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It may be one of the hardest conversations you’ll have to have with your boss.

Asking for a recommendation can certainly be stressful, awkward, and a bit unpleasant. After all, you never know what your boss’ reaction might be to the news that you’re essentially looking to leave the company. But if you’re in the market for a new job, you’ll inevitably need a referral from your current jefe.

Here’s how to ask your boss for a recommendation.

If you’ve been showing up to work day in and day out and being a model employee, asking for a recommendation will definitely raise eyebrows. Even if you’ve been keeping your job search a secret, asking for a rec is a red flag that you’re on the hunt for a new job. So if you think your job search is still under wraps, think again.

Once you’ve asked for a recommendation, your boss officially knows you’re either interviewing or planning to leave. So plan accordingly.

Asking for a recommendation ahead of time can create confusion and a whole lot of unhappiness at the office. To eliminate any unnecessary stress from the situation, it’s best to wait to approach your current boss until a potential employer specifically asks for a referral from your current employer. That way, you’ll still be able to work pleasantly at your job without your boss feeling like you’re abandoning the team, the company, and most importantly, him.

You also don’t want your boss to start looking for a replacement for you before you’re ready to leave, either.

Even though you supplied a variety of recs and referrals from previous bosses and colleagues, your prospective boss wants something current. There’s no getting around it—you need to ask for a rec from the boss you have now. So take the time to speak earnestly with him or her. Let him know how much you’ve enjoyed working in your current position, but now you’re looking to move on. If possible, point out the aspects of the new position that interest you that you don’t currently have in your job. It will show your boss your decision to leave is to ultimately advance your career (or even to transition to a new career), and not because you dislike your job or him.

Then ask if he can give you a referral you can share with the hiring manager. To sweeten the deal, offer up any potential job-seeking friends who could be a good fit for your job. If you don’t know of any, then tell your boss you’ll give him advanced notice if you do get hired for another position, and that you’ll train your replacement, too. That way, your boss won’t feel like he has to scramble to replace you, and you’ll leave your present position on much better terms without burning any professional bridges.

Your boss may feel a bit blindsided by the news that you’re seeking employment elsewhere. So in order to get a referral that you can really use, submit a document post-meeting highlighting some of the key points of your tenure at the company. After all, you don’t want a generic “She’s a great worker” recommendation. By refreshing your boss’ memory, he’ll (hopefully) appreciate all the time, energy, and effort you’ve put into your work and give you a great recommendation.

And be specific about what you need. Most likely, you’ll need a recommendation on company letterhead, but you may also need a LinkedIn referral, too. So be sure to cover all bases so that you can avoid having to ask for a recommendation twice.