First up, congratulations! Having your first one on one meeting with an employee is a big step. It means you care about having meaningful connections with your team, being a great manager, and making your organization an engaged and desirable place to work. Kudos to you!

The goal in this article is to get you prepared for your first one on one meeting. We’ll dig into a number of topics, including:

• Starting one on one meetings with an employee
• Preparing for your first one on one meeting
• Sharing context for your one on one meetings
• Creating your first one on one meeting agenda
• 65 questions to ask in your first one on one meeting
• 5 key takeaways for preparing for your first one on one meeting

Let’s get started.

Starting one on one meetings with an employee

Most commonly, there are three times when you’re having your first one on one meeting with an employee, including:

1. You’ve been promoted into management and are now leading a team
2. You’ve started on a new team and are leading new team members
3. You’ve hired someone or a new employee has joined your team

Whichever your case may be, you will want to let the employee know you’d like to have a one on one meeting. In doing so you will want to share a brief purpose for the meeting and the idea of having them on a recurring frequency to continually stay aligned. Before sending an invitation let’s discuss setting a schedule.

Although it’s a nice idea to think you can catch up with your direct reports on the fly, that’s harder to do in reality. By making a commitment to a schedule, whether once a week or once a month, both parties will better prepare and take the meeting more seriously.

— Via The Secret To Effective One-On-One Meetings With Direct Reports

Scheduling your one on one meetings

Scheduling your first one on one meeting requires a few key logistical components, including the who, what, when, and where.

Who

The participants for a one on one meeting are you (the manager) and the employee (your direct report). As tempting as it may be to invite others, be it other stakeholders, leaders, or team members, the meeting should only consist of two participants—you and the employee. Keep the meeting small and intimate for a more engaged conversation, creating a deeper connection and trust between you two.

What

When it comes time to send an invitation, it is worth highlighting what a one on one meeting is and the desired purpose for the meeting. You don’t need to go too deep initially and can share more context once in the meeting. A good start here includes mentioning you’d like to have a routine time for the two of you to connect and for the first meeting you’d love to get to know them a little better.

When

As for when, there are a few meeting components to identify including the day of the week, time of day, length, and frequency.

If possible, find a day in the middle of the week to meet one on one (preferably Tuesday or Wednesday). This allows everyone to get up to speed on Monday and not be too tired on Friday. Holidays and vacations often fall on Mondays and Fridays too, so those days are good to avoid.

The best time of day to have a meeting is when you’ll both be engaged and ready to connect. The exact time of day is more preferential and is worth discussing with an employee to see if they have a specific time preference.

Length and frequency for your one on one meetings can vary. At a minimum, it’s best to meet for at least 30-minutes. Part of this can depend on the frequency of your meetings. For example, you may prefer to meet for 30-minutes every week or 60-minutes every two weeks. As with the time of day, it is worth asking an employee if they have any preference for how often and how long they’d like to meet. If you’re not too sure where to begin, 30-minutes every week is a good starting point.

When employees know they have a standing meeting, they are less likely to barrage you with a ‘constant stream of interruptions.’

— Via How to Make Your One-on-Ones with Employees More Productive

Keep in mind, different people have different preferences and your one on one meeting schedules can vary by employee. It’s important to work around an employee’s preference to make them comfortable. Know that this can change over time too. You may find you need shorter or longer meetings from where you originally begin and you can change your meeting preferences again and again over time. Frequency can change too, although regardless of the exact cadence you do need to meet consistently to keep your relationship growing.

Where

Lastly, look for a private room where you can each speak freely without worry of others overhearing your discussion. Meeting in a common area can unintentionally limit the conversation, preventing either one of you from having the depth of conversation you’d like. Being creatures of habit, employees may often find comfort in having a consistent room to meet in. If you find your one on one meetings growing a bit stale, however, it is worth changing the location or perhaps going on a walk or out for coffee for one of your meetings.

With the logistical details in place, let’s prepare to send your first one on one meeting invite.

One on one meeting invitation template

Getting all of the logistics in order can be difficult, especially with busy schedules. Don’t give up though. The value of one on one meetings far outweighs the hurdle to scheduling the meeting.

Once you’re ready to send an invitation, you will want to share both the logistics and value of a one on one meeting with an employee.

To help make the process of sharing the point of a one on one meeting a little easier, please feel free to use the following meeting invitation template.

Preparing for your first one on one meeting

Before jumping into a one on one meeting, be it your very first one on one meeting with an employee or your hundredth, there are a few areas of preparation that will go a long way to help make the most out of your time together.

Keep the following recommendations in mind as you start any one on one meeting. Revisit and reference these same recommendations over time too, to refresh yourself.

Be mentally prepared and fully present

Life in management can be a bit hectic, fast-paced, and the days can seemingly disappear before you realize it. Some days that’s great as your accomplishing many great feats. This isn’t how you should approach your one on one meetings though. They are not “just another meeting” or “task to do.”

Before heading into a one on one meeting slow down and mentally prepare yourself to be fully present. Set the stresses of the day and any to-dos aside. This meeting is for the employee and you need to do your best to be fully available to them, not preoccupied with a thousand other thoughts running around in your mind.

If it helps, schedule alone time for yourself before each one on one meeting to write down what you need to do after the meeting to get it out of your head. In the meeting, keep your phone out of reach and your computer off (unless you’re using them for notes, and in that case only use them for notes).

Your goal is to connect with an employee and your best chance to do so is by being mentally ready and fully present for them.

Research an employees work and goals

As part of getting mentally prepared, one of the best ways to put yourself in a proper frame of reference is to review and get up to speed on the work an employee has been doing before sitting down with them. One on one meetings are not intended to be status updates, so there is a chance you won’t discuss the work, however, the familiarity with it will provide additional context to your discussion.

At the same time review the notes from your last one on one meeting, as well as any notes you’ve taken between the two meetings. This is the perfect time to check in on an employee’s goals, where they need accountability, the feedback they’ve given you or received themselves, and generally where you can be of value to them.

In a one on one meeting, you’ll want to stay open and flexible to discuss what the employee wishes, although being prepared will show them you are invested in them while putting yourself in a better position to help.

Start a one on one meeting document

One of the most critical items of a one on one meeting is a shared place for both you and the employee to define an agenda, take notes, and outline decisions and action items. This document sets the stage for your one on one meeting and keeps a running archive of all your previous meetings.

Very quickly, this document helps you prepare for future one on one meetings and provides a reference for employee reviews, career conversations, and employee focused conversations.

The document itself can be Google document or a tool like Lead Honestly, which is specifically designed to help facilitate one on one meetings.

Embrace awkwardness

There is a good chance you’ll encounter some awkwardness in your first one on one meeting, and potentially in many more one on one meetings thereafter. That’s okay! If the conversation has a moment of awkwardness the conversation is likely reaching a point of meaning. Step into this, and don’t shy away from the moment.

If the conversation has a moment of awkwardness the conversation is likely reaching a point of meaning.

With any awkwardness there is an opportunity to learn something deeper about one another, to grow your relationship, and to build a sincere connection. Take advantage of this opportunity.

Arrive early

This may not seem like a big deal, however, do your absolute best to arrive early for your one on one meetings, especially your first one. Being early shows you care about the employee, their time, and your relationship.

Arriving early also sets the context that you take these meetings seriously and will be expecting the same from the employee. Start on time to show you value these meetings, and thus you value the employee. All of this will go a long way in keeping the employee engaged.

Sharing context for your one on one meetings

One on one meetings are a slightly different type of meeting than most, so it’s helpful to share some context and a few small ground rules for you and the employee.

These ground rules aren’t meant to be hard and fast rules and can evolve over time. The idea is to outline the setting and purpose for the meeting, sharing and setting expectations for both of you from the very beginning.

What an employee should expect from you

For managers, there are a number of ground rules to keep in mind to make the most of your one on one meetings. Truth be told, there are more rules for managers than there are for employees.

A good one on one meeting is owned by the employee and as a manager, the rules for you are focused around ensuring the employee can lead the conversation. These rules include:

• Listen more than you speak
• Focus on the employee and what they want to discuss
• Accepting feedback
• Take notes and follow-through

Listen more than you speak

The best one on one meetings you have will be the meetings where you’ve said very little and the employee has lead the discussion.

As a manager, it’s more important to have the right question than know what to say. In a one on one meeting ask questions to get the employee to open up. Let them come to their own answers, reflecting, learning, and building accountability along their way.

It’s more important to have the right question than know what to say.

Embrace awkward silence too. This will be hard and you will be tempted to fill the uncomfortable silence. By letting it linger for a minute you will often be surprised by what the employee has to say next (and uncover new learnings yourself). Give the employee the opportunity to fill the silence first.

Focus on the employee and what they want to discuss

Given this is the employee’s meeting, let them drive the agenda with items they want to discuss. Ideally, these topics revolve around their happiness, productivity, career, team, and allow you to learn more about how they are feeling.

These meetings should not be a status report or project management focused where you get an update on all things work-related.

Now, that’s not to say you shouldn’t discuss a project either. In fact, it’s very likely you will. Projects matter in the context of how an employee is feeling, thus you will want to dig in there. Don’t go into the meeting seeking an update though.

Accept feedback

One on one meetings should become a place where you receive feedback from an employee. Encourage them to provide you feedback and ask them questions to further explore their comments. You may consider the questions “Where could you use more support?” or “What could I have done differently to help you?”

If helpful, consider adding receiving feedback as a recurring item on your one on one meeting agenda.

Treat feedback as a gift. Listen, don’t react. As hard as it may be, do not interject. Being open to and accepting of feedback will help ensure you continue to receive it.

Treat feedback as a gift. Listen, don’t react.

Take notes and follow-through

Throughout a one on one meeting, look for ways to make the meeting actionable by taking notes and creating todos. At times your conversations may make you feel like a bit of a therapist, especially as you listen and ask questions to create self-reflection for an employee. While you want to provide a space for an employee to express themselves, you also want to make the meeting productive.

Take notes and create to-dos to turn discussions from a one on one meeting into action and accountability for both you and the employee.

Most importantly, follow through. Worse than not taking notes and making a one on one meeting actionable is making the meeting actionable and never following through. You will erode trust and motivation with an employee and accountability will fall.

What you should expect from an employee

While there are a few ground rules for managers there is one basic rule for employees, that being the employee owns the one on one meeting.

It is the responsibility of the employee to help create the agenda and bring any items they wish to discuss in the meeting. Employees don’t have to set the whole agenda and managers are welcome to add discussion topics to the agenda too. First and foremost, though, one on one meetings are the employees meeting, and they have priority.

Set this context with an employee, letting them know this is their time and you want them to bring items to discuss.

This meeting isn’t about you. It’s about an employees needs, wants, desires, and aspirations. While there will be dialog back and forth, keep the conversation focused on the employee and helping them.

Creating your first one on one meeting agenda

While your first one on one meeting will be a little different than your recurring one on one meetings to come, broadly, the agenda will be close to the same. This includes starting with sharing your gratitude, briefly catching up, digging into a discussion, outlining key action items, and ending on a high note.

A loose agenda for your first one on one meeting, including time frames for different types parts of your conversation, can be:

• 10 minutes before: Prepare for your meeting
• 1 minute: Start with sharing your gratitude
• 4 minutes: Catch up and check-in
• 5 minutes: Share context for one on one meetings
• 15 minutes: Have a discussion, listen, and learn
• 4 minutes: Outline the next steps and action items
• 1 minute: End on a high note

(To note, this is for a 30-minute meeting. For longer one on one meetings it’s best to expand upon your discussion time.)

10 minutes before: Prepare for your meeting

Come prepared to your one on one meetings with an understanding of what an employee has been working on, what their career goals are, where they’re looking to improve, and where you can help advise, coach, and advocate for them. In your very first one on one meeting, you may spend time learning these goals, aspirations, and preferences. If you don’t know them already, no worries, your first one on one meeting is a great time and place to learn them.

Before heading into your one on one take a few notes on what you’d like to discuss, questions you can ask, and feedback you can share. Keep in mind, this is the employee’s meeting and they have the first right to drive the discussion. Be prepared with context to their day to day and be mentally prepared and fully present.

1 minute: Start with sharing your gratitude

Share your gratitude with the employee to kick off your one on one meetings. What have they done recently that really helped the team or organization? Any recent wins for them? Why are you excited to have them on the team? What difference do you see them making? Whatever the answer may be, tell them! All too often we tend to focus on the bad and don’t share enough of the good.

All too often we tend to focus on the bad and don’t share enough of the good.

Start every one on one meeting by expressing and sharing your gratitude. You’ll build energy and set the tone for a positive discussion.

4 minutes: Catch up and check-in

Be personable and friendly in your one on one meetings to prevent them from feeling transactional. Take the time to see how the employee is doing in and outside of work, and what’s been going on in their lives. If you already happen to know something going on, take a quick minute to ask them how it’s going.

Showing and remembering details of an employee’s work and personal life continues to show you care, and taking a few minutes to catch up allows you to build an open relationship.

5 minutes: Share context for one on one meetings

Being your first one on one meeting, take a few minutes to expand upon the context of the meeting. When you sent the initial invitation of the meeting you shared a little context as to why you’d like to meet and some of the logistics of it, now is the time to go a bit deeper.

Outline the setting and purpose for your one on one meetings. Share what the employee can expect from you and what you expect from them. Most notably, make sure the employee knows this is their meeting to which they are welcome to bring in any topics or questions they wish to discuss.

15 minutes: Have a discussion, listen, and learn

The bulk of your one on one meetings will be a discussion where you listen and learn the most. At times you may provide quick updates, although this is the time for the employee to share their challenges, seek out feedback and support, and bring any questions they have to the table.

For your first one on one meeting you should bring questions to start the discussion, focused on where you can learn more about an employee. To help get a sense of their hopes, desires, and preferences, there is a full list of questions below.

Be flexible on time as the discussion will be the bulk of your meeting. 15 minutes may work for your first one on one. Then you should leave at least 20 minutes for future one on ones (as you will get 5 minutes back from not needing to reshare the context for your meetings after the first).

As you have one on one meetings feel free to change and expand this time accordingly, keeping in mind different employees may want different lengths of time to talk.

4 minutes: Outline the next steps and action items

Before ending your one on one meeting use a couple of minutes to outline any next steps and action items. Define commitments made during the meeting and items that require follow up.

Take the time to also take any personal notes. Note areas of potential coaching, preferences or patterns you’re seeing, and items you feel you will want to reference later.

1 minute: End on a high note

End on a high note by expressing your gratitude once more, much like the meeting started by sharing your gratitude. A good one on one meeting can be a bit awkward, vulnerable, and you may find yourself having some difficult conversations. Slowing down at the end for even a minute to say “thank you” and express gratitude allows you to end on a positive note, creating motivation and appreciation for one another.

65 questions to ask in your first one on one meeting

There are a few key areas where you can learn more about an employee during your first one on one meeting, including their previous experiences, career goals, personal preferences, and entry to the team or role.

To help kickstart the conversation, please feel free to use some of the 65 questions below. Keep in mind though, this should be a conversation and the employee has priority. Let them do most of the talking and leave room for them to ask you questions too. All goes well, you won’t need all 65 questions.

(Looking for a simpler way to ask these questions? Try checking out the Lead Honestly Onboarding Playbook.)

Personally connecting

To start building a relationship it’s important to get to know the employee on a personal level and what their life outside work looks like. Doing so provides you with more context to them as a person, allows you to connect with them on a personal level, and shows true appreciation for them.

Questions to connect personally:

1. Outside of work, what do you like to do? Any hobbies?
2. Given additional time, what would you enjoy spending more time on?
3. As a child, what did you want to do when you grew up?
4. Where is your favorite place to visit?
5. How would you describe your personal values?
6. Regarding our company values, what resonates with you the most? What’s unclear?
7. How do you like to describe yourself to others?
8. How do you think others would describe you?
9. What keeps you up at night? Anything causing worry or concern?
10. What gets you excited? Anything you’re looking forward too?

Employee preferences

Your first one on one meeting is the perfect opportunity to learn about an employee’s preferences for how they like to receive feedback, recognition, what creates stress and happiness for them, when they work best, and so forth. Spending a few minutes to build an understanding of preferences allows you to build a relationship on shared values.

Questions to identify an employees preferences:

1. How do you like to receive feedback and how often would you like it?
2. How do you like to receive recognition and praise?
3. What typically frustrates you? How can I tell when you’re frustrated? How can I help when you’re frustrated?
4. What should I know about your working style to help us work together?
5. How can I and other teammates best communicate with you? Email, instant messaging, phone, etc.?
6. Are you more productive in the morning, afternoons, or evenings?
7. Is this your first time having one on one meetings? If so, what do you hope to get out of them? If not, what did you like and dislike about your previous meetings?
8. Regarding one on one meetings, what time of day, length, and regular meeting cadence is best for you?
9. What is one thing that puts you in a bad mood?
10. How will I or the team know when you’re not in a good mood?
11. How can I make sure you have everything you need to be successful?
12. How can your team make sure you have everything you need to be successful?

Previous experiences

One of the best ways to learn about an employee, and to further understand some of their preferences and working style, is to ask them about their previous experiences. These questions will build upon what you’ve learned so far and help you identify trends within their answers.

Questions to learn about an employees previous experience:

1. In your previous jobs, what have you enjoyed most?
2. What types of people have you found easiest to work with?
3. What experiences give you the greatest sense of happiness at work?
4. What experiences give you the most stress at work?
5. What is a project or task that you worked on that made you feel satisfied and fulfilled?
6. What is a project or task that caused frustration or you hope you don’t have to do again?
7. What have you liked or disliked about your past managers?
8. How have others shared feedback with you, and what did and didn’t work?

Career goals

Your first one on one meeting is a great time to learn about an employee’s career goals and aspirations. As they grow and evolve in their career these goals can change, so it’s important to check-in, ask questions, and have a conversation around their career frequently.

In your first one on one meeting, hitting on some of their high-level goals is a great place to start.

Questions to gather an employees career goals:

1. When it comes to your career, what are your current goals? Have you thought about where you want to be in work and in life in 5 years?
2. If you had to pick a goal to accomplish within the next year, what would that be?
3. How could you break down your goal for the year into goals per quarter?
4. What could you achieve in the next 30 days to kick start your goals?
5. Where would you like your career to go in the next year, 3 years, and 5 years?
6. What skills do you need to grow and expand upon to accomplish these goals?
7. Thinking about your current strengths and skills, how would you like to uniquely help the team?
8. How do you challenge yourself on a regular basis to continuously improve?
9. What do you feel could get between you and success (perhaps systems, processes, team structures, etc.)? How can we get rid of those barriers?
10. What is the first thing I can do to help you on this journey?

New to the team or role

When meeting with an employee who is new to the team or role there are a handful of questions you can ask to help welcome them to the team, learn about their desires, clean up areas of confusion, and successfully help them onboard.

Some of these questions are great for your first one on one meeting, and many are questions to follow later in subsequent one on one meetings.

Questions to help someone new to the team or role:

1. Do you have any questions about your job? Anything I can go over with you?
2. Do you have clear expectations for your new role? What can I clarify?
3. What are you looking to learn and where are you looking to grow in this new role?
4. What was it that originally attracted you to this new role?
5. Are you worried about anything or do you have any concerns about your role?
6. What were your first impressions of our team?
7. What would you change or what could be improved with our team?
8. How has your onboarding been? Is there anything you wish was different, or anywhere we can improve?
9. Has your training been relevant and do you feel prepared for this role?
10. What have you enjoyed most since starting? What have you enjoyed the least?
11. What has been the most surprising or striking with your new role?
12. Is there anything you wish you’d been told or prepared for before joining?
13. What impact have you had since starting this new role? What have you learned?
14. Are you receiving enough help? Can I lend a hand?
15. Who has been the most helpful in getting you onboarded to this new role? How have they helped?
16. What aspect of your role can I provide more feedback on?
17. Have you had any issues making decisions? If so, what were they?
18. How can I or other team members best support you?
19. What has been the hardest part of adjusting to your new role?
20. What has been the most frustrating part of your new role?
21. How do you feel about your current workload?
22. What has been the best advice you’ve received since starting this new role? Who shared it with you?
23. How would you describe our company and culture based on your recent experiences?
24. Are your ideas being valued and considered by the team? Any examples?
25. If you were to make a change today to help us separate ourselves from our competitors, what would that be?

5 key takeaways for preparing for your first one on one meeting

Starting one on one meetings is no small feat, and neither is continuing them. As you set off to start your one on one meetings with an employee keep the following ideas and recommendations in mind:

1. Cover the who, what, when, and where when starting your one on one meetings with special attention to when (be it the time of day, length of time, and cadence)

   🔑 Recommendation: Use the meeting invite template

2. Prepare for your first one on one meeting by doing research beforehand, being mentally ready, and embracing any awkwardness

   🔑 Recommendation: Create a shared one on one meeting document for notes

3. Share context for your one on one meeting by ensuring the employee understands this is their meeting first and foremost, and that they are welcome to bring any topics or questions to discuss

   🔑 Recommendation: Focus on the employee and what they want to discuss

4. Start and end your one on one meetings on a high note, sharing gratitude or a special thanks, and leave the bulk of time for discussion, not updates

   🔑 Recommendation: Meet for at least 30 minutes and adjust the time and frequency as an employee desires

5. Before your first one on one meeting, come up with a few questions to help you kickstart your conversation

   🔑 Recommendation: Use some of the 65 questions recommended