letter was at pains to point out that the practice has tried to absorb rising costs as much as they can, but they’re an independent practice and they’ve reached the point where they’ll have to pass on some of the costs to their patients. That’s how you do it properly.

      You don’t do it like my previous car insurer, who quoted me a ridiculous sum on renewal and could not have been less interested in a) discussing why and b) lowering the price at all. So guess what? I went elsewhere.

    4. boof*

      I think this is the art of it – on the one hand it can be a bit of a bad habit to overjustify relatively straightforward business decisions; what if costs stayed the same, but the service became more valuable? Etc etc. But, it’s probably a good idea to give folks some sense of what to expect – I actually think a yearly price review and update would make a lot of sense. And the review should include a survey of what the market rates are; not that one has to be beholden to the market rate alone, but if you’re going to undercharge, ask yourself why; if you think you’re better* than average, take that into account too.
      *better could mean faster so if the fee is per project rather than per unit of time that might balance out without a higher rate.

    5. Coffee Protein Drink*

      I wouldn’t say, “I need to” either. Simply, “As of date, I will be increasing my rates to $X.” I think 3 months or one fiscal quarter is sufficient time.

    6. spiffi*

      Honestly, it doesn’t matter *how* OP frames it – there will be customers who complain and demand to know WHY – even though it really isn’t relevant.

      Our small company recently let one of our Fortune 100 customers know upon renewal that we were raising our prices – the first price change in 24 years – and they were all offended “why are you raising the rates? OMG!” Like, seriously – our contract is a TINY drop in the ocean of money they spend in a year…

  9. Dysana*

    LW1: I wonder if the emails with attachments are getting caught in spam/security filters? it would explain you sending them but him not receiving them, even though you’re successfully able to send emails back and forth about the issue. He should be able to recruit someone in IT to investigate if that’s happening

    1. LW1*

      LW1 here! He was strangely able to get documents for the other related project with no issue (that I sent from my email), and a colleague also had to send him documents the previous week where there were no problems. It was bizarre!

      1. Tiny Soprano*

        I’ve used the “oh this must be a terrible IT problem! Let’s get it fixed right away!” tack on an older snarky PM once. It was easier given it was within company, but the way all the blood drained from his face when he realised he’d been caught out… and that he was going to have to look like an idiot in front of the (very scary) IT manager! Priceless. And he was on his best behaviour for me thenceforth.

      2. Pandas*

        It could have been one of the specific documents you were sending, possibly the file size or type. That would explain why that was the only one that didnt go through. Even if he really wasn’t recieving the emails though, that’s no excuse for his attitude about it. If someone tells me they sent files I didn’t recieve, I believe them and start trying to troubleshoot it. I don’t make them resort to send me screenshots…

        1. The Younger Woman*

          I don’t know. From what I understand the communication is mostly done via email, which is a good way for tones to be misinterpreted (I myself am not in the habit of using exclamation points in emails, which give the impression I’m a serious, if not sullen, individual) and for a misunderstanding to head south quickly.

      3. Astor*

        I am have had this happen where there’s something in one email that gets caught by the filter, even though all my other emails are going through. On the cases I’ve seen: forwarding that email again, replying to it, and using my mail client’s resend options will all still disappear their end. I think even copy/pasting is risky; I can’t remember what my testing showed. But creating a new email from scratch works.

        It happens really rarely, but one of those times was a situation where I had access to both accounts and so could see that’s actually what happened. The email wasn’t even making it into the junk mail folder. And I’ve had it happen with generally trustworthy colleagues. Less than once a year, I’d guess, but not much more rare than that.

        So even though “lost in their email” is generally the more likely situation when someone doesn’t reply, I do tend to handle my follow up to reflect that it’s possible that one email thread is just not getting through, even though it seemingly makes no sense.

        1. Bast*

          Yes, I’ve had plenty of spam end up in my inbox, and legit emails that end up in spam. It happens.

        2. Miette*

          Yes, this. I’ve had emails from trusted sources wind up in the spam filter at the mail server level, and had to ask IT to check/release it and whitelist that sender’s domain so it wouldn’t happen again. Updates to networking and collaboration software, changes at the router level, unrelated spam somewhere along the network and more can be the culprit for this kind of thing, even with trusted senders. It’s not you–and possibly not even Pat one or two times, though the way they handled it was bizarre, not to mention the fact they did not acknowledge the error for DAYS even after you asked.

      5. boof*

        At the risk of overly justifying someone who may just be bad at their job (and blaming it on you), I find outlook at least a nightmare to work with – maybe it’s some setting etc but it does NOT sort things in a way that I find easy to find or that makes sense to me, and it can be very easy for me to miss update emails that are part of longer threads.
        Obviously that’d be on Pat to figure out, not you, but FWIW on my end sending a new / fresh subject line that doesn’t cluster with the old ones (but still has project keywords somewhere) tends to be a lot more visible than something downstream of multi-email subject thread

      6. theletter*

        I had a manager who demanded email triggers on a certain proess. I implemented it, but not in the exact way he wanted, and boy oh boy, he maintained that he never received them, for about two years. Even when his manager was getting them. Even when his manager was on the phone with him, describing the emails, double checking the notification systems, waiting with him while the trigger occurred. De nada. It was pretty obvious to me and eventually his manager that the guy was just in denial about the fact I’d implemented this toolset without his help or direction.

    2. MissMeghan*

      I’ve had this happen a few times and it can be incredibly frustrating, especially because it’ll happen with people or companies that everything else is getting through. But it’s like traffic, it’s such a common occurrence that it’s also a convenient lie, and you want to give someone the benefit of the doubt until you can’t. If it’s a one-off assume it’s the truth and both parties got frustrated. If it’s a recurring issue and no effort is made on his end to solve it, time for some side-eye.

      In any case, it’s odd and rude that he didn’t apologize for his snark if it was an honest issue once LW1 sent the screenshots.

  10. MassMatt*

    #5 I’ve been there. It helps if you are confident in your worth—look at not just average rates in your area for what you do but the quality. Do you offer more personalization, higher quality, or quicker turnaround times?

    Keep your value in mind when you talk about your rates—know your worth, stay positive but firm. Most clients understand that costs rise (especially lately) and will take it in stride. If you sound overly apologetic or uncertain, you will probably get more push back.

    IMO having the lowest costs for your service as your main competitive edge is not generally a good place to be in the long term.

  11. Katz*

    LW1: I used to forward the original emails to show that they had been sent before. It was easier than creating anew email with attachments that might be forgotten. Makes it more obvious that it was sent and when.

    1. LW1*

      LW1 here! I did also forward Pat the original email, to which he apparently never got. The whole situation was so strange!

      1. boof*

        Honestly this really reminds me of my outlook inbox being a nightmare to see threaded messages in. But you did the right thing sending screenshots of all the attachments you sent; it’s on Pat to figure it out. I suppose if it was the sort of work where it’s appropriate, you could give pat a back up phone number or chat to call/text so it’s easy to say “hey, I sent the attachments, let me know if you can’t find them” in a different format

      2. Miles of Olau*

        It’s not strange. I’d bet you he didn’t search his email when you said you sent it and blamed you instead of himself. Some people are like that. They make assumptions and forget that there might be a record.

      3. RunShaker*

        lol, now understand why you did screen shots……I think it’s user error on his side and/or being disorganized.

      4. Katz*

        He got them. He just didn’t want to look for them.

        I worked for a man who had time frames in mind for responses he was waiting for. When the reply came in before he expected it, it didn’t register for him to look for it. I started the subject line with “Info you requested” which got his attention.

  12. Jinni*

    One freelancer raised rates last year from $175/hour to $200/hour. She simply said, over Zoom, effective on x date my new hourly rate will be. I like her work, so I shrugged and have paid it ever since.

    Another freelancer I’ve worked with for 16! years hasn’t raised rates. It drives me bonkers, so I simply pay her more. (I haz thoughts…but I keep that to myself).

    One last (editor) doubled her rates. Her error rate was too high for the new doubled per-word rate, and I let her go.

    All this to say your rates are your rates. People will act according to their priorities which may not be yours. Take the leap (assuming you have some tolerance for a shake up). I’m thinking now that my friends still hire/work with the first person and I have no idea about the editor…

    1. Sandman*

      I think the expecting to lose some clients and planning accordingly part is key- I would be shocked with 20 clients if you didn’t lose at least 2, and that is probably ok!

    2. MigraineMonth*

      I think there are polite ways to share your thoughts with the freelancer who hasn’t raised their rates in 16 years. Sharing info about the market/usual pay rates/her quality compared to others may give her the confidence to charge her other clients more as well.

      Another freelancer shared a story of a client who heard her rates and then countered with, “The usual rate for this type of work is [much higher rate], so I’m going to write the contract for that.” Since the freelancer was just starting out, it gave her valuable information about the market and how much her work was worth.

  13. Nodramalama*

    I can see why it would seem petty to screenshot the send the proof for LW1 but I would also be quite concerned if there was actually some issue with particular emails sending!

    2. I Have RBF*

      Yeah, because if there really was an IT issue, then Pat could go to his IT and say “These are screenshots of mail with attachments that was sent to me that I never got, with dates, subjects and addresses. Please figure out what is happening.”

      I would look at it as “If there really is a problem with Pat getting my emails and attachments, what would he (plus his IT plus his manager) need to try to solve the problem.” I would include the manager because if Pat is a bit disorganized, his IT may not want to work with him unless the manager demands it.

      Malicious compliance? Maybe. But as an IT person, when I need to troubleshoot email problems, one of the things I want is copies or screenshots of the sent mails, with full headers and timestamps.

      So assuming that it is a technical glitch, and providing data accordingly, is not passive-aggressive. Adding too much snark in the email is, but the solicitous “Oh, no! Here are screenshots and headers so that your IT can help find the problem. I’ve also put in ticket #12345 to my IT in case there’s a problem on this end.” is right if there is an IT problem, and right if there isn’t, because they’ll know you have called their bluff.

  14. Editor Emeritus*

    LW2: If youre in England, Scotland or Wales, you could consider an ACAS training course. Online courses are free. Regionally-based, in-person courses are also available. It’s a government organisation, so it costs less than private sector training.

    1. LW2*

      Oh thank you – I knew they had templates etc (I’ve used them!) but not spotted the training. Great idea.

  15. abnormal_distribution*

    OP1, you did the right thing. I’ve done this myself a couple of times (i.e. sent the screenshots) and I must admit it did feel a bit petty right afterward, but then I realized it was the constructive approach. The only people who have a problem with laying down all evidence are the ones who want to cover their mistakes. This reminds me of an anecdote I had years ago as a junior employee (I was the one who didn’t receive an email, but the same principle holds). My team lead (who has previously bullied me in various ways) claimed he had sent me an email. I didn’t know what he was talking about, so he reprimanded me for not seeing it because it was about something important. I was 99.9% sure I hadn’t got it since I read each email very carefully, but I decided to check one more time. So I said “OK”, he got back to his office, and I went through emails received from him (there weren’t many of them so it was easy). Then I told him I had gone through my emails, that it wasn’t there, and asked him to find exactly when he had sent it so we could investigate. He made a very long, uncomfortable pause, so I realized he didn’t want to do it and gave up. From his behavior, it was pretty obvious he hadn’t sent it at all.

    1. The Younger Woman*

      I don’t know, I feel like sending screenshots is similar to using those Outlook read receipts. You would notice it because that’s not the default setting, and you may understand why a person would do it, but even in best-case scenarios (which would depend on your overall relationship with the person), you’d still roll your eyes when you get THAT little pop-up box.

      That said, I’m not a confrontational person and have developed a mindset where I just want to work for the paycheck and go home.

      2. Elodie*

        *shrug* There’s only so much (sparing, occassional) nonsense I’d be okay with tolerating for the sake of the paycheck, though.

  16. Green great dragon*

    LW5 do raise your rates enough that you won’t be wanting to raise them again in a few months time. You’ll need to either raise them significantly every few years, or plan on smaller increases every year. But sounds like you’ve overdue a decent bump now either way.

  17. Future*

    Detractors is such an odd and loaded word. I would imagine I don’t have very many detractors, and those who I think may be my detractors I don’t put much stock in, because they are irrational like the boss in the letter from yesterday who was always jumping to conclusions, or a handful of clients who are known cranks and complain about everyone. I like to think I mostly am surrounded in my work life by people who like and respect me but may be aware of my faults, and imagining what those people think of me is a lot more valuable.

    1. Myrin*

      I don’t live in an English-speaking country and although I’m fluent in English this is actually the first time ever I’ve encountered the word “detractor”! I’ve looked it up in the dictionary and it’s giving me several translations which all go in the same general direction but are still pretty different from one another – someone who criticises, an enemy, someone who bitches about stuff, a whiner, someone who slanders, and someone who denigrates. I’m fascinated.

      1. The Unspeakable Queen Lisa*

        Yeah, the connotation is definitely “people who actively tell others negative things about you”. Not just that they passively think badly of you, but that they feel a need to share it with everyone they meet.

        It’s way more negative than just “what would other people say are your weaknesses?”

      2. Paint N Drip*

        I would say the enemy/slanderer is closest to most English-speaking usage of the word – so it’s a pretty intense word choice!

      3. fhqwhgads*

        Yeah, it’s more like all those things at once, rather than any of them. Like, someone who criticizes you perhaps because they are your enemy or just opposed to you in general, and it could involve slander or not, but someone who is loud about their poor opinion of you. Generally only used in context of public figures – or frankly even political figures or leaders, or maybe giant corporation head honchos too.
        Like…Nixon had detractors. Heck it wouldn’t even be odd to say Oprah has detractors. It is very odd to say random candidate for average human job has detractors.
        I get in the net promotor score framework how it’s used commonly in business, but even then, it’s about the company as a whole having detractors, not an individual within (unless it’s the CEO or founder), so even if folks are asking the question with that word because they’re used to the term in the net promoter score context, it’s still using a chainsaw where a butter knife would do.

      4. Irish Teacher.*

        I’d take it to mean somebody who puts you down, minimises your accomplishments and criticises you. The sort of person who if you told them you got a promotion would tell everybody you must be a nepotism hire or that you must have bribed somebody or that your interviewers clearly weren’t very good at their job to promote you.

        In this case, I assume it means “what criticisms would those who judge you harshly/criticise you a lot make of your work?”

        I assume it’s basically a way of asking “what legitimate criticisms could be made of your work?” but it is just…a really bad way of asking it because it’s hard to answer it in a way that doesn’t either sound like you are playing things down or else making it sound like you are legitimately bad at your work.

        Like if asked “what legitimate criticisms could be made of your work?” one could answer that “I’m not very familiar with X programme” or “I take a lot on myself and don’t always delegate when I should” or something onto those lines but…when phrased as coming from a detractor, the first sounds ridiculously minor, like you are making out that even somebody determined to find a fault could think of no worse than that and the second either sounds the same way or else like you freeze people out of projects making them angry.

    2. Wings*

      It’s Net Promoter Score speak so for someone used to seeing customer feedback grouped under “what do our promoters say”, “what do our passives say” and” what do our detractors say” it didn’t raise even half an eyebrow.

      1. Paint N Drip*

        THANK YOU for this clarification!! That framework absolutely takes the intensity out of it for me

    3. Pretty as a Princess*

      Agreed. “Detractors” when talking about a person is oddly confrontational. It implies that people are working against you/taking positions against *you* with enough focus and frequency that it’s a *property* of them. I think it’s a crappy way for an interviewer to frame the question. The question is supposed to get not just at “your weaknesses” but at what people push back at you about – that’s different from being a “detractor”. There are people I work with where we have definitely conflicting opinions about how to prioritize and execute certain things, but we wouldn’t classify ourselves as “detractors” of one another. I can have a whole lot of respect for someone but also recognize they have a weakness (say they are nonconfrontational to the point of ruinous empathy at times) but that doesn’t make me a “detractor.”

      If I were asking someone to parse critical feedback they receive, I might ask “What kinds of critical feedback are you most likely to receive in your current position?”

      1. Irish Teacher.*

        If I were asking someone to parse critical feedback they receive, I might ask “What kinds of critical feedback are you most likely to receive in your current position?”

        That’s a good way of phrasing it and leaves an opening for lots of different answers, even more than “your greatest weakness,” I think.

    4. Laura*

      Yeah, I get what they were going for, but detractors is an aggressive word to me and I’d definitely be thrown if someone used it this way in a job interview. I also think that the only people who have detractors are public or quasi-public figures and I am neither.

  18. Cheap ass rolling with it*

    LW #5. I’m a freelancer. I raised my rates, and below is a rough template of my email (personal details removed). I left my email open to negotiation. My client immediately accepted the new rate and did not negotiate.
    —-
    Hi xxxx,

    (A sentence thanking them for a recent interaction/project, etc., especially if it’s new work that was beyond original scope)

    I’ve been meaning to talk to you about my compensation. With the inflation situation the prices of everything have gone up.

    In view of this, I would like to revisit my consultation rate. For the past xx years I have charged a rate of $xx/hour.

    In view of inflationary pressures, I propose my normal rate of $xxx/hr starting with this month’s invoice. Please let me know what you think.

    Thanks,

    1. Overthinking it*

      Don’t use “like to!” You’re not negotiating with a boss, you’re informing a customer. Say, “I have decided to. . $XX.00/whatever.” (If you want to sften a bit, add “I hope that’s going to be ok for you. I’d like to keep working with you.” And don’t say “rising costs” just “inflation” Everybody understands that! You need enough to live on. (Corporations say “rising costs” but it’s understood that one of those rising costs is paying employees enough to live on, so they don’t quit.)

  19. Workaholic*

    LW1: obviously not the issue since Pat did acknowledge receipt of your email eventually. But humorous story – a number of years ago I reached out to the City of Toppenish for documents, and they sent them. I kept calling because I never received them. The lady was getting frustrated so I had her send to a coworker thinking maybe I was having email issues. Still nothing. Then I realized the problem. Our system was blocking emails with the word p*nis in it (TopPENISh). I had to reach out to IT to add them as an approved sender. Took a few days to figure out and resolve the problem, and it was a great laugh after the fact, and… yay firewall? But seriously LOL

    1. EvilQueenRegina*

      The UK town where I lived as a toddler is notorious for this problem (different word) – I won’t name it here to avoid going into moderation, but I think the UK readers will know the one I mean!

      2. Hastily Blessed Fritos*

        If it’s the one I’m thinking of (starts with S, ends in “horpe”, with the problematic part in between) it’s known even in the US among people who pay attention to these things! Learn how to match on word boundaries, filter writers, it’s not hard!

        1. starsaphire*

          Oh my gosh yes, the S****thorpe Problem!

          I had never heard of that particular city until this happened. Now I’m kind of hoping to go visit there someday and send postcards to all of my friends who like to send me postcards from similarly naughtily-named places!

        3. Irish Teacher.*

          The town of Effin in Ireland got people’s facebook accounts suspended for mentioning it. Apparently, thought that mentioning Effin town was an attempt to insult the town.

    2. Observer*

      Took a few days to figure out and resolve the problem, and it was a great laugh after the fact, and… yay firewall?

      This is why one of the first things we do when someone claims that they sent something that didn’t show up is to check the spam filter. We do filter with a light touch, because we REALLY need to avoid blocking some serious stuff, but still it occasionally happens.

      And it’s been decades since we used a filter that could create that problem.

    3. Pizza Rat*

      Oh wow…I’m glad you got it figured out. You also demonstrated what Pat should have done if he wasn’t being deliberately obstructive. You investigated until you found a solution.

      Thank you for the morning laugh. :D

    4. BikeWalkBarb*

      I work for a public agency in Washington state and am now wondering if my coworkers and I have ever missed any emails. I don’t think our spam filters are quite that prudish but I’m going to check.

    5. Minimal Pear*

      Reminds me of the online archaeology (?) conference a few years ago where the overzealous filter was catching “bone”.

      1. metadata minion*

        Paleontology. There’s also a famous fossil site that had to be renamed the Heck Creek Formation for the duration of the conference :-b

  20. General von Klinkerhoffen*

    LW5, it may reassure you to hear that when I revised our fees earlier this year, using an official inflation calculator (eg if we charged $100 in 2015, that would be $150 today), we were also nervous about the reception.

    But every client has written back to accept the new rates, and it has made no difference to the amount of work coming in.

    1. Macro Husbandry*

      Yes, fwiw, as someone who works on the budgeting side of thing, we always budget for a 5-7% inflation increase and are (pleasantly, admittedly) surprised when rates don’t go up from everyone.

  21. Retired But Still Herding Cats*

    Re #1: Pat is either disorganized *and* a jerk, or Pat isn’t sufficiently tech savvy to check his spamcatcher.

  22. Astronaut Barbie*

    Thee way I raise my rates is to start with the higher rate for new clients. Then get in the practice of regularly raising rates (meaning on a time frame, say every 2 years, or whatever you choose) by a little it to keep up with market rates. But start with the newer clients. And if there are no new clients, then start with new projects from existing clients.

    1. Sloanicota*

      I agree, I’m not sure what kind of work OP does, but it was easier for me to bid a higher rate on new projects and just start charging that. It would be nearly impossible for me to revisit the existing rate on previously bidded projects – better to simply finish those up.

  23. cabbagepants*

    #1 maybe because the petty runs in me, too, but I think you were fully justified in sending screenshots of all the emails. Your point isn’t that you did your nominal duty by sending one email; your point is that you’ve been busting yourself trying to get Pat to do his side of the work and he still hasn’t done it. If Pat had been being more reasonable and polite then yes, just the one email would have been appropriate.

    1. The Younger Woman*

      I mean… if what you do is sending the same email over and over in hopes of getting a different result… not only is an Einstein reference due here, but all you do is still your nominal duty (even if you’re doing it more than once).

  24. HailRobonia*

    “What would your detractors say about you?” – that’s so much worse than the “weakness” question. The way it’s worded really makes the smartass in me want to answer “nothing, I destroyed them all!”

    Honestly though, if I were smart, I would, in addition to doing the “this is something I’m not 100% at and what I have done to remedy that” I would say something like “I would hope I don’t have detractors – I value open communication and collaboration and ideally if someone had an issue with my performance or other workplace issue they would feel comfortable discussing it with me so we can resolve any misunderstanding.”

    1. Bast*

      I would find the answer funny if it was then followed up on essentially the same way the “weakness” question was. I always liked when people showed personality during their interviews. HR was a big fan of the standard strengths/weaknesses questions, although she’d usually phrase them slightly different. The only time a funny issue would be a real issue is if the person claimed then not to have any weak points (which a few did) or expressed a dislike or weakness for something that was a major function of the job.

    2. BikeWalkBarb*

      That’s a winning answer in my interview process. The follow-up would be “Describe a time when you had a difference with a coworker or member of the public and how you resolved it. How was your relationship with them going forward from there?”

  25. I should really pick a name*

    #4
    Since you’ve already spoken to your manager about your issues with Jane, I don’t think that bringing them up when you leave is going to change anything.

    Also, good work on having spoken to your manager about it already! Some people go straight to leaving the job without taking that step.

  26. Catwhisperer*

    LW3, if you feel it’s important to explain your rate change but don’t feel comfortable saying it’s due to inflation or rising cost of X, you can always say you’re raising them to be more in line with market rates. If you do that, though, just make sure they actually are within market rate for your area! That would be smart to do regardless of the reason, so you have a better idea about what others in your area are charging. And who knows, maybe you’ll find you’re severely undercharging and it’ll reassure you that the raise is appropriate.

  27. Tech VP*

    #1- I’m probably showing my age (40) but the only thing you did wrong IMO is fail to pick up the phone and call Pat.

    You were right. You sent the docs. Either he can’t find them or is making up nonsense, but either way a quick phone call would solve it without all the email back-and-forths and cc’s to your bosses. As your boss in this scenario, I’m just annoyed to be copied on what clearly should be a phone call. If you are worried about CYA just separately forward me the initial email with “fyi the vendor is acting like he never got my docs but I sent them on X date; I’m on it and will make sure they get uploaded.”

    1. WellRed*

      I felt the same way. All the to and fro and CCs and then the screenshots. When could communication is failing, communicate in a different manner to see what’s going on.

    2. Jennifer Strange*

      I’m sincerely curious how you think a phone call would help with the issue? In my mind the LW calls Pat and he just says “Nope, never got them” and that’s the end of the phone call. By being able to send screenshots the LW is covering her own ass, and either Pat recognizes he did actually get them (and they were in a spam folder, he read them and forgot, accidentally deleted them, whatever) or he and the LW recognize that there is a tech issue at hand and both can investigate further with their tech departments.

    3. Coffee Protein Drink*

      I’m not sure if a phone call is a step here. It was important for the LW to prove to Pat that the original emails and attachments were sent. That means forwarding or screenshots.

      2. Myrin*

        Also, the documents still needed to get to Pat eventually, so better find out if there’s something preventing that sooner rather than later.
        (And I say that as someone working at a phone-heavy place and preferring that. It’s just that I don’t think it would be the best mode in this particular case.)

      3. The Younger Woman*

        Well, I assume the screenshot was one of the later steps after some resentment had built up (because why would you want to “prove” you were right if you were still on friendly or at least neutral terms)?

        LW mentioned below they don’t have Pat’s number and email is how they’ve always communicated. Thing is, of course Pat DOES have a phone number, and after the first 2-3 emails, what I would’ve done is find that number one way or another and CALL HIM. The only time email-only communication would be acceptable is if Pat was based in India or something, and even then I’d try to find the time when we were both awake.

        1. Coffee Protein Drink*

          Friendly has nothing to do with do it. LW was doing exactly what she needed to be doing. She needed to prove that she had done and was doing her job because she was being accused of not doing it.

          Pat is the problem here, not the letter writer.

    4. LW1*

      Hi there – LW1 here! I couldn’t call Pat because the only method of communication I had for him was email, and that’s been the standard since we started working with him.

    5. Generic Name*

      I agree. After the 3rd or so email on the same topic without making any progress, it’s time to make a phone call. I know some people would rather die than call anyone and think all meetings could have been emails, but that’s just not the case all the time.

    6. anon tech writer*

      You know, I get that – I’m in my mid-50s and I also remember when there was no such thing as email – but for my entire (large tech) company, we don’t even *have* phones.

      I wouldn’t even have considered the possibility of calling – I’d have done the exact same thing as OP, because how do you send a screenshot of your proof over the phone, unless you’re in a Teams call?

  28. I treated you like a son*

    In 2024 I think it’s ok to say you are raising prices due to higher costs. The cost of living these days is so high, and everyone knows and talks about it, so I don’t think you need to find a nice euphemism for a price increase.

    My barber just raised his fee with a two month notice – rising costs, nobody batted an eye

    1. fhqwhgads*

      It’s not that it wouldn’t be OK to cite it. It’s just completely unnecessary.

  29. Yup*

    LW#1: Sometimes I feel like the extent and prevalence of sexism in the workplace doesn’t come across enough on this page to explain behaviours like this. You were clearly gaslit over and over again with the intention of making you look foolish–and Pat assumed he could get away with it and put you in your place. Whether you’re reaction was overkill or not is besides the point. What are women (or other targeted groups in the workplace) supposed to do to counter behaviour like this? Of course you’re having doubts about how you reacted–that was sown by Pat in the first place. You were put in a position that made you doubt your professional behaviour, which was nothing but impeccable until the situation turned impossible for you.

    This is all on Pat’s shoulders and I think we need to highlight sexism in the workplace instead of critiquing the way women and others are forced to push back.

    1. Myrin*

      I’m sorry but the prevalence of sexism in the workplace gets brought up here daily and even on letters where there is no indication whatsoever that that’s what’s going on. I don’t know if you’re a new reader or have only ever encountered letters where sexism wasn’t a topic but if you want to criticise AAM for something, “not highlighting sexism in the workplace” is almost the only the thing you couldn’t use because it gets brought up literally all the time.

  30. Hyaline*

    lol the “detractors” phrasing would make me want to shrug and say “haters gonna hate” because it’s worded like an elevated version of high school drama!

    It also seems like it really opens the door to “my perceived weaknesses are strengths” answers or even “here are ways people are wrong about me” and those are probably less than helpful. Who comes up with these questions!?

    I agree with a pivot to “here is something I’m conscious about working on” or maybe even describing how I’ve dealt with conflict in the workplace but sheesh.

    2. Irish Teacher.*

      Yeah, this may be just me, as I tend to be fairly literal, but I kind of feel that virtually any answer to that sounds like a “here’s why everybody who criticises me is wrong” or else like an egregious issue or else so minor that it sounds like you are deliberately choosing something minor.

      Like “I lack experience with X” sounds like a reasonable answer to “what are your weaknesses?” but to “what would your detractors say?” it sounds like “I’m so good at my job that even somebody out to criticise me could think of nothing beyond I wasn’t immediately skilled at something new. And mentioning anything interpersonal, even a minor thing, sounds like it’s really annoying your coworkers and making them into “detractors.”

  31. Lizabeth*

    #1 One trick I found helpful: adding a received receipt and read tag to certain people’s emails (Outlook). That enabled me to say “Oh, but you opened the email on xyz at 9 am.” Or I simply forwarded the notification to whomever in question. Most of the time “someone” wasn’t willing to go through their emails to find stuff in spite of having a search option as well.

    1. I should really pick a name*

      Unless they’re like me and always click “No” when asked to send a read receipt.

      1. Salty Caramel*

        I don’t do read receipts either. I just answer my email in a reasonable period of time. If I have a day full of meetings, I say so if I can’t.

        I remember a client who was utterly stunned that I would usually be able to get back to her in an hour or two. “My last vendor wouldn’t even get back to me on the same day.”

    2. The Unspeakable Queen Lisa*

      I don’t think this works for people outside your office/internal network. So since this was a 3rd party vendor, it wouldn’t change anything.

      Also if their settings are “mark all incoming emails as read” you’re going to get false positives.

  32. Alton Brown's Evil Twin*

    OP1 –
    It seems like you understood that there was confusion between the two projects relatively early in the process – did you explicitly call that out to Pat? When there’s a mixup along that line, I like to surface it very clearly, in a separate email thread.

    “Hi Pat, I think we’ve got our wires crossed. The files I sent you Friday are for Llamatronics (customer #00000), not Amalgamated Alpacas. We won’t have anything more for Amalgamated Alpacas until October.”

    I think Pat has a mental shortcut that links your name (or your company name) to the Alpacas, and he needs to get pulled up out of his routine to see that there’s something else going on.

    1. Salty Caramel*

      I think you’re being kinder to Pat than he deserves. If that was truly the case, he could have cleared this up at the first mistake. LW stated the project name was in the subject line.

  33. Jennifer Strange*

    #1 reminds me of a donor who claimed he had never received an invitation to an opening night, even though we could see that it had been sent to his email. When we suggested he check his spam folder he responded with “I don’t have a spam folder.” It was only when we sent a screenshot that he stopped blaming us and started blaming technology (so a win, I guess?)

  34. TKC*

    LW1 Pat would be about to get a “per my previous email” email. That lack of organization/competence/accountability is just… really bad and if there’s any chance it can fall back on you then you really have to cya and call Pat out in the process. That’s on her.

  35. Former Mailroom Clerk*

    For #5 – With the way your contracts are laid out, can you tell your clients that your new rate will be $XX as of DATE for all new work, but all currently contracted work will be completed at the current rates?

    It’s probably harder to do that if you have an open ended contract, rather than for a specific piece of work.

    I’m not sure this would work, but you could also set an (even higher) rate for new clients, and tell your existing clients that because you value their continued relationship, they’ll be receiving the “VIP Client” rate, which is a bit lower than the (even higher) rate, but still higher than your current rates. (Also not sure if this is necessary)

    1. Long-time Freelancer*

      This is how I do it – I’ve been freelancing for almost 20 years in several industries, and every time I raise rates I implement:
      1) Big rate increase for new clients – This is the one I quote from then on.
      2) Email to existing clients that this is my new rate moving forward, so please keep it in mind if referring me out, but that they will (either, depending on industry) be grandfathered into the old rate, or that they will be receving “Loyalty Discount” for the next 3 mo/6 mo/whatever time frame seems doable to make the change.
      3) I also have a secret “Friends and Family” discount that I use for someone that was quoted the old rate either by myself a long time ago or a referral and really pushes back against the new rate. This one is somewhere in the middle, and I only pull it out if I really do want to work with this client or really do feel bad about them getting blindsided.

      I tend to make my increases quite big (like, double) because I hate raising rates and tend to price myself too low out of fear of losing clients, so while this means I have a lot of numbers to keep track of at any given time, my loyal clients always feel like they’re getting a deal, I don’t feel like I’m exploiting anyone, and I end up averaging out to about market rates. When I start having way too many clients, I know I’m too low again and up the rates go…

  36. I treated you like a son*

    Agree with the main advice for the “detractor” question – it sounds like it’s wording taken from the NPS (Net Promoter Score).

    Don’t take it literally, all it means is basically what are your weaknesses

    1. Observer*

      You’re probably right. But this is a misapplication. Because when you are talking about PR / Comms / public perception / networking what people *say* about you is important regardless of whether those things are true.

      If you’re trying to get your product into people’s consciousness as the “default” whatever, for instance, you need to know that people are *actually* saying about your and your product, regardless of the truth of those comments. You *also* need to know what the genuine issues are, but that can be a totally different thing.

      So it’s a poor application of a sensible concept.

    2. linger*

      Would have been called a Total Promoter Score except nobody would complete the reports.

  37. Art3mis*

    LW4 – I left a job because of a co-worker, but really it wasn’t just her, it was management allowing her behavior to continue when they knew it was an issue. They knew why I was leaving, telling them again wasn’t going to fix anything. They didn’t care that they had created a toxic environment.

  38. Someone Else's Boss*

    LW #3 – it’s a very common question to come out of a search firm. I can promise they will ask your references this same question. I would advise you (and honestly, all job seekers) to think of that question themselves when selecting references. If they were asked to point our your weaknesses, what would they say?

    1. fhqwhgads*

      Weaknesses is a common question. I think it is very reasonable the phrasing “your detractors” is what’s throwing LW3 off. If someone asked me about my detractors, I’d be thinking “is it normal to even have detractors if you’re not a well known public figure?” I mean, I do realize anyone who criticizes you is literally a detractor, but that term has a connotation of something larger. Even asking “what would your critics say” sounds less, I donno, dramatic? But seriously, I don’t think of myself as having detractors because I don’t have a following. Referring to people who have ever criticized me ever as “detractors” seems overblown.

  39. The Younger Woman*

    For #1, just make sure the file itself isn’t the problem by sending it to yourself. I had this issue once when a word file wouldn’t go through Outlook. The project manager sent me a screenshot as “proof” and everything and re-sent it via Teams (while clearly assuming I was lying when I said I never got his email), and later when I emailed him the file back the same issue happened and neither of us knew he never got the email until I supposedly missed the deadline.

  40. Florp*

    OP5: I work with a tiny marketing agency that raises their rates every January, even if they don’t really need to. When you sign on with them they explain it as part of the general contract. They send out reminders in November and December. They work mostly in ecommerce, so their clients can get through their holiday marketing under the old rates and adjust to the new rate in January, which is conveniently when their bank accounts are full of money from holiday business.

    They are very matter-of-fact about it, and the increase isn’t much–COL and market adjustments, mainly. They peg themselves in the mid to high range of the market. They are good at their jobs, and they are pretty fast. The higher rate and quick turn around means they can have multiple clients, and they never have to pad their hours to make a living. The stable companies deal with it just fine. The only companies that have a problem with it are the ones that are full of bees anyway, and you want those to fall off. A client will waste your time if they are only paying $50/hour, but they will get their act together when they are paying $150/hr.

  41. Student*

    The way to handle #1 is to treat it as if there is obviously some sort of technical problem related to emails (even if you are pretty sure that it is just a disorganized, blame-throwing person instead). Tell them there must be some technical problem with emails, and then send them the info you would provide to help troubleshoot if it WERE an email problem – which happens to be info on the number of emails you sent, the approximate times/dates you sent them, which ones had attachments. Get a quick confirmation from the people you cc’d that they saw all of the emails, and add that for good measure. Maybe even contact your internal IT help desk and ask if they can also confirm the emails were sent out of your organization correctly from your business’s email server, so you can emphasize to your contact on the other end that the problem is not on YOUR end.

    This has a few advantages:
    (1) It lets everyone save face – you’re blaming the email system, not the person you’re in contact with. Even if you both know that’s a little bit of BS.
    (2) It lets you show the person on the other end that you keep careful records. You are not going to put up with bullshit if that’s what they’re peddling. You are going to out-maneuver them if they are playing blame games, so they better knock it off.
    (3) It also allows for the very real possible problem that this is IT-related! It’s possible some or all of your email attachments were too big for them to receive. It’s possible your contact needs to whitelist you in their IT system to receive attachments from you, and didn’t realize it or didn’t do so. It’s possible that your attachments got sent to your contact’s spam folder and they didn’t think to check. It’s possible that either their or your business is having a genuine email server problem unrelated to all of these plausible issues I’ve listed, either temporary or prolonged. Email is remarkably complicated. You’re likely used to it being reliable, but it is not the post office – there are lots of situations where it can go wrong.

  42. Fluff*

    LW # 5 – Recommend raising rates, use your value and also consider giving advanced notice to your established clients. Question for the freelancers though.

    Me = client. (and freelance musician but that is different)

    For freelancers, I was wondering about this from a client view. I personally am much happier with a larger bump that stays stable for a while than yearly smaller bumps. I realize that may be a personality thing but it does helps me budget. With enough notice it seems fine and I want to be supportive and pay people well.

    What are appropriate notice times? Do they vary by field? Asking as an established client (vs new ones or intermittent ones). I would be unhappy if the rate increased with the next invoice vs. later. It happened once by a chunk and I had to drop services for 4-6 weeks until I edited the budget. Then I was back on a regular schedule. With heads up it would have been much more doable.

    Am I being too picky as a customer? Is that common to be the next invoice vs a few months out? I wonder if I should work on my expectations if I am out of the norm.

  43. Is this working?*

    LW5 (freelancer raising rates)

    I’m a former freelancer who has had to raise rates. On top of the great advice you already got, I would add two pieces of advice:

    – look for new clients at your new rate. As Alison noted, it’s a normal progression to raise your rate and also to lose some clients as you do. One of my first clients when I started out used a lot of beginner freelancers alongside a team of more experienced employees in-house to review their work. In line with that, they paid beginner rates. We had a good collaboration for a couple of years but at some point, I recognized that I was ready to raise my rates beyond what made sense in their business strategy. So although I liked them, our path diverged. Conversely, one of my new clients at the time paid a fairly high rate but they also expected a more polished, turnkey product. So that client wouldn’t have been available to me when I first started. So there can be a rollover as your experience, profile, and rates increase and that’s ok. If you recognize that, you can accept that losing clients is natural and that they’ll need to be replaced. Given that need, you can start looking for new clients right away, without waiting to lose some. Getting your first new, higher-paying client will put you in a better financial position to take the risk to lose some lesser-paying clients, as their income will already have started being replaced. Plus it will give you more confidence in your new rates, your value, and your ability to find clients at that rate.

    – stagger your rate increases, not by doing too small increases but by doing an appropriate increase with a smaller number of clients. There’s no reason why you have to increase your rate equally for all of your clients. Especially since you aren’t doing a first day of the year/financial year raise. Since it is scary for you, you can start with one client. Pick the one you are least afraid of losing based on income, ease to work with, etc. Tell them you are raising your rates to X starting Y (always give some notice). Once either they pay your new rate or you replace them, tell the next group of clients, and so forth. This mitigates your risks of having a short-term or long-term income loss. If the market can’t support your new rates, then you’ve only lost one or a few clients. If on the contrary, it’s well-received, then you will feel a bit more confident every time you do it. And even when a client refuses and drops you, here and there, it will hopefully change your internal narrative from “oh no, I shouldn’t have done it. I’m losing clients.” to “oh well, clients A, B, and C are willing to pay X. If client D won’t pay that rate, it doesn’t make sense to keep them on, as I could use that time doing higher-paid work for my higher-paying clients”.

    1. Digital Bohemian*

      All of this!! I tie my rate increases to my clients’ anniversary with me, so I’m never raising rates for all clients at the same time. It’s a great way to mitigate risk. I also throw in a “long-term client discount” for most of my clients, which is a great way to make them feel valued while allowing me to set rates for brand new (and pain-in-the-butt) clients much higher.

  44. Mango Freak*

    “My detractors would say nothing but what is written on their gravestones, for lo all foes taste my blade and my boot, and none tell tale again.”

    At least that’s how I got my current job.

  45. filicophyta*

    LW5, if you work from home, you also pay rent, electricity and internet and phone. Chances are, these expensive have gone up, not just coffee.

  46. Mytummyhurtsbutimbeingbraveaboutit*

    My biggest detractors would say I’m too loud, intruding in their view, and don’t share my food, and are worried I’ll invade their space

    They’re also my neighbor’s dogs, so take that as you will

  47. theletter*

    LW5 – look at the 80/20 rule! Often, the clients who are only providing 20% of your revenue are using 80% of your time. Undervalued service can often lead to higher scrutiny and larger demands. These are the clients you eventually want to replace with the 80% revenue clients, who use 20% of your time. These are the clients who appreciate your service simply as it is. They will be expecting rate changes along with normal inflation.

  48. Mermaid of the Lunacy*

    I will always, always cover my butt when it comes to emails. Too often “I didn’t get/see the email” is used as an excuse as to why something didn’t get done and I don’t play that. If I’m doing my part of the process, you don’t get to pretend you didn’t get or see an email. And I insist people send me requests through email and not chat so when I reply I have a record of that email sent. There’s no shame in CYA and letting people see you have your sh*t together and can’t be taken advantage of to excuse their lack of organization or planning.

  49. K in Boston*

    #2 I’m not a businessperson/person who runs a larger organization, but I spoke to a small business owner once who was telling me about their business mentor. Perhaps there is something like that where you are? Not that you need to have one before you hire (especially since you need to hire sooner rather than later), but it might be helpful to feel like you have someone you can talk through these things with!

  50. AnnyFlavash*

    LW2, I feel your pain. When I joined my tiny nonprofit, I was employee #3 – and I was brought on to train under and eventually take over for the Executive Director. We knew we would need to grow, and that meant I was going to have to do some hiring. Nothing about running the business scared me like hiring!

    And, in fact, I did massively mess up one of my first hiring decisions. I hired someone on the recommendation of a board member who thought she would be a great assistant to one of the original 3 of us, who was expecting to retire soonish. But we didn’t ever sit down and write up a job description for this person, and worse, we didn’t ask the old employee if she even wanted or needed an assistant. She also is a terrible trainer (by her own admission) and would just expect this poor assistant to watch her do her thing and intuit from that what parts she could take over.

    It was a mess. I handled it poorly because I had no idea what to do. (This is before I found AAM!) Finally, the assistant resigned and had a painful (for both of us) exit interview, at her request, where she really laid out all we had done wrong. I felt awful the whole time.

    But here’s the thing: I got through it. I learned a ton, and I have now grown my staff to 8 people and learned more with each person we brought on. I still dread hiring (I have another employee retiring and I am dreading filling his place ad we speak…), but I also know I can do it and we will be okay.

    Even if you do mess it up royally, it’s not the end of your organization. You can recover, and you can learn from it, and you can do better next time. But you can’t do better next time if you don’t do it this time.

    1. LW2*

      Thank you. “Remember this isn’t a lifetime commitment signed in blood” is something I have to remind myself of quite often, in lots of contexts. You either succeed, or you learn.

  51. Ann*

    Letter #1
    I can be petty. When I send something, with attachments, and the recipient comes back later saying they never received it – invariably with a CC to my manager/stakeholder – I just pull up the original message and forward it…complete with sent headers and all. Accompanied by the simple message “Please see below”. Being petty I CC my manager/stakeholder, of course.

    I had one particular co-worker who this always happened with. Instead of calling and asking or, heaven forbid, doing a quick search of their inbox, their default was the “I never got this”, CC manager email. I created a separate sent folder for just them.

    1. Orange You Glad*

      I do this too. We use Outlook so I am able to add the original email as an attachment to the follow-up chain with all the powers-that-be CC’d.

    2. Kendra Logan*

      In the interoffice mail era, an admin colleague was dealing with one professional who always said “I didn’t get that” when Colleague directly interofficed paper documents to her.

      Colleague resorted to sending those documents by way of our copy center, even a one-pager. The delivery would include a copy of the request to send the document, which stopped the recipient’s denials.

  52. JennG*

    Just popping in to ditto the recommendation for Managing to Change the World – I read this book with all my people I was promoting to supervisory and managerial roles (like an in-house book club) and it really helped the transition.

  53. Aspiring Chicken Lady*

    LW#2: Make the hire. I’m guessing this person will be your initial “right hand.” Sit down with them in the first days and lay out the things you plan for them to do and how you see that happening. This is a new position, and between the two of you, you can create the role and the ways that the team works — especially in anticipation of future new hires.
    Make sure that you’ve got regular check-ins to get their feedback about how the work is going, and specifically how you as a manager can support them as a staff member, in the same way that they will be supporting you as the manager.

    Presumably you have good vibes about this individual or they wouldn’t have been your pick. Here’s your chance to create some good team culture by being transparent and open to suggestion.

  54. tinyhipsterboy*

    To piggyback on #5, if I may, what would you do if the company sets the rate? I’m fairly certain I’m misclassified (but there are only 2 US-based people on my team, so the company would know if we reported it), so maybe it’s a moot point, but negotiating rate increases has basically been the company either telling me they’re increasing my rate, or me going to them and asking about rate increases and then waiting for them to confirm. Essentially, like you’d see in an employee position. Does that make me SOL for actually getting a rate increase to pay I deserve for the work done and sector?

    1. fhqwhgads*

      If you’re a freelancer – as in you’re an independent contractor because you set out to be and have clients etc – you set your own rate.
      If you’re a contractor – as in they have a contract position that brings their own equipment, sets their own schedule, etc, but is for a specific role they designed and set out to hire for, usually they’d set the rate and you agree to it or not.
      There’s a lot of nuance I’m not getting into here and variations depending on a lot of circumstances, but broad strokes if you’re wondering “am I misclassified?” then you’re in the second bucket, not the first. If you never set the rate to begin with, then you don’t get to raise it independently. Whereas if you have multiple clients you invoice, you set the rates before taking on the project.

  55. Orange You Glad*

    #1 – when you sent the documents the second, third, etc times were you replying back to an email chain or starting new emails? If I knew email communication was working (he replied to your follow-up for an update), would probably default to hitting reply to that message with the documents attached “here they are again”. If it were getting extreme, I would probably attach the entire original email w/ attachment to the email chain (“here is the original email sent on 5/1”). I find this helps because if it really is an email filter issue, then the other person has all the information they need to ask their IT department about it (they have the original email with time stamps, etc).
    If I am reading this right, Pat works for an outside organization that the organization you work for hired to perform a service. If there are concerns about that service, it’s worth documenting so the company can address it and evaluate their continued use of that service. I think it’s great that you are already in the habit of checking in for updates, especially now that you know there could be ongoing issues with Pat.

  56. Immortal for a limited time*

    LW #2: I’ll bet the terror is not really about managing someone, but about the bigger picture in which you’ve created this organization, the work you do is important, and now you’re affecting two lives (your own and your potential new hire’s) in service of it. This sounds a lot like anxiety of the avoidant kind, which I recognize all too well. Sure, things could go wrong (that’s just true of life in general!) but you will be fine. Trust yourself!

  57. Salsa Verde*

    Is LW#4 saying that she would prefer text messaging on the phone rather than Teams messages: using Teams for work-related discussion instead of text?
    Unless they have work-provided phones, Teams seems like the right choice here?

  58. Raida*

    5. How to raise your rates as a freelancer

    The best approach I’ve seen from my mates with small businesses is this:
    You raise rates as desired.
    You contact existing/long term clients and inform them of the price increase, and that they, as a valued client that is appreciated, are being allocated a permanent discount of xx%.

    Result:
    New clients get the full price
    Old/good clients pay more than they used to *but always see a line item about how much they saved*
    Old clients don’t quote a low price when referring you because that’s *their special price*

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