When You Should Tell Your Boss That You’re Looking For A Job

Saying you’re considering leaving isn’t the same as admitting you’re unhappy or have already made up your mind to go.

When You Should Tell Your Boss That You’re Looking For A Job
[Photo: via Kaboompics]

“I’ve accepted a position at another company.”


For most people, that’s the first moment their boss learns they’ve been looking for a job. But just because this is how things normally go doesn’t mean it’s the best approach. In many situations, telling your supervisor that you’re job-hunting–rather than trying your utmost to hide it–might actually be the wiser move. Here’s why, and how to have that conversation if you choose to.

Risks And Benefits

As a career coach, I’ve seen plenty of top-performing professionals talk candidly with their bosses about changing jobs and walk away happy. But I encourage others to proceed with caution. Of course, if your boss is less than satisfied with your work or has proved unsupportive of your career goals in the past, it might be best to keep quiet. Doing otherwise could strain your relationship or even cost you your job.

But for those who are fortunate to have an open, supportive relationship with their manager, mentioning that you’re considering new options has its upsides. It can help you identify your greatest strengths as a professional, gain some insight into your future prospects at your current company, and open the door for a great recommendation from your boss.


For starters, saying you’re considering leaving isn’t the same as saying you’re exasperated, unhappy, or have already made up your mind to go. Instead, it gives you the opportunity to have a frank discussion about why you’re looking around. Once your boss has this information, he or she can propose some potential solutions.

Maybe you say, “I no longer feel like I’m learning as much as I can be.” Your boss might respond, “Okay—what if we involved you in some new projects or paid for you to take a couple of courses?”

On a more practical level, many companies still want to call your boss for a reference check. In almost a decade of experience as a hiring manager, I’ve always asked my top candidates to put me in contact with their current boss before I’ve extended an offer of employment. When the phone rings, it’s usually in your best interest that it isn’t a surprise.

Finally, telling your boss about your job hunt can alleviate a lot of stress and logistical acrobatics. Ever been handed a major project while you’re in the middle of negotiating a new offer and wondered how you’re going to pass it off to a coworker? Needed to invent an excuse to duck out in the middle of the day for an interview? These situations are far easier to navigate when your boss knows what’s going on.

What To Consider Before You Clue Your Boss In . . .

Even if you’re convinced of the upsides, you may still have some good reason to think hard about how, when, and even whether to chat with your boss about your next move. Ask yourself these questions before you do:

  • What’s our relationship like? Is there a lot of trust? Is my boss generally supportive of my career goals? How much information do we proactively share with each other?
  • What’s my ultimate objective? Is there anything that would keep me at my current job, and if so, what?
  • What’s the likelihood of my boss finding out I’m job searching, even if I don’t say anything? Is this a small industry? Does my boss know people at any of the companies where I’ll be applying?
  • How committed am I to finding a new job? Will I take any new position, or only the perfect one?

. . . And How To Break The News When You Do

If you’ve pinned all this down and feel ready to have this conversation, set up a meeting with your boss “to discuss my performance and future with the company.”

Once you’re in the room, start with something like, “I’d love to discuss the quality of my work. Can you give me some feedback on my strengths and weaknesses as an employee?”

That feedback will give you a feel for where and under what conditions your boss sees you heading. Assuming that it’s mostly positive, shift to career goals for the near future. You might say something like, “In the next six months, I’d love to take responsibility for [X project]” or “In three years, I’m aiming to be [Y position].”


Then ask, “What opportunities are there within the company for me to add that sort of value?” Always focus on the value to the company you want your work to lead to, not just your goals. In order to keep your boss on your side, try to show how your goals might still align with the company’s (even if, at the moment, you doubt they do in the long run).

Your boss may give you brand-new information that makes staying more appealing, or they might give you an answer you’re not really happy with. If that’s the case, follow up with, “Ideally, I’d like to stay at the company, but I think I owe it to myself to look outside the company, if that’s what I have to do in order to reach my career goals.”

Provide as much specific context as you can. I once put it this way to a boss of mine:

I’ve been in my current management role for over three years now, and I want to make sure I can move into senior management within the next one to two years. It sounds like there may be an opportunity or two on the horizon, but I know that nothing’s guaranteed. I’ve thought about looking outside the company for work, but wanted to have this conversation first.

No matter what, ask for your boss’s support. Say, “I’m committed to doing good work as long as I’m here, but I’m hopeful that you’ll support me, regardless of how the future unfolds. Would you be willing to give me a positive recommendation if another company comes calling?” Then the ball’s in their court.

After It’s All Out On The Table

If your boss ends up convincing you to stay, make sure you’re gracious and humble: “I really appreciate what you’ve done to support my career goals. Thank you, and I’m excited to continue working together.”


And if your boss says good luck and sayonara, try asking what you could’ve done differently to make yourself a more valuable employee. At the very least, that might give you a more thoughtful answer when interviewers ask, “Where do you see yourself improving?” Plus, once you do get a new job, you’ll know what to focus on.

Telling your boss that you’re looking around might sound like a faux pas or seem scary, but it could be the key to finding a job you love—or making the most of the one you already have.

Watch this before you leave your job:

Steve Monte is a career strategy coach who uses time-tested methods to help young professionals get hired, get promoted, and earn more. More information about his work can be found at