Handling Departures

I’m writing a book!

I’ve been working on it for a while now, and I’m over 60,000 words into my first draft. It’s a lot of work, but I hope helpful. A friend of mine told me that if I help even just one person, it’ll have been worth it. I think he’s right. That kind of motivation is really helpful, thanks Casey :)

I’m writing the book I wished I’d had the first time I became CTO. It’s a collection of thoughts, pointers, and ideas; things that have worked for me and things that haven’t. I hope it is, if nothing else, a light in the darkness.

Every work thrives on feedback. To that end, I’m going to share some bits in a pieces here from time to time. I hope you’ll let me know what you think! Please leave a comment below :)

I wanted to start with a section from my notes on Performance Management, Handling Departures.

Handling Departures

Sometimes people leave because they’ve decided to move on and sometimes you’ve made the decision. Either case should be handled with grace and dignity. How someone leaves your company is how they’ll remember you, and how they remember you is how they’ll speak of you. That word of mouth can go a long way in your favor or against it.

If you’ve made the decision that it’s not going to work out, you should act as quickly as you can. If you let things drag on, the employee can usually tell that you or your leadership team have lost faith in them. They become demotivated or even toxic. At worst, I’ve seen employees in this “walking dead” state start to drag others down with them.

Act quickly and give your departing employee a generous severance package. Severance is your way of giving that person respect and time to find their next opportunity. There was a poor fit in some way between that person and your job—it doesn’t mean they’re incompetent or incapable. I’ve seen someone I let go go on to become the CTO of another company and be quite successful. It’s all about the person, the company, and the specific time.

I like to say “this isn’t working out, and I’m going to help you find a place where you’ll be happier.” When there’s a bad fit, the departing person is rarely happy.

When you act with grace and are respectful of the other person it carries weight. If your paths cross again it’s far more likely they’ll remember your time together as a positive experience.

If it’s your employee who has decided to leave, you have the option to try to retain them. If they’re leaving because they can get more compensation, then maybe you were off in some way. Review your compensation theory and change your model if you must, but don’t leave your model—stretching to retain a departing employee can be a vector for inequity. If they’re leaving for a different kind of role or an exciting new mission, there’s often very little you can do to change their mind. In the past I’ve countered employees who had an exciting new offer with a large retention package. While I was sometimes successful in retaining them, it often changed the nature of the relationship and turned them into a mercenary. That can be ok to a point, but mercenaries can be known to cut corners and not care as much about the long-term quality of the work. I’d much rather have a team of missionaries.

No matter why someone leaves, when it’s clear they are going to leave let their Squad know quickly so they can start offboarding. Your organization will have an easier time remodeling itself around the loss when you give a departing employee time to finalize any necessary knowledge transfer. Remain respectful in how you speak about the person who is exiting. Thank them kindly for their service and wish them well in the future. If you speak poorly of them behind their back or later it only makes you look bitter.

Change is inevitable. It’s your job as leader to prepare your organization to handle it.

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