Better one-to-ones

Scott Baldwin
May 29, 2015 · 6 min read

Of all the things I do in my job, one-to-one’s are my favourite – yeah I know, crazy eh? I love talking with my team about their ideas, challenges, goals; giving (and getting) feedback; and helping them (and me) grow. And I’m sure they were Captain Kirk’s favourite too.

How can you make your one-to-one’s better? Read on.

1. Pick a frequency and stick with it

It’s easy for many managers and staff to kill or continually move these meetings. Don’t! Set a rhythm and be religious about sticking to it. Not meeting regularly means that you don’t know when there is a problem, until there is actually a problem. If you have to re-schedule, make a point of doing it in the same week and try to look ahead at people’s availability and work on their plate so you can adjust when needed.

What’s the right frequency? Ask your team. Right now I meet bi-weekly with my team, anything longer than that I find to be too large of a gap.

2. Set some structure.

Have an agenda. I have a rough agenda in my back pocket that I like to run through. Having some consistency in the structure allows staff know what to expect.

I usually start my one-to-ones with some discussion on current work, priorities, and recent accomplishments. While I might already know a lot about this, it’s surprising how often other details come out when talking one-on-one. If I have anything I can share about their work (e.g. feedback, things I’ve noticed, kudos) and I haven’t done that already, I’ll do that here too. Dig into any issues/problems that may be standing in their way of being successful in their work asking “why” – our job is to get those obstacles out of their way.

3. Take time to get to know each other too.

Take time to just talk about lives, family, kids, the dog, interests, and life. All work and no play makes Jack a dull boy! Be human.

4. Check-in on career development and learning plans.

Career development and learning often takes a back seat to other priorities (hey we all have lots of work to do). I like to use questions to poke at their plans and progress and solicit commitments (e.g. due dates, next steps) to help them keep on-track.

5. Get ideas about what they think things could be improved — in the team or company.

I guarantee you’ll get some insights you never heard before in other meetings. If there’s good stuff, figure out how to get them involved in making the change happen.

6. Show up.

One-to-ones require two people to show up. Both of you have to be engaged. But this can be easier said than done.

  • As a manager: take some time to prep, don’t just show up empty handed. Look at what you discussed last time and what action items or commitments were made that you need to followup on. Alternately, consider sending out questions a few days before that you’d like them to consider and be ready to discuss.
  • As staff: be ready to chat, do some prep about the topics you want to discuss and let your manager know in advance. Feel free to drive the agenda – show up with a list of ideas about how you can make your role and the company better leverage you. Talk about the responsibilities you have and want, and suggest ways that your skills and the company’s needs can merge.

7. Show some candor.

“Build a culture centered around speaking the truth…[and] have their best interests at heart…[and] push them to being their better selves.”

Share what you know, be honest and open and forthcoming. Welcome candor in your discussions. People like that and it’s remarkably refreshing.

8. Listen.

Honestly. Just shut up and listen. As my colleague and Stuart McLean look-alike likes to say “you have two ears and a mouth, use them in the same proportion”.

If nothing is coming out that you can listen to, use silence to your advantage and wait – I guarantee you won’t be the one to break the silence.

9. Have some questions you can pull from when needed.

Have a list of potential questions at the ready. Use them to start discussions, encourage more forthcoming answers, or just to get over those “what else should I talk about” moments. Keep the questions open-ended, so you can draw out more details not just a “yes” or “no” that you’ll get from closed questions.

Here’s some of the questions I use (by no means exhaustive). You don’t have to do all of these every time. Pick some regulars, swap in others, consider the blind spots or places you want to know more about.

Questions that can tell you about their balance and satisfaction at work:

  • Describe your balance of client time and personal development time since we last met?
  • Are you doing the work that you love?
  • Are you doing what you enjoy?
  • What aspects of your job bring you joy?
  • What would you rather be spending more time doing?
  • How are you feeling about your work and workload?
  • How have you experienced our values recently?

Questions that can tell you what their focussed on right now and where they might need help:

  • What’s your focus right now?
  • What challenges are you facing?
  • Where are you stuck?
  • What have been some of your most difficult setbacks?
  • What is the business doing, or can be doing, to make you more successful?

Questions that can help you draw out accomplishments:

  • What’s going well? Any wins (big or small) this week?
  • What do you think you’re doing well?
  • What are your greatest achievements lately?
  • When was the last time someone said “thank you” for your work?

Questions that can give you insights into how they are feeling:

  • How are you feeling?
  • What thoughts are on your mind these days?
  • On a scale of 1–5, (with 5 being the best) how happy are you? Why?
  • What’s the best thing that happened to you this week, either at work or outside of it?
  • What has you excited?
  • What’s wearing you down?

Questions about career and learning plans:

  • Have you learned any new skills recently?
  • What could you learn that would make you more valuable to the team?
  • What have you done recently with your learning plan? (have them walk you though each of their plans/goals)
  • Where do you need help/support?
  • What’s are your planned activities for the next period to keep these goals moving forward?
  • What do you like most about your current role?
  • What do you like least about your current role?
  • What where do you see yourself in 5 years? 10 years?
  • How are you moving towards your career goals?
  • What do you want your next role to be?
  • What kind of capabilities/skills do you think you’d need to develop to achieve that role?
  • Where do you think you could make a greater impact?
  • What parts of our business intrigue you?
  • What do you want to learn more about?
  • What are some of your personal aspirations outside of your career?
  • What kinds of initiatives would you like to work on in your next assignment?
  • Why do you work at here? What keeps you coming in the door each day?
  • What important to you in your work and what you do?

Questions that can give you insights on what to improve:

  • What is one thing we aren’t currently doing, but could be doing to grow the business?
  • What’s one idea you have about improving the team/company?
  • What processes do you think could be fixed or improved? What’s stopping you from changing them?
  • If you owned the company, what’s one thing you would do differently?

Questions that can illicit feedback:

  • What were some great contributions made by other team members?
  • How would you improve on the way I work with you?
  • How would you like to see the two of us work together?
  • What should we cut back on? e.g., spending, meetings, etc.
  • What are some things I can do to make you more productive?
  • What was the last time you didn’t enjoy your job and what could have happened to make it better?

Another method I like to use is called “Stop, Start, Continue”. You can use this approach to either give or gather feedback.

Example when giving feedback:

  • You should stop doing…{insert thing}
  • You should start doing…{insert thing}
  • You should keep doing…{insert thing}

Example with seeking feedback:

  • What’s not working? (stop these things)
  • What do you need more of or where can I be of more help? (start these things)
  • What’s working? (continue these things)

I hope these ideas are helpful. Now go off and listen (then talk). If there are things that work for you, , I’d love to hear them!

Scott Baldwin

Written by

Dad, husband, ultrarunner, and drummer. By day: #prodmgmt #ux and other hashtags but I'd rather be in my shoes trail running.

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