Gábor Till

about engineering leadership

One-on-one topics & questions

Cover Image for One-on-one topics & questions
Gábor Till
Gábor Till
14 min read

One-on-one meetings are one of the most important events you can attend with your direct report. These are the occasions when you can get to know the human side of them better and find out how you can help them to become a really effective team player. In this article, I will give you some specific topics and questions to ask, along with some other practical tips.

Before the meeting

You should know where you stand and how well you know them, so ask yourself frequently.

  1. Do I know them?
  2. What interests them?
  3. What motivates them?
  4. What gets them out of bed, and what keeps them in bed in the morning?

Calendar invite

Ideally, my direct report should own the calendar invite. This gesture gives them control over this meeting. I would like to also reinforce the feeling in them that they are an absolute priority for me.

Preparation

  1. Review the action items both for me and my direct report.
  2. Pick new questions that are relevant this week.
  3. Think of a specific phrase about something this person did.
  4. Send out the schedule.

General tips

  1. Free your mind from remembering everything by taking notes to capture the essence of the meeting.
  2. Start with your intent, like, “The reason I'm sharing this information with you is that I want you to be seen as a leader. This may be a blind spot that you don't see, and this is something that can help you.”
  3. Don't wait for a one-on-one to give feedback. Give it immediately.
  4. This is not a status update. It's about listening rather than managing.

During the meeting

Break the ice

  1. What's on your mind?
  2. What have you been thinking about lately?
  3. How is your week going?

Topics

The volume of topics below might suggest that you need to talk a lot in meetings, but in fact the opposite is true. Pick one question from a topic and let your direct report do the talking. Try to respond with follow-up questions, so you can go into more detail without you talking.

Short-Term Goals

Focus on things that can be done in the current quarter or month, with projects assigned to that person.

  1. How is the XYZ project going? What could we do to make better?
  2. Is there anything blocking you from getting your work done?
  3. Are there any projects you'd like to work on if you were given the opportunity?
  4. What parts of your job would you like to deepen your skills or get additional training in?
  5. Is any part of your project unclear or confusing?

This is all about getting feedback, so you can improve their day-to-day job and relieve frustrations on their projects. These are intentionally a short set of questions relative to other areas you usually spend a lot less time talking about.

Long-Term Goals

This is all about whom they want to become. Everyone is growing in different ways, and people are happiest when they feel they're making progress on their big life goals. These questions will help you learn what those goals are and see if they think they're making progress on them.

  1. What do you want to be doing in five years? Ten years? Three years?
  2. What are your long-term goals? Have you thought about them?
  3. Do you feel you're making progress on your big goals here? Why or why not?
  4. What's one thing we could do today to help you with your long-term goals?
  5. Do you feel we're helping you advance your career at a pace you would like?
  6. Who do you admire? Why? (People often admire those they want to become)
  7. If you had millions of dollars, what would you do every day?
  8. What are your superpowers? What powers would you like to develop?
  9. What are your big dreams in life? Are you making progress on them?
  10. Could you see yourself making progress on more of your goals here? What would need to change to do so?
  11. What work are you doing here that you feel most in line with your long-term goals?
  12. As a kid, what did you want to be when you grew up?

These questions will help you make sure your people are progressing in the areas that matter most to them. Realize that they will change over time, and it also takes time for people to open up about their dreams, so it helps to revisit them regularly.

Company Improvement

Asking questions about the development of the company can help you find out what people see at work. You can get great ideas for improving your company while asking follow-up questions to better understand them.

  1. What is the company not doing today that we should do to better compete in the market?
  2. What's one thing we'd be crazy not to do in the next quarter to improve our product?
  3. How could we change our team meetings to be more effective?
  4. If you were CEO, what's the first thing you'd change?
  5. Do you think our company is loyal to its employees? Why or why not?
  6. Are there any aspects of our culture you wish to change?
  7. What are your favourite parts of our culture?
  8. Do you feel overworked, underworked, or just the right workload?
  9. Why do you think [employee who recently quit] left? What did they tell you?
  10. What would convince you to leave for a job somewhere else?
  11. Which company values do you like the most? Which the least? Why?
  12. What is the #1 Problem at our company? Why?
  13. Do you feel like you're on the same page with your team? How often do you think you need meetings to ensure you stay that way?
  14. What do you think are the long-term prospects of the company?
  15. How many hours a day do you feel you're productive? How could we help you be more effective?
  16. How could we be more creative or innovative as a company?

You may not always like the answers you hear when you dig in for feedback like this, but that's the point. If you act on the things you can change and help your reports understand why some others are the way they are, you can help relieve a lot of frustration while making people feel heard.

Self-improvement

Creating a culture of learning and self-improvement starts with discussions to help people understand what they should do differently. By discussing them in private, you avoid embarrassing them in a more public setting and coach them through needed changes.

  1. Do you feel challenged at work? Are you learning new things?
  2. What area of the company would you like to learn more about?
  3. What skills would you like to develop now?
  4. Who in the company would you like to learn from? What do you want to learn?
  5. How do you prefer to receive feedback?
  6. Do you feel you're getting enough feedback?
  7. What's a recent situation you wish you handled differently? What would you change?
  8. What additional training or education would you like?
  9. Are there any roles in the company you'd like to learn more about?
  10. What do you think are the critical skills for your role? How would you rate yourself for each of them?
  11. Is there an aspect of your job you would like more help or coaching?

These questions will reveal ways to help people grow and improve them in their job. The key is to realize that the follow-up questions need to include action items and advice for assisting them in making progress on what you just discussed.

Manager Improvement

The saying goes, “People don't leave jobs. They leave managers.” That means receiving and getting feedback from your team members is a crucial part of your job.

Asking your team directly for feedback will help you improve and build the trust that you're as open to feedback as you want them to be. Set a good example with questions like these below.

  1. What could I do as a manager to make your work easier?
  2. What do you like about my management style? What do you dislike? What could I start or stop or continue to do?
  3. Would you like more or less direction from me on your work?
  4. What could I do to make you enjoy your work more?
  5. How can I better support you?
  6. What would you like to know about me?
  7. Is there a situation you'd like my help with?
  8. What is something I could do better? What is the criticism you have for me?
  9. What are the things you need from a manager?
  10. What can I do to be a better manager for you?
  11. How can I be a better manager for you specifically?
  12. Is there anything I can do to help you with your work?

When your reports dare to give you hones feedback, make sure you fully understand it and thank them. It can be scary to say something negative to their manager. If you don't follow through on the feedback, you will lose their trust, and they may start to resent you.

Happiness

Whether it's a work-related issue or a personal one, happiness will significantly impact productivity and morale at work. One-on-one is the best time to dig into any issues affecting them and do things to help.

  1. Are you happy?
  2. Are you happy working here?
  3. Are you happy with your recent work? Why or why not?
  4. What would make you leave this job for another?
  5. What's one thing we do to help you enjoy your job more?
  6. Is your job what you expected when you accepted it?
  7. What worries you?
  8. What's on your mind?
  9. What's not fun about working here? What do you enjoy most about working here?
  10. Who are your friends at work? (Shown to be a key to enjoying your job)
  11. When was the time you enjoyed working here the most?
  12. What do you feel is your greatest accomplishment here?
  13. What do you feel is undervalued that you contribute to the team?
  14. What part of your job do you wish you didn't have to do?

These can be the most challenging issues. If someone is unhappy, they may be reticent, so do your best to give them space and listen carefully. If you help them, you can persuade an employee to stay who might otherwise want to leave.

Personal Life

Your employees are one complete person. No matter how much you'd like them to, problems in their personal life will affect them at work. You don't need to be their therapist, but a little empathy can go a long way with these kinds of questions.

  1. How are you? How is life outside of work?
  2. How do you feel your work/life balance is nowadays?
  3. How do you feel about your current compensation (salary and benefits)?
  4. What's one thing we could change about work for you that would improve your personal life?
  5. Around a holiday: What did you do for the holiday? How was it?
  6. How are your parents/grandparents? Where do they live?
  7. If they have children: How is [name of child] doing? (Ask something related to their age like starting school, playing sports, or other interests.)
  8. What do you like to do in your leisure time? What are your hobbies?
  9. What did you do for fun in the past that you haven't had as much time for lately?
  10. What drives you? What motivates you to come to work each day?

These questions can help you better understand people's motivations and interests. Empathizing with situations like a divorce, sick parent or grandparent, a death in the family, or positive moments like children, a successful side project, or fun activity can all go a long way towards building great rapport for your team. It can also inspire inexpensive ways to thank a team member.

Team Relations

Your team spends 8+ hours a day working together. One of the opportunities for productivity improvement comes from strengthening the interpersonal relationships among team members. Questions like these help uncover problems and opportunities to help every person become a better team member.

  1. Who on the team do you have the most difficulty working with? Why?
  2. How would you describe the work environment on the team? Is it more competitive or collaborative?
  3. How can we improve the cooperation of our team?
  4. Who is kicking ass on the team? What have they done?
  5. Who do you admire on the team? Why?
  6. Do you feel the team and I hear your ideas?
  7. Who would you like to work more often with? Why?
  8. Is everyone in the team doing their part?
  9. Do you help other members of the team? Do others help you when you need it?
  10. What is the one thing we should change in the way our team works together?
  11. What characteristics make someone a good fit for our team? How would you look for those characteristics in an interview?
  12. What's the biggest thing you'd like to change about our team?
  13. What do you like most about working on our team?
  14. Have you ever felt uncomfortable in a team? What happened?

One-on-ones are a great time to coach people on issues with co-workers. You can also use them to uncover problems in your team before they become a big deal.

Work Habits

The more you can learn and understand how each team member operates; the more productive they can become. These questions can help you work with them to realize their work habits.

  1. What part of the day do you have the most energy and focus? When do you have the least? What changes could we make to your work schedule to accommodate this?
  2. What are three things would you buy to improve your productivity if money was no object?
  3. What is a perfect, productive day at work for you? Could you walk me through the day?
  4. What's an inexpensive thing we could do to improve our office environment?
  5. What are the biggest time wasters for you each week?
  6. What makes you excited and motivated to work on a project?
  7. When you get stuck on something, what is your process for getting unstuck? Who do you turn to for help?
  8. What part of your work routine do you find is working best? What area do you want to improve?
  9. Are there any meetings or discussions you feel you should be a part of that you're not? Are you included in any you prefer not to be a part of?
  10. What do you do when you feel low energy or unmotivated?
  11. How can I help you be more productive/happier at work/enjoy work more/etc.?

Often the best ideas come from people working in the field. While you are in meetings, fuss around the office or travelling, they are likely to see things in the office that have a big impact on their productivity (for better or worse). Making changes can have a big impact on team performance.

Career development

Monthly
  1. What skills do you want to work on this short-term?
  2. Is there anyone you want to shadow?
  3. How did your last XYZ go?
Quarterly

Where do you want to be in one year? Where do you want to be in 5-years? What are your career aspirations? How can I achieve those aspirations? What roles or skills do you want to explore?

Questions to ask every one-on-one

None of the things you talk about in one-on-ones matter if you don't follow through and act on them. These two questions will ensure you always follow through with the critical things you discuss in your one-on-ones:

  1. What can I hold you accountable for next time we talk?
  2. What can I be accountable to you for the next time we talk?

Coaching

Something magical happens when somebody thinks that it's their idea. There is so much more willing to take action.

  1. What have you tried so far?
  2. What direction do you want to try next?
  3. What has worked in the past for you?
  4. What hasn't worked?
  5. Where do you want to go next with this?
  6. What is the outcome you're looking for?
  7. What are some pitfalls you can run into?
  8. Why is that?
  9. How do you want me to support you with this?
  10. How do you want me to follow up with you?

Wrap-up

Specific praise

It is essential to end the meeting on a positive note. Mention something your direct report did well and add that it impressed you, and keep up the great work.

Follow up for next time

Repeat the agreed action items for both of you.

After the meeting

Just like the calendar invite, your reports should own the notes. Right after your meeting, share it with them. It will be a friendly reminder of all the things you have discussed, and they can add notes for themselves in the document.

I like to keep a copy of my notes, so I can always go back and check something if needed.

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