Crank Your 1-on-1’s Up to Eleven

Make Deeper Connections by Getting a Little Bit Awkward at Your 1:1 Meetings

Catalyzing high-performance teams means more than just working with the right people.

It’s more than skill and attitude.

These days, more than ever, we need to build and nurture resilience.

That means getting to know each individual more deeply than we did yesterday.

One on ones are all about your people and building a strong, trusting relationship with them. Share on X

While there are plenty of team activities that help – e.q., see Super Powers Team Retro or if you’re really daring Fear and Vulnerability Team Retro

I posit that utilizing the artful 1:1 is often neglected. And I suspect for many, their 1:1’s have turned into a (yawn) status report.

As Mark Rabkin wrote: … “If it’s not a bit awkward, you’re not talking about the real stuff.”

Rebooting Your 1:1’s

Pretend It’s the First One

Years ago Lara Hogan shared a really great list she titled “Questions for our First 1:1

It started with:


  • What makes you grumpy?
  • How will I know when you’re grumpy?
  • How can I help you when you’re grumpy?

In these days of back-to-back zoom meetings, how nice would it be for both of you to know the answers to those three questions?

More Good Stuff to Know on “Day One”

Lara’s 1:1 list goes on to cover

  • Feedback and Recognition
  • Goals and Support
  • The Most Important Question: What’s your favorite way to treat yourself?

But Wait, There’s More!

Jason Evanish piles on with the value of good one on ones:

“One on ones are all about your people and building a strong, trusting relationship with them.”

He has been collecting and organizing his favorite 1:1 questions into the following categories:

  • Short Term Goals
  • Long Term Goals
  • Company Improvement
  • Self Improvement
  • Manager Improvement
  • Happiness
  • Personal Life
  • Team Relations
  • Work Habits

And he’s shared them all via his list of 101 questions for 1-on-1 meetings.

If it’s not a bit awkward, you’re not talking about the real stuff. Share on X

The Random 1:1 Question Selector

To make Jason’s extensive list fun and easy to use, Marc Chapman served things up via a random three 1:1 question selector.

Why not bookmark 1-on-1 question generator and give it a spin at the start of your second 1-on-1!

The Most Important 1:1 Question: What’s your favorite way to treat yourself? Share on X

Mindfulness Hacks for Your 1-on-1 Conversations

Ready to take things up another notch?

My wonderful friends at changehacks created a deck of physical cards that they called “ponderfy.” ​

The cards are more than just conversation starters – they are mindfulness hacks.

Early lock-down, I assembled them online at to make ’em 1:1 conversation starters.

I use them to encourage my colleagues and myself to pause and think about what we’ve accomplished, how we perceive the world around us, and what we have the potential to achieve. Wonderful topics for any 1-on-1, don’t ya think?

Don’t Waste Your Next 1 on 1 Meeting

Don’t make your next 1:1 a status update – #ShouldHaveBeenAnEmail – or worse….

This post is dedicated to the great and amazing Bazoo

Read/Listen More

Great podcast from Radical Candor on how to get feedback at your 1:1’s:

Podcast Season 3, Mini Episode 5: How to Get Feedback

Forming Stronger Bonds with People at Work (HBR) by Monica C. Worline, Jane E. Dutton, and Ashley E. Hardin

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