Daniel Doubrovkine bio photo

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 went through a process of trying to answer this question with the help of an executive coach. He helped me divide my attention into three priorities: people, technology and business.

Because I value people first, I reached out to my four team leads and asked them What can I do for you? Consistently, I heard that engineers that work for them also want more of my time. They felt increasingly further away from “management”. They wanted to discuss their issues and plans with someone who had a broader view of the company and insight into the thought process within the executive team.

I decided to take this request a step further and offer my time to the entire company.

Subject: 1:1 with dB.

Team (on the bcc),

There’s so much great progress being made across Artsy!

The engineering team is nowadays quite self-sufficient and is driving the company forward when it comes to software delivery. We are also building a new product organization, which is very exciting and marks a significant milestone in the company’s rapid growth. There’s momentum everywhere, I have never felt it so strong in any of the 4 startups I’ve worked at, including my own.

With growth and momentum come many new challenges. I find myself having the luxury of a bit more time to focus on new things, and am in a really privileged place where I know Artsy inside-out, having been here for 4 1/2 years. I want to give some of my knowledge back and offer my time to anyone who wants it.

I invite you to schedule a 1:1 with me at your convenience whenever open on my calendar to talk about anything you want. I already do this with every engineer, and it has been tremendously useful. I want it to be recurrent, I think I can do it once or twice a year with each one of you, for sure.

Please do take this opportunity, especially if you’ve just joined! Come prepared with topics and questions. I buy coffee. Looking forward to your calendar invites.

About two dozen people, roughly a quarter of the company, took me up on this offer. I got a lot of excellent responses and many thanks for offering my time. I also tried to create a repeatable process around it, so every time I got a meeting request I asked to make it recurrent, every few months. After several particularly useful 1:1s I asked to make them even more frequent.

Today someone asked me: What do people ask during these 1:1s? This was a great meta question!

Some were quite predictable.

  • How did you come to the company?
  • What did you do before?
  • Why are you still here?
  • What is your art background?
  • Who is your favorite artist?
  • What is the most exciting project in your team today?
  • What is the most interesting project in the company?
  • What do you think are the biggest issues in our organization?
  • What do you think are the biggest issues in the engineering organization?
  • Where do you see the company in five years?

Some were tougher.

  • I am getting very little guidance from my manager, how can I make progress?
  • I have been rapidly promoted to a team lead, but have no idea what I am doing. Can I get help from you?
  • My career path is unclear, what is my opportunity at Artsy?
  • It’s difficult to understand how priorities are set, how is the executive team fixing it?
  • Artsy’s mission speaks to all citizens of the world, but we’re spending a massive amount of resources catering to the 1%. Am I being naive to believe in a grander mission?
  • I am not satisfied with the diversity discussion during the last all hands, what does your team do about it?
  • What is your personal position on the issues of diversity that have been discussed at the last all hands?

My biggest takeaway from all these is that team members cannot get enough time from executive management and that giving this time to them is essential. I am positive that I have helped preempt at least two major issues because of a 1:1 and I have done a full 180° on at least one bad plan within engineering that was born in a place that severely lacked business and customer context. I’ve also connected several individuals across organizational boundaries and was able to dry-run and help steer the upcoming product reorg with some individuals by describing to them the current thinking and gauging their initial reaction in a fail-safe environment of a casual coffee break. And a lot more.

In sum, our job as leaders is to serve the entire organization. Regular 1:1s with a broad range of team members is one thing I now do.