When it’s OK to tell your boss you’re looking for a new job

It may seem counterintuitive, but you don’t always have to sneak around when you’re job searching.
A full-force job search requires time, effort and a considerable amount of maneuvering when you currently work full time.

You may have to take a sick day, or a phone call during lunch. You may even have to get crafty to account for your sudden absenteeism at your current job. Then, there’s the interview suit situation: Next you’re finding yourself changing in your car or a gas station to return to the office in casual mode.

There is another option you probably haven’t considered: Tell your boss.

Believe it or not, there are a slim few instances where it actually makes sense to tell your boss you’re looking for a new opportunity. They are as follows:

You’re being laid off or your contract is expiring
If your boss has been transparent and informed you within a few months your position is being offshored or downsized, feel free to be open in return.

You can say something like, “Since it doesn’t sound like I have a future here, I’m going to start looking externally and actively interviewing. May I include you as a reference?” In many instances, your boss will unequivocally say yes and offer to help you.

You could even take this one step further. Ask your boss to tap into his or her network for help. Say something like, “I don’t want this to sound awkward since I still work here, but I need to land a new job really soon. Is there anyone perhaps in your network and our industry whom I can reach out to for a conversation?”

Feel free to be specific in your requests. “I’m looking to get my foot in the door at this specific company. Do you happen to know anyone who works there?” you might ask.

You may begin to feel ambivalent about your job and current place of employment. And that is your right. On one hand, your work performance doesn't really matter as much as it once did—(You’re probably thinking: “What are they going to do, fire me?”)

So, if those three-hour networking lunches look like they will pay off more than sitting in front of your computer cranking out weekly spreadsheets will, go for them. But bear in mind you do want to get a decent referral and you don’t want to make enemies out of your managers who still need your help, so don’t stray too far from your current responsibilities.

Your job is a dead end
Say you have an honest discussion during a performance review or separate meeting with your boss in which you learn that it would be impossible for you to be promoted. Whether due to faltering revenues or a pending merger, sometimes it’s just out of your hands.

Instead of making your boss or the flat organization part of the problem, make them part of the solution. Ask your manager to see the situation from your perspective. Say something like, “Since it looks like the writing is on the wall, if you were in my shoes knowing my fate here, what would your next course of action be? Should I immediately start pounding the pavement—is that what you would do right now?” While it may temporarily feel like you’re putting management in an awkward position, you’re enlisting their guidance to lead, encourage and support you.

Their answer will likely sound something along the lines of, “Yes, in this situation—and you didn’t hear this from me—you may want to start looking externally.” This is a permission slip that grants you the go-ahead to look with their blessing.

Even if you knew the answer before you asked it out loud, this open dialogue can serve as a catalyst to looking elsewhere guilt-free. You can follow up by saying, “OK, so it sounds like I really have no choice but to look externally. I really enjoy working here but I need to advance my career. Instead of sneaking around, I just want to be up front about it. Would you mind being my reference?”

In either of the above instances, I encourage you to have these open conversations, but you’ll have to do so at your own risk. In an ideal world, your boss and colleagues will be on board and supportive of your need to move on, but everyone’s situation and workplace culture is different. Assess your own situation to see when it makes sense to be forthcoming about your plans, and how best to enlist your superior and colleagues’ help in the process.

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