Effective One-on-Ones

Doug Daniels

VP Engineering at Datadog



"When I first started out as a manager at Mortar Data, I did what a lot of managers do. I held one-on-ones that were mostly status update talks and we would talk about the code or project the engineers were working on. However, what I neglected to discuss was how they felt about work in general."

An employee came to me, ready to quit. I had no prior sense of this, as everytime we had talked we talked about the feature he was working on, rather than issues he was facing that I could have easily fixed.

Actions taken

I was able to fix the problem the engineer was facing, but realized I needed to restructure the way I conducted one-on-one meetings. I read an article by Michael Lopp called "The Update, The Vent, and The Disaster". It suggested that what you should do in a one-on-one is aim to understand how the other person is feeling with respect to their work and the company. In addition, you should get stories from them that they wouldn't ordinarily tell that they need to tell you.

I now rarely talk about projects, unless I'm certain the person I'm having a one-on-one with is happy and is feeling fine. Instead of going in and asking about work, I would start with a softball opener, such as "How are you?". It's also useful to let the employee talk most of the time. I tried not to steer the conversation unless it's going too much towards work. While I still go in with a few questions I'm interested in, I mostly try to get my employees to talk about themselves, about work, whether it's motivating for them, and if they're happy about the people they're working with.

Lessons learned

"It's important to check in with your engineers to ask them how they're going. Often, it's a question that doesn't get asked in any other meeting as you're talking about business, rather than how someone feels. I used to be very formal about one-on-ones, but I found that it helps to make one-on-ones less formal, and to look at the person rather than having a computer there to write notes. Even if you think you understand someone really well, if you don't give them the space to talk, they may not bring up things that they are finding uncomfortable."

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Doug Daniels

VP Engineering at Datadog

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