1-1 Meeting Questions to help kickstart better conversations

1-1 meeting questions
At Friday, we believe 1-1 meetings are one of the most important activities a leader can do on a regular basis to understand what's going on at work. This regular feedback loop can be a wellspring of insights into what you can do to improve, as well as ways you can make work better (and more personalized) for each person on your team.

We believe the effectiveness of these 1-1 meetings hinges on two factors:

  • The employee setting the agenda & driving the meeting
  • Leaders asking the right questions to dig deeper

We've compiled this guide to highlight questions you can ask during your 1-1 meetings. Please treat this as inspiration, not prescription. The reality is that asking questions should not feel forced. It should be a natural part of your conversations.

Warmup questions: starting the conversation

Here are questions to help break the ice at the beginning of the meeting.

  1. How is everything going?
  2. How was your weekend?
  3. What would you like to talk about today?
  4. How should we kick things off?
  5. What did you think about ________?
  6. How did [recent event] go?

Questions about day-to-day work

Below are questions to help you understand the day-to-day work and how you can help.

  • How is [insert project name] going? Is there anything I can do to help?
  • Are you happy with your current workload?
  • Is there anything I can do to make your day a bit better?
  • What's the worst part about your job?
  • What's the best part about your job?
  • What gives you energy on a day-to-day basis?
  • What drains your energy on a regular basis?

Career-development questions

Career-related questions don't need to be asked on a weekly basis, that would feel weird. We recommend syncing up on career-related goals once a month/quarter. These tend to be a bit higher-level and strategic.

  • What would you like to be working on one year from now? 5 years?
  • Are you learning new things at work? How can we better support you in this?
  • Are there any training/classes you'd like to take?
  • Do you feel like you can grow in your career here at [company name]?
  • What are your long-term career goals?
  • What skillsets would you like to develop?
  • What do you think your next career move is?

Questions for team leader improvement

1-1 Meetings can be a wonderful way to uncover where you can improve as a leader. Here are some questions that you can ask to discover areas to improve. 

  • Are there any roadblocks that I can remove for you?
  • What is something I should start doing?
  • What is something I should keep doing?
  • What is something I should stop doing?
  • What is one thing I can do to make work better for you?
  • How do you think I handled [situation]?
  • I have an important decision I need to make about [topic]. How should I handle this?
  • If you could wave a magic wand and improve anything about how I work, what would it be?

Questions for team improvement

The next set of questions aims to discover ways to improve as a team (strengths, weaknesses, etc)

  • Who on our team is going above and beyond?
  • What is the biggest strength of our team?
  • What is the biggest weakness of our team?
  • What do we need to improve as a team?
  • How well do you think we are working as a team?
  • Do you think we are doing our best work as a team?

Questions for company improvement

  • Is there anything you wish you could change about our company?
  • Do you feel aligned with our company strategy?
  • What's the worst part about working here at [company]?
  • What's the best part about working here at [company]?
  • If you were the founder/CEO, what would you change about working here?
  • What is our achilles heel as a company?
  • What is the #1 strength we have as a company?
  • Do you feel connected to what others departments are working on?

Miscellaneous Questions

  • How are you feeling about your workload?
  • What's your favorite activity to do outside of work?
  • What's one interesting thing you've done outside of work recently?
  • What motivates you to come into work everyday?
  • Do you get excited to come into work?

Wrapping up

I hope these questions help you have better 1-1 meetings! If you'd like to learn how to hold more effective meetings, please visit our guide for employees and our guide for team leaders for more information.

Additionally, feel free to try out Friday. We make it easy to ask questions on a regular basis.