GUIDE: Lead Better One-on-Ones

December 27, 2021

Great 1:1s can transform the relationship between a leader and their team.

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Part of this post was originally published a few years ago on the NOBL Collective blog, an organizational design team whose work and leadership I greatly respect. I’ve remixed and added to this version, turning it into a guide for people-managers.

Leading effective 1:1 meetings is far too often a mystery to people leaders. We know we should have regular check-ins with our team, but we often deprioritize this rhythm.

Reasons I’ve heard for avoiding or neglecting 1-on-1s:

  • “I already talk to my team regularly on Slack. I know project status via our stand-up meetings. Why do I need to spend more time one on one?”
  • “This is so time consuming — I have a big team!”
  • “What would we talk about? I don’t know how to take the conversation beyond project updates…”

I get it, but I don’t buy it.

The teammates we manage—or develop, as I prefer to think of it—often crave a consistent opportunity to discuss their work, get feedback, and explore ways to grow. We’re more effective leaders when we deepen relationships with our teams.

There are several simple ways to get from good to great 1-on-1s.

Three ways managers can level up 1:1s

1. Create a framework for 1:1s

This time goes beyond a simple status check on current projects. Ask your team member to drive the agenda: they should show up prepared with questions, concerns and ideas. This empowers them to own the meeting as “their” time. Your job is to ask great questions and take notes on key learnings. The meeting can be split into two parts:

  • GET IT DONE — The first part is pragmatic. Ask questions like, “What big rocks are you facing right now?” or “May I provide some feedback on your client pitch last Tuesday?” This time also allows your team member to discuss obstacles and big updates on projects.
  • THE BIG PICTURE — The second part covers work well-being. You can prompt the discussion by asking, “Do you feel like you’re growing in role right now?” or “What can we provide to make you excited to walk into the office each day?” or “What do I do that helps you? What can I do less of?” Below are a couple dozen options for asking big picture questions.

2. Make 1:1s a priority

Build trust with your team by treating 1:1s as fixed, untouchable time on your calendar. This time is sacred. Only reschedule when it’s absolutely unavoidable. Weekly or biweekly meetings is an ideal cadence.

3. Track 1:1 key learnings over time

Keep high-level, bullet-point style notes after each 1:1. I can hear you objecting from here. “What?! Me, as the manager — I have to keep notes?” Yes. I think the most effective people-leaders take intentional, consistent action to grow their teams, which includes tracking and understanding the big picture of an employee’s growth path.

Review your notes prior to each 1:1 to make sure you’re supporting requests and checking off action items.

Questions for Better 1:1s

Open-ended, provocative, and creative questions are the secret weapon for impactful one-on-ones. If you pick one question from the list below to ask at every 1:1 that you run starting today, your relationships with your team will deepen. (I offer a 100% satisfaction, money-back guarantee on that!)


  • What could I do immediately to make your job easier? What about my job would help lighten your workload?
  • Where are you experiencing resistance? What’s at stake if you ignore it?
  • What are you optimizing for in your day to day work?
  • What, if anything, is going unsaid in your projects/goals?
  • What’s the most likely outcome? What’s the worst outcome?
  • What help could you most use that you haven’t asked for?
  • What should our team be doing differently that could lead to 10x improvement?


  • What’s the first job you had, that’s not on your resume, and what did you learn from that experience?
  • What is the shortest path to [the X thing you want]?
  • What do you want to achieve with your career?
  • Without using the title of your job, tell me what you do.
  • What is a secret skill of yours? (Or – What is a hidden talent that’s being underutilized in your work?)
  • Imagine yourself in three years. What do you hope will be different about you then compared to now?
  • Think about your ideal next role. What are its characteristics — including responsibility, team, and company culture perspective? What characteristics does it not have?
  • What is something you’ve learned from one of your teammates recently?


  • What is your favorite compliment of all the compliments you’ve ever received?
  • If I could free up time for you to do anything, what would you do with that free time (personally or professionally)?
  • What’s something that would surprise me (or teammates) about your day-to-day?
  • What’s something new you’ve learned about yourself in the last three months?
  • What’s a misconception I (or teammates) have about you?
  • What are you looking forward to right now (personally or professionally)?
  • When was the last time you were out of your comfort zone?
  • If there was a global competition with three ‘feats’ to pass, what would be the three things that you would win at above anyone else in the world?
  • What has surprised or delighted you lately?
  • What was the last thing you nerded out on?
  • In your life, who has influenced your leadership the most? How might you bring that influence to this team?
  • Who was the last person you felt inspired by?
  • What small gesture from a stranger made a big impact on you?
  • What experience are you really glad you had, that you are also glad is over?
  • What is something you love doing that you’re terrible at? What about something you really do not like doing that you’re great at?
  • If you could devote a year to researching someone’s biography, who would you study?

Great 1:1s have the power to transform a relationship between an employee and a manager. And by transforming individual relationships we transform the very nature of our work.

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