1. My boss said he submitted me for promotion … but maybe didn’t?
I have worked for my company for eight years. Five years ago, I switched to a new department, a great fit for my skills. In those five years, I got great results, stellar feedback, and a performance grade of “above expectations” four times (and “met expectations” once). I’m good at what I do, and everyone I worked with told me they knew I was the go-to person for near-impossible tasks.
A couple of years ago, I was told that my promotion case would be presented to leadership. After the reviews, however, my manager told me all promotions were frozen due to budget cuts. Fair enough, I thought. Next cycle, same. Again and again.
Last week, a new position opened up in a sister function, two grades higher than my current position. So I approached our function head (my boss if I got the position) to ask whether the grade jump would be a concern. I told them the situation about my pending promotion. They replied, “What pending promotion? I never received your promotion case.”
I racked my brain to make sense of this. My manager seemed to have my back. I always trusted her. The only possibilities I could come up with were that either my manager had a personal beef with me, or I was being discriminated against due to my disability. The disability has no impact on my performance, as seen by my performance grades. It just creates schedule issues during flare-ups. I compensate for lost time with flexible hours.
Meantime, the potential future boss was pushing for clarity, so I gave her an account of my promotion saga and the possible reasons I could think of. She’s now all gung-ho to investigate this. To be honest, my chances of getting the new position are low. If the boss launches the investigation, I know nothing will come out of it. Then there will be a whole “going through the motions “ investigation. Disability discrimination is almost never provable since nobody says “well, you’re not promoted because you’re disabled.” They always find an excuse. So now I face the whistleblower issue. Best case, I will be alienated from my manager. Worst case, he will retaliate subtly.
I wish I had never approached the boss mentioning the pending promotion. I need this job. I love this job and the company culture in general. How do I dig myself out of this hole?
You’re assuming a lot here, and then catastrophizing about things that haven’t happened!
The facts we actually know are: your manager told you she was submitting you for promotion repeatedly, and your function head says they never received it and so they’re going to look into what happened. If your manager was lying about it, that’s something your company’s management has good reason to want to look into (which is why your function head was pushing you for more information). Maybe it’ll turn out that this is a miscommunication and your manager did submit your promotion case and the person you were talking to just didn’t know about it (or forgot, or who knows what). Or maybe they’ll find out that he never submitted it, and he’s been blowing smoke up your ass this whole time. That doesn’t mean that one of your two conclusions (discrimination or personal beef) is correct (it’s possible that he didn’t think you really were qualified for promotion but sucks as a manager and didn’t want to tell you that directly) or it could be but regardless of what explains it, there’s a problem of some sort that your company needs to sort out. Either way, you were right to speak up about it.
Let this play out and see what comes of it before you assume you’re in a hole.
If you do end up in a situation where you think your manager is retaliating against you, that’s something you can escalate; retaliating against an employee for raising good-faith concerns about discrimination is illegal (which doesn’t mean it doesn’t happen, but decent companies usually want to shut it down if they know about it).
2. Can you get through to a combative, defensive coworker?
My friend Anne works in a creative environment where she is paired up with a partner (who I’ll call Tracy) and, for the most part, work on projects that require both of their input (think writing and art). They are at the same level and experience and report to different managers.
Tracy has issues with “soft skills.” While technically good at her job, she lacks the ability to get along with others, be collaborative, accept constructive criticism, acknowledge they aren’t always right, etc. She has been spoken to by her manager, but nothing has really changed. The partnership has been together long enough that they are starting to look at being promoted to the next level. However, because Tracy doesn’t play well with others, Anne is concerned about being held back, as it would look odd to promote one half of a partnership to a more senior title, even though they would continue to still be partners. But this does sometimes happen, so there is hope.
What Anne is wondering is, would it be at all productive or worth it to try and talk to Tracy and get her to see the issues? Tracy has mentioned several times that she wants to be promoted and truly does believe she deserves to be and has even made subtle comments that she thinks Anne is the one holding her back. Tracy’s attitude has been noted by numerous people in the company, so Anne isn’t just imagining it. They have a fairly good rapport with each other, but part of that is Anne knows how to pick her fights whereas Tracy thinks every hill is one to die on. Anne would like to try and point out, kindly and respectfully, that they stand a better chance at being promoted if not every meeting with a client was a battle, and yes, sometimes you may not agree with the feedback but you have to suck it up and make the changes. Sometimes you just have to smile and nod. When you show upper management that you can’t handle feedback and sulk and make passive aggressive remarks, you aren’t showing them you are mature or professional enough to be considered a senior team. How do you make somebody see this?
You can’t necessarily make somebody like Tracy see that — but I’m surprised Anne hasn’t already tried talking to her about it, given how closely they have to work together and the fact that Anne’s own ability to progress is tied to Tracy. She can certainly give it a shot now, although the fact that Tracy has implied that Anne is the problem doesn’t bode well, and nor does the fact that she’s already ignored the feedback from people with actual authority over her.
Instead, though, can Anne talk to her manager about being unpartnered from Tracy? Her manager, who sounds well aware of the issues with Tracy, may assume Anne is willing to deal with her since she hasn’t pushed back on it so far. Anne could argue that she’s put in her time working with Tracy and now she’d like to be able to progress in her career at the company without being permanently tethered to her.
3. Approving a partner’s business expenses
I’m relatively early in my career. Over the last few years, I’ve taken on more operations and accounting responsibilities, including reviewing and approving company card expenses. My boss has generally told me to approve meals and entertainment expenses if they appear to be legitimate business expenses.
Our company has an owner and a few partners. One of the partners, who is not my direct boss, has recently started putting a lot more lunches on the company card. As far as I can tell, they’re legitimate lunches with employees, vendors, or business contacts. I don’t have any evidence that anything improper is happening.
The issue is that it’s usually the same group of employees attending these lunches, and I’m never one of them.
I know nobody owes me an invitation to lunch. I know that’s not the standard I should be using when reviewing expenses. But after seeing receipt after receipt come across my desk, I’m finding it harder to tell whether I have a legitimate concern about the frequency of the spending or whether I’m just feeling excluded and noticing it more because of that.
I don’t want to be the person who raises concerns about a partner’s spending because my feelings are hurt. At the same time, I also feel a little uncomfortable being the person responsible for approving expenses from someone who is much more senior than I am, especially when I don’t have a clear idea of where the line is between reasonable and excessive.
How do I figure out whether this is actually a business concern worth discussing with the owner, or whether it’s something I should recognize as personal and let go?
You said, “As far as I can tell, they’re legitimate lunches with employees, vendors, or business contacts” — and that doesn’t change just because you’re never invited! I think what you’re saying is that this partner’s lunches with employees seem to happen a lot more than you see from other partners, and you’re wondering if she’s somehow abusing her expense account, but you’re also wondering if you only think that since you’re never included. But in general, if she’s taking employees to lunch, you should assume it’s a legitimate business use of the card under the guidelines you’ve been given.
That said, you can always ask your boss for clearer guidelines. You could say, “Should I be approving every lunch that involves a partner and employees, or is there a point where I should flag it for you if someone is having a lot of those lunches? And if so, what is that line?”
But there are a lot of situations where a partner might take the same group of employees out to lunch a lot (like that they’re all working on the same project) and it wouldn’t be odd. There are also situations where who gets invited might not be work-related and is more about social favoritism, but the partner would still be given the leeway to decide that on her own.
4. Do cover letters still matter in the age of AI?
I was helping a friend write a cover letter and brought up your advice about sounding conversational and like an actual human, which raised the question: with so many people using AI in their job applications, do you think writing a great cover letter is still worth it? Because a) does anyone read cover letters in the age of AI slop and applications being bombarded with bots / people using AI, and b) it’s easier to get AI to write a tailored, conversational-style cover letter. What do you think?
Good cover letters matter just as much as they ever did — which is to say, a lot in many fields, somewhat in other fields, and not much at all in a small minority of fields, and much more if it happens to be an exceptionally good cover letter and/or if there are things you want to explain about your candidacy that will strength your application and which aren’t evident from your resume alone.
If anything, a really good cover letter might even stand out more now because so many people are using AI to produce slop, and employers are being flooded with crappy applications.