Effective one-on-one

I spend a ton of time in 1:1 meetings. I meet with my team members weekly, including people I support and peers on my first team. I have bi-weekly syncs with engineering managers from adjacent teams, and I do monthly checkins with a bunch of other folks. I easily spend more than 10 hours every week between attending these meetings and preparing for them. My feelings of how my week goes are largely predicated on the effectiveness of my 1:1 meetings.

Effective, not efficient

You can only be effective with people. You can never be efficient with people. That was the first words of wisdom that Jay Shirley shared with me, and I feel so fortunate to work with him.

As an engineer, I tend to focus on efficiency, which means doing more things with fewer resources. Therefore, I had this innate impulse to optimize my 1:1 meetings when I first became a manager. That was especially true because I spent so much time on them. I wanted to get more things done with less time, but I found it challenging to apply the same mindset. It turned out that, unsurprisingly, people were different from computers.

Huge was the mindset shift to have effective, but not necessarily efficient 1:1 meetings. I started out having 50-minute 1:1s with my team, thinking that I could shorten them to 25-minute ones¹¹ I run speedy meetings which are shorter than the typical one hour or 30 minute long meetings. once we built mutual trust. I was wrong. We did build mutual trust, but the length of the 1:1 meeting should not be decided by how much we knew each other. Instead, it should be long enough so that we could have effective, sometimes insignificant conversations. After having that realization, I no longer optimize for shorter 1:1 meetings. I am so much happier.

I also learned to leverage 1:1 meetings to roll out policy changes iteratively. Take the Project Buddy as an example. It took us four rounds of 1:1s to roll out. I spent time with my team members to brainstorm about the problem space, to socialize the idea of Project Buddy, to discuss the initial trial, and to eventually ask for commitment. A month was probably not efficient by usual standards, but I believed this was an effective way to build rapport and resolve frictions. At the end of the day, a one-on-one meeting is the safest place for people to share disagreements and critical feedbacks.

Toolkit for One-on-One

I crave structures. I need tools to organize myself, more so for 1:1 meetings where I spend a lot of time. I would feel overwhelmed if I did not prepare, and my week would be predictably awful in that case. Below are some tools I have learned over time to help me be happier and more effective:

• Up-to-date recurring calendar invites with an adequately sized room and/or video conferencing setup. The calendar entry should be modifiable by both parties.
• Separate yet overlapped calendar invites as reminders to have career conversations. I prefer to have them once every month while doing weekly 1:1s with my team. This does not apply to 1:1s with other people.
• A shared Google Doc linked from or attached to the calendar entries. This document is meant for preparing agendas and taking high-level notes. Access to the document should be strictly limited to the two persons only.
• A separate weekly plan document for myself. It is useful to write down common talking points across the team. For example, the project buddy discussions would begin with similar narratives for everyone during its rollout phase.
• A help-me-understand-you document for each of my team members to help me support them.
• Some common conversation starters. This list of 1:1 questions was featured on HackerNews a few days ago. I personally like to start with how-is-life and gradually shifts to what-is-holding-you-back-at-work.
• Offering to discuss items on the other person’s agenda first in every 1:1 meeting. I usually mention that I have, say, three things to discuss, but I would first defer.

That is it for now. I hope this post is effective, if not efficient.