guilt about applying for a new job, new hire didn’t negotiate, and more

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

1. I feel guilty about applying for another job

I work in a department of three — me, a coworker with the same title and responsibilities as me, and our manager. Recently my coworker was out on maternity leave and was expected to return after five months. My manager really doesn’t know how to do a lot of the tasks we do and so a lot fell on me, although my manager did try to help here and there. Well, my coworker decided that she wasn’t going to come back at all. My manager has made some comments that seem to imply that we don’t need to hire someone else to replace her and that perhaps we can make some changes to ease some of my workload without hiring anyone else. There hasn’t been any discussions yet on what those changes would be and I’m feeling very burnt out.

I noticed a job opening with a different company that is very similar to what I do now. I’ve heard it’s a great place to work and they are transparent about their salaries, so I know I could be making at least $8-10K more per year if I were to interview and get the job. My guilt is holding me back from applying though. If I leave, my manager will be the only one left and there’s so much that he can’t do. I know he would be disappointed and upset. The thought of even telling him I’m leaving for another position fills me with dread. I like where I work. It’s a great atmosphere and I have a great manager, but I just don’t know how much longer I can sustain this. Do you have any suggestions for how to move past my guilt? It just feels like a crappy thing to do to leave my manager high and dry when we’re already understaffed but I also need to do what’s best for me as well. I’m really struggling with this!

Apply for the other job. If your manager is concerned about being left alone without knowing how to cover your work, he has lots of opportunities to mitigate that risk — like cross-training, ensuring your processes are well documented, and not removing the only other position that does what you do. But even aside from that, this is just not something that should control what career decisions you make. You need to do what’s in your interests, just as your company will do what’s in its. If your manager is in an inconvenient position when you leave, he will get by — people always do! He can hire temp help or all sorts of other possibilities. It’ll be fine. (And even if it’s not fine, it’s not a reason to put your career on hold. That is not the sort of sacrifice you are being paid for. But it will be fine.)

Meanwhile, though, in case this job doesn’t pan out, speak up about your boss’s plan not to replace your coworker! Say that covering for her has been difficult and you were willing to do it while it was temporary but it’s not something you can do much longer-term, and it’s important to you that her role is filled. (And if your boss doesn’t act on that, you should move forward with even less guilt!)

I am positive I didn’t used to get as many letters as I do now from people feeling guilty about leaving their jobs! I’m going to write a book called You Can Leave Your Job Without Guilt, and it will just be that sentence repeated in a variety of fonts for 200 pages.

2. New hire didn’t negotiate

I just hired my first-ever direct report. I’m very excited, but the process was not without bumps.

We offered the position to one strong candidate who tried to negotiate for a salary over 30% higher than what we had offered. That … didn’t work out.

But when we offered the job to our second choice (who was also an incredible candidate), she didn’t negotiate AT ALL and took the salary we offered her immediately. While I am extremely pleased that she’s going to be working for us, I’m wondering if at some point I should say something to her. We did have budget to pay more than our original offer (not 30% more, but a few thousand more). I don’t want to bring it up immediately, of course, and it’s awkward when I’d have a say over negotiating future raises and promotions, but I feel like this woman deserves a pep talk about arguing for what she’s worth!

It’s surprisingly common! A ton of people don’t negotiate when they get a job offer and just accept the first salary offered. More women than men, as we so often hear, but men too.

It would be a professional kindness to encourage her to negotiate at some point, but I’d wait until you have a natural opening at some point — a conversation one day about hiring in general, or a discussion of negotiating with a vendor, or whatever gives you an organic opening to bring it up. (In part that’s because you don’t want it to land too pointedly as, “I had more money to give you if only you’d asked, too bad!” … which could be a demoralizing takeaway, especially when the job is new.)

3. Recruiter asked me to re-take a test on camera

I’m in the middle of job hunting, and recently took a CCAT assessment for a job. The recruiter reached out for a first-round interview a few hours after I took the assessment and requested I retake the assessment on camera with another recruiter watching. I’ve taken the test before but never had this come up. Is this standard practice?

Nope. That’s a recruiter who for some reason thinks you might have cheated and is trying to verify that you took the test without help or cheating.

Feel free to say, “I’m happy to redo it, but was there a concern with my original assessment?”

4. Job opening gets reposted every month

Last year I applied to a job through a third-party hiring organization on LinkedIn. The job was for a company I know and respect. I don’t know the third party contractor, but they seem legitimate (I found them through a trusted aquaintance). I got a polite automated email several weeks later saying they appreciated my interest but were not going to interview me. No big deal.

I put an alert on that particular job title, since it was exactly what I was looking for. Since then, I’ve noticed that exact job posting gets posted every four or six weeks, only on LinkedIn, only by that third party. The opening doesn’t appear on the company’s website. Because it is an area with a high turnover rate (we live in a military town, and this is normal — not really a red flag), my husband suggested they like to keep a pool of applicants ready in case of an unexpected opening. My father, who works in a position where he often does hiring, suggested that it’s an automated system and nobody is looking at the applications at all.

Is this weird? Have you seen this before? I guess I could reach out to the LinkedIn page where its posted, but they’re a large company that has probably hundreds of postings for multiple agencies. I could technically reach out to the company itself, but I’d prefer not to look like a fool in case I end up applying there again. What’s your take?

They could indeed be keeping a pool of applicants if it’s a job they have to hire for frequently, either because of turnover or because they have multiple slots and/or keep increasing the size of that team. (I used to hire a for a position that was posted nearly constantly, because the team kept growing and it was hard to hire for, so we were willing to consider applicants all the time and hire anyone we found who was right.) It’s also possible, though, that this is a weird thing the outside recruiter is doing — that the company doesn’t consider this position currently “open” but the recruiter is advertising it that way to collect resumes … which could be for the legit purpose of being ready to pitch those candidates to the company when the role does open again or could be for the sketchy purpose of finding candidates to pitch to other companies for other openings, which is a thing that happens. The fact that it’s a third party posting and isn’t on the company’s own website, if their other jobs are, might point to that. But it could also just be a coincidence.

That said, I would just ignore the postings! You applied and they appear to have considered your application and concluded you’re not quite what they’re looking for. That can happen even when they’re continuing to actively (and constantly) search for other candidates. I wouldn’t worry about what’s going on with it or contact the company about it; just assume this position isn’t a match right now for whatever reason.

5. Should I send my references gift cards?

I’ve been interviewing for a job. The hiring manager wanted to hear from two past managers. For me, this means reaching 5+ years into my past and asking old coworkers who live in different cities to be references. If they were local, I’d take them out for coffee to say thanks, but they’re across the country. I want to send them a token of appreciation, but does it seem weirdly transactional to send them a coffee gift card?

Yeah, don’t do it! Giving references for colleagues whose work you respect is part of work life; if you offer a gift in exchange for doing it, it risks coming across as … not payment exactly, but not quite in the spirit of references either. Send an enthusiastic thanks and let them know if you get the job — that’s all people really want or expect!

my ex-boss isn’t that into me (but I’m still into her)

A reader writes:

I recently left my old remote job of one year for a role with a new team in the same company. I thought I was close with my manager (messaging regularly for business and casual friendly text chats, Christmas gift, birthday gift — even drove one hour to ship me sweets from my favorite bakery), but she gave me the cold shoulder and a lecture on my last day. Instead of the usual warm fuzzies as you would expect on a last day, she asked for only “business critical” updates. Mind you, this was literally the last 15 minutes we’d talk as manager-employee and my transition plan had already been discussed weeks prior. In the lecture, she didn’t seem too jazzed with my two-week notice (she’d asked before if it could be pushed back). It felt like a bad break-up. I didn’t hear from her until a month later when she messaged me to check-in. I don’t know what to do. My feelings were hurt. Do I let her know? Should I try to clear the air?

It’s worth noting part of the reason I left was that she has an unexplainable allegiance to one of her other direct reports who I think does sub-par work and I often had to pick up the slack. When I started during the pandemic I was told that person could not be expected to prioritize work because she had young kids at home. The greater team culture is also very inclusive where they don’t really point out people’s mistakes and everyone gets a participation trophy for different levels of work/contribution. Also, I felt like I was working around the clock and not being compensated for it other than really big THANK YOUs. So I asked for more money. I phrased it as, “What would you need to see to get me to X salary?” In truth I was hoping for just some acknowledgement of my contributions (other than the all too frequent team thank-yous) or at the very least a counter or rebranding my role (something I’d casually mentioned before). None of this happened. After three months at our quarterly check-in, I was told my ask was out of the range for my role (while also stating she didn’t know the top range for my role) and to look elsewhere. I didn’t really believe she looked into it like she said she did and it made me feel undervalued and dispensable. So I took her advice and looked elsewhere. So that’s why I’m confused about her reaction to my leaving.

Is it worth trying to re-establish a friendship with this person? Can I just ignore any other check-in messages and only respond to business critical questions (which are unlikely)?

Honestly, sometimes I feel a bit used for the last year and it is causing a lot of resentment. Is this normal?

Is there anything I could have done differently to change the outcome? I think my ideal outcome was either to have less things on my plate (unlikely) or more money. I didn’t want to leave, but they seem to be doing just fine without me. That hurts too. What do I do? How can I put this behind me and move on?

There’s lot of stuff going on in this letter!

Most importantly, I think your expectations are out of sync with what the relationship really was. You’re responding as if this were a friendship … but this wasn’t a friendship! Your boss was friendly, but she was your boss. It makes sense that you haven’t had much contact since you left, because that’s how it normally goes when you leave a job! Typically when someone leaves a job, they might never interact with their manager again — or if they do, it’s likely to be very sporadic, more toward the once or twice a year end of the spectrum. Since there was a warm relationship, having her email you to check in about a month after you left sounds pretty normal … but then I’d expect there might not be a lot of (or any) contact for a long while after that.

There are exceptions to this, of course! Some people do stay in closer contact with former managers — but that’s more the exception than the rule, and you shouldn’t read anything into it not happening here.

Generally, manager/employee relationships — even when very warm and friendly while working together — are much more transient than what I think you’re envisioning. That’s true even when birthday and Christmas gifts are exchanged and cookies sent. Those things are just … stuff a manager might do because they have warm relationships with their employees. It doesn’t indicate a personal relationship that transcends the employment one.

I am also concerned that you asked about your salary while hoping for a whole range of other things (more acknowledgement of your work, a rebranding of your role, etc.) and then were frustrated that you didn’t get any of it. It’s legitimate to be frustrated that you didn’t get a raise you felt you’d earned. But the other stuff — if you wanted those things, you should ask for those things! Otherwise you’re expecting your boss to read your mind instead of being straightforward about what you want.

About your feelings that you were used … the employment relationship is sort of about being used. You are using the work to get a paycheck and your employer is using money to get the labor they need. That’s the arrangement in a nutshell. I suspect you feel used partly because you went above and beyond in the expectation that you would get things beyond a paycheck — things like loyalty, more vocal appreciation, better and fairer treatment, etc. Those are reasonable things to want! But if you don’t get them, it’s not personal. It’s just … an employer who sucks at those things, and so then you need to decide if you want to stay under those conditions or if you’d rather take your labor elsewhere. But I also suspect you feel used because you saw your boss as a friend, and she hasn’t been treating you like a friend. But again, she’s not a friend; she was your employer.

Now, it does sound like she mishandled your departure. Some managers respond to resignations as if they’re personal betrayals. That’s unreasonable and generally a sign of real dysfunction in the person’s approach to management, but it happens. If it happened here, it’s on her and not on you. (That would be the case regardless, but it’s especially the case after she told you to job search because they couldn’t meet your salary request!)

You definitely should not tell your former manager that your feelings were hurt by how she’s acted. That’s putting expectations on her that aren’t appropriate for the relationship. Similarly, there’s no “re-establishing” a friendship, for that same reason. If you want to have a warm, collegial relationship going forward, you can probably have that! But it won’t happen if you ignore other check-in messages and only respond to business-critical questions. If you want a warm, collegial relationship, you have to respond to her in a warm, collegial way.

Ultimately, what this sounds like is an employer who overworked you, declined to pay you more when asked, and then was shocked when you left over it. That happens a lot. As for whether you could have done something differently to change the outcome, I don’t think so. You wanted less work (which you knew was unlikely) or more money, so you asked for more money and when you didn’t get it, you found a different job that seems to meet your needs better. That all makes sense.

The thing to do differently is … well, to see work as work. It’s a job! Your boss isn’t your friend (and shouldn’t be — in fact, if she is, that’s a problem). When you want something different in exchange for your labor, ask for it straightforwardly. If you don’t get it, then decide if you still want the job on those terms or not. When you leave, assume they will do fine without you.

Right now you are seeing this all through the framework of a friendship, but it’s not.

my job offer was rescinded — after I already quit my old job

A reader writes:

Well, it happened to me: the dreaded rescinded job offer.

Everything was going great with the interview process for this job. I had gotten to the reference stage and provided information for five people who I knew would represent me well. I got a call the following week from the HR manager, and she asked if the hiring manager would be able to speak to my previous boss.

My previous boss had a personal vendetta against me and made my time working for her really difficult. Eventually, I was moved out from under her to a different team within the same department. So when asked, I simply told the HR person that my previous boss and I didn’t have a good relationship, and that I could not rely on her for a reference.

After that conversation, I got a conditional job offer, contingent on a background check, and then a final offer, containing the following clause: “This final confirming offer remains contingent on satisfactory receipt of a reference from your current manager as of this letter date.” I asked the HR manager for the new job what that was about and she told me that I should give my notice at my current job, and then follow up with my manager’s contact information.

At this point, it’s a done deal, right? My current manager and I haven’t always seen eye to eye but I have always been hard working, professional, and respectful. I gave my notice, and asked my manager if she would be able to give me a positive reference, and she agreed she would. She seemed genuinely happy for me that I would be moving on in my career, and it was a positive interaction.

That was last week. This morning, I got a call from the HR manager for the new job to tell me, quite unceremoniously, that the offer had been rescinded. She was also unable to tell me why, as she didn’t have all of the information, but that she wanted to let me know right away that the offer is off the table.

So now I’m in the awkward position of having to ask for my job back – which of course is in no way guaranteed – or face having to desperately scramble for a new one. My question is, what do I do now? Do I contact HR and demand answers? Do I outright ask my boss if she said anything negatively about me? Do I have any legal avenues to pursue? The state I live in is an at-will state but the new employer basically encouraged me to quit while there was a contingent offer in the works. Finally, what should I have done to protect myself and what should I do in the future to prevent this situation from happening?

You can read my answer to this letter at New York Magazine today. Head over there to read it.

employer wants friends and family to participate in 360 feedback reviews

A reader writes:

Something odd happened to me today, and I wanted to see if I’m the one off-base for being confused by it.

I received a request to fill out a 360 review for my sister. My sister and I are not coworkers; we do not work for the same company (we aren’t even in the same industry!). When I asked my sister about this request, she said she was encouraged to have her friends and family fill it out because some people are different by profession then they are by nature?(!). Her supervisors made her feel that this review will help her get a better view of areas in her life she could improve.

Luckily for my sister, I don’t really have anything negative to say about her, so if I fill out this review, I’m not worried it will impact her career advancement. But I thought it was overly invasive, a point my sister understood but she thought I was being paranoid. I can’t think of any way getting a 360 review from your friends and family will help you in your career, but I can think of a LOT of ways it could hurt you.

So I’m wondering if this is some new trend? Or is this a common thing, and I’ve just never experienced it yet?


No, this is not a new trend. This is inappropriate and boundary-crossing and weird.

It’s none of an employer’s business what an employee’s friends and family think of them, and if an employee wants “a better view of areas in life where they could improve,” they can ask their friends and family for that on their own.


Yes, some people are different at work than they are in their personal lives. (In many cases, that’s a very good thing.) If it’s unconnected to how they operate at work, then it’s irrelevant for work purposes.

This is a massive overstep by your sister’s employer. They aren’t her therapist or life coach. They seem to have a fundamental misunderstanding of what an employment relationship is and what is and isn’t in their purview.

And really, if her feedback from friends and family comes back with issues that she’s never displayed at work, is her manager going to coach her on, like, how to stop arguing with her husband and her need to show up for more family events and why Aunt Meryl doesn’t feel more connected to her? (My hunch is that the answer to that is no — that they’ll leave that stuff alone and it’s just there for your sister’s own personal use, but THIS IS NOT SOMETHING WORK NEEDS TO COORDINATE FOR HER.)

This may be the last time you hear from me because my blood pressure is so high right now that I believe my demise is nigh.

is it ungrateful to ask for more money when you get promoted, my mentee is out of touch, and more

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

1. Is it ungrateful to ask for more money when you get a promotion?

My boss recently told me that you are not supposed to negotiate your salary when you are offered a promotion (that it makes you seem ungrateful). I’ve asked around at work, to those who are discreet and trustworthy, and the response has differed. Some say yes, you most definitely should counter whether it be a promotion, a new role, etc. Others agree with my boss that you are not supposed to counter a promotional offer. What’s the truth?

I’m sure your boss would like that to be the case — it’s certainly in her interests if you believe it! — but it’s categorically untrue.

It is very, very normal to negotiate the salary for a promotion. You get to decide what price would make the extra responsibility worth it to you! You don’t need to just accept what your employer offers you. People negotiate promotions all the time.

And her reasoning is that you should be “grateful”? You don’t need to be grateful when you receive a promotion! Your employer isn’t promoting you as a favor; they’re promoting you because it makes business sense for them. You don’t need to be grateful, any more than you need to be grateful when they hire you or pay you or ask you to take on a project they need to. You can certainly appreciate them if they’re a good employer who go out of their way to recognize and reward good work — as they can appreciate you for doing said good work — but being grateful implies they’re giving you something you don’t deserve.

Your boss has just revealed that she has really weird ideas about the power dynamics of employment. Keep that in mind when you’re dealing with her!

2. My mentee is out of touch with how our office works

I am a year into my first professional job after college. My company has a junior staff mentorship system where each incoming hire is assigned someone roughly a year ahead of them to be their peer mentor. It is supposed to be a casual and informal relationship, to establish a first relationship and get a sense of the company and have someone to go to for advice or tips. There is also a separate, more formal mentorship program where the mentor gives feedback, assists with career advancement, and other more serious things.

My problem comes with my new peer mentee, Jane. Jane is about a month into the job, and I have noticed some weird quirks I am not sure how to handle. Mainly, her manner comes across as a little rude/out of touch, which (I think!) is unintentional, but really rubs people the wrong way. I had heard that she almost didn’t receive an offer after her internship because of her demeanor, so I am not the only one to whom this stands out. For instance, we are expected to meet every two weeks to check in and discuss how work is going for her. She has failed to see/respond to/attend meeting invites with me multiple times, and brushes it off or doesn’t acknowledge the mistake, even when I have hinted that if she is doing this on her work teams, people won’t respond well. She also seems to misunderstand our relationship (despite my describing it to her); for example, once as we were discussing her work, she cut me off and said, “But enough about me, how are YOU doing?” even though the whole meeting is supposed to be about her work! Most recently, after showing up 10 minutes late to our meeting, after about 15 minutes (and before the scheduled end of the meeting) she said she had some other things to do and had to drop off. Normally, if a situation like that comes up, people at my office are pretty flexible (i.e., if an urgent email comes in during a meeting, you can say, “Something just came up, sorry about that, let’s reschedule,” etc). In this instance, though, nothing new came up for Jane, she just decided she was done. At my office you typically don’t do that if the meeting is scheduled for a certain slot ahead of time. Plus these meetings aren’t optional for her!

Essentially, nothing she does is particularly egregious, but it comes off as very presumptuous, not very respectful, and out of touch with our office norms. Since it is nothing crazy, however, and since I am relatively junior and not the one responsible for giving her feedback, what, if anything, should I do to address this? I don’t want to overstep, but in addition to stopping this annoying behavior for my own benefit, I would like to help her adjust to the office since I know I am not the only one put off by this.

Stop hinting and tell her directly! It’s not overstepping to let her know what your office’s expectations are in these regards; in fact, it’s likely that you’re expected to do that. That’s part of the point of mentoring, even with peer mentoring.

Sample script for your next meeting: “You’ve been not responding to the invitations for these meetings and sometimes showing up late or not at all. I want to make sure you know that’s a big deal here; people will expect you to actively manage your calendar and be on time for meetings. You should also plan on us using the full amount of time scheduled, unless we both agree we should end early. I’m setting aside time in my schedule, and I want to make sure we’re both invested in using it fully.” You can say this in a tone of “hey, you might not realize this, so let me me tell you something that will help you succeed here,” rather than a chastising tone — but do say it.

It’s also okay to address other off-key things right in the moment. Like if she says something that indicates she misunderstands the whole point of these meetings, you could just matter-of-factly say, “So, to clarify, these meetings are to discuss XYZ.” I suspect you feel weird doing that (because it feels weird that you’d need to do that), but you’re doing her a service by recalibrating her to your company’s norms if you can.

At the same time, though, don’t feel like you’ve failed if it doesn’t work. Some people are very hard to get through to, particularly if you’re not in a position of authority (and even sometimes then), and as a peer mentor your tools to reach her are limited. Give it a shot because it’ll be helpful for everyone if it works, but don’t stress too much if you can’t get through.

3. My spouse keeps asking me for career advice, and it’s too much

I am in the midst of developing career services consulting to assist job seekers with attaining new employment. Thus far, the process is slow-moving intentionally, but those I’ve shared my interests with are very excited about the venture, especially my spouse. My spouse is in the middle of job hunting themselves, so there have been times where they ask me for advice or insight. Of course, being my spouse, I’m more than happy to help every so often … but now they are expecting that I resolve every issue they run into and answer every minute question that comes up. Sure, my spouse wants to put their best feet forward and I want that for them, too; however, they’re regularly interrupting my daily motions (current 9-5, etc.). If this were any other person, I would have already sent an invoice, scheduled times to interact, and set those boundaries. Should I keep giving my spouse free career advice, stop all together—or do I charge them for my services? (That last suggestion is more joke than not, but it’s something that’s been suggested to me.)

If you were really good at accounting and your spouse kept interrupting your full-time job with constant accounting questions, at some point you’d need to say, “I can help you with this when I’m not working, but I need you to hold all these questions until after my work day is over so I can focus on my job.” And depending on the number of questions you then faced in your off-hours, at some point you also might say, “I’m happy to help you out here and there, but we’re spending a lot of time on accounting when I’d rather be relaxing with you. For the good of our relationship, let’s find you an accountant who’s not me.”

The principle here is the same: it’s okay (and necessary) to set boundaries so that it’s not interrupting your work or overwhelming your off-hours. It’s reasonable to tell your spouse you need your workday to be free of job-search questions, and to set limits on how much you’re up for doing the rest of the time. It also might help to schedule specific times for it — like deciding that you’ll spend an hour on it a few times a week, but it won’t intrude on all your time together.

That’s the nitty-gritty of how to navigate it … but more broadly, this is your spouse! Talk to them about how you’re feeling, and how they’re feeling, and figure out an arrangement that you both feel good about. When you’re at the point of wondering if you should charge your spouse for your help (even half-jokingly) and they don’t realize how put upon you feel, there’s a big communication gap to address!

4. We’re required to forward work calls to our personal cell phones

I work for a large organization in a role that was full-time in-office pre-Covid. Once Covid hit, those of us who could work remotely did so. My team has been high functioning and made the best of the past year, but was hoping to come back to a hybrid schedule, which we were told was approved. However, our department’s director decided what that looked like was giving up our offices and keeping a few hot desks (ugh). Part of losing our dedicated desk space also means losing our desk phones.

We were recently told that we would keep the actual phone number but are expected to have it forwarded to our personal cell phones. Our organization provides services 24/7, and many of our company phone numbers were previously assigned to other departments, so some of those phones ring at all hours. Not a problem when we aren’t in the office, but a very annoying problem when it’s your cell phone ringing at 2 am on a Sunday. Furthermore, they are not contributing to our cell phone bills. I’m super annoyed and don’t feel it’s fair to tell my team that the company will be forwarding calls to their cell phones. Is this normal and I’m just being overly annoyed? Or are phones a cost of doing business and they should be either providing us cell phones or subsidizing our phone bill?

That’s actually a pretty common set-up when people are working remotely or on a hybrid schedule without dedicated desks — although it’s also common for companies that do that to reimburse a portion of your phone costs, and that’s something you should push for. In some states, employers are legally required to reimburse you for business expenses, so you should check if yours is one of them. (More info here.)

The easiest way to deal with the calls outside of work hours, though, is to set up a Google Voice number that the calls forward to, because you can program that to only ring though on certain days and hours and to go straight to voicemail the rest of the time.

5. Formatting business letters sent by email

I have a random, very low-stakes question. Every once in a while I have to write a business letter that’s to be sent by email. Is there a modern format for the “block” on the letter, when there’s no physical address for either party? It always seems to look weird however I format it.

If you’re writing the letter in the body of the email, you don’t use the same formatting that you would with a physical letter — no date, addresses, etc. With email, you just launch in with your salutation (“dear Bob” or “hi Jane” or however you’re opening the letter). In part that’s because email puts the relevant information in the message headers already, and in part it’s because this is the convention with email.

If you’re attaching the letter to the email (because it’s something formal on letterhead or so forth), you’d put the date at the top but it’s okay to leave off the address block if you don’t have the other party’s address.

my boss is angry that I lied about the reason for my vacation

A reader writes:

At the beginning of the pandemic, I started a relationship with my now-boyfriend, who lives in another country. We met online and had been planning on taking a vacation together as soon as the borders of our countries, which were closed due to COVID restrictions, opened . During the summer, I had fallen and broken my foot, as well as had a cyst removed from my tailbone. Towards the end of the summer, when the borders reopened for tourism, I was feeling well enough again and was looking forward to finally meeting my boyfriend in person.

In July, I emailed my boss asking for the last week of August off to take a vacation, which was approved. I work as a librarian in a Catholic high school and have many coworkers who love to gossip and spread judgment, which can create a really negative atmosphere. Because of that, I made the decision to tell my boss that I was going on a family vacation.

A couple weeks before I left, my boss had told me that I was taking vacation at an inconvenient time and while she had approved it this time, I shouldn’t take off during that time period again. I made note of that statement, told my closest friend at work the true nature of my trip, made final plans, checked the COVID policy with my work, made sure I had full coverage, made my social media accounts private, and took my vacation.

Near the end of my vacation, my friend from work notified me that my boss had somehow figured out that I wasn’t actually on a family vacation. In order to get ahead of the issue, I emailed her to explain that I didn’t tell her the true nature of my vacation because I was trying to avoid gossip, and that I had multiple negative Covid tests which would approve me to return to work if that was her concern. She told me that we would discuss this matter when I returned.

Upon my return, my boss pulled me into a conference room and told me that she was angry with me for lying to her and breaking her trust, that if I were to have handled this situation better I would have made an attempt to discuss the reason for my vacation in person (even though I was injured and wasn’t working in person), was upset that I decided to take vacation during an inconvenient time, accused me of lying so that I would get those days approved because I was worried that she wouldn’t approve them, and questioned my dedication to the school and my position. She also mentioned that she didn’t believe that I was trying to avoid gossip and thought I had an ulterior motive. I apologized and said that I would be honest about my plans for time off from here on out, but that I was warranted privacy during my time off and what I do on my own time.

I am fully aware that lying was not the best course of action for this situation, but I strongly believe that what I choose to do on my own vacation time should not affect the approval of my vacation time. Was I fully in the wrong in this situation? Or was my boss’s reaction out of line?

Nah, your boss’s reaction was over-the-top.

In theory you’re right that what you plan to do on vacation shouldn’t affect whether or not it’s approved. In reality, though, it can be more complicated. Let’s say that you submit a vacation request and it’s a hard date to for your boss to accommodate (maybe other people will be out that day and she needs coverage, or it’s the day before a major event and she needs all hands on deck, or so forth). If you just want the day off to the go to the park, your boss might reasonably ask you to find a different day. But if it’s the day of your kid’s wedding, most of us would expect her to find a way to make that work. So we tend to accept that sometimes the reason for a specific set of dates matters.

It gets a lot more problematic, though, when the plans in question aren’t so obviously toward the “my kid’s getting married” end of that spectrum. And most of the time, people are rightly uncomfortable with managers deciding what’s “important enough” to accommodate and what isn’t … even as we also recognize exceptions like weddings.

But it’s possible that your boss considered a family trip closer to the wedding end of the spectrum than a trip to meet a boyfriend would be, and maybe she approved not-ideal dates for that reason. It’s possible that that’s why she’s pissed off now — maybe she went out of her way to accommodate difficult dates because you told her it was a family thing, and now she thinks you lied so she would do that. Her reaction was still over-the-top — this should have been a much calmer conversation — but she would have more of a basis for being bothered. (For the record, though, I don’t think managers should be adjudicating the importance of one trip vs. another like that unless it’s something more like the wedding vs. park example and the dates are difficult ones to approve.)

Or it might not be that at all. She might just be overly controlling and think she’s entitled to know more about your personal plans than she really is. She might be so focused on the lie that she’s not seeing that it didn’t really matter what you were using your time off for because it’s still your time off.

You can probably figure out which of these it is based on (a) what you know of your boss in general and (b) how inconvenient those particular dates really were. If they were seriously inconvenient for your team, it’s probably the first explanation. If they weren’t, it’s more likely the second.

can I turn a request for free help into paid consulting?

A reader writes:

I work in a pretty specific niche area. I was recently at a conference describing my work, and a leader from another organization came up to me to ask me how he could find someone like me to work for him. I emailed him some information about the graduate school I attended, where there are many students who would dream to work for such an organization. I also pointed him in the direction of a popular job board for my field.

But the questions didn’t end there. We then talked for around half and hour about my responsibilities, his organization, recommendations I would make for him at this point, future directions he might look into, etc. Later that same day, he asked me what a fair salary range is for the position he’s hoping to hire.

I’m flattered by his interest, and would genuinely be happy to help him find the right person. But it isn’t feasible for me to join his organization at this time.

My fear, however, is that I’ve put myself in the position of giving unlimited free advice and recruiting. I would be willing to offer limited services (e.g. draft a job description, assist in making a strategic plan) as an independent contractor.

What I am wondering is how I can pivot our current conversations into an independent contracting offer. It feels awkward to say at this point that I’m unwilling to chat with him more for free. It’s one thing to make conversation at a conference, but he mentioned that there would be many more emails coming my way,.

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.

my employee sent me a “letter of intent” to look for another job

A reader writes:

I manage a small department at a state agency. One of my direct reports, who had been having some issues with other employees (faults on both sides, honestly), just sent me a Letter of Intent to look for another job. The letter itself was beyond odd. It listed all of his contributions to the program (which are significant!) and demanded, if we wanted him to stay, a position that doesn’t exist and can’t be created without involvement at a much higher level, a much higher salary than the salary band permitted by the state, and a fancy title that doesn’t exist in our system.

The letter then asked me if I want him to work until December or through spring. The problem? He’s got a year-long contract that runs through June, and it’s utterly unclear whether a letter of intent to apply for other jobs actually constitutes a resignation or, if he can’t get another job by January, we’re obligated to continue to employ him until June. (Note: the probability that he will find another job matching what the letter says he wants by January is slim to none.)

Now, his demands are so off-the-wall that I not only have no desire to meet them, it’s completely impossible for me to do so, even if I wanted to. I have a call in to the contract person for our agency to figure out if a letter of intent for applying to other jobs constitutes a resignation from his contract or not. If he’s not going to be here in January, I need to start the hiring process NOW. If he is, I don’t want to hire someone else for that time period and have no work for them.

Have you ever heard of anyone issuing a letter of intent to start job searching before? Does it constitute a resignation? Does it mean anything? The letter was clearly written in a state of extreme annoyance, but I’m half expecting him to try to walk it back once his blood cools. FWIW, I ran into him in a common area today, and he avoided interacting with me.


People do not give their employers “letters of intent” to announce they plan to begin job searching. They just … begin job searching.

This is not a thing!

My guess is that either:

1. He’s hoping you’ll respond by begging him to stay, which is what most people want when they issue a dramatic Intent To Flounce … but he’s somehow oblivious to the fact that he has a contract through June.

2. He genuinely has no idea of workplace norms and thinks he’s supposed to notify you when he starts formally looking for other work … ? Maybe it’s connected in some way to the contract, like he thinks the formality of the contract demands this sort of formality when he’s thinking about breaking it? I dunno.

I’m skeptical that he has seemed to have a strong grasp of workplace norms up until this point, so I’m guessing you’ve seen other stuff from him that will let you figure out if it’s more likely to be #1 or #2.

As for whether it constitutes a resignation … it depends on whether your purposes are practical or legal ones. For practical purposes and if there weren’t a contract involved, I’d treat it as a resignation — he’s asking if you want him to leave by December or in the spring, so I’d decide which one you want (advice: December, if not earlier) and let him know. As in, “Let’s plan on December then, and we’ll set December 12 as your last day.” Or, if you judge that it would be harmful to have stick around that long because of his work or his conduct, you could say, “Let’s actually plan to have you wrap up by (insert earlier date).”

But there’s a contract involved, so you’ve got to go by what the contract requires in terms of notice on both sides, etc. You can certainly decide to let him out of the contract earlier (and it sounds like you should), but when a binding contract is in play, that’s going to govern how you can respond, at least to some extent.

All that said … if this guy’s work was good up until now and you’d actually prefer it if he’d stay — and if and this isn’t characteristic of his conduct before now — another approach is to just ask him what’s up. Call him in for a meeting and ask what’s going on. Explain you can’t meet the demands in the letter and ask what he wants to do, given that. Talk to him enough to get a sense of what this is all about. Was there some precipitating incident that pushed him over the edge into weird I Am Writing To Notify You I Am Thinking About Leaving territory? Did he feel mortified right after sending the letter and wishes he could take it back? Did he send these letters at all his past jobs when he was ready to leave? Unless the letter struck you as utterly typical of him, it’s probably worth a conversation to find out what’s going on before you do anything else.

I have two bosses, my manager attends a notoriously bigoted university, and more

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

1. How do I navigate two bosses?

I have worked for my organization for two years, as a manager. I technically have one director who I report to (Jane) I report to, and another (Niles) who I also report to but less officially. Jane and Niles have vastly different concepts of how things need to be handled. Niles is not clear and I very rarely understand what he wants. (If I do, it’s because I ask a lot of questions!) I’m not the only one in my organization who has this problem — in fact, most staff do not know how to communicate with him at all. (When I tried to talk to Niles about this, he told me that the entire staff doesn’t know how to communicate and he doesn’t see how that is his problem.)

So, I carry out duties as directed by Jane because (a) I understand what she wants and (b) she is my direct supervisor. The problem comes in when Jane makes a decision and Niles has an issue with it … which inevitably is only addressed by Niles to me, not addressed with Jane. Niles is Jane’s boss, so I sort of have to report to each of them. I can’t simply say something like, “I’m sorry, but Jane has assigned me to take care of the task in this manner. I can’t proceed in the way you would like until I get the all clear from her.”

I’m at my wits’ end trying to get the two of them to communicate and to get Niles to communicate properly with the rest of the organization. Jane is pretty understanding about the situation but it’s starting to get out of hand. How do I navigate two bosses?

First and foremost, it’s not your job to get Jane and Niles to communicate, and it’s definitely not your job to get Niles to communicate better with the rest of the organization. Those two things are both clearly problems, but they’re above your pay grade so free yourself from whatever’s making you feel responsible for fixing those. If the people with the power to fix those them aren’t doing it, you definitely won’t be able to — and you’re just adding additional stressors to your plate that don’t need to be there.

With the conflicting instructions, you’ve got to keep in mind that Niles is Jane’s boss and he has more authority than she does. That doesn’t mean you should just abandon Jane’s instructions when he tells you to something differently, but you also shouldn’t respond with “I cannot do what you are asking” (your proposed language). That comes across as pretty rigid! Instead, just explain she asked you for something different and so you’ll go back to her and relay what he wants. For example: “Ah, let me talk to Jane. She’d wanted X, so I’ll let her know that you’re saying Y.” Or, in some situations: “Jane told me to do X earlier. Could I pull her into this conversation so we’re all on the same page?”

You should also have a big-picture conversation with Jane about the pattern — “Niles sometimes give me instructions that contradict yours. How do you want me to handle it when that happens?”

2. My manager attends a notoriously bigoted university

I’m new to my job (two months in) and so I’m only just getting to know my new supervisor (all virtual/over Zoom). She seems lovely and supportive. But I recently learned that she is enrolled to get an advanced degree at one of the most notoriously anti-gay, anti-trans, anti-civil-rights, etc. etc. evangelical universities in the country. I’ll call it University X.

This isn’t a matter of what’s physically close to her, because it’s all online. It’s not a matter of saving money, because it’s being paid for by employers who would pay any tuition. It’s almost certainly not a matter of academic excellence, because this place just isn’t academically excellent. While I give a lot of leeway to where people get their undergrad degrees — an 18-year-old is functionally a child and most are under the thumbs of their parents — this is a woman closer to middle age who would have made the decision to enroll in grad school at University X with both eyes open and a plethora of other options.

As a supervisor, what is her duty here? Our employer is outspoken about support for the queer community. But I can imagine hearing from her that she was enrolled at University X and feeling super unsafe about talking to her about anything in my life that was even the least bit non-normative. Whether I count as “queer” is sort of up for debate within the community, but this question isn’t really about me so much as it is a hypothetical: What would you advise my supervisor to do here? Should she have chosen a different school from the get-go? Should she omit the name of the school when she discusses her academic work with subordinates? Should she mention the school but insert a disclaimer, “I know that University X has a really awful reputation for being queer-friendly, but I just want to let you know I don’t condone that”?

She shouldn’t attend a school that’s notoriously anti-gay, anti-trans, and anti-civil-rights, period. With the context you gave (eyes wide open and other options), you’ve got to assume she either actively supports their positions or simply doesn’t care (which for all intents and purposes isn’t that different from supporting them) and that’s a real problem for her as a manager (and as a human). If your employer is paying for her to get a degree there, they need to revisit what they pay for.

3. Hiring managers are asking how I thought the interview went before they offer me the job

I’ve recently been job searching and accepted a new job and turned down several offers. One thing I ran into several times was that post-interview, I would receive a call from the interviewer. We’d exchange the usual pleasantries but then they would ask me how I thought the interview went.

Every time this happened, it was incredibly awkward. I had no idea what they wanted from me as an answer and in the moment it felt like answering it wrong might lose me the job. Each time they ended up offering me the job after I answered.

Once when this happened, it was a job that I’d planned to email the next day to withdraw from consideration. They asked me how it went, I said that it didn’t seem to be a good fit for me. They said, “Well, you might think that you didn’t come across well or didn’t answer the questions perfectly but it’s good news — we’d like to offer you the job.” As you can imagine, my politely declining the offer was so much more awkward than it would have been without that spiel.

Is there some logic behind this question that I’m not seeing? What is the “right” answer? Please tell me they aren’t doing this to people they reject?

That is a strange way to open a conversation that’s leading up to a job offer. My guess is that they really mean, “How are you feeling about things?” and they’re expecting you to say that you’re really interested in the job, which they will then respond to by offering it to you.

The problem, of course, is that they don’t seem to be contemplating that you might not respond that way — or at least they’re not adjust their script when that happens, as evidenced by the person who, upon being told you didn’t think the job was a good fit, responded that they had “good news” anyway. It apparently never occurred to them that you might have felt they were not a good fit for you and that you weren’t simply waiting for their judgment of you.

It’s also totally unnecessary! If they want to offer you the job, they can just open the conversation with, “I’m calling because we’d like to offer you the job.” Done!

As for a good response to “how did you feel the interview went?” if you are still interested in the job, you can go with something generically positive, like, “I really enjoyed talking with you, and I’m very interested in the position.”

4. Can I warn a vendor about our difficult IT director?

My workplace has recently identified a piece of software we need to replace, and we’ve selected one that meets our needs well. I’ve been working closely with the vendor during this process to evaluate the software and their proposals and have a very good relationship with them.
The only hurdle we have left is IT approval. The problem is the head of IT is a real [insert not nice word here]. In past interactions with vendors, he’s only been happy when he thinks he’s getting one over on them. I have heard him berate salespeople and hang up on technical reps who he’s specifically requested to be a part of the call. (I’m very happy to not be in his chain of command.) I’m also a woman in a typically male-dominated role (where I’m expected to be THE expert on some things). I’ve had him specifically ask my opinion about things in my area of expertise (which he knows little to nothing about) and dismiss my opinion when I didn’t agree with him.

I will have to keep working with this vendor through the purchase and implementation of the software, and longer if we go with the remote-hosted option that seems the best fit. We have a meeting next week with a technical rep from the vendor and our head of IT to get all IT questions answered so we can move forward. Ethically it seems like I should warn the vendor that the head of IT isn’t particularly nice and may be spectacularly unreceptive to the proposal, but I genuinely have no idea how I would go about that. Is there anything I can say that wouldn’t be badmouthing an exec?

There’s no reason you can’t discreetly say, “Roger can be difficult in these meetings, but you won’t have much contact with him afterwards. I’m the one you’d be working with throughout the purchase and implementation.” If there’s anything you can specifically recommend the vendor do to prepare for the conversation (like “Roger always looks at X really carefully and will likely have questions on Y”), that’s useful too.

5. How do I pass on institutional knowledge before I retire?

I’m a bit over a year from retiring. I currently manage a small environmental regulation group that I was an inspector in for almost 30 years, and when I retire I will have been here for 32ish years. We’re a niche program in a field that really didn’t exist until the early 80s; I got started in it in 1982 at another city, so I was in on the ground floor. In my time here as an inspector, I have always been the subject matter expert here. My three employees total about half my experience in the field.

We have decent policies and procedures, all of which we’re updating/rewriting over the next year. But how do I transfer what’s in my brain? Like I know the answer to something because I read an EPA guidance letter about it 30 years ago that will be difficult to find a copy of, but don’t “know” I know it until the question comes up. We have a good library of guidance documents, and most of them are available online, but half the battle is just knowing where to look and I can’t figure out how to pass that along.

You can’t really pass that kind of thing along. That kind of institutional memory can’t just be written up into a manual or downloaded into someone else’s brain. Even if you had a colleague closely shadow you for the remaining year, you wouldn’t be able to transfer all of that. It would make sense to spend a good part of your remaining time mentoring colleagues, but your bar for success can’t be “they know everything I know”; that just won’t happen.

But this might indicate you could do a few hours a week/month of lucrative consulting work after you’re gone, if you wanted to!

weekend open thread – September 11-12, 2021

This comment section is open for any non-work-related discussion you’d like to have with other readers, by popular demand.

Here are the rules for the weekend posts.

Recommendation of the week: Instead of a book, this week I’m recommending a Netlix series: The Chair, about drama in a college English department. It’s like a David Lodge novel come to life. Highly enjoyable.