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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 and created time to think, asking myself hard questions.

One of such questions was

What is the best thing I should carry over from my previous job as Head of Engineering into my new job as CTO?

The answer came from another question

What kind of leader are you?

That actually gave me pause, turns out I wasn’t sure. I started enumerating things I do, looked for patterns and found one.

First and foremost, I generally try to be helpful. I am a big fan of IFYYFME. I offer rejected candidates help with finding a job. I am an obsessive documenter of technical issues on this blog. Etc.

Why do I do this? A few years ago I wasn’t able to answer this question. Today I can. Turns out, being helpful, for me, is a way of earning trust towards a more useful purpose - connecting people. Helping someone achieve what they need creates a strong connection between an individual and myself, and an opportunity to connect such individuals between themselves to enable magic. This is straight out of Tribal Leadership, where a triad is the building block of a Stage Four culture.

The most valuable relationships are not made of two people, they’re made of three. A third person will always stabilize and grow the relationship between the other two. It’s called a triad, and the more you create, the stronger your network.

Leaders lead when they take positions, when they connect with their tribes, and when they help the tribe connect to itself.

This has always been obvious to me - I’ve only read the book last year. Interestingly, I’ve been called a connector at all my jobs and even Burning Man over ten years ago. I rely primarily on personal experience and try to understand individual motivations. I look for special people to connect with other special people, and the challenge is always identifying what’s special about them. I have no idea how I do that, so for now let’s just say that I use my gut feel a lot.

So, how does one connect people to enable magic?

  1. Establish trust between you and each of the two people for a future triad by helping them individually achieve a personal goal or professional growth. For example, help an engineer with a thorny technical problem. Invite a business manager into an executive brainstorm about the future of a business.
  2. Come up with an idea that could be enabled by the two individuals in a potential triad. For example, a sales manager and an engineer together could unlock massive revenue growth by focusing on an underserved customer segment.
  3. Gently seed the idea to each of the individuals in 1:1 conversations amongst a thousand other important things. Make sure they become aware of the problem you’re trying to solve. For example, an engineer must see that the business manager is failing at serving the customer segment. The business manager must see a large number of new ways software could potentially address this problem.
  4. Create an opportunity for a conversation between you and the two future members of the triad. Direct the conversation into the area of interest. If the idea is worthy, the two people in front of you will spiral into working on it, it will be magic.
  5. Never take credit for the problem, the idea, the solution or the connection, give it entirely to the other two members of the triad. Your role in this should be completely invisible and thankless. You’re just doing your job of a leader. Walk away and look for the next opportunity.

Connecting people with premeditated focus and, thus, enabling magic, is one thing I now do.