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‘My Boss Wants to Know Way Too Much About My Job Search’

Photo: The Cut

Dear Boss,

I’ve been working as an assistant/coordinator at a small company (about four people) for a little over a year now. I like it fine and my boss values me, but I feel like it’s time for me to move on. There’s not a ton of work to do, especially when splitting it with the more junior assistant, and I find myself exceedingly bored throughout the day. I’m early in my career and I’d like to take my next step to a bigger company with more name recognition and opportunities for advancement. I’d also like to work in an office with more people around.

When I first expressed the feeling that it was time to move on (about eight months in), my boss promoted me to coordinator, increased my salary to a just-tolerable wage (assistants and coordinators in my industry are notoriously and grossly underpaid), and promised to introduce me to other higher-up executives. I accepted under the condition that I would only suspend my search long enough to hire and train the new office assistant. One of my stipulations was that I had to be able to tell my boss when I was going on interviews; I had a couple last year but felt strange about lying, and there are only so many doctor’s appointments I can have before things start to look suspicious. 

Recently I started applying for jobs again like I told him I would, but I’ve run into an unanticipated problem: having to tell my boss exactly where I’m interviewing when I notify him that I’ll be out of the office. When I reluctantly tell him, especially when the places are in the same industry, we end up in an interminable round of him trying to convince me to stay while I nod politely and wait for the first opportunity to back out of the room.

It’s yet another issue with working in such a small place: He’s the king of our little four-person castle, and there’s no HR department I can turn to. He’s an older, wealthier (white) man set in his ways, and having built this company from the ground up, he’s used to getting what he wants. He’s also the one who personally signs my checks every week, and I need to stay in his good graces while I keep looking. 

I have an important interview coming up at one of these larger companies. When I tell him, I know he’s going to be upset, because if I’m going to stay in the same industry, why not just stay here? What he’ll hear is that the business he’s built isn’t good enough for me. Which, honestly, is somewhat true — I just don’t know how to say it. How can I phrase it so that it doesn’t come out like an insult to him? Or better yet, what’s a tactful way to ask him not to ask in the first place?

Very small businesses like this one are often run as their own little fiefdoms, rife with norms and practices that wouldn’t fly in other workplaces. That can be tricky even for experienced professionals, but it can be especially dangerous for people early in their careers, when you don’t always have the frame of reference to recognize when something is weird.

I say that because what your boss has asked of you, and what you’ve agreed to, isn’t how this typically works.

Usually when people are job searching, they’re pretty discreet about it. Most of the time, people don’t inform their employer, because there can be serious consequences: You can get pushed out of your job earlier than you want to leave (either because your manager sees you as disloyal — which is ridiculous and yet a thing that happens — or because your employer pushes you to set an end date for their convenience rather than for yours); or you can end up on the top of the list if your company needs to do layoffs because “you were leaving anyway.” Less-dire consequences, like getting shut out of important projects because people assume you might be gone before the work is finished, might still be something you want to avoid.

Because of all that, people don’t often let their managers know when they’ve decided to interview for other jobs. There are exceptions to that, of course. Some managers make it safe to confide in them when you’re ready to move on by demonstrating that they won’t react poorly, push you out, or pry into your plans in ways that would be unwelcome. And some jobs are clearly designed to be shorter term, and it’s openly acknowledged that you should be looking after X amount of time. But generally speaking, the convention is that your job search isn’t your employer’s business and you’re not obligated to announce you’re looking or share details when you do.

Your boss seems to have somehow missed this message. And I’m worried that he’s making you think he’s entitled to pry into your job search in the way he’s been doing.

Now, to be fair, it sounds like you might have initiated this conversation when you told him you were ready to move on last year. And you asked to be open about going on interviews so you wouldn’t have to lie. But that seems to have opened the door to him involving himself in your search in a way that’s not reasonable.

He’s not entitled to know where you’re interviewing. And he’s not entitled to insist on the chance to try to convince you each time that his company is a better spot for you.

If we had a time machine, I’d tell you to go back and be more close-lipped from the beginning. He didn’t need to know you were job searching at all! And he definitely doesn’t need to know each time you’re leaving for an interview.

I get that you felt awkward about lying, and in some ways it’s easier to be able to explain that you’re out of the office for an interview. Except that he’s shown you that it’s not easier, because he’s going to subject you to an interrogation each time you tell him.

So I’d revert to what most people do when they’ll be away for an interview — say you have “an appointment” and if he presses for details, it’s “something personal I have to take care of.” Or try to schedule interviews for early in the morning before work, late in the day afterward, or during a long lunch. But if your employer makes it impossible for you to be vague, they’re pretty much forcing you to use a cover story, and in that case, some people find it useful to say they’re having dental work done, since that can take a series of visits.

When you stop telling him about each interview you’re going on, hopefully you’ll eliminate — or at least cut way down on — the cross-examinations.

If it comes up again anyway, and/or he starts pushing you to stay in your current job, you can say, “I really appreciate that you value me, thank you! I’m sure I’ll move on eventually, but you’ll be the first to know at whatever point that day comes.”

And if he pushes you to justify why you’d want to leave for a larger company … don’t engage. It sounds like he hasn’t been willing to accept your very good reasons for this desire in the past, and there’s no sense in continuing to go round and round with him about it.

If you absolutely must respond — and since you’re concerned about placating him — there’s nothing wrong with saying, “Your input is really valuable to me and I appreciate hearing it, thank you.” That doesn’t say you agree with him or you’ll do what he wants; you’re just being diplomatic in a situation where the dude who signs your paychecks is being overbearing about something that’s none of his business.

And again: None of this is normal! In future jobs, default to keeping any job searching confidential, unless your manager has a clear track record of handling that kind of information well (and maybe even still then; it’s just safer).

Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email Her advice column appears here every Tuesday.

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