Sunday free-for-all – October 5, 2014

IMG_5105It’s the weekend free-for-all.

This comment section is open for any non-work-related discussion you’d like to have with other readers, by popular demand. (This one is truly non-work only; if you have a work question, you can email it to me or post it in the work-related open thread on Fridays.)

Have at it.

I’m in training with a much slower coworker, contacting my boyfriend’s boss, and more

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

1. I’m in training with a much slower coworker

I am training for a position as a quality assurance agent for a surveying company, and it is me and another woman training with a trainer. Today, I’ve been sitting here for more than half the day while the other woman is painstakingly going through her case slowly. I got through four cases in two hours, and she’s gone through one and a half. Is it absurd that I am just sitting here while I have obviously gotten the grasp of the work?

Probably. I’d check with the trainer and say something like, “I feel like I’ve got a good grasp of this. Is there something else I can move on to?” If she tells you there’s nothing more left to learn, then you could ask, “In that case, would it be possible for me to get started on work?” But if she tells you that there’s more training to be done but she can’t move you on until your coworker is caught up, then ask if she minds if you read the news or something else while you wait.

Also, if the training is weeks, this is worth addressing more assertively than if it’s just a day. If it’s just a day, it might just be something to suck up. (But either way, if you have the opportunity to give feedback on the training later, this is a reasonable thing to mention.)

2. Should I contact my boyfriend’s boss?

I have been planning a surprise trip to New York for my boyfriend of five year’s birthday in November. I had him ask for a total of three days off work. He is fairly new at his job, having only been there for four months, but he is given so many vacation days that he is to use by year’s end. When he mentioned the vacation days to his boss, they stated, “It should be fine, it’s your vacation days.” My boyfriend was specific about the dates I told him, but still told them that he’d confirm the days via email.

I am now only a month away, so since they told him that he should be okay to take off, I purchased flight, hotel, and tickets for a Broadway show (about $1700) without insurance. And of course, a few days afterwards, the bosses told my boyfriend that those dates are not good dates. Once he told me, I explained (without telling him where the trip was) that I have already made the purchases and to try to see if he can do anything else about it. He mentioned it right away to his boss, who then stated that we should not have jumped the gun but that he would ask anther manager for their opinion. It’s been a week and they have not brought it back up yet and since my boyfriend is still so new, he does not want to bring it up himself.

This situation needs to be figured out soon so that I can figure out what I need to do to try to get some money back. Would it be unprofessional for me to email his boss and explain the situation and that it was my fault for making purchases and whatnot?

Whoa, definitely do not contact his manager yourself. This is his to handle and you risk making him look bad by interjecting yourself into his own work situation. If they had given him approval (real approval, not tentative “email us the dates and we’ll confirm” approval), then he should talk to them and point out that nonrefundable tickets were purchased based on their okay. But if there’s any chance that their okaying the dates was tentative, he may need to let it go. Either way, though, you’ve got to leave this to his judgment to handle, since it’s his job and his relationship with his boss, and he’s the one who can best judge how to approach this.

3. Should I let my friends know I’m on the hiring committee that will be evaluating their spouses?

I was asked to be on the hiring committee for an open position in my division. These committees are a new strategy, and sometimes word gets around as to who’s been asked to participate, but there’s no real announcement of any sort. I just got the packet of applications to review, and it turns out that two of my coworkers’ spouses have applied for the position. I’m friendly with both coworkers in and outside work, but don’t know the spouses. My instructions say to keep the candidates’ names confidential, but should I mention something to my work friends out of courtesy or in the interest of full disclosure?

I wouldn’t. They don’t really have a stake in knowing, and you risk making things awkward if you end up thinking the spouses should be rejected. It’s hard to see any good that comes from letting them know, and there’s no assumed obligation to alert them. If you’re asked directly, that’s one thing — but I don’t see a reason to go out of your way to announce it to them.

4. When is it appropriate to update LinkedIn with a new job?

At what point in time after receiving and accepting an offer at a new employer is it appropriate to update your LinkedIn page (to the new employer and title)? I am within my last two weeks at my current employer, but am generally wondering if there’s a protocol for this.

I’d wait until you start, since before that it wouldn’t technically be accurate to list the new job as your current employment. But any time from your first day onward seems reasonable to me.

5. Can an employer forbid employees from talking to each other?

My husband is in an extremely hostile work environment. He just told me that the supervisor forbade the 50+ employees from talking to each other. On top of being horrible for morale and utterly dumb, I am wondering if this is even legal.

Yep, it’s legal, as long as they’re being forbidden from talking across the board. It could be illegal if the employer is only banning certain topics, and those topics are, for instance, wages and working conditions. The ability to discuss those topics is protected under federal law. But they can certainly ban social chit chat if they want to. It’s a silly thing to do, and pretty much guaranteed to create a highly disgruntled workforce and drive away good people, but they can do it if they want to.

how long should a cover letter be?

A reader writes:

I have the most basic of questions, but I’ve received a different answer from everyone I ask. How long should a cover letter be?

I tend to be more concise in my writing, so I would be okay submitting a half page cover letter. However, I feel like that appears too short and should be about a page. Because I always strived to submit a full page, I think a lot of my cover letters may have ended up wordy/contained a lot of fillers.

Would hiring managers be happier with a shorter cover letter, that’s more direct to the point?

Different hiring managers have different preferences. Most prefer about a page, but you’ll also find managers who prefer something shorter (although I think these tend to be ones who don’t place a major emphasis on the cover letter at all). Few if any would tell you that they prefer more than a page.

Really, though, it’s less about length than it is about content (assuming you don’t impose on people’s time and get too lengthy). The perfect length for a cover letter is the amount of space that it takes to explain why you’re an unusually strong candidate for the job aside from what’s on your resume. Half a page isn’t usually going to be enough to truly do that — although there are exceptions to that. One page is usually about right — but you also shouldn’t be writing to hit a certain word minimum, since that’s a recipe for a bad letter. And if you find yourself adding filler or fluff to lengthen it, that’s a flag that you’re not really doing what you should be doing with a cover letter. (And while we’re on the topic: 99% of job applicants write cover letters that just summarize their work history. That’s relatively worthless. Stop that.)

Being a certain length isn’t what makes a cover letter effective; it’s what it says.

The litmus test is this: Does your letter make a compelling case for why you’d be awesome at the job, without repeating your work history?

If your letter does that but it’s longer than a page, look for ways to edit it down without losing its essence. If it’s half a page or less, you should just be damn sure that it’s truly passing that litmus test. It’s hard to meet that test if you’re writing very short. Not impossible, but a lot harder.

And really, there are exceptions to every rule. Hell, at least one example of a real-life great cover letter that I’ve printed here is longer than a page, but it worked, and when something works, the rules don’t matter. But if you’re looking for guidelines, about a page is usually right.

open thread – October 3, 2014

It’s the Friday open thread!

The comment section on this post is open for discussion with other readers on anything work-related that you want to talk about. If you want an answer from me, emailing me is still your best bet, but this is a chance to talk to other readers.

my employer revoked everyone’s telecommuting status, my coworker copied my LinkedIn profile, and more

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

1. Can I lie about my hours to get a better salary at a new job?

I have been working at the same company for 10 years, from a junior role to managerial position. It’s a very small company (less than 5 people) and has been hit in recent years by the economy; people have been laid off. I’ve only had a few small pay raises in that time, and a couple of years ago I asked for a pay increase and was refused as the company wasn’t doing well. I managed to negotiate working a four-day week along with no drop in holidays for the same pay (I do the same job but just more efficiently).

I love my job but obviously there comes a time when you have to move on and start earning what I believe is deserved. When job hunting, I’ve been told my pay is very low (about £15k + less than it should be). I’ve started lying to agencies about my salary with the intention of suggesting that would be my salary if I worked full-time. However this is still lower than I’m aiming for.

I’m now wondering if I can lie about my hours, i.e. say I work three days a week instead of four and that I freelance elsewhere in between (which I do, although I don’t earn much from it). I’m not comfortable with lying but really want my next role to be in line with the industry standard. Would a future employer ever find out my working hours, either through pay slip or reference? Or would there be a better route to getting such a huge increase?

What?! No, you can’t lie in the interview process. It would raise huge issues about your integrity, for obvious reasons, and yes, it’s easily discovered. Employers that base salary offers on what you’ve been earning are often employers who ask for verification of that information, either as part of the reference-checking stage or by requesting tax forms, pay stubs, or other documentation. And moreover, sometimes they do it after you’ve already accepted a job offer as part of their new hire paperwork, which means that you risk them pulling the offer after you’ve already accepted it and resigned your current job.

You’re better off keeping the focus on what the market rate is for your work.

2. My employer just revoked everyone’s telecommuting status

I work for a bank in a southern city. I work as a telecommuter and live 2 hours from the office. There is no public transit. I was hired under these conditions and signed up for a program called MyWork. I go in once or twice every two weeks. A lot of my hours are out of standard hours (I can be working at midnight on an issue) and I work from home during these as well.

This bank just revoked everyone’s telecommuting status. Everyone in my major metropolitan city. Thousands of people. Some of us are being offered relocation if we don’t live in the city (like me). Regardless, that disrupts families in mid school year and spouses with jobs. We’re having to deal with this during the holidays! It is obvious that if we say no, we will lose our jobs. The question is, will they fire us for cause for this? Can they?

That wouldn’t typically be considered being fired for cause; “cause” generally means a performance issue. This would be something more akin to a layoff; the nature of the role is changing so dramatically that it’s essentially being eliminated and replaced with a different one.

But if your question is more about whether you can lose your job over this and less about what it would be called: Yes. If they’re committed to eliminating telecommuting, they can require that you move or otherwise work from their office. However, you’d almost certainly be able to collect unemployment, and you should try to negotiate severance as well.

3. My former coworker copied my LinkedIn profile verbatim

A former coworker and I held the same position at different times at the same company (she was in this role first, then was laid off and I moved into that position a year later, and now have a new role). I noticed recently that she updated her LinkedIn profile about that position to be practically identical to mine. Her tagline is verbatim the unique tagline I had until a few months ago as well. Do I say anything or assume it’s a coincidence?

Unless your wording was very generic. I wouldn’t assume it’s a coincidence; it sounds like she stole your wording. But I don’t know that it’s worth speaking up about. I’d file this in your head as evidence that your former coworker kind of sucks, and move on.

4. Do I really have to spend so much time reconciling my business credit card expenses?

I travel a tremendous amount for a national nonprofit. I have a company credit card, which I am able to use for all my business expenses. There are some months when reconciling my credit card for our accounting department takes me 3-5 hours. The spreadsheet has 50-60 items on it. and I despise having to do it. I don’t have anyone else to help me and I don’t have any one to blame. When I object to the spreadsheets, the copies of receipts and the cumbersome process, I am told that our auditors demand it and the IRS demands it. I just dont believe them that I need to explain every expense – a $2 metro card? Am I just crazy? Should I just suck it up, pour some wine, and reconcile away?

What is the easiest way to do this? Am I daft?

Pouring some wine and settling in for a few hours of reconciling sounds right to me. Reconciling expenses does need to be done; otherwise, someone could scam your organization out of significant amounts of money over time.

But you might look for ways to streamline expenses — for instance, rather than having to record a $2 metro card every time you go to a meeting, see if you can buy a $50 metro card for the month and categorize it as “traveling to meetings.” (They might not let you do that if they want more specifics than that, but it’s worth asking since you’re in such a travel-heavy job.)

5. My temp-to-hire job hasn’t given me any details about salary or benefits

I’ve got a “temp to hire” job, but no details on wages, timeline, benefits, etc. have been offered, casually mentioned by coworkers, etc.

I recall a past agency explicitly forbidding its employees asking about being hired, if they will be hired, the wages if hired, etc. The working conditions aren’t the best (having to second-guess construction site addresses when Google can’t find them, no designated work area, bad lighting, etc.) and not being able to find any details on compensation (not even on the ‘net) makes me inclined to ask my agency to pull me out. It may be a wonderful job with incredible benefits, but I haven’t heard a peep about them.

Why not ask your staffing agency? It’s true that they don’t usually want you approaching the client about this stuff directly, but it’s perfectly reasonable to ask your agency for details. I can’t see any rationale for asking to be taken off the job without first telling your agency specifically what you’re interested in finding out.

your workplace is gross

A reader shared this disgusting internal email from his workplace:

Subject: Restroom Walls, Conference Room Tables, & Boogers
Importance: High

Good Morning All,

As you can read from the title this is a very unusual request to be sending to a group of professionals. Yes, we are talking about boogers this morning.

As I and my staff travel through the halls and rooms of our shared office, we occasionally find some rather unusual “treats” left by those that have inhabited the areas before us. Unfinished drinks, food and paper are tolerable; albeit still wrong, and as adults we should be cleaning up after ourselves. What is intolerable, and increasing as the weather starts to change, not to mention childish and disgusting, is the amount of boogers found rubbed on the restroom partition walls, tile, grout, and occasionally the underside of choice conference room tables.

So my request to all of you this morning: Please dispose of your boogers using Kleenex, toilet tissue, or paper towels, and please do not smear them on the walls of the restrooms or the underside of the conference room tables.

Thank you and have a fantastic day!

Gross.

Does this kind of memo ever help anything? I mean, it’s not like the perpetrators thought that they were engaging in socially acceptable behavior but this memo will open their eyes. Anyone who smears … bodily matter around their workplace pretty much knows they’re doing something gross.

I suppose it’s possible that this memo could shame people into better behavior … but I’d argue that when you’re at the point where this has become such a problem that it’s memo-worthy, the war has already been lost.

3 ways to build accountability on your team

If your staff is missing deadlines, not following through on work, not taking responsibility for mistakes, or simply not producing high-quality work, you’ve probably got an accountability problem. Here’s how to fix it.

1. Talk explicitly about your expectations – not just about what people do but also how they do it. Managers often make the mistake of having a whole set of expectations for how employees will behave but keeping that information to themselves – and then being frustrated or surprised when employees don’t act in accordance with those expectations, even though they never shared them. But unless you manage a team of mind readers, part of your job as a manager is to do the work of getting your team aligned with what you expect from them.

Some of this happens in the hiring process, of course – you screen for people who have a strong work ethic, take initiative, exercise ownership, and so forth. But a large amount of expectation-setting also needs to happen afterwards, as well. For instance, if you’ll get antsy if people aren’t responding to emails within a business day, tell them that. If your deadlines of “by the end of the day” really mean “by 5 p.m.,” be explicit about that. Whatever your expectations, get them out of your head and articulate them for your team. Otherwise, you’ll end up frustrated that people aren’t performing in the way that you want, and your team will end up frustrated that they’ll be held to standards they were never told about.

2. Give feedback when you see things you like and things you don’t like. Too often, managers keep their thoughts about employees to themselves. They’ll be impressed and delighted at how a staff member handles tricky clients – and might even praise her to others – but neglect to tell the staff member directly how great her approach is (or even better, specifics of what makes it so great). Or they’ll be annoyed that a staff member always turns in unpolished work, but never actually tell the employee, “When drafts come to me, they should be fully polished and ready for publication, which means no proofing errors and no fact-checking still left to be done.” That can lead to employees not feeling accountable for the types of things the manager would like them accountable for. Which leads us to…

3. Ensure that actions have consequences – both good and bad. If people feel like great work goes unrecognized, over time they’re less likely to continue going out of their way to do truly exceptional work. And if people feel like great work isn’t recognized but problems are always called out, people will wonder how it is that you always notice the bad without seeming to observe the good, and then you’ve got a recipe for plummeting morale on your hands. It’s important to ensure that you’re providing recognition and rewards when things go well, as well as consequences when they don’t.

And keep in mind that “consequences” for problematic performance doesn’t have to mean something formal, like a write-up or disciplinary action (and those things can often be overkill). Rather, a consequence can simply be a conversation with you, asking about what happened and what the plan is for avoiding it in the future. On a healthy staff, that should often be all the consequence you need to reinforce accountability and get things back on track. (Of course, there will be times when that doesn’t solve the problem, and then you’d escalate in seriousness from there – but that’s usually the right place to start.)

Originally published at Intuit Quickbase.

is this job rejection a load of bull?

A reader writes:

I had a question about being rejected for a job. This is the first time I’ve encountered this rejection reason.

Basically, I had a phone screen with the HR person and she said she would share my details with the hiring manager to work out some times for a second phone interview and should get back to me by Tuesday with times (the interview was the Friday before). I asked it it was better for me to provide times instead, but she said no (I thought that was odd already).

I follow up with her Tuesday night and she gets back to me Thursday morning to tell me that she shared the details with the hiring manger and unfortunately, they are too far down the hiring process with other candidates to move forward with me.

To put it bluntly, this sounds like a load of crap to me.

Here is the email:

“Thanks for reaching out! I have shared the details of our conversation with our hiring manager, but unfortunately we’ve started to move forward with candidates who are a bit further down the road in the interview process than you. That said, if another BLANK role opens up, I’ll reach out to resume the process.

Best of luck in your search!”

Should I try connecting on LinkedIn? Any suggestions? I don’t want to burn any bridges but who knows, I might end up interviewing for the same company.

That doesn’t sound like BS to me.

That kind of thing happens. If they’re pretty far in the process with other candidates, the hiring manager may think she’s likely to make an offer to one of them, or simply that they have a sufficient number of strong candidates already in the interview pool. Sometimes the subtext of this is that looking at your materials, she doesn’t think you’re likely to be as strong as them, but sometimes it’s nothing more than “we’re already talking to plenty of strong people, and no more are needed.”

Or who knows, maybe the hiring manager looked at your materials and decided she wasn’t as enthused about you as the HR person had thought she would be.

There’s no way to know — but it also doesn’t matter. It’s not personal, and you shouldn’t agonize about what the “real” story is. As a job candidate, you can rarely be sure that you know the real story behind a rejection, no matter what form it comes in — but you also don’t need to, despite the fact that it would be awfully satisfying to know.

As for whether you should connect on LinkedIn, sure, if you feel like it. There’s no reason not to. You could also send a gracious note back thanking her for letting you know and reiterating that you’d love to be touch in the future.

But really, this kind of thing is pretty normal. I wouldn’t read anything into it beyond “it just didn’t work out this time.”

should I ask for a lower salary, my boss wants me to inflate people’s performance ratings, and more

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

1. My boss wants me to inflate people’s performance ratings

My organization really prioritizes feedback. Every month, each employee gets an individual meeting with their manager to talk about progress, performance, goals, and ways the organization can better assist the employee in achieving his/her goals.

I oversee about 20 remote employees, and I report directly to the executive director. Last week, I started working on formal performance reviews, and he asked to speak with me about my scoring. He told me that while he agrees with my scores, he thinks it will anger and frustrate people to receive a satisfactory or average mark, and therefore I should give higher scores to keep people happy even if they don’t deserve it. To me, this seems to defeat the purpose of performance reviews. I tried to explain my position to my boss, but he didn’t agree. I’m hoping to revisit the conversation soon and I’m looking for advice on how to explain to him that feedback is completely useless if it’s falsely high.

I love that our organization gives feedback, but there’s no point if I can’t discuss concerns. I know that he’s my boss and what he says goes, but I feel like it’s really important to be able to give accurate feedback. (And his personal management style tends to be “don’t give feedback until there’s a huge issue,” which I tolerate but don’t agree with.) Any advice on how to convince my boss that accurate feedback is essential? He wants our team to be successful — I just wish he’d see that accurate feedback is the only way to get there.

Wow, your boss is incredibly wrongheaded here. The purpose of feedback is to talk to people accurately about how they’re doing and where they could do better. What he’s suggesting is a horrible disservice to employees, because it would deny them the benefit of actually knowing where they stand — and potentially sets them up to be blindsided by the consequences (which could be anything from what kind of raise they receive to whether you have to let someone go at some point). It’s also a horrible disservice to the organization, because it means that people aren’t being set up to succeed in their roles (which requires being aligned with you about how they’re doing and where they could do better) and people will get worse results because of it. It’s also potentially laying the groundwork for legal hassles later — if someone is led to believe that they’re doing a great job when they aren’t and then ends up being fired or denied a promotion or given a lower raise than their peers, and decides that reason is a discriminatory one (i.e., based on their race, sex, religion, or other protected class), you’re going to have a hell of a time defending yourself against a discrimination lawsuit if you have written documentation saying their performance is awesome.

You should point all of this out to your boss. You should also point out that the way you “keep people happy” isn’t by blowing smoke up their asses — it’s by treating them well and, among other things, being honest and up-front about problems and areas for improvement. You also don’t treat people well by ensuring that lower-performing coworkers don’t get feedback about the problems; in fact, most high performers will tell you that that will quickly demoralize and frustrate them, if not drive them out of the organization.

But I don’t have high hopes here. Your boss’s thinking is so disordered on such a major piece of managing well that it’s hard to see his leadership of the organization going well in the long-term.

2. Should I ask for a lower salary?

I’ve spent my career at small companies, knowing I make less money there than in “corporate America.” I have enjoyed the intimacy and the variety in the work I do. Even with a smaller salary, I’ve always been comfortable in my life and am not greedy. When I was hired, my boss agreed to my salary expectations. But from then on, she frequently let me know that I made more money than other people in my department. As such, I did not ever ask for a raise and made sure to never complain about my salary, even though I heard gripes from my colleagues regarding discontent with theirs.

Fast forward six years, I was laid off. I feel the salary issue may have been one of the causes on why I was one of the first to go.

I was recently offered a job where I asked them to match my ending salary. To my dismay, they made a higher offer – so much higher that I am uncomfortable. This is for several reasons. First, should there be a layoff I don’t want to be in that situation as I was before. Second, that prior atmosphere was so demeaning, and I am terrified of experiencing that again. Lastly, I have many years of work left, and would like to stay with a company. I don’t want to max out (even with annual adjustments). Are you allowed to negotiate down?

Accept the salary they offered you. If it was higher than they were comfortable paying, or if it was outside their typical salary structure, they wouldn’t have proactively offered it you; they would have simply matched your last salary, as you asked them to do. They offered you a higher one because they want you fit appropriately within their existing salary structure and don’t want to pay you less than others at your level (which is smart, both in order to retain you long-term and because otherwise they risk opening themselves to later perceptions of paying less because of your race, sex, religion, or other protected class).

Don’t be haunted by one bad experience. This company is making you an offer in good faith; there’s no reason to ask for less (and doing so would come off pretty strangely).

Read an update to this letter here.

3. Should I limit the use of “I” in cover letters?

I have seen a bunch of articles cautioning the job-seeker to limit the use of “I”, “me”, “my” in cover letters, but I’m having trouble rephrasing my sentences without falling into the trap of sounding like an informercial. I was wondering what your take was on this. Any suggestions?

That’s terrible advice and makes no sense. The whole point of a cover letter is to talk about why you’d excel at the job. There’s no way to do that if you’re avoiding talking about yourself.

4. My boss brought up my absences in every performance review category

When I received my performance review, my boss was bringing up just one thing over and over and over: missing too many days.

Team player – bad because I was not there enough. Customer service – great with people but she misses too much work. Knowledge of job – Has knowledge of job but she misses too much work.

Can he do that? It seems that he should bring it up under one category.

Legally? Sure (assuming that you weren’t missing all those days due to FMLA or another legally protected form of leave). Should he, from a management perspective? It depends. It’s certainly possible that if your absences are really numerous, they’d truly be part of any reasonable person’s assessment of your performance in these areas. Or, if you didn’t really miss that much work, it’s possible that your boss is being a little obnoxious. Regardless, though, it doesn’t really matter: The message for you that’s coming through loud and clear is that your boss has serious concerns about your attendance and wants you to make pretty significant changes there.

5. Can employees refuse to go home when it’s slow?

I work in an emergency and specialty animal hospital in Connecticut. If I send non-salary employees home because it is slow, can they refuse because they want to “make their hours”?

Nope. That said, if you’re finding you often have to send people home because it’s slow, it’s worth reexamining how you’re scheduling people. If it happens regularly, you’ll start losing good people who will be rightly annoyed.

I was hired to run a department — but the old boss is still there, 10 months later

A reader writes:

I took a job under perhaps unusual circumstances and was hoping for a little insight on how to move forward.

I was recruited by a company, in a situation where the director of teapots was looking for a new job and wanted to have someone in place to take over his role once he left. The Big Bosses were fine with this and appreciated his advance notice and planning (the director had been there several years in this high-profile role, so they understood why he wanted a change).

The director created a new assistant director of teapots position for me and brought me on with a sense of urgency, indicating that he’d probably be gone in the next few weeks and wanted to make sure he had time to train me. He said he was interviewing other places and had things “in place” to be leaving shortly. He pushed HR to fast-track my materials so I could start ASAP. The assistant director role was a lateral move for me, and I only agreed to it because he would be leaving so soon, and I’d soon get a promotion into his Director role (this was all discussed in advance — this isn’t speculation on my part).

Fast forward 10 months, and the director still hasn’t left yet. I realize that there was no guarantee that he’d ever actually leave, even though that’s the express purpose that he brought me on board. But, I never wanted to work for him or in this particular role (i.e. a #2 instead of a #1), and I can’t shake the general annoyance I have every day that he’s still here. We have very different working styles and are driving each other nuts, so that’s adding to my annoyance. We work extremely closely, as our job duties are identical – he just made up the assistant role as an excuse to bring me on board.

Now that I’m approaching my 1-year mark with the company, do I bring this up with him somehow? As in, asking whether he’s still job searching and planning on leaving soon? Perhaps in my annual review? Do I just try and find a new job? Or do I stick it out silently as to not make things awkward between us? I’m frustrated and want to leave (this isn’t what I signed up for!), but I’m not sure if I’m being too impatient.

You absolutely should address this. You were brought on board under one set of assumptions, and those assumptions proved wrong quite a few months ago. There’s no need to wait for a formal review to have this conversation; it’s one that probably should have happened eight months ago, so don’t delay it any further.

As for awkwardness, yeah, it might be awkward. It’s an awkward situation. That’s no reason not to discuss it, though. And you can minimize some of the awkwardness by framing it not as “hey, when you are going to leave?” but rather as “I’m trying to figure out what makes sense for me” (which is indisputably your purview).

I’d say something like this: “I’d like to talk to you about what the future for my role looks like. When I originally came on board, you were planning to leave fairly soon, and I took the assistant director position on the understanding that it would soon be transitioning to the director role. Since our plans have ended up changing, I’m trying to figure out what makes sense for me. I wouldn’t have accepted a #2 position if I’d realized it was going to be long-term. I realize that plans are never written in stone, though, and I’m trying to figure out what makes sense for me now. I’d love to hear your thoughts.”

Before you have this conversation, though, you need to figure out how you’ll respond if his answer is, “Yeah, I changed my mind. I’m not going anywhere.” That seems like a pretty likely outcome, given that his actions are already basically communicating that, so you want to figure out how to respond to that ahead of time.

In addition to that, you should figure out what you’d want to do if you were told that the director is never leaving and plans to stay in the role for many more decades. Would you stay and be reasonably happy in your current role? Or would you start actively looking to move on? Regardless of what your director says when you talk to him, it might make sense to move forward with those plans — because at this point, any promises from him to move on aren’t credible enough to stake your own career planning on, short of “I formally resigned yesterday and my last day is Friday.”

Read updates to this letter here and here.