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One-On-One Meeting Template: Top 10 Questions to Ask

Tips on standard one-on-one meeting questions. Plus, other questions to sometimes use for deeper conversations.

One-On-One Meeting Template: Top 10 Questions to Ask
Rob Lennon
Customer Education Lead at Hugo
Marketer and author with 18 years experience in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

A lot of people wonder how to prepare for a one on one meeting. In particular, this boils down to one big question—the question of all questions, you might say.

What are the most important questions to ask in a one-on-one meeting?

Because one-on-one's aren't about sitting someone down to lecture them for half an hour. They're supposed to be meetings where managers and their direct reports open up about how the work is going, and how they can help each other make it go even better.

“What often fails to be appreciated by everybody is just how significant an act of leadership it is, simply to give somebody your undivided attention for a while.”
― Nick Robinson, Great One-on-One Meetings for Busy Managers

So, in this post, I will be going over what you should consider as the most important questions to ask during a one-on-one meeting. Each of these are strategic questions that you should consider asking employees to get the most out of your meeting.

Ultimately, the best business relationships are built on trust. The best way to build trust with your co-workers is to understand their needs and concerns and how you can provide them with the best solutions you can offer.

In this article:

Basic questions to ask in every one-on-one:

What's new in your world?
While this may be the most basic question you can ask, it's often one of the best ways to kick off a meeting. When someone asks you this, they're not asking what's new with your business or how your day is going. They're asking about the things that are taking up your attention at work, which are probably different from last week.

What are you feeling good about?
If someone feels good about something, you want to ask them about it. That's because it's much easier to build on strengths than it is to fix weaknesses. This is also an opportunity to ask questions about things that are not going well.

What are you stuck on?
This is a great one-on-one question because it's just as much an opportunity to find out things that aren't working as it is to find out what's not working. Also, since this person feels powerless over their situation, they will respond positively if you give your honest opinion about the situation.

As a psychologist, I can tell you that there are people who look very good in a group, but they're very different in a one-on-one situation.
—Dr. Henry Cloud, Clinical Psychologist

What are you committing to?
This is a great question to ask in one-on-ones because it's an opportunity to find out what people are anticipating working on next. It's a way to participate in how they prioritize their work without micromanaging every aspect of it.

Joanne Mika Hayashi, President and Co-Founder of Breast Cancer Hawaii uses these questions in her one-on-one meeting agenda template that she has kindly shared for everyone to download or copy:

One-On-One Meeting

⭐ Checking in

What's new in your world?

🎉 Recent Wins

I'm feeling good about...

🚧 Current Obstacles

I'm stuck on...

📍Other Topics

Include any additional discussion items

🗓️ Next 2 Weeks

I'm committing to...

While routine one-on-one meeting questions help you set a consistent and recurring meeting agenda, it's good to expand your conversations during one-on-ones to other topics. This will help you really explore how an employee is doing, and allow you to help them develop in their role.

To that end, here are some extra questions to work in. You might keep these as personal notes, not putting them in your official one-on-one meeting agenda.

Ask these questions in your one-on-ones periodically:

1.  Is there anything not on the agenda that you want to accomplish during our one-on-ones?
When you know what your co-worker wants to accomplish, it will be easier for you to determine what approach on how to bring the best results. This way, the meeting itself will be worth your time. Since one-on-ones are often recurring meetings with similar questions (and therefore similar one-on-one meeting agendas) each time, it's easy to fall into a trap of avoiding or missing certain discussions. So go ahead and ask the question: What else should we talk about?

2.  What is your opinion of this project?
This is a great question to ask because it will lead into other questions about why they have a certain opinion about the project. This way, you can better understand their needs and concerns, and how your employee thinks. If they have a negative opinion of the project, ask them why and see if there's anything you can do to change their mind. Conversely, if they're overly sunny about something that isn't going well, it may be an opportunity to reset the

3.  What do you like to do outside of work?
This is a good question to ask to gain insight on their personality. This will help you determine what type of person they are and also what they like to do for fun. It's important to know the person's personality, as well as how it can affect your job performance and relationships.

4. How was your weekend?
Some managers like to kick off one-on-one meetings with a bit of light-hearted small talk. Others are all-business. If you're in the latter group, maybe, occasionally, you can find it in your heart to talk about something other than work, even if only for thirty seconds.

5.  What is your biggest frustration with your job?
When asking this question, it will give the impression that you care about them as a person and not just as an employee. It's important for your co-worker to know that you are there for them if they have any problems. This will only strengthen the relationships that you have with your co-workers.

6.  What are you looking forward to / not looking forward to?
This can be a great question to ask if you want to understand what motivates the person. If the person is looking forward to something, then you will want to know why they are excited about it. If they aren't looking forward to something, you will want to know why they aren't excited about it. These are questions that are great for deeper levels of understanding about their likes/dislikes and how it may affect their work performance and can help you distribute future responsibilities and projects more according to a person's interests or aptitudes.

We trolled the internet and asked our peers to submit ideas for other questions like the above, and the result was this database of over 300 great questions for one-on-ones. If you want to add some variety to your one-on-one meetings, take a look.

One-On-One Meeting

⭐ Checking in

What's new in your world?

🎉 Recent Wins

I'm feeling good about...

🚧 Current Obstacles

I'm stuck on...

📍Other Topics

Include any additional discussion items

🗓️ Next 2 Weeks

I'm committing to...

Tips on how to ask questions during a one-on-one

One-on-ones can be scary for a lot of employees because there is an inherent power imbalance. It's personal time with the boss and it always feels like some kind of negative performance evaluation might come out of left field. You'll want to take this into account.

It's important to remember that when you are asking questions, your one-on-one meeting is not an interview or an interrogation. Treat it as an opportunity for both of you to gain insight into each other and create better business relationships. And if you do have something difficult to discuss, here's some advice on having tough conversations.

Here are some one-on-one meeting tips:
1.  Ask open-ended questions as opposed to yes-or-no questions or ones with a clear correct answer. You want to get your employee talking, and an open-ended question like, "how can I help you?" can be answered in so many different ways, it gives them an opportunity to reveal to you what is most pressing.

2. Be aware of your energy and tone. Your tone can determine how people respond to you and even what they decide not to say in response to your question.

3.   Pay attention to physical cues like body language and facial expressions. If your employee is fiddling with something on their desk or avoiding eye contact, that can give you clues into how they are feeling about the question you just asked. This also goes for yourself. Try to be relaxed and open with your posture.

Go Further 🚀
Use a meeting management tool like Hugo stay organized as you prepare and take notes in 1:1s.
meeting management software Hugo user interface

4. If you're a new manager, remember that asking questions is how you get things done in your job. Work can be isolating and impersonal. It might feel strange or intimidating to actually have a real conversation with someone at first. Try to get over any hesitations. Take it as an opportunity to get to know your co-workers. If they're having trouble opening up, you might find that some subtle encouragement can help.

5.  Keep an open mind about what you hear. It's easy for your own biases to get in the way of understanding how someone else feels about something if it is different than what you would think or feel in their situation.

6.   Find out how they are doing on a personal level. If they are facing some personal challenges that are having an impact on their work, this will help you to understand how to better support them through these times. They may appreciate your concern.

7. If the conversation becomes stilted or awkward, take a break and try again later or on another day. Even the best conversations can sometimes feel uncomfortable at first until you both get used to it. Say the meeting has been going on for forty-five minutes and has been a challenge, and you still have some difficult feedback to deliver or challenging questions to ask. Consider whether it would be useful to save those issues for another day.

25 more sample one-on-one meeting questions:

1. Is there anything we should be doing to create a better team environment?
2. What has been the biggest challenge you've faced recently?
3. How is your work going on this project/task/area of responsibility?
4. Do you have any concerns or questions about how we work together overall?
5. Are there any particular challenges for this project or organization that I should know about?
6. What do you think of our company/team/products/services? What can be improved upon?
7. What is your preferred communication style? How can I best communicate with you?
8. What do you like most about working here?
9. What is one thing you wish more people would do, or stop doing, in our company?
10. If you could change something in our company, what would it be?
11. How closely do you track your tasks/goals/milestones on this project?
12. What is the most challenging aspect of this project?
13. If I can improve, or add to, anything that you are working on, what would that be?
14. What are some groups or departments that you feel are competing for resources/resources not being used effectively? How can I help?
15. Are there any additional responsibilities that you would like to take over?
16. How do you process tasks/projects/information on this project?
17. What do you think about our new systems or project management methodology?
18. How would you describe the culture of our organization/team/team members? What are some of your experiences with that culture?
19. Do you have any new goals or aspirations for your work in the next few months?
20. What has been one of your biggest wins or success stories?
21. If you could have two things changed at the company, what would they be?
22. Who would be an example of someone whose skill set you feel is under-utilized within the company?
23. Who are your mentors or role models at work? Why do you admire them so much? What have they taught you about being a good leader/manager etc.?
24. In your opinion, what is the biggest challenge facing our company today?
25. What do you wish was different about your job?

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Rob Lennon
Customer Education Lead at Hugo
Marketer and author with 18 years experience in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

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