Resigning can be tricky, especially if you’re worried about your boss’s reaction. In this episode, I share real-life stories and strategies to help you navigate a potentially awkward conversation.

From internal moves to competitor switches, this episode covers how to prepare for every type of resignation—and what to do if your boss doesn’t play nice.

Episode Transcript


Hello and welcome to the Daring to Succeed Podcast. I’m your host, Julianna Yau Yorgan, and today we’re going to talk about when resignations go wrong.

A few episodes ago, I talked about this from the perspective of leaders who have employees who resign…without much grace.

Today, I’m going to get into the employee side: when your boss or employer doesn’t take YOUR resignation that well.

First, of course, if you’re in the thick of it and things have gone sideways, definitely get yourself a local employment lawyer who can make sure you’re protected.

Luckily, the worst I’ve seen is a coaching client who was accused of sending herself company materials—which she absolutely was not—and had to prove it. Because she was in the right, she had nothing to worry about. She knew she was only sending herself her performance reviews, and no matter how much they went through her emails, they wouldn’t find anything else.

So before we get into the juicy stuff, I’ll assume you’re listening to this because you’re getting ready to quit your current job and are worried things might not go so well.

Maybe you’ve been working on an internal promotion for a while, and finally got a better role somewhere else instead.

Or maybe things have just been tense between you and your boss, and getting a job outside the company was your best way out.

Or maybe things are mostly fine, but you’re going to a competitor and not sure how they’ll take it.

In any case, you’ve been working towards an exit for a while and know that you’re going to need to talk to your boss about quitting…and you’re pretty sure it’s not going to be a great conversation.

Let’s start with an internal move.

At every company I’ve worked with and most clients I’ve coached, your current boss is likely to already know if you’re about to go to another team. This could be a leadership-only practice where they start to plan transitions between managers, and some companies also require that you discuss your candidacy for another role after you get to a certain point in the interview process.

For these situations, there’s limited fallout that can happen. If your boss is terrible, they may not recommend you or push for a looooong transition period, but beyond that there’s not a lot they can do.

I personally was in a situation early in my career where my boss lied to me and said I couldn’t apply for another role—which is pretty extreme. I only found out because I innocently asked my HR rep when I could apply for another role, and she said they had discussed my situation and my boss was told I could apply.

But short of these career-damaging moves, leaving a team for another one could just be super uncomfortable at most.

A good thing to do before you speak with your boss is to get a list of everything you’re working on, which things you’ll be able to finish before you leave, and which things will need a new owner. This way, if things start to get awkward, you can use that list to focus the conversation on transition and making sure your current team and the work that needs to get done is taken care of.

But what if you’re leaving the company altogether?

Being walked out of a company right away is normally unheard of…but, I do still know of people who are being “exited early”—either later that day or week, after the leadership team and HR has had a chance to review the situation.

It used to be that this would only happen if the employee was irate, already had performance problems, or was going to a competitor.

But in the past few years, I’ve seen employers be much more risk adverse and ask the employee to leave before their notice period. I’ve even coached managers who didn’t know how to handle this situation because they advised that their employee was not a risk, but were told to send them on their way early anyway.

So if you’re worried this might happen, like my client, you may consider carefully taking copies of only what is rightfully yours—performance reviews, and honestly not much else. Any actual work that you’ve done for the company belongs to them—whether it’s as simple as a template or as complex as an entire product. Client and even co-worker information is also hands-off territory.

What you may want to do is draft a “farewell” email with your personal contact information that you plan to send after your departure is made “public”. Short of that, most of what I’m seeing now is people connecting with their closer work friends on whatever social platform they use and try to keep in touch that way.

Managing a potential outburst from your boss is a little bit more tricky. If this is something you’re really concerned with, I encourage you to try to resign through a video call (so that you’re not at any physical danger) or in an office or meeting room that others can see into. If this is a serious concern, especially if you worry about your safety, definitely consult with your HR team and/or an employment lawyer to find out what your options are.

At the end of the day, resignations usually are uneventful, and when they go sideways it’s only a bit of pettiness that stings a lot at the time, but will heal over time.

The important thing is to make sure you’re not doing anything that will get you into trouble later, like gossiping, telling people before you tell your boss, or taking anything from the company—even things you did for them during your employment.

You can also keep the conversation short and professional by giving just enough information, and nothing else. Resigning “to pursue another opportunity” is still commonly accepted and most employers aren’t allowed to press for more information than that.

So if you’re on your way to a better job, congratulations, and I hope this episode was helpful. If you’d like a little help with navigating this situation, just reach out to me by email or on LinkedIn.

And remember—it may be a rough departure, but you’ve got better days ahead of you.

Okay, that’s it for now.

I’ll see you next time!  

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