March 28, 2021

1:1 Conversation Ideas

A look at some conversation ideas that you can use in your next 1:1 session

1:1 Conversation Ideas

Running an effective 1:1 can be quite difficult and at times you may feel like you have nothing to talk about. I regularly search the internet for some conversation ideas and below are some of them that I have accumulated over the years.

Opening Questions

The point of this is to learn about the individual and give them the opportunity to say anything that is on their mind or to see if they want to direct the conversation in a particular direction.

  • What did you get up to on the weekend?
  • What would you like to kick off with?
  • What's something I should know, but don't?
  • How things going on at home/with the family?
    Note: Write down their family members name's, it just makes it more personal
  • How is (Child) doing? (If they have children)
  • Who do you really admire? Why? (People often admire those they want to become)
  • What has been going on for you this past week?
  • Where is your family from? How are they doing?
  • Is there anything on your mind you want to talk about?
  • What can I do that will make your day/week better?
  • What is something different you have been doing lately?
  • What do you want us to focus on in this meeting?
  • (Christmas/Easter/Holidays) Do you have anything planned for (Holiday)?
  • What do you in your spare time/hobbies?
  • Do you have any personal project? How are they going?


These questions tend to focus on the other person, so you can learn more about them and find out what you can do to help them

  • What are your hobbies that you do to relax?
  • What do you feel your greatest accomplishment is personally? And at the company?
  • Are you feeling fatigued or worn down?
  • Are there any areas that you are looking for feedback on?
  • Do you feel like you receive enough feedback? When do you feel like you got valuable feedback? When do you feel you got bad feedback?
  • Are there any items hindering you on achieving your goals?
  • What skills do you have that you think are underutilized?
  • How are things going for you outside of work?
  • What else can I do to help you advance in your career?
  • What are the biggest time wasters for you each week?
  • Do you feel comfortable/stretched/stressed in your current work?
  • What did you want to be when you grew up?
  • How is your current work helping or hurting your professional development?
  • Have you ever felt undervalued at work?
  • In a typical day, how many hours do you feel you are productive? What can we change to make that better?
  • Do you have any personal projects you are proud of?
  • How do you feel you are coping with your current workload?
  • Which part of the day do you feel most productive? What can we change to make you work best?
  • Is there any training that you would like to attend to grow your skill set?
  • How do you feel your work/life balance is?
  • Are there any projects you would really like to work on if you had the choice?
  • What are your current goals that you are aiming for?
  • Who in the company would you like to work with? What do you want to learn?
  • Are there any areas of your job that you would like coaching/mentoring with?
  • What motivates you to do the work that you do?
  • What sort of progress have you made since our last catchup?
  • Are you happy with your recent work? Why?
  • Who in the company do you admire? Why?
  • Are you being the best you that you can be?


As with the personal questions, the team questions are there to help see if there are any issues within the team and what you can do to help them.

  • What sort of overall personality would describe your team?
  • Are there any aspects of your team culture you wish you could change?
  • Do you feel your team gets constructive feedback?
  • Has anyone on the team ever made you feel uncomfortable? If so, what happened?
  • I’ve noticed X about the project. Can you help me understand that better?
  • Do you feel like you’re on the same page with the team? If not, why?
  • Is there anything slowing you down and preventing you from being your most effective?
  • Do you think that your team is working as effectively as they can?
  • Do you feel that your team works well together?
  • Who in the team has been doing an excellent job lately? What have they done?
  • Do you feel that you communicate well as a team? If not, why?
  • Do you feel you can give any of your peer's constructive criticism? If not, why?
  • What worries you most about the team?
  • Are there any meetings you feel you should be a part of that you’re not? Conversely, are you included in any you don’t want to be a part of?
  • Do you feel you are psychologically safe in the team? If not, why?
  • Who in the team would you not like to work more again? Why?
  • Who in the team would you like to work more again? Why?
  • Looking back, how could we have improved X for the team?
  • How could we change our team meetings to be more effective?
  • Do you feel that there is any division within the team, including any client staff?
  • Is there anyone in your team that you find it difficult to work with? Why?
  • If there was one thing you could change about the team, what would it be and why?
  • What attribute do you feel you add to the team?
  • Is there anyone on the team that you feel isn't pulling their weight?


These questions are nice to ask every few months, or whenever a major change happens, to gauge how the people are feeling about the company.

  • What is the biggest concern you have about the company?
  • What could we do to make the company more creative and innovative?
  • What part of the townhall/lighthouse do you think provides little value?
  • How is the new situation/development affecting your work? What could be getting in the way of your being effective?
  • What is an inexpensive change that we could do to the office to improve it?
  • What is your feeling on the company's future overall? Why do you say that?
  • How are you feeling about the latest news that was announced?
  • If you could improve the company in one way, what would it be?
  • What part of the lighthouse do you find most beneficial?

Leadership & 1:1s

Lastly, 1:1's are meant to be a two-way street, so this is an opportunity for you to find out how you could be doing better.

  • What would you like to know about me?
  • I'd like to improve as well, so for our next meeting could you share some feedback on one thing I could do better?
  • At what point in the past week were you most frustrated with or discouraged by your work? What can I do to help you manage that?
  • What can I do to make things easier for you?
  • What have your past mentors done that you’d like me to also do or not do?
  • What would you like me to stop, start, or continue doing?
  • What are your impressions of our 1:1s? What could we do differently or better?

Until next time...keep learning!