Angela ended the conversation with, “You’re going to write about this, right?” My response: “Well I am now. But I’ll change the names to protect the innocent.”

What were we talking about? Angela had decided it was time to quit her job, and understandably she was nervous about the conversation with her boss. So nervous that she hadn’t slept much the night before, hence the quick coaching session the following morning.

What was making it hard for Angela was this wasn’t the “I quit!” type of situation. Her boss wasn’t being a jerk, the work wasn’t terrible, she loved the company, and she adored her team. She knew, however, that what the company needed and what she had to give weren’t in alignment. It had been that way for a while, and it was time.

We’d talked before about how to approach the conversation. The following is what Angela asked I share with you.

It’s time to be practical, but practical from the other person’s perspective. You’re about to mess with someone’s world, so put yourself in her shoes.

We tend to think (or not sleep) a ton about the emotional reaction of the person we’re breaking up with. How will they react? Will they get mad? No one wants an emotional or angry response. I often find the best thing to do is to pretend you’re the person hearing the news. What questions might they have? What are their next steps going to be? What might worry them?


Frequently you’ll find some of the more common things are the following:

  1. They’re going to have to communicate your departure. Put together a comms plan for employees, management and maybe even customers.
  2. They might be worried about current projects or initiatives. You know how we’re often asked what we’d do with our first 90 days on the job? Flip that around and consider how you’re going to transition things off.
  3. Give them some control. By announcing you’re leaving you’ve basically taken control of the situation. While there are things companies and managers can do to change someone’s mind, usually in this type of situation your mind is pretty much made up. For example, give more than one option as an exit plan. (The two weeks notice standard is just that, it’s not a rule.) I’m a HUGE fan of what I call the “chocolate and vanilla ice cream” approach to providing options. It gives the listener a choice. If they have a choice, they have some control over the outcome. Come up with a couple of options for a smooth transition or how to complete a project. People like to have options, but not too many. If you give them more than two options, then it opens up the discussion to options, four and five and can often make things confusing and halt discussions.

So what about the emotional stuff? What if you’re worried the conversation isn’t going to go well? What if historically the person doesn’t react well when someone leaves?

With everyone I’ve spoken to about leaving, this is the part where everyone gets stuck. We tend to assume the worst is going to happen. Don’t forget that you’ve built a great relationship with this person over the years and who actually cares about you as a person, very much.

Every single one of my clients who followed the strategy and plan above reported back that her boss said something to the effect of: “They were totally awesome. They understood. They were so supportive.”

I think you’d be surprised.

That said, you should never go into an awkward conversation like this without a plan. This plan should have answers to the following questions because they might happen:

They’re mad, so mad that they ask you to leave immediately. Have you gotten everything in order? Nothing is worse (and yes I’ve seen this happen for entirely emotional reasons) than getting frog-marched out of a building with no way to communicate with your co-workers, your customers, or your network. This doesn’t mean you should communicate with them before your supervisor; I’m just saying you should have a backup plan.

They start yelling or some other emotional reaction. You don’t have to take this. You actually shouldn’t. I made my last client memorize the following statement. Memorize it in a calm and gentle tone. “I’m sorry this has upset you so much. I’d like to give you some time to think about this news. Let me remove myself until you’re ready to talk. I’ll be at my desk.” Shouting back is the last thing you want to do. If you’ve taken care of the first situation, you’ll either get a “get out” or a rational person eventually.

The last emotionally charged question you need to be prepared for is the question you’ll receive from more than just your supervisor: “What are you going to do?” Even if your plan is to do NOTHING you need to have an answer that works for you. Remember you don’t have to share ALL the information, and you can (as a wise mentor once told me) answer with, “I’m going to learn how to play tennis.” It’s an answer.

Remember, your last impression is as important as your first impression.

I’m a big fan of exiting gracefully even if the situation might not be that graceful. And yes, this whole “breaking up with a job” thing is often really hard and quite emotional. It’s important to remember that you date a job. An awesome date with lots of amazing memories and lovely friends, a date that might have felt like a marriage once in a while.

So give everyone a break in this process because breakups are hard.

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