The Art of the One-on-One

A primer for managers, mentors, and senior developers

As a senior person in a technical organization, people look to you for leadership and direction. Generally that comes in the form of a “one on one” meeting that happens regularly. One on ones (or 1:1s if you don’t have a lot of time) are a little less structured than scrum ceremonies but should have more structure than a casual chat at the bar. As a manager, I regarded 1:1 time as one of the most important things I could do for the team as I saw them as opportunities to energize, be energized, and align personal growth goals with team goals. I enjoy doing 1:1s so much, I thought I’d share some tips for other managers to help you and your team get the most out of them.

Mechanics of a 1:1

As a manager, at minimum, you should make yourself available for 1:1s with your direct reports at least weekly and their reports as a “skip level” at least monthly. I say “make yourself available” as not everyone will require regular 1:1 meetings; and that’s OK too.

The 1:1 is owned by your directs and they should set the agenda. Depending on the pace of the organization, the 1:1 could be discussing current events or big strategic direction. Whatever it is, the 1:1 is a judgement free discussion that is driven by the person on the ground with the most information (i.e. your direct).

Leave time to discuss performance related items. I like to mention something they did well or impressive since the last time we spoke and/or bring up a performance concern, as it may be occurring in a blind spot for them or they may be hesitant to bring it up themselves.

Finally, schedule the 1:1 sometime after lunch for 30m to an hour and leave a buffer at the end. I’ve found that when people are really passionate about something the conversation can go long. Depending on your relationship, you might even duck out to a bar or a coffee shop to make the conversation more honest and genuine.

What to Cover

As I said, the detailed subject matter is driven by the report, but that doesn’t mean you should ignore performance related items. At beginning I like to bring up the status of any professional development goals. You should figure out what the person wants to do long term (e.g. are they looking to get on the management vs individual contributor track) and use that information to align the organization’s goals with those of the person.

For instance, when a person isn’t sure about management, I recommend they check out The Manager’s Path as well as the company’s career ladder guide to get an idea of what it means to be in management. Then if they think management is interesting, assign a leadership task and ask them how they’re feeling about it in each 1:1.

Ask your directs broadly how they’re feeling on the whole about the work they’re doing.

  1. Are they interested in the work they’re doing?
  2. Do they feel empowered?
  3. What are their obstacles/concerns?
  4. What would they be doing differently if they were calling the shots?

You should be thinking about these responses in the context of your direct’s professional growth, as well as looking for patterns from your other 1:1s.

Finally, your direct should come with an agenda. They might be pushing for a promotion or on a performance improvement plan. The takeaway for them is that they should feel seen, and feel like you’re taking an interest in helping them be better at their craft.

What a 1:1 is Not

Unstructured screw off time — It should be a focused meeting about career growth and aligning that with the organization’s goals, not an aimless discussion

Status meeting — we have enough of those. You can have discussions in the context of ongoing work, but encourage your direct to not just come to talk about the same things they talk about at stand-up.

To be disrespected — Life happens sometimes and it’s not unheard of to push a 1:1 or to be late. However, if re-scheduling or tardiness becomes the norm, it shows that you’re not as invested in your team as you say you are. Other teams should be respectful of your existing engagements so the company can grow and retain talent.

Parting Thoughts

As a leader, conducting a thoughtful and intentional 1:1 with people is one of the most important things you can do. The very nature of work is constantly shifting and recently, people are interested in doing work that is fulfilling and beneficial to their growth. The 1:1 is the most important retention and growth tool in your arsenal. Hopefully you found these guidelines or management musings useful and will frame your next 1:1 meeting with these in mind.

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