Level up your one-on-ones with these 31 questions

Want to listen and connect more deeply with your direct reports? Keep this list handy!

Today I want to explore one of the most powerful tools in any leader’s toolkit: the one-on-one meeting.

How you handle regular meetings with your direct reports can make or break your business. They’re vital if you want to:

  • Keep projects and initiatives on schedule
  • Engage your team in your overall mission
  • Spot issues and fix them early
  • Find untapped opportunities and new ideas
  • Identify and develop future leaders
  • Retain your top talent

But a lot of managers don’t fully understand how to use their one-on-one chats. They see those meetings as a burden on their schedule. They show up with no real plan or agenda. Or they just offer critiques and commentary instead of asking questions and listening for insights.

So in this edition of Insiders, I want to break down the five key objectives that one-on-one meetings can help you accomplish. Then, I want to give you a list of questions for each area to help you get more out of every conversation.

One quick caveat: I’m going to list LOTS of questions for you to consider. Not all of them will work for you, nor should you try to just cram a bunch of rapidfire questions into your next one-on-one. Your employee may think they’ve stepped into an interrogation instead! 

But as you prepare for meetings with direct reports, keep this list handy. Reference it often. It will help you ask better questions and listen more thoughtfully.

And that’s key to creating the kind of trust and dialogue you need to drive your business forward, one conversation at a time.

Ready? Let’s get started.

Staying clear on goals and priorities

One of the primary purposes of one-on-one meetings is to help you and your team stay aligned on objectives.

These conversations are the perfect setting to create accountability and track progress toward big goals. You can also talk through roadblocks and make adjustments when circumstances change.

Best of all, each team member can see how their individual work contributes to the overall mission.

Here are some questions you can ask to prompt healthy conversations about goals and priorities:

  • What are your top priorities right now, and how can I support you in achieving them?
  • Are you waiting on me for anything?
  • What obstacles or challenges are making work harder than it needs to be?
  • Are there any long-term strategic goals that you feel may be getting overshadowed by more immediate tasks?
  • Are there any competing priorities or conflicting demands on your time that we need to address?

Featured Insight: Explain how short term goals ladder up to long term vision >> Evan Spiegel

Optimizing performance

Your one-on-one meetings are a great way to make sure everyone’s at their best. 

Every team member faces unique day-to-day challenges. There are always issues and questions about processes, people, and strategy. If you want to know what they are—and how you can resolve them—then you’ve got to ask the right questions.

Try these prompts so you can use your one-on-one meetings to optimize performance:

  • How’s your workload right now?
  • What tasks in your current workload feel like they’re a waste of time?
  • What communication or collaboration challenges are you experiencing with colleagues?
  • What is our team’s biggest strength?
  • What is our team’s biggest liability?
  • If you could snap your fingers and fix one thing on our team right now, what would it be?
  • What would you do if you had my job?
  • What about [Project XYX] isn’t working well? (Thanks to Frank Blake for this one!)
  • If you were in charge, what's one thing you would change?

Featured Insight: One question to boost honest feedback >> Frank Blake

Keeping an open line of communication

Sometimes, in the daily grind, it can be hard to find space for more difficult or honest conversations with team members. That’s yet another powerful reason to prioritize your one-on-one meetings.

Set the expectation that your one-on-ones are a place where it’s safe to both give and receive feedback. Set an example of honesty and vulnerability. When you’re intentional about feedback and communication, you create a culture where people are more likely to share what really matters. 

Here are a few prompts that might help you keep that open line of communication:

  • How can I get better at giving you feedback in the way you prefer?
  • How do you feel about the level of autonomy you have in your role?
  • What’s something you did this week that you’re really proud of?
  • What tough lesson are you learning right now?
  • What are my blind spots?
  • What’s one thing about your job that you wish everyone in this organization understood?

Featured Insight: Embrace constructive confrontation >> Ken Chenault 

Creating a path of development

One of the top reasons people leave their job is not feeling like they have a path forward in their organization. (We’ve talked about that before here on Insiders!) 

Devote time in your one-on-one meetings to understanding your team members’ goals for professional growth. It’s how you can make sure your best talent grows as your organization does.

These questions can help you spark great conversations about career growth and development in your one-on-one meetings:

  • What areas of the business are you interested in learning more about?
  • What skill or training would you most want in order to do your job better?
  • What are your long-term career aspirations?
  • What’s a strength of yours that you wish you got to tap into more often here?
  • If I gave you two weeks to work on anything you wanted here, what would you do?

Featured Insight: Create development plans for your people >> Carol Tomé

Making a personal connection

I always say that people don’t care how much you know until they know how much you care. Leave space in your one-on-one meetings to get to know what your team members enjoy and what really makes them tick.

Here are some simple prompts to help you make a personal connection:

  • How’s everything outside of work?
  • How are you thinking about work-life balance these days?
  • What motivates you to excel?
  • What do you enjoy most about the work you do? What do you enjoy the least?
  • What’s a book, podcast, or TV show that you’ve gotten into lately?

Featured Insight: Show your team you care about them >> John Calipari 

With just a little bit of intentionality, preparation, and creativity, you can make one-on-ones a powerful force of growth and development in your organization.

I hope these categories and their corresponding questions have gotten your wheels spinning about how to do just that. 

Of course, you can’t JUST ask questions in your one-on-ones. There will always be specific notes and feedback you need to bring up, too. 

But I hope you’re feeling inspired to devote more of your meeting time to listening and coaching and less of it to directing and correcting. 

Now, it’s your turn. What are the major topics and themes in your one-on-ones? What has your experience taught you about how to make that time effective?