let’s talk about passive-aggressive notes at work

In any office, you’re likely to find at least one passive-aggressive note — whether it’s the note scolding whoever keeps leaving dishes in the sink, or the frustrated sign in the bathroom reminding you to clean up after yourself (generally placed there after someone has not).

Often you can feel the rage emanating off of these notes. They’re not just matter-of-fact reminders; full of all caps, bold fonts, and underlining, they’re salvos in an ongoing war for consideration of others.

What are some of the funniest/weirdest/most dramatic notes you’ve seen at work?

coworker keeps saying I’m too muscular, boss suggested I work on a sick day, and more

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

1. Coworker keeps saying I’m too muscular

I am currently working in an allied health field as a practitioner in a private practice, and am (mostly) very happy with my job and my career. I am also an avid gym-goer, which has led to this problem.

We have a practice manager, “Jane,” who is not really my boss as I don’t report to her, but she is the head of the administrative side of things which I guess puts her higher up the ladder than me. We didn’t often interact until recently due to office re-arrangements.

We now see each other much more often. Jane has begun to make several comments on my body, saying that I am “too muscular,” and that she doesn’t “like men that big.” Jane has also stated that my tattoos are inappropriate (two sleeves of snakes, skulls and flowers, nothing outrageous) and insinuated that I am “intimidating” to clients, saying that clients may be physically intimidated by my physique and tattoos and also that clients who are not in good physical shape may feel insecure about my fitness. Furthermore, Jane has made comments to myself and others that I might have outbursts of “roid rage.”

I do indeed use steroids, but I have no difficulty with temper and am in fact a very quiet guy. I did not tell Jane this though, and fail to see how it’s any of her business as long as it doesn’t affect my work.

I am unsure of what to say to her, as Jane is senior to me and I hate confrontation in general, and was hoping you could help me with a script. I am especially worried that she already sees me as potentially unprofessional and aggressive, and am hopeful you can give me something that will convey that I want her to drop the issue without giving her more ammunition.

Whoa, she’s really out of line. In theory the next time she makes one of these comments, you say, “Please stop commenting on my body” or “I don’t want to talk about my body at work and it’s weird that you keep bringing this up.” Or if you think she’s the type to respond better to this, “You keep commenting on my body and it’s making me super uncomfortable and self-conscious. I just want to get my work done and your comments are making that hard.” (To be clear, you shouldn’t need to soften it like this! But I want to give you a few options because she has power and also sounds out of her gourd.)

Ideally, though, you’d skip all that and go over her head. Small medical practices are notorious for not having real management structures in place, and I’m guessing you don’t have anything like HR or even a person above Jane you could go to. But if you do, skip everything above and go to that person. If you don’t, is there someone else who’s high enough up for Jane to listen to who you could talk to about what’s going on and enlist them to speak to her?

Read an update to this letter.

2. Should I pay a service to improve my resume?

I’m hoping you can give me some advice on whether or not I should spend money to help better position myself to find a job. I graduated from college just before the pandemic and was not able to find a position in the journalism or communications fields I’ve been attempting to enter. I recently had a paid internship but it stopped at the end of January. I’ve been seriously job-hunting for the last three months and have had zero interviews despite sending out dozens upon dozens of applications. Frustrated, I happened upon a website last week that offered to evaluate my resume and ran it through an artificial intelligence software that it claims many companies use to screen applicants. Unequivocally, the results they offered said that my resume is actively hindering my job search. Thankfully, this same website/company offers a full resume overhaul, done by professionals for $200.

Given how little interest I’ve garnered for jobs I’m definitely qualified for, I’m considering coughing up the money, However, a longtime reader of your website (my mother) has encouraged me to reach out to you first. From reading your website, she believes that many of these companies offer bad advice and are often scams. I agreed to reach out to gauge your opinion on these sites and to see if they’re a good use of my money. I’m also attaching my resume and a sample cover letter to see if you agree with their assessment of my materials.

Your mom is right. (I so infrequently get the opportunity to say that!) Those sites are scams; as far as I can tell, every resume evaluation they do reaches the conclusion that — surprise! — you need to pay for their help. Once you do, the advice they provide will generally be generic and no more useful than what you could find in 20 minutes of googling on your own. Definitely don’t give them your money.

Your resume is … fine. It’s fine in that it’s exactly like 95% of resumes out there, which means that it looks professional and well-organized but it just summarizes what you were responsible for at each job. Because it’s just like 95% of resumes out there, it’s not going to stand out — especially for someone at the start of their career without a ton of experience yet. If you want to improve it, the way to do that is to include what you achieved at each job — not just the activities you performed, but the accomplishments you had. Think outcomes, not activities; there’s advice on how to do that here. (For breaking into writing fields, what you really need are published clips, and it looks from your resume like you have those.)

3. My boss suggested I work from home while still taking a sick day

I was recently discussing my options with my manager on a day I felt too bad to be in the office but had a lot on my plate that I was worried about having to reschedule. We’ve previously had a fair bit of flexibility, including the ability to work from home if too ill to come into the office but okay enough to stagger on in terms of getting work done, but that has been officially withdrawn. Knowing that I was concerned about my workload, my manager suggested that I mark the day as sick time in the leave system, but work the full day anyway, “to allow me to work from home.”

Ultimately I just took the sick day, of course, but that suggestion feels wrong to me. Is it illegal? Is this something I should bring up later in a “hey, maybe educate yourself on what’s legal and not” way? I’ve done a bunch of googling around labor laws in my state but I can’t find a definitive answer as to legality, and I checked the leave policy statement on my (large) organization’s HR site and found nothing about taking sick leave but being asked to work anyway.

It’s legal in most states, but obviously incredibly messed up — if you’re going to be charged a sick day, why would you bother working from home? Sick leave is for days when you’re not working, not just when you’re working from a different location. What your boss was suggesting was that you take a hit to your accrued leave while the company still got the benefit of you working — all upside for them, all downside for you.

It may or may not be worth bringing back up with your boss now, but it certainly wouldn’t be unreasonable to say, “I was surprised you suggested I work from home while taking a sick day since it doesn’t make sense to me to lose a day of leave when I’m working the whole day.” If her thinking was that you had important stuff to get done that day even though you couldn’t come in, maybe she can use that as impetus to advocate for switching your WFH policy back to what it used to be.

4. How much prodding should I do as an interviewer?

I’m a newer manager currently hiring at my job for an entry-level role, meaning some of the folks I’m interviewing have maybe never had an interview before. I try my best to make sure my questions are worded as clearly as possible and I’m happy to provide clarification if a candidate is unsure of what I’m asking. But when a candidate doesn’t fully answer my question, gives an extremely short answer with no elaboration, or gives a response that doesn’t get at what I’m asking, am I supposed to prod them for more?

For example, I asked a candidate for an example of how they handled making a mistake at work, and instead of giving me a specific example, they generally spoke about how they handle mistakes. (I start by saying “can you tell me about a time when…” so I think it’s clear I’m looking for a specific example.) I had another candidate who answered most of my questions by giving examples from their prior job in a different, unrelated field but without connecting them to what I was asking about for this job. Some of my questions related to work style or communication style also got really short answers, like “I prefer X” with no elaboration.

In these cases, should I have asked them to give a specific example / clarify the connection for me / elaborate? I am not sure if I’m meant to take their slightly off answers as an answer in and of itself, or if I should let them know they didn’t really answer it for me. If I do have to prompt someone more, is that something I should note about their interview? There were a few instances where the answer was so off I did clarify — for example, one person misunderstood the question completely so I re-explained and got a proper answer. In another instance, I asked a candidate how they would manage their workload within the somewhat unusual schedule at our workplace, and their answer was basically that they would not follow that schedule, so I clarified for them it was not optional to not follow the schedule and given that, what would they do instead.

I’m only having these issues with a small portion of the folks I’m interviewing, and I do have a lot of great candidates who are having no problem answering my questions in the intended way. I just want to make sure I’m not being unfair to people who are new to the working world, since this is an entry-level job.

Yes, if someone doesn’t fully answer your question or it’s clear they misunderstood it, you should prod for more or clarify. That’s true with candidates at any level, but especially with entry-level candidates since they often won’t have the frame of reference that will help more experienced candidates understand what you’re looking for. Basically, you want to set candidates up for success (within reason); if a little guidance helps them give you a better sense of how well they’d do in the job, it makes sense to provide that guidance.

I do think it’s fair to take it into account if someone seems to need a lot of guidance and prodding — not for cases when they just need a little (people are nervous or inexperienced and natural misunderstandings happen), but if you have to struggle to get more than one-sentence answers out of someone for the entire interview, that’s relevant data about what it might be like to work with them.

5. Asking for a new office chair when you’re too short for the one provided

I have a quibble I’d love your take on. This is my second job where the office chair is an Aeron, and I freaking hate them. They’re sized chairs, and I’m too short to fit the standard size that every workplace seems to order. As a result, I’ve been having excruciating wrist and neck pain, and have had to take muscle relaxants for the first time in my life.

Is it reasonable to ask my job to either find the the smaller model of the Aeron or cover some/all of the cost of a new chair? It’s not the end of the world to have an uncomfy chair or buy my own, but I’m frustrated with all office stuff being designed for taller people (i.e., men).

Yes, this is a really common and standard request — even from people who aren’t having the painful effects you’re experiencing!

“Our standard chairs don’t fit me and I’ve been having severe wrist and neck pain as a result. Can I get a smaller chair? There’s a smaller model of this one if we want them to match, or I can look at other options.” And go in expecting them to cover the full cost, because they probably will.

my intern is way too passive

A reader writes:

I am currently supervising an intern, Lauren, who is completing a postgrad professional degree in my field. The placement with my organization is a mandatory part of her course, and she is here to learn high-level skills with an emphasis on critical thinking and creativity. My field is one that most people enter out of a passion for the work (there’s not much money in it!).

Lauren has been with us for a few months now and she is still just … completely passive. She will complete concrete tasks (to a pretty uninspiring standard — sometimes seeming to give up if her first attempt doesn’t work) if I assign them to her, and she watches me do my work, and that’s about it. When I ask about her learning goals or interests, she has none or seems to make up a generic answer on the spot. When I ask her to keep me updated on her workload and let me know when she wants a new project, she says nothing (which makes me wonder if she’s just slacking off; we’re working mostly remotely so I don’t have a lot of oversight). When I ask her to choose which of a few projects she’d like to be involved in, she just says she’ll do whatever I need her to do. I’ve tried explaining to her that she’s here to learn and not to be my assistant (frankly, she’s not very helpful anyway) to no avail. I’ve explained the importance of being proactive, creativity, critical thinking, etc. I’ve done everything I can think of to allow her to feel safe asking questions and expressing opinions. If things don’t change soon, I can’t give her a passing grade (I haven’t said this to her yet, but I plan to this week).

What would you do? I’ve never been in this situation before — all of my previous students have been thrilled to be here and constantly asking questions — so I’m stuck!

I think it will help to think of it this way: the internship is supposed to be a learning experience for Lauren and you have an opportunity to teach her things that could really help her professionally … just not in the way you’re used to. Your previous interns might have needed to learn field-specific skills; what Lauren needs to learn is how to communicate in an office, how to take initiative (and that she needs to, and what that looks like), and how to engage with the people guiding her work.

If she doesn’t learn those things now, it’s likely to cause her real problems in future jobs. You have an opportunity to help teach them to her!

There’s no guarantee that your efforts will work, of course. She might not be in a place where she’s receptive to what you’re trying to teach. But you should give it a shot.

Since she needs to make significant changes in order to get a passing grade, that gives you a really easy framework to use. You can sit down with her and say something like this, “I want to talk about some concerns I have with your work. Right now, as things stand, I would not be able to give you a passing grade for your internship. But there is time for us to change that, and I think you can succeed here if you’re open to making these changes. What I need to see is…”

And then be really specific — more specific than you probably think you need to be. For example, don’t just say “be proactive” because she probably doesn’t know what that should look like. Explain the broad principle you want (which could be “be proactive”) but then give multiple concrete examples of what that should look like (“for example, when we meet about the taco campaign on Friday, I want you to bring three ideas for social media promotion — here are some social media ideas interns generated in the past, so you can see the format and nature of what I’m looking for”).

Also, be explicit about the things you have asked her to do that she’s not doing — “I have asked you to keep me updated on your workload but haven’t heard anything after that. I’d like you to send me an email every Monday morning listing your priorities for the week, things you completed the previous week, and any questions or things you’re getting stuck on. We’ll plan to meet every Monday at 2, so I’d like the email no later than noon.” (Or whatever.) I’m guessing this is a lot more prescriptive than you had to be with previous interns — and you might not want to be this prescriptive — but it sounds like Lauren doesn’t know what it means when you ask her to keep you updated, and you’ll be doing her a favor if you paint a clear picture of what it looks like to do it successfully. (Then do the same for all the other most important things you want to see her do.)

And then say this: “Without you making these changes, I can’t give you a passing grade. But I’m confident you can do this, and the support I can offer to help is ___.” (Fill in some ideas there, because I would bet significant amounts of money that she doesn’t know what she could ask for.)

From there, it’s up to her. But you’ll have set her up for success as much as you could, by spelling out really clearly what she needs to pass, and offering her help to get there. If she doesn’t meet the bar you laid out, then you’ll have made the consequences clear. But if it does help her learn how to navigate work, it might have even more of an impact on her future than what your previous interns learned.

should I insist my employees get comfortable with public speaking?

A reader writes:

As a director, a large part of my role involves public speaking and training, which I enjoy and am good at.

Two junior people I supervise are not public speakers. They, each to varying degrees, hate it to the point that they will avoid it at all costs. It gives them a tremendous amount of anxiety, and if asked to present to a crowd larger than a small meeting, they react with refusal, anger, and sometimes tears. I was asked to present the strategy for our team at an all-staff meeting next week, and when I asked my employees to present with me, they both declined. One of them sent me an email yesterday suggesting other ways that staff members can share information, for “those among us who just aren’t cut out for public speaking.”

I believe that not being able to present is a career limiting move, and I have encouraged both of these staff members to work on their fear. But that comment made me wonder — does everyone in an office environment need to be able to speak in public? Does my employees’ inability to do this specific thing reflect badly on them, or on me as a manager as well? Certainly, it is not ideal for me to be the sole member of my team who can present (nobody to fill in if I’m out sick, etc.) but in addition to asking about strategies to help them through this, is it possible that some people just aren’t cut out for it, and is that acceptable for two people early in their careers?

I answer this question over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

new manager keeps pushing hard for me to be his friend

A reader writes:

I have a situation that is annoying me with a new manager at our sister company, George. He was hired with no notice into the role that I had been promised would be my career progression within the company. I have spent the last five months training him on the basics and fundamentals of that entire part of the business, which someone being hired into his role should already have known.

Since he started, he has been strongly pushing for personal connections with employees, including me, and is ignoring polite professional cues and boundaries, and it is making us all uncomfortable.

One example I can give is that he wants me to spend my legal, mandatory, unpaid lunch breaks with him going out for lunch together. I do not want to. I have put him off, brushed him off, been non-committal, pointed out that my rather short lunch break doesn’t allow for that (going out for a sit-down meal within 30 minutes including 5-10 minutes of driving). I have even told him that I am too busy for X number of weeks. His solution? He went to the company directly, arranged for me to use my own leave to take three times as long of a lunch break, and spoke to the director about my workload to get approval for me to shuffle things around, then emailed me afterwards and told me that he had done so while also telling me that the director strongly approves of it.

Another example, if I am off sick, he will call to check on me when I get back, and I will simply brush it off — “yes, fully recovered, thanks, so what can I do for you?” said in a professional-friendly, polite manner. He will then push, “You’re all better? Is everything okay?” And I will counter again, “Yes, nothing major, I am all better, so what were you calling for?” to which he will reply “nothing major…” — once again, ignoring that I have answered, shut the topic down, and turned it back to work. He acts awkward and mildly offended that I won’t go into my private medical details, and it takes two to four “now, back to work topics” attempts before he will accept it and move on. Rinse and repeat for how my weekend was, how my holiday was, etc.

He also pushes staff to share their hobbies, tries to plan friend-group style boardgame nights/days for evenings and weekends, tries to get the details of any groups or clubs we are in, and tries to push us to sign him up for them.

In short, he just pushes and pushes professional and personal boundaries. He is also overly ridiculously flowery and “nice,” prone to going into longwinded over-the-top carry-ons complimenting people for doing their basic job tasks, and the type to be shocked and apologize for 10 minutes straight and then six more times after that if he thinks he has done something wrong, so he is anxious and just too much in general and will definitely make a fuss if I say, “Back off please, you’re being rude/not taking the hint/stomping my boundaries.”

How can I handle this?!

My real worry is that it will irreparably damage the relationship, because I cannot figure out how to tell him he needs to respect boundaries and back off without him being immensely offended. I also have to protect my own image in the company and not come off as an unfriendly, bitter witch (which is a possibility given that people know I was meant to be in that role).

Oh my goodness.

If he were just a little too friendly and oblivious to hints, that would be one thing … but he’s pushy and overstepping on top of that. Arranging for you to take longer lunch breaks so you could eat lunch with him, without your knowledge or consent?

Some of this you’re going to have to accept as just his personality — he’s annoying and interactions with him will take longer than they should, and there’s probably nothing you can do to change that. But some of this you can push back on, depending on how forthright you’re willing to be about it.

At a minimum, you should say something to him about his lunch break interference, because that was a wild overreach and you want to make clear he shouldn’t do something like that again. You could say, “I don’t understand why you sought out Jane’s permission for me to triple the length of my lunch breaks — that’s not something I wanted or asked for, and I’m going to need to go back to her and let her know I don’t need it. Please don’t do things like that without my involvement.” (I am assuming here that while George is a manager, he’s not your manager.)

You could also use this as an opening to raise some of George’s behavior with your director. If you let her know you didn’t ask George to change the length of your breaks and are concerned he did that because he’s been pressuring you to socialize with him, that might easily segue into some of the other problems you’re seeing. (I know you’re concerned about seeming biased because he got the job you were promised, but this really is such a weird overstep, particularly after so much pressure to socialize with him, that it’s unlikely to look like just sour grapes on your part.)

Beyond that, you can set a lot of boundaries in the moment — keeping in mind that “boundaries” refers to how you behave, not what he does. In other words, you can’t change him, but you can change your own responses.

For example, when he calls you and wants to ask repeatedly about your health or your weekend, you can say — cheerfully and briskly — “I’m on deadline right now, but what can I do for you?” or “I’ve got to get to a meeting in a minute” or “I don’t have a lot of time, but did you need me for something?” Those are all things that convey, “I am busy and cannot have a leisurely conversation.”

You can do something similar when he’s embarking on a 10-minute apology — cut him off and say (again, briskly and cheerfully), “It’s fine — we’re both busy today so let’s move forward.” If he keeps going anyway (as it sounds like he might), are you someone who could pull off a firm but cheerful, “GEORGE! I said it was fine! Stop apologizing”? There’s a way to do that where it’s warm, not chilly — but still firm enough to make the person stop.

In fact, if you can manage that vibe, it might be really helpful with him in a lot of these situations. In many cases you can be pretty damn blunt as long as you sound warm and cheerful.

But I also think there’s room for a bigger-picture conversation with him, especially since you’ve been training him on the job. That gives you some standing to say, “Hey, I’ve noticed you’ve been pushing the staff to share things about their personal lives and to hang out outside of work, and that’s not really our culture and is likely to make people uncomfortable.”

Or, you could just speak for yourself: “I’m really not into hanging out with coworkers after work and I like to have lunch on my own. It’s not personal. I wanted to explain so you know where I’m coming from and that I’m not ever going to be up for that stuff.” That would be a lot to hit someone with the first time they extended you a social invitation — but at this point, when he’s been pushing and pushing, it’s kinder to just spell it out for him so he knows where you’re coming from. (Yes, he should have taken your 5,000 hints but he hasn’t, so it really is more humane to clearly state the boundary you want him to respect.)

You’re not going to come off as a bitter witch for pleasantly explaining something like that (and it sounds like everyone around you is well aware of why George would have made that conversation necessary anyway).

About your worry that George will make a fuss if you say something direct like that: that might be perfectly fine. You’re delivering a reasonable message, and if he has a Big Response to it … well, that’s his to work through. Obviously it’s different if you think it will cause real work problems for you, but it sounds like he’ll just make everyone in the vicinity uncomfortable for a brief period of time, and he’s already doing that anyway.

my coworker thinks I need to calm down when I don’t, can’t give two weeks notice, and more

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

1. My coworker misreads me and tries to calm me when I’m fine

I am emotional, expressive, and passionate. Think a “movie-typical Italian” telling a story. Nothing wild, just a loud voice, expressive face, etc. In my 9-5 job, this is required. I over-emote all day long to support the people around me. It is what makes me good at this job.

However, in my after-hours second job, I have a coworker who constantly is offended by my expression. She will see an expression on my face and jump to emotionally coaching me off the ledge — “deep breath, it’s okay, we’ll figure it out” — and I’m … fine. I find it frustrating that I have to mute my personality with her or be publicly talked down when nothing is wrong. To note, no one else responds the way that she does or feels I’m overreacting at all, I’ve checked. I know this is her problem, not mine, but the constant correction and public redressing is frustrating. Can you offer some words I can share with her to professionally tell her to back off?

“You keep saying that to me when nothing is wrong. Please trust that you are misreading me and I don’t need to be talked down.”

And then if it happens after that: “This is what I asked you to stop doing. It’s really weird that you keep trying to talk me down when nothing is wrong.”

Related:
my coworker misinterprets all my facial expressions

2. I can’t give two weeks notice when I quit

For the past five months, I have been working at a job that I can’t stand. The day-to-day functions are what was expected, but I’m working under the worst boss I have ever reported to. He’s a micromanager, loves to publicly shame under the guise of “transparency,” and every day I wake up to 40 urgent messages he sent during the night. In addition, the company changed their policy from two days a week in-office to four right after I started, and I probably wouldn’t have taken the job if I had known that. I could go on about why I wanted to leave, but it really boils down to how horribly it has affected my mental health.

But I recently accepted a new job! This job has a hard start date. I am waiting for my background check and drug test to come back, but I know how long those can take. I don’t want to give notice until everything at my new job is finalized, but that doesn’t leave me enough time to give a full two weeks, probably only one week. I of course want to put my full two weeks in, but my new job isn’t flexible on the start date. This job has caused me insurmountable anxiety and stress, but I feel guilty for not giving the corporate standard notice. As I haven’t been here that long, do you think this will follow me through my professional career? I don’t even know if I plan to keep this job on my resume in the future but the idea of quitting a job this soon is freaking me out and not giving a full two weeks is making it even worse!

You’ll be fine. Often when you haven’t been in a job that long, there’s not a lot of point for the employer in having you work the full two weeks anyway — but even if they want you to, you can say, “I’m so sorry, but I asked and unfortunately there’s no flexibility on my start date. I’ll of course use my remaining time to document everything and leave things in good shape.” This isn’t ideal, but with the sort of job and boss you described, it’s nothing you should feel guilty about — and again, your short tenure means they may not even care.

That said, while this doesn’t apply in your case, generally you can and should push back when a new job tries to insist you start without enough time to give two weeks notice. In most situations it’s reasonable to say, “I need to give two weeks notice at my current job, just like I would do for you. As soon as you clear my background check and drug test — neither of which I expect to pose any problems — I’ll give my notice here and can start two weeks after that, but I don’t feel right leaving without proper notice to them.” (There are rare situations this legitimately can’t happen, but they’re extremely uncommon exceptions to the rule.)

3. Shouldn’t job applicants visit our studio before applying?

I’m looking for perspective on what importance to apply to whether or not a job applicant has ever interacted with my small business.

I own a yoga studio where anyone can come take a class (for a fee ranging from free to less than $20). Our website and our limited social media presence both convey that in-person interaction is a core tenet of the studio’s culture. For example, we do not offer online classes.

The vast majority of job applicants—whether prospective yoga teachers or front of house staff—have never taken a class or come to the studio in person. I am A) befuddled by local applicants who initiate interest but have never visited, and B) downright skeptical of those who gush enthusiasm (“I love your studio and it’s exactly the type of environment I thrive in!!!”)… but have never walked through the doors.

To me, it feels like applying for a job at a restaurant because of how much you love the menu posted online … but in reality, you’ve never even tasted a bite of their cooking. It also seems like such a missed opportunity for the applicant to do their own due-diligence to find out if we really are who we say we are! Should I mention this in some way in our standing job posting? Or is my expectation skewed here?

It’s not a realistic expectation. Your applicants are presumably applying for dozens, even hundreds, of jobs and won’t hear back from a large portion of them. It’s unreasonable to expect they would visit each place in person before applying. There’s a tendency on your side of this equation to think, “But we’re different — our business is so personal and the environment matters so much, and our online presence makes it clear how essential in-person interaction is to our culture” … but that’s something you do for your customers; it’s not something you should expect of your job applicants. Candidates should indeed do due diligence, but generally not until they’re in your interview process; doing it at the application stage would be a waste of time for most people, since only a small handful of them will be moved forward. (And job applicants tend to be acutely aware of that.)

Certainly if someone talks as if they have firsthand knowledge of your studio when you know they don’t, that’s just puffery and can be ignored (although I’m not sure how you’d know that for certain). But it’s also pretty common puffery for the context. Choose not to be swayed by it, yes, but it’s not something to penalize someone over unless it’s truly over-the-top or inaccurate.

4. How can I set boundaries in my volunteer job?

Less than six months ago I started volunteering with a nonprofit. Due to some staffing struggles for the organization, plus my interest in potentially moving into their field full-time, I’ve taken on a lot more time commitment and scope of work than what I initially signed up for.

As they rebuild and bring new people on, some of those people are now looking to me as they get their feet under them. Near daily meeting requests, onboarding and more. Essentially I now have a part-time internship in addition to my (demanding) full-time job.

Some of this is fine, as I’m gaining a lot of valuable experience and I was willing to take on a pretty heavy lift for this org. while we were in recovery mode because I care about their mission. However, I’m struggling to integrate acknowledgement of my serious time limitations into my (frequent) daily communication.

I’m approaching six months of doing this work and while we’re getting back on our feet, it’s taking a while. I need to start regularly asserting that while I am happy doing far more than a regular volunteer would, my capacity is limited and I need to start pumping the brakes. I’ve mentioned this need in passing, but the requests just keep on coming, hence my thought that I need to start reframing the way I interact with the org as one of taking on specific projects, not handling regular admin.

Talk to whoever’s in charge and say this: “I’m finding new people are turning to me for a lot more than I have time for — things like XYZ and near daily meeting requests. I can take on specific projects like ABC but I can’t handle the regular admin. Can you make sure people know that?”

And then as you continue to get requests outside the limits you’ve set: “I don’t handle that sort of thing. I’m a volunteer and only do ABC. Check with Jane.” You’re actually doing people a favor by spelling this out clearly! If you try to be accommodating and help out, you’re preventing them from figuring out what structures actually will work for them longer-term. Being clear about your limits is a service not only to yourself, but to the organization too.

5. Found an amazing internship … but I already graduated college

I graduated college a year ago and have been working in a field related to my degree (engineering) ever since. However, I am also a self-taught photographer with years of experience (taking photos for fun, and doing paid gigs). Although I enjoy my job and would like to keep working in my field, I am truly passionate about photography. It is more than just snapping a shutter for me, and I love studying lighting, perfectly composing a photo, editing, and knowing that I just nailed a shot … so I am open to switching my career to photography one day if the income/opportunity/timing is right.

In addition to my day job, I am always on the lookout for photography-related side gigs like grad photos, engagements, and family portraits. Recently, I found a job posting to be a part-time photography intern at a nearby professional sports team. I would love to apply for this position, as I am not overly experienced in sports photography and would love the chance to break into this part of the industry, but am unsure if it is acceptable to apply for an internship when not in college (and when I did not study photography in college). Note that the job description does mention that candidates should be in a degree seeking program in a related field.

My engineering job has slightly atypical hours, so I am not overly concerned that this would interfere with my current job. I think this internship would be a great experience, and could open doors for me in the future. Since this position mentions being in college currently, is it even worth applying for?

Typically when internships say that applicants should be enrolled in a degree-seeking program in a related field, it’s because the internship is for college credit and/or it’s to help ensure the employer complies with legal requirements for internships. There are internships where that’s not the case, but when it’s listed as a requirement in the ad they generally mean it. (That said, if it’s a paid internship, it won’t be subject to the same legal requirements and they might have the ability to be more flexible.)

You could always apply and see, or even just email them to ask.

my company cut our pay after we met our goals and says we shouldn’t be upset

A reader writes:

I work in a position that is the butt of a sales organization. I don’t mind it, but I don’t make a ton and deal with a lot of nonsense.

On Thursday, they called a meeting for me and the six other people or so in my position and spent 30 minutes telling us how bad the economy is, how bad sales currently are, and how our team “loses money for the company.”

But that isn’t true. We surpassed our goals, even the lofty one investors didn’t think we would hit (which included doubling our revenue in a single calendar year). It was not a small feat. All because of my team and another team we work with.

I thought they would perhaps restructure our plan but they just straight-up cut our pay, equivalent to about $3-6k per year, which is not a small amount of money!

They were too afraid to tell us as a group, so they pulled us aside individually. We all checked with each other after and we all got the same exact pay cut.

Whenever we try to speak to our bosses about it, they just tell us it’s normal for goals to change every year. But none of us are upset about the goals changing, we’re upset about being paid less for more work.

When I confronted my boss about it, she told me it’s only $250 a month. But we’re not even paid well to start with! If it is only $250 a month, then why did they remove it at all if it’s such a small amount of number to her? We’re already paid $10k below the industry average for our position.

All our bosses got promotions and raises because we hit our goals. They also told us the pay cut was to ensure that we did not have to fire anyone, but as recently as new year’s, they hired another person for a position we weren’t even hiring for — he’s a friend of the boss.

Furthermore … the entire company got bonuses, some deep into the five figure range. The reason given is because the sales team exceeded their goal. We were excluded from this bonus. It was paid out the same day our pay cuts were announced.

I don’t have a single drop of motivation to ever put any extra effort in this job ever again. Is this normal? I feel like I’m going crazy. They’re gaslighting us, right?

I feel like my trust has been violated. Our bosses kept telling us we would cool down after a few days, but today is day 3 and I’m probably angrier than I’ve ever been. Sales involves dealing with things outside of work hours, doing a lot of research effort on my own, and we don’t really have anyone supporting us and we took a pay cut. It’s beyond a slap in the face.

I feel like they are using the recent large layoffs to scare us, but we aren’t those companies. They paid out bonuses and gave promotions, while cutting our pay.

Just tell me this isn’t normal? And what should I be doing moving forward? Most of us want to quit but our bosses are trying to proceed like everything is normal. Our output cut by almost 70% since the announcement, but I know some people are going to go back to normal because they don’t have any other choice. But I don’t want to.

It’s not normal, and it’s not okay.

Your company is lying to you, and your managers are trying to confuse you about what’s really happening.

To be clear, there are times when companies genuinely do need to cut pay. It’s a really big deal, but sometimes it’s unavoidable. Generally companies that have to do that understand it’s a big deal and risks destroying morale, and they’d usually try to be more thoughtful about the optics of cutting pay at the same time that they’re awarding bonuses, creating a position for the boss’s friend, or giving your managers promotions and raises because the team getting its pay lowered hit their goals.

It’s also BS that when you’re upset about a pay cut (which is a very normal thing for people to be upset about, even in circumstances where it’s necessary), they’re responding by telling you it’s normal for goals to change. They’re intentionally missing the point so they don’t have to engage with what you’re actually saying.

So yes, it is both normal and reasonable that you’ve lost your motivation to put in extra effort for this job. People put in extra effort when they trust their company. They stop doing that when they see their company is screwing them over. They really stop doing it when they see that extra effort not only won’t be rewarded but will be met with slashed pay.

As for what to do: Look around and see what else is out there. Meanwhile, it’s smart to do enough to keep your job, but they’ve clearly signaled that there’s no value in doing more than that.

when should I tell an interviewer I need disability accommodations?

A reader writes:

I have a question regarding asking for disability accommodations when getting a new job.

I have a circadian rhythm disorder that basically makes me a clinically diagnosed night owl and causes me great pain when getting up at what would be a normal time for most people. When I’m able to sleep on my own schedule, I sleep well and feel well-rested upon waking. But when I shift my sleep schedule to get up earlier, my body’s desire to keep sleeping in the morning is so strong that I will turn off my alarm without actually waking up, press the snooze button for hours, walk to another room to try to wake up only to lay down in there and fall back asleep, be unable to interpret the numbers on the clock, and if I do manage to force myself awake basically feel like I’m having a heart attack. It took me a long time to realize that this was a disorder and to get a diagnosis.

At my current job, I have a delayed start time, which improves my quality of life immensely, but I’m looking to leave this job for something more interesting and lucrative.

There’s only so much medical intervention that can be done. I’ve tried the most effective treatments (light therapy, melatonin) and they help keep my sleep regular and pull my wake time earlier by an hour or two, but I can’t push it past that. The only other thing to try would be taking prescription stimulants every morning to wake up, which I’ve heard a lot of negative things about from others with my disability. I am willing to try this route for the right job, but would much prefer to have a delayed start time, and if that’s not feasible for a particular position, I would like something in writing that allows me some extra grace around showing up late more often than most people would.

Bringing this up wasn’t an issue with my current job because I had worked for them in temporary positions previously, before my diagnosis. They saw the difficulties I faced first-hand and I was able to talk about it openly in the interview process.

In my search for a new job, I’ve been asking in the interview process how much flexibility there is around work hours but not telling them that I would need flexibility or have a disability.

Is this something that I should talk about in the interview process, or should I wait until I have an offer? Or even wait until I start and then talk to HR about this? On one hand, I’m worried that if I disclose it in the interview process, I could get passed over because they don’t want to deal with my accommodation. On the other hand, people have told me that it could cause friction with my manager if I wait until I’m hired and then drop this on them. One person I know who is a manager told me that if someone waited until they were hired to disclose this, they would feel put off and like the employee didn’t trust them, and that could cause ill will. However, I see no reason I should trust a manager I don’t know yet to treat me fairly, and I’m more concerned with my ability to get a good job and be protected under the law than I am with my potential manager’s feelings.

What are your thoughts here? Should I disclose early and often? Should I bring it up before accepting an offer? Or should I set myself up for maximum legal protection by waiting until the paperwork is signed?

Wait until you have a job offer and then bring it up as part of your negotiations.

You shouldn’t bring it up earlier because you’re right that it risks biasing employers against you, even if only unconsciously. That would be illegal on their side — by law, employers aren’t permitted to factor disabilities into their hiring decisions as long as the applicant could do the job “with or without reasonable accommodation.” But as we know, illegal discrimination happens all the time and can be tough to prove.

Frankly, when I’m interviewing candidates, I’d much rather they not disclose disabilities until we’re at the offer stage. I don’t want to worry about it influencing me unconsciously, and if I end up rejecting that person for legitimate, job-related reasons, I don’t want them to wonder whether it was because they disclosed a disability. Since it’s not something employers can legally take into consideration, you’re doing them a favor by waiting until the offer stage so that you and they can avoid all those traps.

Not every manager will see it that way, of course. You’ll run into people like your friend who will feel you should have raised your need for accommodations earlier. But they’re wrong — the law makes it very clear that you don’t need to disclose sooner and that they couldn’t have taken it into account even if you did. And show me someone who would be affronted that a job candidate didn’t trust them, a stranger, not to have bias around disabilities and I’ll show you someone who hasn’t reckoned much with prejudice in general.

By waiting until they’ve already made an offer to mention the accommodations you need, you’re significantly lowering the possibility of hiring discrimination. Yanking the offer at that point would open them up to serious legal liability for violating the Americans With Disabilities Act. (The ADA is the federal law that requires employers to offer reasonable accommodations to employees and prospective employees. Of course, make sure that you’ll be covered by it; it kicks in only when employers have 15 or more employees, though some states have additional protections that cover smaller employers as well.)

Once you’re offered the job, express your interest and then say something like, “I’d like to discuss schedule options with you. I have a disability that, in the past, employers have accommodated with a delayed start time. As a medical accommodation, would it be possible to work a schedule of [fill in with details of your desired schedule]?” If they have concerns about how well that would work for this job, they can raise them at that point, and you can engage in what the law calls the “interactive process,” in which you both try to figure out if there’s an arrangement that will work for you without causing undue hardship to them.

Note, too, that the law is clear that “undue hardship” on the employer’s side would need to constitute more than “We don’t like it.” They would need to demonstrate a genuine burden, often financial, or that the accommodation would conflict with the essential duties of the role, like if the opening were for a breakfast cook and you wouldn’t arrive until the afternoon.

Assuming you can reach an agreement, at that point it’s smart to get the accommodation in writing so there’s no question about it later. That can be as simple as sending an email to your manager and HR rep summarizing what’s been agreed to. Make sure you use the words “accommodation under the Americans With Disabilities Act.”

All that said, there’s an argument to be made that it’s better to have this conversation during the interview process on the basis that if your would-be manager is going to hold your need for accommodations against you, you don’t want to work there anyway. If that’s ultimately where you land, that’s your prerogative. Personally, I’d contend that there’s a ton of bias out there and you’re not obligated to put yourself at risk of it … and since the law offers you protections, go ahead and take them!

Learn more about accommodations based on your role at the Job Accommodation Network. Charges of employment discrimination on the basis of disability may be filed at any U.S. Equal Employment Opportunity Commission field office. To find the EEOC field office in your area, contact 800-669-4000 or go to eeoc.gov.

Originally published at New York Magazine.

my mentor falsely accused someone of sexism on my behalf without my knowledge

A reader writes:

I recently moved into a senior leadership role at my organization, which was a big jump for me. To help me get acclimated to the role, our CEO assigned me a mentor, Jane. She’s someone I’ve known and respected for a few years, although sometimes she strikes me as kind of a gossip, but she has a lot of institutional knowledge so I figured I could glean some helpful insights from her. We’ve been meeting once a month or so for informal chats.

This new role has been more challenging than I expected and I’ve also had a lot of difficult things going on in my personal life. In the midst of a really tumultuous week, I made some mistakes on a project, which were caught by our VP, Bill. The mistakes were caught early enough that they didn’t have much of an impact on anything, but Bill was obviously annoyed with me. It was upsetting for me because I’m used to being a very high achiever and it’s not like me to make mistakes at work. I also felt like I’d lost a lot of credibility with Bill.

A couple days later, I had a check-in with Jane. I mentioned I’d had a really rough week and told her about what had happened with Bill. She reassured me that I shouldn’t take it personally and that Bill can be kind of a jerk. She also said she sometimes thought Bill treated women differently and mentioned some other women who had issues with him, suggesting that was going on here as well. I was surprised to hear that, but said it was interesting and maybe she was right.

I worked really hard to redeem myself with Bill and things also calmed down a bit in my personal life, and I realized I’d overreacted about the situation with him in a way that I wouldn’t normally have if so many things hadn’t been going on.

I’d put it behind me, but then this morning our CEO, Melinda, asked to meet with me. She said that Jane had told her that I felt like Bill was treating me badly because I was a woman, and that she (Melinda) had been in touch with HR to start the process of filing a grievance against Bill. The way Melinda presented it, it sounds like Jane told her this as though I had come up with it myself and complained to her about it, which I absolutely did not. I would never have even considered that gender had anything to do with it if Jane hadn’t brought it up first.

I was horrified and told Melinda that I didn’t think that at all and that it was Jane who had suggested it, not me, and that I absolutely did not want to file a grievance against Bill. She reassured me that HR hadn’t started an investigation yet and she would tell them not to move forward but encouraged me to come to her if I ever had any issues with sexism in our very male-dominated field, no matter how minor it seemed.

I’m really upset this happened and have no idea how to move forward. I’m worried Melinda now looks at me differently because of this. I don’t even know what I would do if it got back to Bill that I thought he treated me badly because I’m a woman. He’s highly respected and I feel like it would reflect poorly on me if people thought I was accusing him of sexism. I’ve completely lost trust in Jane and feel like I made a huge mistake confiding in her when I know that she tends to gossip. Do I bring this up with her or just make sure I’m careful about what I say to her in the future? What if she’s been telling other people about this as well? Should I follow up with HR to make sure they know I’m not accusing Bill? How do I recover my credibility with Melinda? Moving into this role has been hard enough as it is and I’m just devastated that this has happened.

This is almost certainly not as big of a deal for you as you’re worried it is.

That’s not to say that it’s okay that Jane misrepresented what you said. It’s not! But misunderstandings happen, you cleared it up, and it’s very unlikely that this has harmed your credibility with Melinda.

There’s no reason you can’t address it with Jane, though. You could say, “Melinda told me that you told her I felt Bill was treating me differently because I’m a woman. I was really taken aback by that, because I didn’t say that to you when we spoke. How did you end up telling her that?”

To be fair, it’s possible that Jane genuinely misunderstood you. You only told her that maybe she was right about what had happened between you and Bill, but for someone who’s already concerned about a pattern of sexism from him, I could see her mentally adding you to her list of people Bill had mistreated without realizing she needed to clarify whether or not you actually saw it that way. And if she genuinely believed it, she might have had an obligation to escalate it (particularly if she’s a manager, which does obligate her to report discrimination if she becomes aware of it). Now, obviously if that was the case, she should have let you know she planned to do that — but who knows, maybe she was making a broader complaint to Melinda about Bill that didn’t focus on you, but included you on a longer list of people she’d seen affected. (She still should have alerted you that she was going to do that! But this might have gone differently than what you’re picturing.)

In any case, it’s reasonable to ask her about it, and it’s reasonable to say, “Please don’t make complaints on my behalf, especially without looping me in. I don’t want to have another situation where a misunderstanding leads to something being reported on my behalf that I don’t agree with.”

You can also say, “Have you mentioned this to anyone else? I want to correct the record with them if so.”

Since Melinda said she’d follow up with HR to make sure they know you don’t have concerns about Bill, I don’t think you need to follow up with them yourself, although you can if you want to. It wouldn’t be weird to do that if you prefer to, and it sounds like it might bring you more peace of mind.

But yes, you should be careful about what you say to Jane in the future. At a minimum, she’s shown she’s prone to misunderstanding what you say and then acting on it in ways you object to. Combine that with the fact that you already thought she was a gossip, and it doesn’t make sense to treat her as a trusted confidant in any way.

I do want to say … it’s possible that Bill really does have a record of treating women differently. Jane’s behavior here doesn’t preclude that. That’s not something you need to sort out and it doesn’t change how you should proceed, but keep in mind that it’s possible for Jane to have flubbed this specific incident but still be right about the larger pattern.

Relatedly, if people did hear you had reported sexism from Bill … obviously you don’t want that to happen since it’s not correct, but it’s also not a disaster for you if that did happen. Sometimes something looks like bias when it’s not, and it’s better to bring those things to the surface so they can be examined than not to do that, even if it turns out there was nothing there. Again, of course you don’t want people saying that when it didn’t happen, but you sound like you’re having a really strong reaction to the idea that someone might think that. Generally, when you’ve been able to set the record straight, the fact that there was an initial misunderstanding would be more on the “aggravating but not devastating” end of the spectrum — but you’re saying “devastating” so I think that’s worth looking at.

I wonder if you’re thinking of “hey, this feels like there could be gender bias going on” as a massive, career-destroying thing to say about someone — but it’s normally not, and if people see it that way, the barrier to reporting potential discrimination will get even higher. (It will also make people a lot more defensive if someone raises those questions about their actions, when what we want is for them to feel it’s safe to listen with an open mind and think about ways they could do better.)

Read updates to this letter here and here.

friend doesn’t believe in different dress codes for different situations, applying for a job where my landlord works, and more

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

1. My friend doesn’t believe there are different dress codes for different situations

I have a younger friend who works for a well-known leisure apparel company at their headquarters. Many of the employees still work from home the majority of the time and when they are in the office, it’s not unusual for them to be wearing their brand apparel. So, pretty darn casual for this old timer who grew up on suits, stocking, and heels! All that is well and good but there are occasions where they may need to do presentations to other divisions, be in meetings with high level executives, etc. Do you think the dress code changes in this situation?

Her grandboss made a comment about her wearing athleisure attire to a meeting (something along the lines of “That’s what you’re wearing to the meeting?”). She doesn’t seem to think it’s a big deal since they didn’t come out and say, “Don’t wear that to this meeting.” I think it is very clear that her grandboss expects more. I’ve tried the “dress for the job you want, not the job you have” approach. I suggest she have one really great pair of black slacks and a jacket on hand for these meetings. She isn’t hearing me. She has said that I “just don’t understand” that wearing their branded clothing is part of the culture. While I don’t disagree with that, I think there is a time and a place for certain items. And I think she could pair quality slacks with their branded shirt and still be part of the culture.

Maybe I’m all wet. If I am, I am happy to back off. But if I’m not, I’d really like some words of wisdom or a relevant article I can point her to.

Well, you’ve got to keep in mind that she’s much better positioned to know what’s acceptable in her office culture than you are — and there are indeed offices that don’t expect you to dress up for higher-level meetings and presentations. So pushing her to change what she’s doing just based on a general belief that people shouldn’t wear athleisure to those meetings would be an overstep; you don’t know the culture at her company firsthand and she does. (And it sounds like you might have a blind spot about the fact that there are companies where this would be fine.)

But her grandboss’s comment sounds like a clear indication that in this office she is expected to change what she’s wearing for some meetings. So you’re probably right in her particular case! But you’ve tried to point it out, she’s not interested in hearing it, and and it’s not your place to keep pushing.

That said, if you hadn’t already been pushing her on this, you could point out that her boss was sending her a clear message that her clothes weren’t acceptable for that context … and it would make sense to say that clearly rather than using “dress for the job you want, not the job you have,” which she clearly doesn’t think applies in her situation. But at this point, when you’ve already been trying and she disagrees, the best thing to do is to drop it and assume she’ll figure it out on her own eventually or someone who works with her will tell her more clearly.

2. Is it OK for managers to send mild reprimands in an email?

Are mild reprimands over email an appropriate avenue for small errors? I manage students and staff members who work all hours of the week — hours when I’m off the clock as well. We go over common expectations for job performance in training, and sometimes I’m notified of a small work-related issue about a student who won’t be working hours when I’m normally available. Is it appropriate to send a short email addressing the possible issue and reminding them of my expectations, or should all conversations involving job performances and mild reprimands be in person?

It depends on what you mean by “reprimand.” Frankly, I don’t think managers should need to be doing a lot of reprimanding, so if you find that you are, it’s a flag to look more closely at what’s going on — it could be that people need more training or supervision, or you need to have a more serious performance conversation or even have the wrong person in the job, or your managerial style needs to be recalibrated.

But it’s fine to give guidance in email, or relatively straightforward corrections or reminders. Something like “it looks like you missed the X row in this spreadsheet — can you fix that and make sure you watch for it in the future?” is fine in email. Something like “you’ve continued to miss the X row even though we’ve talked about it repeatedly” should normally be a real conversation (in part because at that point you need to have a real conversation about what’s going on).

3. Is a company’s bad screening system a reason not to take the job?

I recently applied for a job through the company’s website. It’s a relatively high level position, and I thought I was a perfect fit for the job, but alas I never heard back. These things happen.

I forgot about it until a month later when a former coworker told me they had reached out for him to have him consider the job. He wasn’t as qualified as me (he was missing one of the key qualifications), but they’re relaxing some criteria because they hadn’t filled it. They reached out because he had applied for a job in the past.

Hearing this, I figured my application and resume were held up by a finicky screening algorithm. So I reworked my resume and reapplied. Still no response. Which I thought was weird, and I figured maybe they had found someone after all.

Fast forward three weeks. My friend said they asked him if he knew anyone he could recommend for the position and he sent my resume. Within 30 minutes, the recruiter called me and within a week I had interviews set up with the leadership. They are very excited and the process is proceeding very quickly.

Should the fact that they couldn’t find my resume (one they admit is highly qualified) in their own inbox after two applications be a red flag? At the very least, I figure after a failed search they would go through rejected resumes to see if there was something they may have missed. If their hiring practices are dysfunctional, I worry about them being able to get good talent in the future. And if the only way to get through screening is to have a connection, I think this raises serious diversity and equity issues. People without connections tend to be from groups that have been marginalized in the past. Am I overthinking this, and it’s just wonky software/algorithms? Should I mention something about it? Is this a reason to not take a job?

It’s not a reason not to take the job. It’s a reason for them to reassess how their applicant tracking system is working (they should look at why you were screened out and who else has been screened out recently to figure out if it was a one-time fluke or part of a pattern, and whether their system can be tweaked to work correctly or needs wholesale changes), but it doesn’t indicate on its own that the company is dysfunctional. Lots of places that are fine to work have crappy application systems (or some other crappy software that doesn’t reflect the organization’s competency more generally). You’re right about the diversity and equity implications though, and if you end up working there in a position with some influence, that’s definitely something you should point out.

4. Do I need to ask my landlord if it’s okay to apply for a job at her workplace?

Some of my friends have encouraged me to apply for work at their organization. The only sort-of catch is that my landlord also works there.

Is it rude/wrong/inconsiderate to apply without consulting my landlord first? She works in a high position in the company. I’m not sure where she is on the org chart, but I would more than likely work as an underling, definitely not as an executive if they were to hire me. My landlord doesn’t know I’ve been laid off yet because I have savings and my husband works full-time so there’s no issue with not paying rent. I’m not sure what the etiquette is for this situation. We have a great business relationship through my renting from her, but I feel weird putting her in a position to possibly have to vouch for me or a position of intermingling her various businesses with her day job.

You don’t have to mention it to her, but it could be smart to — if for no other reason than if it’s going to cause problems, it’s better to know that now while you can still factor it into your decision-making, rather than after it’s too late to do that. For example, if it turns out the position is in her chain of command, they might not be able to consider you for the job (because it would be a conflict of interest for her to oversee someone who she also gets rent money from). You could wait until you’re a little further along in the process though (maybe after you’ve been invited to interview).

5. Contacting a hiring manager before a job is posted

I work in a niche field that doesn’t have regular turnover. Recently, someone at another company in my same line of work, though more senior, has left their job. I interacted once at a networking event with the likely hiring manager of this role. Can I reach out to Potential Hiring Manager to share my interest if they plan to fill the role? And if so, what is the best way to do so without sounding too eager?

Yes! I’d say it this way: “Hi Jane! We met a couple of years ago at the Oatmeal Association’s annual conference and chatted about the work you’ve been doing on instant oats. I saw that Jane Burtlebot recently left her position with you, and I’m interested in throwing my hat in the ring at whatever point you’re considering applicants for the role. Your project on breakfast grains is exactly the sort of work I’m hoping to tackle next. I’m attaching my resume and I’d love to talk with you if you think I might be a match for what you need.”