Should You Tell Your Boss You’re Looking for a New Job?

There’s nothing like secretly job hunting to make you feel like a total secret agent. You keep a change of clothes in your car so you don’t need to wear a conspicuously “interview-approved” outfit into the office. You schedule phone interviews over your lunch break. And, you’re smart enough to never use company time or internet to search for new gigs.

But, if you’re one of those people with an obnoxiously loud conscience, job hunting when you’re already employed can begin to eat away at you. You feel sneaky, manipulative, and conniving—even if that isn’t at all true. And, you’re constantly stifling the urge to fling open your boss’ office door and yell, “HEY, YOU! Just so you know, I’m looking for another job!”

Hey, sometimes that upfront honesty is recommended. And, in other cases? Well, you’re going to deal with a lot of fallout. Whether or not you explain to your supervisor that your job hunting is really an individual decision that depends on your specific situation.

But, if you’re currently wrestling with whether you should spill the beans or not, there are a few things you should evaluate to help you make the decision.

1. What’s your relationship like?

Superior and subordinate relationships are really an individualized thing. Some people enjoy particularly close relationships with their bosses—they go to happy hours together, gab about each other’s families, and are even Facebook friends. Others? Their bond with their supervisors remain strictly professional. They talk only about work—aside from that occasional polite conversation about the weather while in line at the coffee maker.

Needless to say, your relationship with your boss will have a large impact on whether or not you feel inclined to tell him or her about your current search. Do you consider your manager part boss/part friend who you want to share your thoughts and large life events with? Or, is your relationship more distant and cold? If that’s the case, the news of your job hunt might not only be ill-received—but totally out of leftfield. Your boss will likely be left wondering why you even felt the need to spell that out for him or her.

2. What’s your company culture like?

Do you work in a small, tight knit, family-like office that people rarely leave? Does everybody operate with the understanding that you’re all “lifers” at that company? Or, is turnover actually pretty common in your organization?

Take some time to think about your company culture. If your boss isn’t used to people frequently moving on to bigger and better things, he or she might take your job search as a personal attack or criticism.

But, if your organization sees people come and go frequently, the fact that you’re searching likely won’t be a surprise. In fact, your boss very well might wish you luck and offer up a recommendation if you need one.

3. How has your boss reacted to previous employees leaving?

If you’ve experienced previous employees jumping ship from your team or department, how did your boss react to those departures? Did he roll his eyes, mutter under his breath, and then proceed to gossip and complain about that employee once he or she was out of earshot? Or, did he shake that worker’s hand, wish her well, and let her know how much she’ll be missed?

Past behaviors are usually pretty good indicators of what you can expect in the future. So, if your boss threw an all out tantrum the last time an employee decided to go a different direction, looping him or her in on your job search likely isn’t the best idea.

4. What’s the potential fallout?

When considering all of these things, you should also take some time to think about the potential fallout of letting your boss know about the fact that you’re searching for a new gig. Would he or she take it personally, and only serve to make things more difficult for you? Would your supervisor be so offended that she begins freezing you out—making team meetings, projects, and your job duties that much more uncomfortable and complicated?

Of course, you also need to think about the potential implications of not being upfront and honest with your manager. Is it becoming overwhelmingly difficult to keep your search a secret? Would you rather have your boss hear the news directly from you—rather than through the grapevine? Your mom was right. Sometimes honesty really is the best policy.

Needless to say, weighing all possible outcomes is important when deciding whether you should share the news or keep your lips sealed.

5. How do you feel?

As selfish as it may sound, you need to look out for yourself. After all, if you don’t do it nobody else really will. So, think about how exactly you feel about sharing that news or not. Chances are, you already have a gut feeling about what you want to do.

If you don’t think it’s necessary to update your manager, and it would only end up causing more issues for you, then your decision is made. But, if you feel like you’re distractedly walking on eggshells in the office and constantly trying to weave together elaborate lies about why you took such a long lunch, you might be better off being upfront and honest. At least you can go into work everyday knowing that everybody is on the same page about where you currently stand. Plus, you’ll avoid having your stomach leap into your throat every time your cell phone rings while you’re at work.

Deciding whether or not you should tell your boss that you’re looking for a new job is really a personal one. But, you should still make an effort to make the most well informed and logical decision that you can.

So, ask yourself these questions first in order to analyze your circumstances and decide whether or not you should let the cat out of the bag. Hey, if nothing else, you can rest assured that you’re refining your secret agent skills. If that’s a requirement for your next gig, you’ll be well prepared.