Do One-on-Ones, Like a Boss

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Photo by Brooke Lark on Unsplash

There are millions of articles and books about the importance of one-on-ones for managers and leaders. When I was a new manager, it’s something I read about and put a lot of effort into. I didn’t feel like I was good at them, and I didn’t look forward to them.

But — like many things — the more you do them, the better you get. This is the story of things I’ve learned with time and experience.

Make Time to Prepare

This is the piece of the puzzle that I was missing for too long. The secret to good one-on-ones is preparation. Make it part of your morning routine to prepare for each one-on-on you have that day. Eliminate distractions and dedicate focus to each person you’re meeting with.

The secret to good one-on-ones is preparation.

How do you prepare for these meetings, though? It’s a combination of looking back and looking forward. Review notes from the previous meeting, reflect on interactions and contributions, and think about the person’s life outside of work.

First, you need to make sure you’ve dealt with anything you signed-up for last time to demonstrate accountability and build trust. If you missed something, that’s okay — there’s still value in bringing it up as something you couldn’t get to, provided that you don’t lose track of things and deliver more times than you don’t.

Next, think about the person and how they’ve been since you last met. Have they completed important work? Has there been conflict? Have they raised complaints? Have they been engaged? Have they been visible? As part of your preparation, identify positive and negative things to call out. These can be individual or team items, too.

Finally, look ahead to the future. What short and long-term goals does the person have, and are there things you can do to help them make progress? Some examples would be to follow-up on a commitment they made last time, give feedback on a instance where they exhibited a specific positive or negative behavior, or provide advice or reference materials that could help them.

The one-on-one is also your time to solicit feedback from them. How do they feel about recent changes the team has made? How is the current project going? What do they think about the direction of the team? You can — and should — also ask them about you. What could you do to help them or the team? What would make you more effective as a leader or manager?

Preparation checklist:

  • Did you take care of action items from last time?
  • Are there positive or negative things to call out?
  • How can you help with their goals?
  • What feedback do you want to solicit?

Be Persistent and Dedicated

Preparation is critical for effectiveness, but the most important thing is to actually have the meeting. Sometimes the biggest hurdle is just getting the meeting on your calendar. I’m an introvert, and one-on-ones are mentally and physically exhausting. The thought of another recurring meeting on my already-busy calendar was demoralizing. Don’t procrastinate. You know you need to do it, so just get it on there!

Making the appointment is nothing without keeping it. It’s important to put forth your best effort to make sure they happen. Don’t treat them as your lowest priority. Things will inevitably come up, and you’ll need to reschedule your one-on-ones sometimes. When that happens, favor rescheduling over canceling, and reschedule sooner than later; not showing or canceling at the last second sends the message that you don’t care.

It’s not always easy, but force yourself to have the one-on-ones. Arguably, the harder it is to have the meeting, the more important it is. Relationships that are most strained are ones that stand to benefit most.

Take Notes

If you’re anything like me, you’ve got a lot of meetings with a lot of people. It’s impossible to remember all the commitments and action items in my head. Take notes! Taking notes has multiple benefits beyond simply having something to refer back to, more so if you write by hand. It forces you to listen and be engaged which helps demonstrate to the other person that you care and makes distractions less… distracting. Research has shown that writing things down helps you remember, so you’ll naturally retain more of the conversation. And, lastly, taking notes gives you the obvious benefit of having something to refer back to. Taking notes is immensely valuable even if you never look back at your notes.

If you want to be a next-level note-taker, take handwritten notes during your meetings, then immediately re-organize them into a digital format that you can refer back to during future preparation and that can also represent a running history. Make sure to flag action items or mark things for follow-up, too. Depending on how you work and organize, you may want to add items to your calendar or task lists. The “secret sauce” here is that you’ve now written it twice — so you’re less likely to forget it, anyway — and you’ve got some fail-safes in place to make double-extra sure that nothing slips through the cracks.

Set the Agenda

I’ve covered preparation, scheduling & commitment, and note-taking during the meeting, but what about the conversation itself? Here are some things to keep in mind as you conduct your one-on-ones.

Let them go first. This is the standard one-on-one format: they get 15 minutes then you get 15 minutes. Their part is your chance to listen, take notes, and understand what’s happening with them as a person. If people aren’t opening up, try asking questions like, “How are things outside of work?” or give them a choice of where to focus like, “How’s life, at work or away from work?”

Prioritize topics. Treat them like people first. If last time you spoke to them, you learned they had sick family, don’t jump right into grilling them about the reports they’ve been working on.

Be direct. If somebody isn’t meeting your expectations, say, “You aren’t meeting expectations,” and explain your expectations and why they aren’t being met. If you don’t address problems, they won’t improve. If you only focus on positive things to encourage good behaviors, it’s going to be received as, “[you] didn’t have anything bad to say!”

Highlight positives and negatives. It’s easy to worry about negative feedback and improving performance so much that you forget to celebrate the good things. It can be a drag to only hear about what you do poorly, so be sure to shine a lot on positive behavior, personal growth, and team victories.

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Image by Free-Photos from Pixabay

Whether you’re a new leader or you’ve been at it for years, one-on-ones are an effective way to build trust, gain influence, and promote team & individual growth. It doesn’t come free, though. You need to do your part to ensure the effectiveness of these meetings, and that means more than just showing up.

Prepare. Commit. Take notes. Set the agenda with empathy. Do these things, and you’re sure to maximize the value of your one-on-ones!

I’d love to hear from you! What tips am I missing that make your one-on-ones most effective? What differentiates an okay one-on-one from a great one, or what things have you seen from the best leaders in your career?


Originally published at https://adamprescott.medium.com on November 13, 2020.

Author: Adam Prescott

I'm enthusiastic and passionate about creating intuitive, great-looking software. I strive to find the simplest solutions to complex problems, and I embrace agile principles and test-driven development.

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