Replacing Your Head of Engineering

I’ve written previously about firing your CTO in a hostile situation and how to survive your CTO leaving. In this post I’d like to talk about the process you as a CEO should go through before deciding to replace your current head of engineering / CTO in the case where it just doesn’t seem to be working like you’d hoped. As with any senior position, replacing the head of engineering can be very disruptive to the organization, so proceed with caution.

There are many paths to get to this decision point, but the most common are:

  • You’ve realized the current person is not a good cultural or personality fit for working with you and the rest of the team.
  • They were a great fit for getting you to where you are now but you’re questioning their ability to lead the way forward
  • You’re not getting what you need from them, despite repeated asks, and you believe it should be different
  • Others on your team have repeatedly expressed frustration in working with this person.

What frequently happens next is that you start the process to look for a replacement without fully understanding why the current situation isn’t working, which has several potential consequences:

  1. It’s possible that a significant part of the problem is you and how you’re relating to this person.
  2. You’re not really sure what you should be looking for that’s different from who you have now, so you might end up with someone as bad or worse.

How do you determine if now is the right time to make the move?

Review Your Hiring Artifacts

If you were responsible for hiring the current CTO, you hopefully used a job description and scorecard as a part of the hiring process. If you did, this is a great time to pull those back out and revisit them. Given what you knew then about the role and what you thought would be important, how did you score them during the hiring process? How would you (and perhaps a few others on your team) score them on that same scorecard today? This helps to answer a few critical questions in a quasi-quantitative way:

  1. How good are you at hiring for this role? Should you have someone else involved the next time around?
  2. What ended up being important that you missed in the process the last time around?
  3. Did you get what you thought you were getting? If not, why not? What did you miss, or what’s changed?

Update Your Job Description and Scorecard

The job has likely changed since you last hired, so now is a great time to update the JD and scorecard for the position. In the event that you have to make the change, you’ll need both of these things anyway, so you may as well do it now.

Next, re-run your evaluation using the updated scorecard for the current CTO. How do they measure up for the role today and over the next few years? Again, to remove your personal bias, it is best to have others do a similar evaluation. If there is a board member who’s close to the situation and your current CTO, ask them to fill it out as well.

Make the Decision

Once you’ve done the work, make the decision quickly and get moving. Both you and the current CTO will be better off if you’re confident it’s the right time to make the move. There’s a better than average chance they’re feeling some of the same things and questioning whether your company is right for them as well.

End Well

In most cases, your current CTO has made material contributions to your company. In spite of your current frustrations, it is incredibly important to remember this as you go through the process of letting them go. Your company’s reputation in the local engineering community is at stake.

Here are a few things I’ve seen work well over the years:

  • Be generous in your severance package, including options vesting and benefits. They likely have a family and obligations, just like you, and they’re going to be worried about it.
  • Thank them privately and, more importantly, publicly for the work they’ve done. Not just generally, but specifically. “Andrea helped us deliver X and Y that were critical to our success in the past couple of years” kinds of things.
  • Offer to connect them with a recruiter to help them find their next gig.
  • Provide a written recommendation, if appropriate, that they can take with them and use in their search.

If you handle this part right, they are out in the market saying something close to “It wasn’t a great fit for me but they treated me incredibly well.”

What else have you all seen work when it comes to making this kind of decision? I’d love to hear from you, as it’s such a deep topic and one that I continue to learn more about time I go through it.