Preparing to Tell Your Boss “I Quit”

Telling your boss that you’re leaving is one of the hardest workplace conversations you can have, and it’s difficult to predict how they’ll respond in the moment. The authors outline five possible reactions and how to respond in each case: if your boss gets angry, if they badmouth your new opportunity, if they make a threat, if they try to guilt trip you, or if they counteroffer. By reviewing these scenarios and strategizing in advance, you can greatly increase the likelihood that you’ll be able to handle their reaction — whatever it may be — with thoughtfulness and grace.

Like many professionals these days, you might be planning to leave your company. One recent study reveals a full 44% of workers are looking for a new job. Making the decision to quit is challenging — but what often feels even harder is actually telling your boss. What should you say when you’re sitting there face to face with them, whether it’s over Zoom or in person?

Leaving a job is a fundamentally awkward circumstance. After all, your decision upsets the status quo and workload for everyone. Ideally, we’d like to hear our manager respond to our departure with unconditional support and say something like: “I’m so happy for you. This is a great next step for you — of course I understand.”

But people are human, and that doesn’t always happen. Many employees, even if they know quitting is the right thing to do, feel trepidation around telling their boss — and especially how to handle it if they respond in a negative way.

In our work as executive coaches, we’ve seen five common emotionally loaded reactions that managers may have when an employee announces that they’re leaving. Hopefully your boss will respond in a supportive and encouraging way. But to prepare yourself just in case, here’s what you can say to your boss in each circumstance to help ensure you don’t leave on a bad note.

If they get angry.

Depending on their emotional state at the time of your conversation, your manager may become immediately upset, or even furious that you are resigning. They may feel a sense of betrayal, as well as anxiety about how they will manage the workload without you. Those who don’t know how to manage their temper may feel triggered by your news and lash out at you. “I can’t believe you’re doing this after how I’ve supported you!” they might say.

Oftentimes, this is a temporary stress reaction, and with a little time, they’ll cool down. You want to be gracious and give them space to process the new development and reassure them that you aren’t leaving them in the lurch. “I know this is a surprise,” you could say. “I want you to know how grateful I am for your support and encouragement. The new position was an opportunity I felt I couldn’t pass up, but I want you to know I intend to do everything in my power to make this transition as seamless as possible.”

If they badmouth other opportunities/criticize your aspirations.

A boss who feels insecure may offer unsolicited criticism of your future plans. We’ve seen examples of managers choosing to dampen their employee’s excitement about their next chapter by disparaging their future employer in the guise of “coaching.” One of our clients was told by her boss that moving to a (much better known) company was a huge mistake because “no one likes working there” and “its brand has really declined.”

If you find yourself in this situation, don’t try to argue with them. Instead, try to change the conversation to get this off this tack. “I really appreciate your concern,” you could say. “I’ve decided this is the best course for me, and I feel good about that decision, but thank you.”

If they make threats.

Another reaction that your boss may have is to intimidate you as a way of making you second-guess your resignation. One of us had an executive coaching client whose boss, upon receiving her resignation, threatened her by reminding her about her weaknesses and saying, “I don’t know if I feel comfortable recommending you to anyone I know in the future.”

Your resignation conversation isn’t the time to debate past performance reviews or to try to change someone’s mind about you. If someone threatens you, they’ve actually done you a favor by letting you know that they are not an ally. “I hear you loud and clear,” you could say. “Thank you for letting me know.” And then get out of there quickly.

If they try to shame or guilt trip you.

One of the hardest maneuvers to resist is when your manager makes you feel guilty about your decision. One of our coaching clients, upon his resignation, was told by his manager, “Do you know how many times I protected you?” She went on to enumerate the lengths to which she’d gone to shield him from the organizational peril. Especially if you have a close relationship to your manager, you may already be feeling bad — so hearing guilt-inducing stories from them may drive the dagger in further. “I know how much you’ve supported me,” you could say. “I truly appreciate everything you’ve done for me. It wasn’t an easy decision to reach, but I truly feel it’s the right time for me to move on and I’ll always be grateful for our work together.”

If they counteroffer.

Finally, it’s not uncommon for managers to ask you, what will it take for you to stay? Or, what if I can match what they are offering you and increase it? Of course, this isn’t a negative reaction — it’s actually a very positive testament to your role in the organization. But it can feel discomfiting nonetheless if you’re not prepared to respond.

It’s important for you — before you have your resignation conversation — to think through how you’ll respond. Are you a definite no, and “all in” on your next chapter? Or if your existing company can better your circumstances, financial or otherwise, would you reconsider?

If the former, you could say, “I truly appreciate you asking. I’ve really thought this through and feel confident that moving on is the right step for me, but I’m flattered you asked.” If the latter, you could say, “I didn’t come into this conversation looking to leverage an offer. It’s my intention to accept the new position. But it’s true — I do love working here, and if it really were possible to match what they’re offering, I’d love to stay.”

Telling your boss that you’re leaving is one of the hardest workplace conversations we can have, and it’s difficult to predict how they’ll respond in the moment. But by reviewing these scenarios and strategizing in advance, you can greatly increase the likelihood that you’ll be able to handle their reaction — whatever it may be — with thoughtfulness and grace.

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