Improving at One-on-ones

Massimiliano Pippi

Agent and Integrations Team Lead at Datadog



I used to struggle with leading one-on-ones, so when I was promoted to the role of team lead, I had no idea how to do one. I am naturally an introvert, so I found them extremely difficult - my only experience with them had been as a team member, with my manager leading the discussion. The problem was that the goal of these meetings is to gain insight into the health of your team, so it was important to have these meetings.

Actions taken

Usually, my interactions stop with "How are you?", and with my former manager this had been the case too. However, to gain value from the one-on-ones I needed to dive deeper. When I first started, it was a little awkward as I didn't really know what to say. Every single time, the discussion would steer towards something technical, rather than being focussed on more personal aspects of what the team member was going through. When someone has a big personal problem, then it's pretty easy to lead a one-on-one meeting because they are direct, and will look to you to help solve it. However, what is missed is your team's expectations for the future. I asked for advice from the Director of Engineering, and while he gave me a lot of practical advice, as an introvert I was still struggling. One day, during a technical meeting, my team had a big argument with me about some technical topics. I felt really bad, because I was supposed to be the team lead but I couldn't lead anyone, as everyone disagreed with me. I was really upset by this, so I spent a few days just reflecting on what had happened. I decided to be direct during my next round of one-on-ones. I admitted what I had done wrong, expressed my discomfort with what had happened, asked questions, and talked about more personal topics. This was like a breakthrough. I was able to prove to myself I could have effective one-on-one's and could talk about personal things with my team. From that point on, I have always tried to steer the conversation back to personal topics whenever the topic is steering towards technical topics.

Lessons learned

Holding one-on-ones in the right way is important, and approaching them from a personal perspective is much better. By using this technique, I was able to get new information, and am able to address issues my team has before they snow pile into huge problems.

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Massimiliano Pippi

Agent and Integrations Team Lead at Datadog

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