How to Survive Your CTO Leaving

I had a call the other day with the CEO of a fast-growing company on the west coast. He was really struggling with a delicate situation involving his CTO, who was a co-founder.

The CTO was transitioning out of the business by mutual consent, and they had hired his replacement. However, the transition was dragging on and getting a bit messy, for various reasons.

The developer(s) who get your company launched may not be the developers who can grow with the business and build a team. It takes a special kind of developer to handle all of the stress and uncertainty of the early-going. Developers by their nature are logical and tend to like clarity, and of course there is little clarity in those first few months. Those who thrive in that early environment often struggle with loss of control as the team grows.

This particular situation was made even more complex because the outgoing CTO was the only one who knew certain parts of the system (very common particularly in small teams).

Here’s three things that must be handled during this kind of transition:

  • Make the change known as soon as possible
  • Plan for knowledge transfer
  • Expect extra effort

Make the Change Known

The tendency will be to keep the fact that your CTO is leaving quiet. I’ve always found that people tend to know what’s happening even if you try to keep it quiet, and the fact that you’re keeping it quiet induces more worry and concern. If you need to, create a temporary role for the outgoing CTO such as “Special Projects” or “Head of R&D”, and announce their move to that position.

The key is to make it clear that they won’t be working with the rest of the team day to day, and that the transition starts as quickly as possible.

Knowledge Transfer

The hardest part of an early key employee is that so much knowledge walks out the door with them unless you make it a priority. More than likely there’s very little written down because what’s true today was not true yesterday. And, let’s face it. Everyone hates writing documentation except people who write documentation.

Here’s how you manage knowledge transfer:

  • Plan to take at least one full sprint cycle, and preferably two, to make the transition
  • Have the outgoing CTO stop writing new code and instead work with others to share knowledge or provide additional test coverage. They don’t fix bugs. They don’t create new features. They’re just a resource, which forces everyone else to acknowledge where the gaps are and get them addressed by remaining team members.
  • Whoever is replacing the CTO should have adequate time to get meaningful brain dumps. Have your outgoing CTO make a list of everything they can think of that must be known as the starting point.
  • Make sure that all system access is properly transitioned to the new leader

Expect Extra Effort

It’s time for the remaining team members to step up. Set expectations accordingly. There’s no doubt going to be conflict during the transition as new leadership steps in. The change in style will be welcome for some, and unwelcome for others. Everyone must focus on getting through the transition, after which you can deal with the smaller problems.

Insisting on cooperation to make the transition smooth, and checking in regularly with all involved, is a key part of your role as the overall leader of the company.

Just Remember

Every time you go through this major of a transition, the business is at risk. By making the change known early, planning for knowledge transfer, and expecting extra effort, you can drastically reduce the duration and severity of these kinds of events.

Your Assignment

If your CTO or lead developer walked in tomorrow and told you they were leaving in two weeks, could you survive it? If your answer is “I don’t know” or “No”, here’s a simple exercise to immediately get in better shape.

Sit down with your dev team and ask “If you left tomorrow, what would all of us need to know in order to carry on?” Have everyone involved write up as much as they can in an hour or two, and publish it to a shared folder. In two hours, you’ve de-risked your business significantly.