if you're unhappy with a change at work, should you bring it up before you start job-searching?

A reader writes:

My fiance, Jim, works at a successful but relatively small nonprofit. He’s the head of his department of one, and is the only person who’s ever been in his role; he was hired to start the department about two years ago and by all accounts has been very successful.

About four months ago, there was an internal restructuring, and he ended up with a new boss who’s now making changes. Jim was fully remote until two months ago, when he started having to go in three days a week, which was a bit disappointing but overall fine. However, now they want to change his hours. His hours are 9-5, but he’s a morning person and on the days he works from home, he often starts work at 7 am or 8 am because it’s when he works best and he prefers to have more free time later. He does have to be “on call” functionally until 5 pm when he does that though. Most people at the org work 10 am – 6 pm, and they want him to change to match. He hates this idea. He said it might be workable on WFH days, but he’s in the office more than half the week and he’ll be miserable getting home from work at 7 pm. The day he found out about the change, he started putting together his resume and putting feelers out in his network to find out about other openings.

My question is: if you feel that strongly about a change, is it worth it to bring it up before you leave to see if they’re willing to be flexible? I know there’s risk involved with that, so I guess I’m asking how you weigh risk vs reward here.

Yeah, if you otherwise like the job and something changes that makes you want to leave, it often makes sense to bring it up and see if it’s fixable before you quit over it.

That doesn’t usually mean saying outright, “I am going to quit if this doesn’t change.” Sometimes it might, which I’ll get to in a minute, but usually you’re better served by something like:

“I appreciate the reasons you’re asking me to sync my hours with everyone else’s, but I work a lot better starting earlier in the day. Is there any room for flexibility on this?”

“X is really important to me — it’s one of the reasons I took the job initially and have happily stayed here as long as I have. Would you be open to trying __ instead?” (In some cases you could propose trying your suggestion just for a few months and seeing how it goes.)

When you say something is really important to you, the subtext is already there that you might end up leaving if you don’t get it, so you don’t usually need to spell it out. But in a small number of cases, it can make sense to anyway — usually when you think that clearly stating that could change the outcome and you’re confident you can safely say it without retribution. That last part is really key, because some managers will react really badly to anything that feels like forcing their hand, and you don’t want to get pushed out earlier than you would have left on your own or sour the relationship with your boss for whatever time you remain. But there are some situations where you can safely say, “I want to be up-front that this is important enough to me that I’d likely move on if we can’t do it.”

To be clear, none of this means you’re obligated to talk to your boss if you’re unhappy enough with a change to leave over it. You’re allowed to decide that you don’t feel like expending the effort or the capital. But in a job you otherwise like, it often makes sense to try.