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Daniel Doubrovkine

aka dB., @awscloud, former CTO @artsy, +@vestris, NYC

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In my past CTO life I directly managed a VP of Engineering, who managed 2 directors, who managed 6 managers, who managed 30 or so engineers, had peer VP of Product, Head of Design, Head of Marketing, COO, CFO, 2 Heads of Business, a Head of People and a CEO. Each had at least 2-3 very important direct reports. This quickly added up to 60 people that I would have wanted to have a 1:1 with, at least once a year, 20-30 people that I needed to be talking to at least quarterly, and a dozen people that I had to talk to at least monthly. I would also get weekly pings from new hires for a 1:1 and maybe a weekly urgent, everything’s on fire, 1:1 from someone wanting to vent or to quit.

In my current individual contributor life I work with even more people across multiple divisions, so this is not an exclusively managerial problem.

My full time job isn’t 1:1s!

At first, I tried to think of my 1:1 schedule as a bit-packing problem, squeezing everyone on some regular schedule as tightly as I could. Instead of a solution I ended up in a crazy game of calendar Tetris. Something more important would always come up that would require rescheduling a 1:1, then eventually canceling 1:1s as the newly rescheduled 1:1 dangerously approached the next occurrence of itself. I was getting dizzy from doing entire days, sometimes weeks of 1:1s. And I was seriously overdosing on coffee.

I called bankruptcy, erased all recurrent 1:1s, and tried to improvise the schedule completely, telling my team, my peers and the entire company that they could and should always schedule a 1:1 with me as needed, sharing the calendar responsibility with me. But many people thought a 1:1 wasn’t needed, or didn’t want to bother me because I was too busy, and simply didn’t schedule any, which was the opposite effect of what I was trying to achieve. Several individuals would also constantly attempt to schedule recurrent 1:1s, which re-created the problem above. Finally, a few team members scheduled 1:1s too frequently, getting a lot of attention for themselves, but unfairly penalizing others.

I then introduced a tracking spreadsheet that recorded when I had a 1:1 with anyone.

name days since last 1:1 date of last 1:1 date of previous 1:1 date of older 1:1
Bob 42 2019/01/05 2018/09/03 2018/04/03
Jane 21 2019/02/03 2018/05/01 2017/01/03

Sorting by date of last 1:1, oldest first, told me who to prioritize. This was a huge win.

I was then able to stop scheduling recurrent 1:1s altogether (except for my direct reports) and spent half an hour scheduling 1:1s once a week on a Friday, a week in advance using the data in the spreadsheet, my own judgement and everybody’s available time. I could do fewer in a busy week and more during summer months. One-off 1:1 requests fit well in this system too, because those would be recorded on the sheet.

I made my life easier by creating a standard copy-paste for the meeting request.

Looks like we haven’t had a 1:1 in a while. This is your time to discuss any issues, concerns, ask any company-wide questions and tell me about your work. Please come prepared with topics. Coffee is on me.

I could manage my own volume and generally scheduled no more than two 1:1s per day, usually after 3pm, and would diligently prepare for each with at least one question that I wanted to ask.

To avoid stress and running out of time in the usual case when a previous meeting ran late I always scheduled an entire hour, while often keeping the actual meeting to 45 minutes.

Finally, I tried to never express to my team frustrations around the volume of 1:1s, or whether they were a chore. In general, I always enjoy talking to people, learning about their work, gathering actionable information and helping them in any way I can.