Departing Employees: Regret, Learn and Be Better

By on September 25, 2019

For better or worse, I don’t think there are many jobs in the corporate world where you come in, do your work and go home. I guess that says a lot about our culture and our attitude toward work, but if there’s an upside, it’s because of the emotional effort, engagement and investment that’s required, you end up forging deep relationships with the people you work with. I always bristle at the “work family” analogy, but I don’t think it’s hyperbole to say that some of the most important relationships we have in our lives are with our co-workers.

Of course, the downside is that when people leave, it hurts — it really hurts. You’re left not just with a loss of talent and brainpower, but the powerful relationship you’ve built with that person. It’s part of the work game, and while we all know that it’s going to happen and happen more often than we’d like, it sure doesn’t make it any easier when the day comes.

I’ve recently begun a management thought experiment that I’d like to share with you. Full disclosure: I’m not sure how practical it is as a business model, because it involves a good amount of second-guessing (and what’s more annoying than a Monday morning quarterback?) and (I am embarrassed to admit) a bit of magical thinking. Stay with me, and see if you find this exercise useful when a good employee leaves.


Part One

Think about the last ten key employees that have left, and what it would have taken to keep them at your organization. We’re going to put them into two groups. Obviously, sometimes when an employee leaves there really isn’t anything (within reason) you could have done: perhaps they wanted a career change, wanted to relocate where you don’t have an office, needed a fresh start, etc. When that’s the case, it stinks, but you can’t do much more than wish the person well and hope they will consider coming back if their circumstances change. This is our first group.

Pro Tip: If the “thing” that would have kept them at your company is more than 2-3 items, they probably belong in the first group.


Part Two

Now for our second group – and here comes the magical thinking part. If you could do the one or two things today that would have kept that employee, would you do it? Would you give them that raise/promotion? Send them to that conference? Move them into the role they expressed interest in? Make them feel more supported and connected? Again, sometimes the answer is no. Other times —and I would argue it’s most of the time for key employees —you’d do it in a heartbeat.

Okay, I know what you’re thinking. Sure, it’s easy to say that once they leave, hindsight is 20/20, etc. But is it really hindsight? Be honest: Did you really not know what would have kept the employee? If you say no, well, first of all, I don’t really believe you, and secondly, if you didn’t know what this key employee wanted, isn’t that kind of your fault too?


How are you doing?

So how does this exercise map out over the ten employees you picked? If you find that most times they fall into the first group and you couldn’t/wouldn’t do the thing needed to keep them, good for you and sleep well tonight.

If however, key people have left and you consistently find yourself wishing you had done what it takes to have kept them … well, like a lot of us, you’re screwing up my friend. And unfortunately, you’re in good company these days. The reason I wrote this blog is that I believe most managers can do better by their key employees by having those important (sometimes uncomfortable) conversations, being more proactive and spending more time on their employees. Spend time helping employees map out their career journey, developing a learning and development roadmap and getting them involved with new employees and/or mentors. I know I can do better. I bet you can too.

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