We’re all going to leave our job for one reason or another, and thinking through that eventuality is a valuable process. As a manager, it’s important that you know your reports’ perspectives on their eventual exit plans.

Why talking about exit plans is important 

If you don’t know the reasons someone might leave your team, every departure is going to come as a surprise. On top of that, it’s much harder to mitigate the reasons a person might leave if you never know what they are. You could find yourself optimizing for salary growth when what they want is new experiences (or vice versa). Having these conversations openly gives people on both sides the opportunity to effectively plan for the future.

How to discuss exit plans as a manager

Entering this conversation with a report, you must set a foundation of trust to help enable meaningful discourse. Even if your relationship with your team is already trusting, you still likely need to ease into the conversation. 

For me, that’s often meant taking the time to bring up the topic in advance. Set a meeting with your report and, roughly one week ahead of it, raise that you would like to discuss potential reasons that they might leave the company in the future. Acknowledge that this conversation could be daunting and that it's okay if they don't currently know what their exit plan is. Regardless, it’s important to have the discussion anyway. There is potential for this conversation to be unnerving even with preparation, so you need to be ready to calm some fears.

Once you sit down for the talk, start broadly. I like to ask, “What’s your exit plan?” Every person is going to take this conversation in a slightly different direction, and keeping the initial question as broad as possible allows them to chart the path. In turn, you can respond and follow along. But not everyone is going to seize that opportunity on their own.

For those folks that find it a little more difficult, you’ll need to figure out how to get them to open up. You can go about it two ways, depending on the person. The first is by flipping the script and talking about your own previous exit plans, and the second is by asking narrower and narrower questions until there’s something they latch onto.

If I decide to go with the first option, I normally try to pull examples from my past. Anything tied into the current era might make them nervous that I’m thinking about leaving. If you don’t have examples to pull from your history, then you might need to refer to more present circumstances, but just be cautious that in doing so you don’t disturb the foundation of your relationship with your report.

For the second option, I start throwing out different scenarios. Figuring out what technologies your report would like to work with, their salary goals, or even if there’s a dream company they would like to work for can inform your future decisions as their manager.

Knowing these interests allows you to get a bigger picture as to why they might consider leaving, or, if you would like to retain them for as long as possible, how you might be able to “sweeten” their deal to get them to stay. Once the conversation is underway, it also gives you more threads to pull on to help them think through their exit plans.

In rare cases, you’ll get someone who absolutely refuses to engage with the question. In these scenarios avoid trying to browbeat someone into a discussion, as that will end poorly for everyone. Here, my goal becomes understanding why they won’t engage with the topic, and then trying to address those concerns head-on. There’s no exact formula for this, but I usually acknowledge that I won’t bring it up again unless they want to talk about it. I also add that I hope to get to a place where they’re comfortable discussing the topic.

As managers, it’s important that these conversations reflect a culture that supports people and promotes transparency. However, even in the perfect setting, not everyone will open up. If someone is choosing to keep details private, that’s their right. But if they keep quiet because they don’t trust me or the overall environment, then we have a problem to address.

As the report

If your manager has gone through the steps that I’ve outlined above, then your role is easy: show up and talk through your thoughts. But in my experience, not every manager is going to bring up the topic and that’s where the onus can shift. 

If you’re the one broaching the matter, the most important thing for you to do is to make sure your manager is aware of the context. This normally takes the shape of you saying something like, “This week I’d like to talk a bit about my exit plans. Don’t worry, I’m not looking at leaving any time soon, but I want to make sure we’re on the same page about why I might eventually leave.”

Even with that context, your manager might be scared that you’re already on your way out the door, so you should be prepared to calm some fears. Once you’re past that point, I recommend focusing on your future goals through three specific lenses. 

First, opportunities that you think you can get in your current role. Second, opportunities you think you can get in your current company. And third, opportunities you’ll need to go elsewhere to get. Discussing what you believe your options are may lead you to learn that you were underestimating what’s available to you – or perhaps overestimating. The important thing is that you have a starting point for the conversation. 

Once you and your manager have settled on the picture of what’s available and what isn’t, you can use that to talk through which of those gaps you can accept and which of them will spur you to start looking elsewhere. But it’s important to know that this isn’t a one-time conversation. If the expected opportunities aren’t appearing, then maybe you and your manager need to revisit things down the line. 

On the other hand, an opportunity may crop up in a place that neither of you expected. All of a sudden the thing that you thought you’d need to leave the company to get becomes available within the same org (or even team). Or, maybe you and your original goals are the ones that change, meaning the reasons for which you thought you would leave no longer hold weight. In any case, this is something that needs to be regularly refreshed and revised, because none of us are static.

Final thoughts 

Even in the best circumstances, conversations about exit plans are hard to have. You’re asking the other person, either your manager or report, to help you think through your career beyond the bounds of your current company. This can be uncomfortable. But if everyone can get past that discomfort, a better environment for the report, and a better experience for the manager can be reached.