Maximizing Connection: 25 Powerful Questions for Meaningful One-on-One Meetings

Team engagement and performance improve when we take the time to ask important questions.

One-on-one meetings give team leaders and team members time to connect personally and talk privately about their hopes or concerns at work. At least, that’s what they’re supposed to do. Unfortunately, for many teams, one-on-ones are a boring obligation neither party enjoys.

Cisco studied engagement in over 15,000 teams and found that well-designed one-on-ones based on just two questions reliably boosted employee engagement and team performance.

What are your priorities this week?
How can I help?

At Cisco, team members write the answers to these questions and send them to their team leader. The team leader then responds, ideally in a weekly one-on-one conversation that becomes core to their relationship.

These two questions do a great job getting the conversation started. They create an excellent foundation when you want to drive scalable, repeatable performance–and given Cisco’s over-15,000 teams, you can bet they make scalable performance a priority.

That doesn’t mean, however, that these two questions are all you can or should talk about.

Why You Should Ask More Questions

I was watching Amy Edmondson, the Novartis Professor of Leadership at Harvard Business School, speak about her pioneering research into high-performing teams. She found that teams enjoying psychological safety (a term she coined) outperform others. She explained that you can tell psychological safety exists when team members feel they can raise concerns, risks, and point out errors without fear of retribution.

Many people feel like they can’t bring up risky topics at work, and often this has nothing to do with a realistic fear of punishment. People who work in places where they say “no one ever gets fired” may never speak up simply because no one else does.

More importantly, no one asks them to.

If you are fortunate enough to have time dedicated to meeting one-on-one with your colleague, seize that opportunity. Ask questions that make talking openly about your team’s hopes, fears, and “so crazy it just might work!” ideas the new normal.

Here are 25 questions team leaders and team members can ask that make your one-on-one time more valuable.

Questions Leaders Might Ask

To learn what’s working well so you and your team can do more of that:

What do you feel best about in the work we’re doing?
How can we set each other up for success?
When did you recently get an opportunity to learn and grow? How can we create more of those?
Have you seen someone else doing something you felt worked really well? What was it?

To learn how you can best support your team member:

What should I know about you that would help me support you better?
What are you doing here that you feel is most in line with your long-term goals?
What are you doing here that you wish you could set aside so you can concentrate on your most important work?
Is anything holding you back from doing the best work you can do right now?

To invite questions and feedback about working with you:

If you were coaching me to have a greater positive impact, what would you tell me?
What can I tell you about myself that might make it easier to understand me and work with me?

To invite ideas for improvement:

Is there any part of the company you wish you interacted with more?
Have you seen something recently and thought to yourself ‘I wish we’d done that’?
Is there something outside your current role where you feel you could be contributing?
What rules should we be breaking?

Questions Team Members Might Ask

To learn more about the leader’s perspective on work:

What was your career path?
What would you love to be true in how this team works together?

Questions Anyone Can Ask

These are questions managers might typically ask, but this is one meeting team members should try to drive. Besides, just because one person has the job title, that doesn’t mean they’re naturally gifted leaders when it comes to this part of the job.

Whether you’re the manager or the team member, you can take the lead by asking these questions.

About the work:

What’s become apparent since we last met?
What vibrations (news, rumors, dynamics) are you picking up that you think I should know about?
What’s our biggest miss, and how do we resolve it?
What do we need to do today to pull ahead of our competition?
What do you feel is our biggest risk right now, and what’s the plan if that happens?

About your working relationship:

Is there anything at all about which you are curious, wondering, anxious, or concerned about in regard to working with me?
Are there other conversations we should be having?

And because the teams doing the best work are full of people who trust each other, care for each other, and enjoy an above-average level of being treated like a human being at work: