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Daniel Doubrovkine

aka dB., CTO at artsy.net, fun at playplay.io, NYC

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A few months ago I asked myself: What does a CTO do?. I divided my attention across three priorities: people, technology and business, spent a lot of time with the entire team, beyond Engineering, created time to think, and learned to connect people in a more systematic way.

Why do so many things I do seem obvious in hindsight?

I define leadership as creating an environment in which people do their best work, in contrast with one where people are told what to do. It’s a creative and a committed role, and I expect that the organization I serve fosters creative and committed individuals. The role of a leader is to see possibilities. Turns out that is rather difficult, so we do our best, collect as much information and feedback as possible and generate possibilities. In many ways leadership is about expanding a company’s limits through new options. With the right kind of leadership we can constantly push these boundaries and therefore achieve growth.

A good concrete example of successful leadership is turning a demotivated exceptional Engineering team member around, someone on the verge of quitting because they feel like they have reached a good stopping point and don’t see the much larger opportunity ahead, or at least one that is exciting enough to commit to for another term. I patiently look for something amazing for that individual to do, and stay motivated through multiple false starts. These “great” suggestions get a weak “meh” response at best. I keep digging, because I believe that something can be found. I take lots of input and one day find myself talking to two other senior executives about a big customer problem around an unrelated subject. Suddenly all the dots connect! How did I not see that our problematic team member was perfect to attack this very important problem before? Incredibly, I am also seeing a 10x business opportunity enabled by solving this problem. It takes work from the entire group to strategize our approach to the said team member, who is as excited as I am once shown this opportunity.

In hindsight, the opportunity and the fit was completely obvious.

My biggest challenge is to turn hindsight into foresight.

I do this with pattern matching, taking in as many disconnected pieces of information and trying to find repeatable patterns. The above example is fairly straightforward and 20/20 in hindsight.

  1. A Engineering team member is demotivated.
  2. Someone in a customer-facing organization has a recurrent problem that concerns them every day.
  3. The recurrent problem is also a big business opportunity.
  4. The team member is not sufficiently motivated by just solving the recurrent customer problem because it feels too short term.
  5. The team member is reenergized with the big business opportunity but requires a real short term customer problem.

Every single time I have a demotivated team member, I look for an immediate business problem with a long term 10x opportunity. The hard part is to connect the dots.