35 One-on-one Questions to Ask Employees (+ Free 1-on-1 Meeting Templates)

It’s not uncommon for leaders to want to ensure they’re preparing for their one on one meetings in the best way possible. When run properly, one on one meetings can be a fantastic way to build trust with your direct reports, set expectations, and empower your employees to do their best work.

Asking the right questions can make all the difference when it comes to setting up your 1-on-1 meetings for success. These questions can help you gain insights as a leader, and understand where your employees are at both personally and professionally. In this article, we'll discuss:

Essential 1-on-1 questions to ask employees
Periodical one on one questions to ask employees
25 One on one questions for employees by category
7 templates for one on one questions
Tips for asking great 1:1 questions

Essential 1-on-1 questions to ask employees every time you meet

As a leader, the importance of regularly checking in with your employees is vital. While there are some bigger picture related questions that can be asked at more infrequent intervals, some questions are good to ask each time you meet with your employees. Here are some examples:

What’s new in your world?

Asking an employee what’s new might feel a little obvious, but the formatting of this question ensures they understand you’re interested in what they might be dealing with both professionally and personally. It gives them a chance to open up to you and share the events going on outside of work.

What are you feeling good about?

Questions meant to pique positive reflection are great assets to include in every meaningful one on one meeting. Building a habit of positive self reflection when it comes to work can help boost your employees’ self esteem and identify wins among your team.

What are you stuck on?

Unblocking employees is one of your biggest strengths as a leader. You bring a unique perspective to the table, and something that might feel daunting for your direct report could very well be an easy fix when tackled as a team. Asking this question regularly helps keep your employees as productive and efficient as possible.

What are you committing to?

The word “commitment” has a lot of power behind it, and asking a question like this is a great way to see what your employees are planning on tackling next in their workflow. This way you can be an active participant in how your direct report prioritizes their work while also empowering them to set their own goals.

Bonus tip

Because these questions are best asked in every 1-on-1 meeting with your employees, leveraging a tool that attaches a meeting agenda to your recurring 1-on-1 meetings can completely change the way you run them.

Fellow is the all in one AI meeting management solution that’s built to help you have more effective one on one meetings. With Fellow, you can easily track your one on one meetings in one place, and set a recurring meeting agenda template with the best questions to ask your direct report.

What’s more, Fellow’s AI Meeting Copilot allows you to record, transcribe, summarize, and share your meeting notes with your direct reports. Then from that information, you can Ask Copilot to synthesize information and third party insights to help you get the most out of your 1-on-1s.

Periodical one on one questions to ask employees

Now that you’ve got the basics covered, it’s time to move on to some broader questions that can be asked more infrequently depending on the needs of your employees and your relationship with them.

Is there anything you want to accomplish during our one-on-one that’s not on the agenda?

Ideally, every one-on-one meeting you have should be accompanied by a clear and concise meeting agenda that covers everything you want to discuss. However, periodically asking this question can help prompt your employees to reflect on what they want to get out of the meeting, and leaves space to discuss anything that didn’t make its way onto the agenda prior to the meeting.

Can you give me your honest opinion about X project?

Asking for feedback is the mark of a great leader. When it comes to projects, it can be helpful to get the honest opinions of your employees so you can make better decisions in the future. A one on one meeting is the ideal place to ask this question because it’s a safe space for employees to share with their direct managers.

What do you like to do outside of work?

This is a great question to ask every once in a while in order to keep up to speed with your employee’s personal interests and hobbies. Taking an interest in your employees helps build trust and relationships.

Pro tip: When you use Fellow for your 1-on-1s, you can add personal info to the “private notes” section of your meeting agenda, so you can easily refer back to it at a later date.

How was your weekend?

While it’s great to ask your employees about their weekends and personal time off, asking this question too frequently runs the risk of becoming repetitive. You can ask this question often enough to stay in the loop, but use it sparingly enough so it stays relevant and not glossed over.

Are there any frustrations you’re currently experiencing with work?

Staying in tune with your employees frustrations can help prevent burnout, workplace disagreements, productivity dips, and more. It also shows that you care about their job experience as a leader, facilitating trust and relationships.

What are you looking / not looking forward to in the future?

Asking this question offers you the opportunity to see what’s exciting your employees and what’s giving them feelings of dread. Understanding this can help you identify projects and initiatives that motivate your team and discover ways to keep them excited in the future.

25 One on one questions for employees by category

Ensuring that you’re asking a variety of different questions is ideal as a leader. Below are more example one on one questions divided into four categories:

Personal growth and development

1. What’s one challenge you’ve recently dealt with at work?

2. Do you have a preferred communication style? What’s the best way for me to communicate with you?

3. What are some additional responsibilities that you’d like to take over?

4. In the next few months, what are some of your goals or aspirations you’d like to achieve?

5. What do you think the biggest challenge is that’s currently facing our company?

Feedback

1. Tell me about our company, team, product, or service; What do you think can be improved?

2. Can you tell me about your most recent win?

3. If you had the power to change two things about our company, what would they be and why?

4. Who is someone whose skillset you find isn’t being used to its fullest potential in our company?

5. What is one thing you wish was different about your workflow?

6. Do you have any role models that you look up to when it comes to your work? What are some things you’ve learned from them?

Project Tracking and Prioritization

1. How is work going on X project, task, or responsibility?

2. Is there a specific challenge or blocker for this task that I should know about?

3. How are you keeping track of progress and tasks for X project?

4. What are you finding the most challenging about project X?

5. What are your priorities for the week? How can I support you in succeeding with them?

6. What would be one thing I could add to or improve upon when it comes to what you’re working on right now?

7. Where can I see the tasks and relevant information about this project you’re working on?

8. Is there something that can be improved upon when it comes to processes for project X?

Improving Team Dynamics and Culture

1. What is one thing we could do to foster a better environment for our team?

2. What is your main concern when it comes to how we work together as a team overall?

3. What’s your favorite thing about working here?

4. If there was something our team could do, or stop doing, what would it be?

5. When reflecting on the culture of our team, company, or organization, how would you describe it?

6. What’s one thing you would change in our team if you could?

7 templates for one on one questions

Another great source for example questions to ask in your one on ones is via templates. Not only can these serve as inspiration, but they can be directly applied to your one on one calendar events by using Fellow.

When you sign up for Fellow with your work email, it connects to your calendar and allows you to browse the 500+ template library and apply whichever one feels right to your 1-on-1 meeting agenda. Below are some example one on one meeting agenda templates:

General One-on-One

This template comes with three 1-on-1 questions built in to the first section of the agenda, which is great for setting expectations clarity.

One-on-One Sync

This template is divided into four sections, including what to cover first, updates, wins, and action items.

One-on-One: Catching Up

This template is great if either you or your employee has been away for a bit and need a structure for updating each other.

One-on-One: Coaching & Mentoring

Because there is an art to coaching and mentoring, this template sets up any 1:1 session for success, including sections for planning, feedback, and follow up.

One-on-One Goal Setting

There’s nothing like a good goal setting session to spark motivation. This template will help guide both you and your employee to setting goals and keeping each other accountable.

One-on-One Remote Employee

1:1 meetings that are held remotely versus in person can vary in both formatting and tone and energy. This template is designed to keep remote sessions synchronous and efficient.

One-on-One Skip Level

One of the most nerve-wracking types of one on one meetings can be the skip level. Using a template for structure will help ensure everyone comes to the meeting relaxed and ready to engage.

Tips for asking great 1:1 questions

While one on one meetings can feel like just another part of the workday for a leader, the same cannot always be said for employees. The reality is some direct reports feel dread surrounding one on ones, whether it’s because of the power dynamics, uncertainty, required time commitment, or all of the above.

To ensure your one on ones are a positive and productive experience for everyone, here are some tips for crafting great 1:1 questions.

Ensure your questions are open ended

Asking questions that can be answered with a simple yes or no aren’t conducive to sparking conversation. The point of one on one meetings is to get talking and build trust, so be sure to structure your questions so that they prompt open-ended answers.

Monitor your energy and tone

It’s best practice for direct reports to run their one on ones, but as a leader, the tone and energy you bring to the meeting can make all the difference. Using the right tone and energy when delivering your questions can mean the difference between a good, responsive interaction, or a cold and unproductive conversation.

Pay attention to physical cues

Body language and facial expressions can tell you a lot about how your questions are being received and how they make your employees feel. If their body language seems nervous or tense, you can use this insight to follow up with reassurance and also curate how you structure your questions in the future.

Find the balance between personal and professional questions

While 1 on 1 meetings are a great way to get to know your employees on a more personal level, it’s important to keep them professional. Asking too many one on one questions can become an unproductive use of time, and make your employees uncomfortable. At the same time, remember to have some friendly or personal questions every so often in your one on one conversations to show your employees that you’re interested in them as people.

Keep an open mind when it comes to answers

Questions that ask direct reports to be honest about their opinions and feelings can sometimes elicit responses that aren’t exactly what you want to hear. It’s important to maintain an environment that’s emotionally safe for your employees to express themselves, and keeping an open mind to their responses will help build trust in your relationship.

Leverage AI

While you work on building relationships and fostering efficiency within your team, it can be tough to track insights and continually come up with new questions to keep conversations fresh and impactful. Leveraging AI to help ideate or synthesize information can save you time and help you be more efficient and effective as a leader.

Fellow not only has a personal AI meeting assistant that you can ask for insights and information, it also has an AI powered agenda builder that can generate suggested topics and talking points based on context from the meetings.

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