How I Learned to Run Better 1-on-1 Meetings
By: William Anderson
Tags: Management, Work, Meetings, Mentorship, Leadership

How I Learned to Run Better 1-on-1 Meetings

Most of the magic happens in the 30 minutes I take to prepare

Photo by LinkedIn Sales Navigator on Unsplash

I had a boss years back who was a fantastically natural mentor and coach, and to whom empathy was seemingly innate. Having one-on-ones with her was formative and provided a template that I would follow for years to come.

Unfortunately, I lacked the magic she had.

My kickoff question for the longest time was simply, “So, how’s it going?” I thought this was incredibly natural and casual, but sometimes casual just doesn’t work.

As I developed experience managing people of varying personality types, I started to encounter more and more office introverts. For them, a natural response was simply “fine.”

I was shocked.

For most of my career, I worked in agencies. I’ve also owned my own, led engineering departments at others, and did a tour as an IC.

In agencies, everyone is an extrovert. You kind of have to be to survive.

Shifting to product companies with significant heritage, however, that wasn’t the case. Teams and people are way more varied in the day to day and looking for different things.

My “How’s it going?” just wasn’t working anymore. So I started to prepare more ahead of time.

This may seem intuitive, but it’s not. I have worked with and spoken to very few managers that take the time to prep for one-on-ones with their team members. And if I’ve ever had a manager that did it, they hid it well.

Taking time to review the state of a report’s work and previous several one-on-ones lets you cut out useless questions. If you can get the info you need some other way, it’s a waste of valuable mentoring and coaching time to repeat yourselves.

This review time leads to me having between four and five solid, challenging, and mutually beneficial questions or talking points per session. These range in topic from industry in general, opinions on strategy, questions about their career, the company, and more.

The answers I get often challenge my reports to question themselves, myself, and step up. They push me to do the same.

We never get through all the questions, but that’s not the point.

So now, for each weekly, 30-minute, one-on-one, I set aside a full 30 minutes to prepare, and I learn a lot in that time.

I’ve found that genuinely preparing for one-on-ones not only helps mentoring and development, but cuts down on other meetings too.

I get the info I need as I dig into what they and I need to work on. I track every question and answer, as well as notes, in a little black book, with a single page per session.

I stay question-focused and let them lead. It’s their time, and I want to hear what my team members have to say. The questions I ask are just to help steer or dive deeper down their train of thought.

All this I learned from my mentor.

My one-on-ones are electronic free and have become more focused, providing value to my team, myself and my employer. They should never been seen as overhead, and, if prepared for, they will quickly shift into your most valuable meetings as well.