What makes a great CTO?

I have been asked this question many times. Great CTOs build amazing cultures, where engineers build amazing products.

Let's get to the details by sharing two relevant experiences.

Great CTO is someone who governs by serving the organization. Set clear goals, empower, enable, and get out of the way.”

Stellar performers return to great CTOs

A few years ago, one of my senior software engineers, “D”, and I had a career discussion. “D” was a terrific engineer, wanting to advance his career very quickly. Perhaps too quickly. Yet I knew “D” was under compensated and asked him to be patient.

“D” was considering a very good offer: well compensated with the role and title exactly what “D” wanted to have. “D” asked for my advice. Some of you are wondering why would an employee be asking his boss for career advice which may in fact cause the employee to leave. The answer is simple: if I fail to build the most desirable culture and a great place to work, then I fail as a leader. Employee would leave anyway. The best part of my job is to see great people grow, leave, and then … return to my organization.

Despite my advice, ‘you are not ready’, “D” left. We stayed in touch. 6 months later, “D” called me told me that his job was in trouble. “D” admitted the organization was very complex and many urgent issues had very little to someone’s ability to apply their technical depth. “D” was clearly not succeeding.

‘May I come back?’, asked “D”. “D” returned, learned a lot more, and became one of the most committed employees in my organization. I cannot thank “D” enough for all contributions over time. In every customer success story, “D’s” contributions can be easily noticed. By the way, “D” reported to a Sr. Director of Engineering in my organization, or “G”. “G” was a stellar engineering leader, capable of so much more. “G” left for a better opportunity but we stayed in touch.

Interviews with great CTOs are short

My phone rang. It’s “G”. “G” is one of the candidates being considered for a CTO position. However, “G” also shared with me that the executive recruiter considered “G” to be candidate number 10 our of 10 candidates. Not a good position to be in.

“G” asked for my advice, “what makes a great CTO? How can I impress the company?”

I told “G” the challenge was not to impress anyone. Simply tell your story, knowing that you are the best. Then you will no longer be a candidate, but someone who will be hired almost immediately. Stop being a candidate. Stop.

Great CTO is someone who can …

1. Create and execute a multi faceted plan which supports business strategy. This plan is not just a technology plan. This plan must address three elements of success: people, process, and then technology. In this very specific order.

2. Practice innovation / speak innovation / inspire innovation. This is the most difficult task of any CTO. How does one innovate in the era of constrained budgets and tactical priorities? Don’t stop trying and always be transparent. The world of software hasn’t forgiven many CTOs who failed to match the rhetoric with the right culture and realistic budgets. As one engineer told me, “how can I innovate if I work 60 hours a week. My innovation time is now sleeping time”.

3. Deliver great results in a thoughtful, anticipatory manner. Delivering something that works on time and on budget is not enough. Deliver something which doesn’t need refactoring and can support the needs of future customers without 5 emergency releases. Have the vision to do it and ignore those who say this is not necessary.

“G” finally had the interview and called me 2 weeks later with disappointing news. The company elected to hire someone else.

“G” did everything right. He told his story which was a story about a great CTO. I advised “G” to be patient.

Four months later, “G” called me with terrific news. “G” had an interview with another company.

“How did it go?”, I asked.

“Well, the CEO stopped the interview and asked me when I could start”, “G” answered.

“What did you tell him?”, I asked with great interest.

“I told him a story about “D” who left, realized it was a mistake, came back, and become an amazing employee. Do you remember that story?”.

Yes, I do. That’s what makes a great CTO. Great CTOs build amazing cultures, where engineers build amazing products.