Preparation is key to having a productive conversation. Whether you’re a first-time manager or you’re a one-on-one veteran, it doesn’t hurt to be prepared. Use this checklist to keep your one-on-one meeting relevant, organized, and meaningful.

One-on-one meeting checklist

1. Create a recurring schedule and set the context

• Discuss the importance of one-on-ones with your direct reports.
• Let your direct reports co-create and own the agenda of the meeting.
• Set up a weekly, bi-weekly, or fortnightly cadence for 30 to 60 minutes. What’s important is to maintain the frequency.
• Agree on a broad structure that is flexible and allows room for deviation.
• Decide on where you will meet. (E.g.: conference room, Zoom, etc).

2. Prep for the meeting in advance

• Go over the agenda shared by the employee (typically a day before the call).
• Note down any achievements that should be commended or any feedback you might want to deliver. Consider taking some time out to phrase the feedback.

3. Create a comfortable space to have the one-on-one

• Be punctual and kind. Remind the employee that this is a safe space and encourage them to communicate openly.
• Stay present and engaged. Avoid distractions and make the person feel like they are the priority.
• Avoid shifting the conversation to yourself - ask open-ended questions that might encourage the individual to be more candid.
• Take notes so you can raise appropriate action items and follow up in future one-on-ones. 

4. Be mindful during the meeting

• Ask about their general well-being and do an overall work check-in.
• Confirm that the agenda is as planned.
• Circle back on the previous one-on-one’s action points and learnings.
• Discuss key highlights of the week and acknowledge wins.
• Ask about their wellbeing, growth and learning, and work relationships.
• Get feedback on your role as a manager.

5. Round up the one-on-one

• Do a quick summary of the meeting and mention the action points to be discussed in the next one-on-one.
• Reflect on how the meeting went and if there’s something you should take over to the next meeting.

Quick tips for remote teams

• On one-on-ones with remote teams, ask about their productivity levels (do they feel productive at work?), wellbeing (how are they pacing themselves when working from home?), and connectivity (do they feel connected to the team and the company?)
• Try to replicate an actual in-person meeting. Ask your team to switch on their videos and work with your People Ops team to ensure remote workplaces are set up well.

One-on-one meeting templates

Depending on who you are meeting with and the goal of the conversation, you might want to ask different questions. We’ve compiled here a template of questions for different scenarios. For more templates, check out our blog post that covers what questions great managers ask people in one-on-ones.

General check-in

Goal: To build a relationship, celebrate wins, and resolve issues.

1. How are you feeling this week? What are you most excited or worried about? 
2. How did your past week/month go?
3. What immediate questions or concerns do you have?
4. Are there any roadblocks for you at work? How can I help?
5. What went well with the team recently? Who supported you? What are you thankful for?
6. How are you feeling about your job overall?
7. How would you describe your current mindset?
8. What does your daily routine look like?
9. On a scale of one to YouTube cat videos, how productive were you at work this week?
10. On a scale of 1 to 10, how valued do you feel at work?

First one-on-one with a new joinee

Goal: Lay the groundwork for a collaborative relationship and future one-on-ones.

1. How did your first week/month go?
2. What are your greatest superpowers/strengths?
3. How do you like feedback - scheduled in 1:1s, or as-it-happens?
4. Let’s talk about the team and how we work.
5. Are there tools your colleagues use that you don’t know how to use or have access to?
6. What new skills would you like to develop?
7. What could you teach others from your last professional development experience?
8. Is there anyone in our organization you’d like as a mentor?
9. What training do we offer internally that could help you in your development?
10. What kind of support do you need to achieve your goals?

Goal-setting one-on-one

Goal: Collaborate on a list of OKRs and follow up on these in subsequent one-on-ones.

1. What has been your progress on the OKRs we had set?
2. Is there anything on your plate that is not in line with your short-term goals?
3. What circumstances helped or hindered you in meeting your goals this month/quarter?
4. A year from now, what do you want to have accomplished?
5. Is there anything I can do to help you improve your day-to-day tasks?
6. What accomplishment are you most proud of so far this year/quarter?
7. How will you measure or track your progress on your goals?
8. What professional development opportunities are most in line with your long-term goals?
9. What is one skill that is hard for you that you could work on?
10. As things stand, do you think you will be able to achieve your goal? Why?

Career development

Goal: For employee development.

1. If you were not a <role>, what would you like to be?
2. Do you feel like you’re learning and growing at work?
3. What opportunities for advancement are you interested in?
4. What’s a project that you’re proud of? What other project would you like to work next?
5. What other areas of the company do you want to learn about?
6. What is a recent situation you wish you had handled differently? What would you have changed?
7. How would you like to use your strengths in the future?
8. How would you like to make a bigger difference?
9. What rewards and recognition matter most to you?
10. What knowledge and skills do you need to get to the next stage of your career?

Job satisfaction

Goal: To check the level of employee engagement.

1. I’ve noticed that you’re feeling a little <adjective> than usual. Is there anything you want to talk about?
2. Are you liking work? Do you enjoy working here?
3. Is there anything you’d like to do that you feel that you don’t have the time for?
4. Do you feel like you have a good work-life balance?
5. What things about this company, presently or in the future, would lead you to see yourself somewhere else?
6. Do you feel connected to your teammates?
7. How transparent do you feel the management is?
8. Do you think that work is distributed evenly across your team?
9. Do you get company news in a timely manner?
10. How open to change are we as an organization?

Feedback and coaching

Goal: To get upward feedback.

1. How can I make work easier for you?
2. Which skills would you like to continue working on?
3. What can we do to improve our 1:1s?
4. Are there any areas of work where you need more/less direction from me?
5. Are there any resources you need help with?
6. What are three actions you can take that would make sense this week?
7. What can I do to help you be more effective and engaged?
8. What areas are you struggling with in managing your team?
9. What ideas do you have on growing as a manager?
10. What do you like/dislike about my management style?

Company growth

Goal: To get insights on how to improve the company.

1. How do you think the team is working together? What can we do better?
2. What do you feel about the company’s future? Why?
3. What do you love the most about our product/service? What is your least favorite feature?
4. Is there any opportunity you feel that the company should capitalize on?
5. Do you have questions about the company’s strategy?
6. If you could change one thing about our company, what would it be?
7. How do you feel about our company culture?
8. What is fun/not fun about working here?
9. What could be improved in your work environment to help you produce high-quality work more efficiently?
10. Are there company values that resonate better or worse with you?

Want to know how to build a one-on-one culture that empowers your teams to do their best work while driving consistent and structured coaching conversations? Book a free demo with Mesh today. 

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