Hiring a CTO… and Letting Them Go

Problem

Hiring our own boss is all about striking a balance between the status quo and out-of comfort change they should bring. They are brought in to change things and push you to be better, but not to change the company’s distinct culture and those things that made it successful in the first place. Thus, finding a candidate that can align with your company culture while still pushing that culture forward is immensely challenging.

We recently went through a process of hiring a new CTO; we did interviews involving multiple candidates as we tried to get a feel for what they were like and ended up hiring the CTO. Then we started to roll some changes out, but some of the changes they were pushing for were not things the company was comfortable about.

Actions taken

After the new CTO came in, they started introducing changes that focused on things they thought were important. After a while, we could see discontent bubbling up as a consequence of those recently introduced changes. That forced us to inspect them more closely and critically evaluate where we were making misses on some of the changes we thought would work well out.

One of the key indicators that something was wrong -- and which we didn’t value as highly as we should have -- was a misalignment in communication. Communication is exceptionally important at the leadership level, and if the communication style is misaligned, the message will be lost, and distorted interpretations will erode trust. Some of the communication glitches may look trivial, but they made a significant impact. For example, we are a Slack-heavy organization, and our new CTO had a strong preference for using email. They tried to enforce their communication style on the organization, which didn’t align with how we were used and preferred to communicate. That ended up being a larger problem than we could expect because people viewed email communication as far more formal and rigid. As a result, all the communication coming through that path was interpreted as formal and not-negotiable, forcing the message to come across completely differently from what was the intention.

Furthermore, some of our longer-employed staff members were grumbling about some things, and we didn’t dig deeper to see how big of a deal it was, mostly because their discontent was quite vaguely articulated. We should have been aware that if someone was grumbling about something, it may have been a tip of an iceberg that we should have investigated. Oftentimes, something that one person is complaining about is what ten others are thinking about but not expressing openly. In this particular case, we underreacted and underestimated their complaints. As we later dug deeper, many of those things turned into larger problems, and by not addressing them timely, we jeopardized much of our trust. As a result, some people became disengaged and unhappy with the company because we were not listening and solving their problems.

This was tightly connected to the problem of finding the balance. The outcome of many interviews was that we knew candidates were not the perfect fit for the role, but we were somewhat excited that they were not the perfect fit because we wanted to push our company to change. Having a growth mindset implies that you should be uncomfortable every now and then, and we were looking for someone who would make us slightly uncomfortable and help us grow, learn and make us better than we were. We were uncomfortable with some ideas the new CTO was pitching, but we liked others, and balancing the discomfort with critical evaluation was missing. We should have dissected the pieces that made us uncomfortable and identify if we want to pursue our growth in that direction.

After we let them go I ended up taking their email and the projects they were working on only to realize that half of those projects no one knew were happening. This was when we asked ourselves who should have been keeping tabs on a new hire -- even that they were in the leadership role -- to make sure they were working on the things that were important. That was lacking from the very beginning, and that responsibility should have fallen on the department they were in charge of. The department should be aware of the direction its leader is trying to move things and ensure that the team is heading in the right direction.

Lessons learned

• Don’t assume that someone who is more experienced than you knows better than you. After hiring your own boss, don’t unconditionally trust them only because they have more experience than you do. You still need to be keeping tabs and monitor what they do to make sure that, even if they are bringing change, that is the change that will make the company better. Also, make sure that their influence will steer the company in the direction the company should go, not where they think it should go.
• Even if you are hiring your own boss, you will still have to treat them as not your boss. You can’t neglect onboarding and check-ins. You still need to keep maintaining one-on-ones and skip-level one-on-ones to make sure that the things that are happening are making sense for the department and not only the leadership of the department.
• Communication is critical in leadership roles. Our future hiring process for those roles will put more emphasis on how a person will relay a specific message. We could do a case study on how a person would roll something out by doing a mockup of how they would communicate their message. That will allow us to early on establish if a candidate’s communication style and path align with ours.
• During the interview, critically evaluate the areas where you want to grow as a company and if that aligns with a candidate’s proposal. Also, make sure to have your boundaries clear in terms of being pushed into something where discomfort outweighs the actual benefits. For example, in the SaaS industry, optimizing efficiency and reducing cost is important, but we, as a company, are not looking at how we can cut our costs to the lowest possible but instead how costs could be cut with efficiency. If a candidate is trying hard to save every last penny, they won’t align because those are not the cost savings we are looking for.