Ask a Manager

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.

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

1. I manage a manager who makes too many assumptions about everything

I manage a manager, Jane, who openly for all to hear assumes motivations for our clients, consumers, and employees on everything. It’s not only unhelpful, but it also is incorrect. For example, we had a project that was having some difficulties and Jane said in a team meeting, “Oh, they’re going to ask us to work the weekend,” when this was never mentioned. It not only put all others in the meeting on their heels and made them nervous, but it also made it seem like our clients were overly demanding. They never asked us to work through the weekend, nor did we need to. Her throwaway comment stressed a lot of employees out and also put our client in a false bad light.

Another example is when an employee Jane manages asked about a glitch she found on a project when she was reviewing it. I had more interaction with the glitch, so I asked her to compile all the feedback she received from different individuals experiencing the glitch, and then we could look at it as a whole. In response, Jane said, “It must have been a one-off situation,” but it wasn’t. There were a lot of people who experienced it, and we needed to come up with a solution – but her comment downplayed the seriousness. I appreciate if she was trying to bring levity, but she is always interjecting assumptions without any basis, and it’s not helpful at all. How do I approach this without knocking the wind out of her sails? Other than this, she does good work – but her additional anecdotes are becoming a lot to piece through.

Name the pattern! And explain that people put a lot of weight on her comments because she’s a manager, and so she needs to be more thoughtful about not making throwaway comments that people are taking seriously or rushing to conclusions without first asking questions. For example: “I’ve noticed a pattern recently that I want to bring up to you. You’ll sometimes make what I think you’re thinking of as a throwaway comment, not one you’ve necessarily thought through or expect people to act right away on. But because you’re a manager, your words carry a lot of weight — and when you haven’t thought through what you’re saying and are working from an assumption that you haven’t taken the time to confirm, it can send people down the wrong path, stress them out unnecessarily, or leave them with the wrong impression. For example (supply examples).”

Obviously, you don’t want the result of this conversation to be that she clams up and never speaks again because she’s afraid of doing what you’ve described, so there’s going to be some art in working with her on this. And it’s unlikely that a single conversation will solve it — but it will flag the issue and provide the framework to make it easier to talk with her about it when you see it happen the next time. It’s likely going to be an ongoing process of coaching (because at its core it’s about judgment), and you’ll need to talk through what she should be doing instead (asking more questions, probably), but this framework should help you name what you’re seeing and why it’s a problem.

2. Was it inappropriate for an employee of a client to invite me for drinks?

When I was 20, I worked at a consulting firm. I worked for a client overseas and worked mainly with a team, but occasionally I had to interact with other employees of our client company. One of those times, a female employee really appreciated some help I gave her and we talked a bit. She mentioned that she would be in my city for a work trip and that we could go out for some drinks if I wanted.

I felt a bit uncomfortable and didn’t answer and then we both pretended nothing had happened. I didn’t want to meet because I thought it would be weird (we really didn’t know each other and I suspect she didn’t know how young I was — she never saw my face) but I also felt it wouldn’t be appropriate. As a man, I didn’t want anyone in my company to think I was trying to hook up with employees of our client (even if this wasn’t the case; I think she was just being friendly). This happened many years ago and while I praise myself for my caution I still wonder if I was right in thinking this was inappropriate.

It doesn’t sound particularly inappropriate; people often meet up for drinks when they’re traveling through the city of someone they work with. I’d assume she was just being friendly and/or networking. If she’d kept pushing you to meet up after you’d declined, that would have been inappropriate — but it sounds like she just suggested it, you didn’t take her up on it, and that was that. Which is also fine! You’re under no obligation to agree to invitations if you don’t feel comfortable or just don’t want to go. Ideally, though, you should decline gracefully — citing other plans is an easy way to do it — so that no one feels awkward about it.

3. Coworker wants to spend sick leave in Cancun

I have a coworker who’s having a medical procedure done and is taking a week to recover. The second week he’s going to Cancun but wants to include that as sick time, not PTO. Can he do that? It seems like if he’s well enough to fly, it should be considered vacation.

It’s possible for someone to be well enough to fly but not well enough to work — depending on the physical and mental demands of the job, and also on what recovery entails (i.e., being laid up in bed is different from just being too mentally fuzzy from painkillers to work). But most employers are going to be awfully skeptical of someone submitting sick time while declaring they’re spending a week in Cancun. Your coworker is pretty much asking for pushback on it.

That said, if you don’t manage him/aren’t in HR and his absence isn’t going to significantly impact you, it’s not really your business and you shouldn’t get involved.

4. My new boss is in my D&D group

I work for a government organization with many departments. During the pandemic, a few semi-official hobby groups were created to allow people across different departments to socialize, including but not limited to a book club and a D&D group. They still exist “post-pandemic” and I’ve been part of the D&D group for about a year. We don’t meet during work hours, and we avoid discussing work during gaming sessions.

Earlier this year I interviewed for a higher position in a different department, and just got the news that I got the job! During the process, after I’d already interviewed, a new person joined the D&D group, and it turns out she’s going to be my supervisor for this new position. She’s fairly new to the position herself.

I know from past letters that you’ve cautioned people about getting too casual with their supervisors and reports, and because of the nature of tabletop RPGs, the group is pretty informal with each other. What’s the best way to avoid any professional missteps or awkwardness when my supervisor and I are pretending to be wizards together in our off hours?

I can’t speak to D&D-specific missteps (although I bet some readers can in the comments) but assuming you’re, you know, a reasonably well-behaved person and not the boor of the group, this is more of a potential landmine for your manager than for you. She’s got to be thoughtful about ensuring that others on the team don’t feel you’re getting special access to her or that work conversations are happening during these get-togethers that they’re not included in. You don’t need to manage that for her, though; that’s hers to navigate.

5. Asking for a raise: a success story

I wanted to share a success story with you! I’ve been at my current job about 18 months now, and am a mid-career nonprofit professional who freelanced a bunch before getting this steady gig because I needed a more stable income. I realized recently that I need a raise as I was taking on new responsibilities, and had already received a new title (budget issues at the time of the title bump meant asking for a raise was not prudent). But the budget has steadied out, and I figured it was time.

I read all the stuff I could on your blog about how to ask for a raise and then sent my boss an email asking for a salary discussion to be put on the agenda for our upcoming 1:1. In my email, I mentioned the accomplishments I’ve had recently and new projects I’m taking on that she’s expressed happiness with, and provided research about the market rate for my position, which my salary was at the low end of. My boss agreed to the discussion, and it turned out: the discussion didn’t need to happen. She showed up with a salary memo from HR in hand, with a 12% bump in my pay.

The hardest part was getting up the confidence to just ask for it! I knew I wasn’t going to leave over it, so I figured it couldn’t hurt to have the conversation. And I’m so glad I did!

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

1. Coworkers message me “hi” with no indication of what they need

I find myself very frustrated with many of my coworkers. We use Teams, and I often receive messages that just say “Hi Name.” If I’m available, I can respond right away and get to their request. But sometimes when I step away for my lunch hour, I return to see that right after I left, I got a “Hi Name” message. When I respond, they’ve often stepped away and it may take another hour for them to get back to me with their request, two hours from when they originally reached out to me.

To me, it seems that people think that Teams chats follow the social etiquette of walking up to somebody’s desk. You both say a quick hello, then get to whatever they needed. However, I view it more like leaving a Post-It note on somebody’s desk. It’s visible, but if they aren’t there, it might take some time to respond. And to leave me a Post-It note that just says “Hi” on my desk, then to expect me to go to yours to leave one as well before giving any details, frustrates me. When I reach out to people, I generally send them “Hi Name, I’m reaching out to you about X. Do you have Y information?” — closer to how I would write an email.

I’ve been at this company for two years, I like it and feel valued, this is just a big pet peeve of mine, as I feel that it is less efficient, and if somebody messages me when I’m away, I now have to spend time tracking them down for their request. I’m also autistic and there’s a chance that there’s something about social cues and unwritten rules that I’m just not understanding. This is a large company, and this communication style is common between people of all ages, managers, coworkers, and contractors.

I’m sometimes tempted to just not respond until they do send the information over, but I also don’t want to come off as rude or unresponsive. I also have thought about addressing it individually with the people that I work closest with, but I’m not 100% sure how I should say it.

Yeah, this is just a Thing That Happens in almost every office. The people who do it think it’s friendlier, and everyone else thinks it’s inefficient and a little annoying. It’s very unlikely that you will be able to solve it, so it’s easier to decide not to care. Write back “hi” and figure that if their communication style means it takes an extra day for them to get the info that they need, that’s on them; it’s not on you to draw their needs out of them.

That said, if you work frequently with someone who does this, there’s nothing wrong with saying, “By the way, feel free to just launch in with what you need when you first message me. If you just say hi and wait for me to respond, it could be hours before you hear back, depending on what else I’m working on — but if what you need is in the first message, I can often get it to you faster.”

Related:
how to respond when coworkers IM me “hi” with no indication of what they need

2. My younger coworker thinks I don’t know anything about computers

I am older (mid 60s) and on my way to at least semi-retirement. We have on our staff a new younger (30-ish) woman who is in a leadership role. I have no issue with that – she’s good and she knows her stuff; I’ve learnt new things from her. But she seems to have it firmly in her mind that I am a sweet little old lady who cannot possibly know anything, especially in the field of computers. When it comes to software, or tech generally, she
is very patronizing towards me and tries to hold my hand through elementary steps. The thing is, I have been working with computers since the mid 1970s and helped design and set up the system we currently use. In this area, I’m good and I know my stuff.

My manager has taken her aside (he tells me) and spoken to her about the way she is treating me, and others on staff have commented as well, so it’s not just me. How can I make her see that I am competent in this area, before the sweet little old lady turns into a cranky old battleaxe on the warpath (which wouldn’t be good)?

The next time she does it: “I’ve been working with computers for decades and helped design the system we use now.” Use an amused-sounding tone.

If it continues: “I’m not sure if you realize you’ve been approaching me like I need remedial help with anything tech-related. So to let you know, I don’t.”

If it continues after that, consider talking to HR about it and using the words “age discrimination.” Or if you want to give your boss one more chance to handle it first, have that conversation with him instead and ask if he wants to do a more serious intervention himself or if it’s time for you to bring in HR.

3. Should I correct students who address me as Mrs.?

I am a faculty member at a major state university where I teach large undergraduate classes in a male-dominated discipline. I have been teaching for quite a while and have achieved the highest faculty rank (Professor). While I am not particularly concerned about being addressed as Professor or Dr., which are correct given my faculty rank and education, I take issue with one way that I am increasingly addressed by students — about half of the hundreds of student emails I receive each semester. Rather than start their emails with Dear Professor Green, Dear Dr. Green, or Dear Ms. Green, students increasingly refer to me as Mrs. Green. To add an irrelevant fact, I am not married.

It has always been my understanding that “Mrs.” is used to refer to a married woman, or a woman who has been married, without a higher or honorific or professional title. And that “Ms.” should be used to refer to a woman of unknown marital status or when marital status is irrelevant. Of course, I believe Mrs. should always be used to address anyone who indicates that preference.

My students will see my name written as Dr. Jane Green on a variety of university and course materials, but that does not seem to change the frequency of emails addressed “Dear Mrs. Green.” I hesitate to correct students for fear that it will be taken as an indicator of self-importance and give me a reputation for being condescending or unapproachable. However, I am sensitive to the misogyny involved. While I don’t think students should call their instructors by their first name, I don’t want to insist that students call me Professor Green or Dr. Green. I would be fine with being called Ms. Green – it’s only “Mrs. Green” that really bothers me.

Do you see this as an important “teachable moment” for college students entering the workforce (in addition to being a personal pet peeve)? My thought is that students should learn not to use Mrs. as the default title for women in the workplace or in addressing professional correspondence since marital status should be irrelevant in these situations (and also that perhaps it is a good idea to avoid offending others like me when trying to be hired for or advance in a position).

I think that if I had confirmation that this reasoning is correct, I would feel more justified including an explanation in my course materials and providing reminders in my responses to student emails. I am willing to take the possible blowback if it will help students in their eventual careers!

Yes, absolutely. Referring to a woman as Mrs. without any indication that she uses or prefers it is a good way to alienate a ton of us — since it’s rooted in the sexist notion that a woman’s marital status is relevant when a man’s is not. It will also hit a lot of ears as old-fashioned.

These students should learn that now so that they don’t address their cover letters that way, greet networking contacts that way, or otherwise annoy and aggravate the many, many women who use Ms. who they’re going to meet in their careers.

I’d say it this way: “It’s Ms. or Dr., please.”

You could add as a parenthetical: “Mrs. is not a title used in professional contexts unless the person has previously indicated she uses it. Default to Ms., or to Dr. when that’s correct.”

4. Can I leverage interest from other employers into a higher salary at my current job?

I’m in an enviable position: I’ve worked my way up to a fairly senior position in a smallish industry, and I have a specialized role that’s currently in high demand. And now—after climbing the ladder and working hard for 20 years—recruiters and hiring managers are calling me nonstop to try to entice me to move. I know, poor me. But I really like my current job! I’ve been here six years, I’ve had some nice success and built a strong program from nothing, and I feel appreciated and—I think—am fairly compensated. I don’t want to leave, but I find myself wondering: Is there anything I should be doing to leverage this interest with my current job? What would I even ask for, assuming I am paid well and well treated?

So far I haven’t even mentioned anything about all this interest to my current manager. But last night a competitive manager took me out to drinks and told me she wanted me to come over to work for her and I should “name my price.” I don’t want to be a cliche of the woman who never negotiates. But I also don’t want to be unfair to my current, very appealing job, where I ultimately want to stay. Any advice?

I’m not a fan of counteroffers, but that’s not what you’d be doing. You’d just be saying, “I really like my work here and want to stay. I want to be up-front that I’m being approached about other jobs that pay more than I’m currently making. I really don’t want to leave, but I wondered if we can take a look at my salary.” You could even use that exact wording.

One thing to note is that it doesn’t sound like you necessarily know what these other jobs would pay; it’s possible some of them would actually pay less well or be less desirable than your current role in other ways. It could be interesting to talk with some of them and progress a little further with them to try to get a better understanding of how they really stack up against your current position.

5. Repeated weekend reminders from a reference-checking company

I want to see if I’m unreasonably annoyed by this situation.

I got a message on Friday after 5 pm from one of the paid student leaders in a program that I help manage. She was letting me know that she had been offered a full-time graduate role that starts next year and they wanted references from managers by the end of that day. She told me she had put me down as a reference and apologized for not being able to ask first.

I was okay with this and was very happy to provide a reference for her. I had seen the message as I often work a later schedule.

I come in on Monday morning and discover four emails from the reference-checking company that has been contracted by the employer. The first email was sent on Friday at 6:41 pm, the second on Saturday at 7:02 pm, a third on Sunday 7:02 am and the fourth on Sunday at 7:01 pm. I’m not in a U.S. timezone, but even in the U.S. all but the initial email would have been on a weekend. I’ve included the text of the reminder emails in a screenshot.

I felt very pressured by this and that if I didn’t get it done quickly I would be hurting the student’s chances of getting this role. It seems to only be giving you three days to respond and those days don’t seem to be business days.

I would expect a system that collects references to account for business days, no matter when the candidate submits their reference request. I completed the reference request (which was 26 questions long and a totally different irritation) but have a lingering irritation about the way this communication occurred. It seems very disrespectful of my time and also unprofessional. Am I wrong to be this irritated?

Nope.

Those reminders were almost certainly automated messages programmed to go out about 24 hours apart, without anyone thinking to leave space for weekends. That doesn’t make it any less annoying, though, or any less demanding. They’re just asking for people to hit that “decline” link.