Firing Your CTO

So, you’ve fallen out of love with your CTO, have you? Ready to pull the trigger and make them exit stage left?

Not so fast.

Every senior-level person in a company carries with them a certain degree of risk if you need to make a change that is contentious or hostile, but few carry the risk of a CTO in a technology company. If you fire your top sales person, you can still call every customer personally and step into those relationships. If you have a bloody ending to the dismissal of your CTO, the damage can be permanent.

“But we’ll just sue them!” you say. That won’t help you if your product is offline and customers start leaving. The damage will be done.

How do you fire a CTO in a hostile situation?

Prepare

The most important work you will do in this process will be BEFORE you have the conversation. Extensive planning and preparation is required.

Create a full system inventory. This post tells you how.
Make a list of all of the areas of the system where the soon-to-be departing has specialized knowledge and think through how you’ll handle getting things done in those areas going forward.
Create a playbook that you will walk through step by step as you let the person go. More on this below.
Identify the key individual that you will immediately transition all of the work to, even if it’s a contractor, and give them time to ramp up. This individual should be able to step in and manage your production environment at a bare minimum, including making small code changes to fix bugs and getting them deployed.

Creating the Playbook

In the moment, you’ll be so stressed out and worried that you will forget key pieces. The purpose of your playbook is to have a checklist of all the things you need to do at the time of execution. Every. Single. Step. With as much detail as possible so that you can read and do, not think. Some examples:

“Login to xyz system and disable the user credentials for Mr. X by running the following commands:”
“Make Ms. Y the new administrator of our Github organization. Login to Github, go to <menu> and click <link>…”
“Meet with Joe and Caroline on the team and explain what has just happened and what you expect from them in the next 48 hours”
and so on…

By creating the playbook, you’ll force yourself to think through all of the moving pieces and eliminate as much of the risk as you can from forgetting something important in the moment.

Execute

Schedule an in-person meeting to make the decision known. If your CTO is remote, go to them. Why is it important to do this in person? If you do it over the phone, the person you’re firing has full access to the systems in your company and you can’t see what they’re doing. While you’re talking they can be doing irreparable harm. If you’re sitting in front of them, they can’t do anything to harm you in that moment.
During the meeting, your key individual helping with the transition is executing the playbook you created ahead of time. By the time your meeting is over, the playbook should be completed and all access revoked.
If the company owns the computer being used, take possession of it immediately. You can transition any personal data later.
If in an office, escort them from the building.

Transition

What you’re going to find is that new development often grinds to a halt post-event, particularly on small teams. There’s usually a lot of knowledge that exists only in that person’s head and it takes time to sort that out. You need to set your expectations appropriately. If you can keep the system running, fix bugs and deploy new code in the week following, you’re in great shape.

The rest will be picked up over time, but it will take time.

It’s impossible to cover all of the corner cases and things that can go wrong in this process in one article. Your job is to do as much preparation as possible, ask trusted advisors for help with the details, and get through it.