The Art of the One-on-One Meeting

The definitive guide to the most misunderstood and yet powerful tool for managers. With a foreword by Lara Hogan, author of Resilient Management.

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What’s inside this free guide:

Foreword Lara Hogan, author of “Resilient Management” (only available in the PDF version)

Chapter 1 The purpose of one-on-ones and why great managers have them.

Chapter 2 Best practices on how to set up your one-on-ones for success.

Chapter 3 Specially crafted templates and questions that will boost productivity.

Chapter 4 The secret skills that will make your one-on-ones 10x more effective.

Chapter 5 Bringing out the best in your team: Career conversations & feedback.

Chapter 6 The 7+ deadly sins to avoid in one-on-one meetings.

Chapter 7 Completing your manager’s toolkit.

1.1 What is a one-on-one meeting?

In most cases, how your direct reports feel about you (their boss) dictates how they feel about the company and their job. That’s why one of your main responsibilities as a manager is to develop positive relationships with them — your fellow teammates.

As Kim Scott, a former leader at YouTube, Google, and Apple argues in the book Radical Candor, the most important thing managers can do to build a culture of trust is meeting with each of their direct reports on a regular basis:

“Holding regular 1:1s in which your direct report sets the agenda and you ask questions is a good way to begin building trust”, says Scott. “1:1s are your must-do meetings, your single best opportunity to listen, really listen, to the people on your team to make sure you understand their perspective on what’s working and what’s not working.” 1

What is the definition of a one-on-one meeting?

A one-on-one (a.k.a. 1-on-1) is a dedicated space in your calendar for you to connect with each person reporting to you and stay in the loop about priorities, team issues, and potential roadblocks. Most importantly, it’s an anticipated moment where employees can ask in-depth questions, receive coaching on their strengths and weaknesses, and provide feedback — three things they wouldn’t be able to do in a public space or at a team meeting.

Julie Zhuo, Facebook’s VP of Product Design and the author of The Making of a Manager, argues that the most precious resource you have as a manager is your own time and energy…

“…And when you spend it on your team, it goes a long way toward building healthy relationships. This is why one-on-one meetings (1:1s for short) are such an important part of management,” says Zhuo. 2

If you’ve heard about one-on-one meetings before, you’ve probably heard that “they are the direct report’s meeting” and not the manager’s.

“The fundamental reason the one-on-one exists is to give a platform to the direct report to allow them to communicate to you,” say Michael Auzenne and Mark Horstman on the Managers Tools podcast. “In order to effectively develop relationships with our directs, we’ve got to spend time communicating about things that are important to them.” 13

In the book Resilient Management, Lara Hogan (the former VP of Engineering at Kickstarter) says that managers and individual contributors can aim to accomplish the following four things in their one-on-one meetings:

What type of questions should you ask in order to build trust with your employees? What is the ideal frequency of one-on-ones? Are there any mistakes you should avoid in order to make the most out of these meetings? How can you encourage your direct reports to come prepared with talking points to discuss? You’ll learn the answers to all these questions as you read through this guide!

1.2 The benefits of one-on-one meetings

Some managers and employees give one-on-ones less importance than these meetings deserve: They schedule them just because they have to, come up with a couple of last-minute questions, share some light updates, or (sometimes) don’t even have them at all.

However, great team leaders acknowledge the importance of meeting frequently with their direct reports, and the potential that one-on-one meetings have to empower their fellow teammates and the organization as a whole.

Here are some of the reasons why great managers have regular one-on-one meetings – and why you should too:

1. One-on-one meetings boost employee productivity

One of the primary benefits of one-on-one meetings is that they increase your team’s productivity and quality of work.

As Andy Grove (former CEO of Intel) argues in the book High Output Management, meeting regularly with your employees allows you to coach them on their priorities and develop a common base of information – which will help your team stay in sync and produce better results.

“Let’s say you have a one-on-one with your subordinate every two weeks, and it lasts one and a half hours. Ninety minutes of your time can enhance the quality of your subordinate’s work for two weeks, or for some eighty-plus hours, and can also upgrade your understanding of what they’re doing,” says Grove. 4

Not all employees are great at prioritizing their time or have the experience necessary to understand what activities will bring the highest return on investment (ROI). That’s why you should meet regularly to set clear priorities with each one of your direct reports.

There’s another way in which one-on-one meetings can boost productivity across your company. Apart from empowering individual contributors to be more productive, they also help managers allocate their time more wisely:

“One of the first things that happen when you start doing one-on-ones is you notice you start getting less questions during the week,” says Mark Horstman, on the Managers Tools podcast. “Things aren’t quieter… People just aren’t coming to you with hundreds of small questions because they know they can wait until the one-on-one.” 13

Do you feel that you never have enough time to finish your tasks because you’re always getting interrupted with “quick questions” from your direct reports? One-on-ones can help you fix that.

“Establishing a consistent one-to-one meeting schedule is a critical tool to improving time management,” argues productivity expert Dave Crenshaw. “The biggest reason is that most people in the workplace are treating each other like human vending machines. They’re constantly peppering each other with quick questions, and these quick questions have a lot of switching cost. Also, it’s getting in the way of people doing their own critical thinking.” 5

In summary, one-on-ones make both managers and employees 10X more productive.

2. One-on-one meetings foster positive work relationships and engaged employees

Relationships can’t be built over the course of one day. Just like you can’t expect to get to know a partner (or friend) if you see them only once or twice a year, you can’t expect to develop a good relationship with your employees if you only sit down with them for yearly or quarterly performance reviews.

This is why companies like Deloitte, Adobe, Microsoft, and IBM replaced annual reviews with frequent check-ins — the best way for managers to build positive relationships and trust with their direct reports.

Studies show that this is the right approach if companies want to boost employee engagement and retention. For instance, Gallup’s State of the American Manager report says that employees who meet regularly with their managers are almost three times as likely to be engaged in their jobs as employees who don’t:

“Communication is often the basis of any healthy relationship, including the one between an employee and his or her manager,” says the report. “And while all forms of communication are effective, managers who use a combination of face-to-face and electronic communication are the most successful at engaging employees.” 6

Do you want employees to feel engaged and happy because their company and boss care about them? Start by scheduling regular one-on-one meetings.

3. One-on-one meetings help you discover and address issues proactively

One-on-ones empower you to unearth issues before they become full-blown problems. Imagine these two scenarios:

This is just one of many examples that show how one-on-ones empower you to proactively fix situations before they become big problems. From helping you solve team issues to allowing you to coach employees when they should be focusing on different priorities… one-on-one meetings can help you defuse workplace bombs before they explode. As Andy Grove argues:

“The meeting should cover anything important that has happened since the last meeting: current hiring problems, people problems in general, and- very, very important- potential problems. Even when a problem isn’t tangible, even if it’s only an intuition that something’s wrong.” 4

Just like managers in the world’s most innovative companies, you can use one-on-ones as a powerful tool to stay updated about issues and provide your team with ongoing support.

4. One-on-ones provide the ideal environment to exchange feedback

Imagine getting an email from your boss saying “we need to talk.” Unsurprisingly, receiving an email like that would cause many of us to freak out a little, and immediately think that we are in trouble (or the feeling of being sent to the principal’s office…). To try and prevent your team from these mini heart attacks, you can exchange feedback during your regularly scheduled one-on-ones.

One-on-one meetings are the ideal scenario to ask for feedback about the company, the team, and your management style. Similarly, they’re the perfect moment (a private, face-to-face conversation) to give your employees helpful feedback on their performance. We discuss specific ways to ask for feedback and provide constructive criticism in chapter 5.

. . .

To sum up, there are many benefits you’re missing out on if you still haven’t scheduled regular one-on-ones. A few of them include increased productivity, better relationships with your teammates, and the ability to address issues proactively and exchange ongoing feedback.

If you’re feeling motivated and ready to start scheduling, we think you’ll enjoy reading the next chapter!

2.1 One-on-one meeting frequency: How often do great managers meet with their employees?

Before communicating your decision to schedule regular meetings with your teammates, you should spend some time deciding if you want to do it weekly or biweekly.

Why not monthly or quarterly?

Think about all the things that happen at work during one month. An employee might go through ups and downs, experience new challenges and feel the need to request feedback from you. An issue that is distressing someone can become a big problem if you, as their manager, don’t hear about it earlier in the month. Similarly, receiving praise can feel hollow if it’s received a month or two after accomplishing an important milestone.

There’s so much to talk about, and so many things that can happen in just four weeks. Besides, if you meet with an employee for 30 minutes each month, you’re only spending six hours per year with them – that’s clearly not enough time to develop a great relationship.

What’s the ideal one-on-one frequency?

If you’re curious about the ideal meeting cadence, our research shows that you should hold one-on-one meetings biweekly or ideally, once a week. Here’s what some of the world’s most recognized management experts have to say about the topic:

As you can tell, there is no “one-size-fits-all” approach. Some managers like to hold weekly 30-minute meetings, while others prefer biweekly one-hour-long sessions. In the end, it’s up to you and your team to decide what works best for you.

There are three factors you can consider when making this decision:

  1. The size of your team: We recommend meeting for 45-60 minutes if you have five or less direct reports, and for 25-30 minutes if you manage more than five people.
  2. Your direct report’s task-relevant maturity: If someone is new to a role or has a new responsibility, they’ll need more help and guidance from you. Make time to meet with them once a week. On the other hand, you can schedule biweekly meetings with more experienced employees.
  3. The frequency in which you work and communicate with your team: Some teams work more closely than others. If you have frequent project update meetings and talk to your direct reports in different settings during the week, bi-weekly meetings are a good fit. In contrast, you might need to meet on a weekly basis if you don’t see or talk to your direct reports very often – or if one of you works remotely 🏡.

Here’s our first action item for you!

Action Item: Open your calendar and schedule recurring one-on-one meetings with all your direct reports.

2.2 Pros and cons of the 3 most common one-on-one meeting locations

Now that you’ve scheduled frequent one-on-ones with each one of your direct reports, you might be asking yourself: where is the best place to meet with them?

Some managers wonder if it’s a good idea to go for a walk or grab lunch with an employee during their one-on-one time. Our answer: Meetings don’t have to be boring – try different styles!

Choosing different settings based on your direct report’s preferences can add excitement to your meetings and help you strengthen your work relationships.

In order to help you decide where to meet with each teammate, we compiled the pros and cons of the three most popular one-on-one settings:

  1. Meeting at the office
  2. Meeting at the park
  3. Meeting at a coffee shop or restaurant

Meeting at the office



Pro Tip

“A supervisor can learn a lot simply by going to his subordinate’s office,” says Andy Grove. “Is he organized or not? Does he repeatedly have to spend time looking for a document he wants? Does he get interrupted all the time? Never? And in general, how does the subordinate approach his work?” 4

Meeting at the park


“When planning a difficult conversation, try taking a walk instead of sitting and talking,” says Kim Scott. “When you’re walking, the emotions are less on display and less likely to start resonating in a destructive way.” 1

“Outside, when we run out of things to say, we have to get back to the office anyway, so we have to come up with something to talk about,” says Avi Arfin, an engineering manager at Quora. “Sometimes those ‘add on’ conversations end up being the deepest ones and let us explore important topics we wouldn’t have otherwise.” 8


Pro Tips

Meeting at a coffee shop or restaurant


“Every once in a while, though, offer to change the setting. Think of it as a chance to interact with your team member more as a human being than as just the stodgy old boss,” says Russ Laraway. 9


Pro Tips

There you go. Three different settings where you can hold your one-on-one meetings. Remember that switching up your location will help you get more creative, have different types of conversations, and build rapport with your teammates.

Action Item: Ask your direct reports if they’d like to have their next one-on-one over coffee, lunch, or a nice walk in the park.

2.3 Convincing your team to see the value of one-on-one meetings

Now that you’ve figured out the logistics (meeting length, frequency, and location), it’s time to communicate your decision to schedule regular one-on-one meetings. You can do this during a team meeting or via email.

In order to get your direct reports on-board with this initiative, you must reassure the team so they don’t feel intimidated. How? By letting them know what you expect each one of them will get out of these meetings.

You can tell them you are going to schedule recurring one-on-ones because you want to:

Here’s a draft email you can use to communicate your new plan (or get some inspiration if you decide to talk about this during a team meeting):

Hi [name],

I wanted to let you know that I’ll be scheduling recurring one-on-one meetings with everyone on the team. We’ll spend this time discussing priorities, sharing feedback, working on career development, and answering any questions you might not be able to ask me during the week.

You should know that these one-on-one meetings are your time with me, which means that your talking points will be the primary focus of the meeting. Here is some further information on how you can get the most from your one-on-ones:

Please let me know if you have any questions.



Action Item: Let your team know that you’ll be scheduling regular one-on-ones and explain the benefits that the team will get out of them.

2.4 The 3 basic (yet overlooked) steps to prepare for your one-on-ones.

Whether it’s your first time scheduling a one-on-one or you’re looking for ways to improve your existing ones, the following steps will help you get ready to have more meaningful and effective conversations:

1 Review previous meeting notes

A great place to start is to review the last one-on-one you had with the person you’re about to meet with. Spend a few minutes reviewing the things you discussed in the past and getting up to speed before the meeting, rather than during it.

Are you aware of the projects and initiatives that your direct report has been working on recently? Is there a conversation or piece of feedback that you’d like to follow-up on? Are there any action items from the previous meeting that haven’t been completed? These are all things that you should review prior to your one-on-one.

In The Manager’s Path, Camille Fournier recommends using a shared document to track your work interactions with staff:

“For each person you manage, maintain a running shared document of notes, takeaways, and to-dos from your 1-1s. This is helpful for you to keep context about what has happened, and is useful for remembering when and what feedback was given,” says Fournier. 7

If you’d like to use software to do this, you can check out

2 Collaborate on a meeting agenda

In The Making of a Manager, Julie Zhuo argues that it’s rare to have an amazing conversation when nobody has a plan for what to talk about. This is why you should always come to your one-on-ones prepared with things to discuss.

The most important part about this step is that you are not creating the meeting agenda – you are collaborating on one, which means that both you and your direct report will come up with talking points and questions before the meeting starts.

As a manager, you’ll be attending and organizing a lot of meetings. However, this shouldn’t be an excuse to show up unprepared. If you’re struggling to find a time to prepare for your meetings, you can do it in the mornings, as Julie Zhuo recommends:

“Every morning, I’ve gotten into the habit of scanning my calendar and compiling a list of questions for each person I’m meeting with,” says Zhuo “Why questions? Because a coach’s best tool for understanding what’s going on is to ask.” 2

Another great way to prepare for your meetings is to write down what you’d like to ask your reports throughout the week – as opposed to coming up with questions for the sake of adding something to the agenda the morning before the meeting.

You can create a new document as soon as your one-on-one ends, and start writing down thoughts for the next meeting as they come to mind. These ‘random thoughts’ will generate much better conversations than the talking points you make up a couple of hours before the one-on-one.

How can you encourage employees to prepare for your one-on-one meetings?

First of all, you need to ensure that they know the reasons why you’re having one-on-ones (something we discussed in the previous section). If they understand that your main goal is to help them, they’ll probably come up with better discussion points and questions.

Another way to encourage your direct reports to prepare is by sharing a list of topic examples with them. Suggested topics can jog ideas and bring permission to bring up things that otherwise might feel too risky or awkward to bring up.

Here’s a list of one-on-one meeting questions that you can share with your employees.

Finally, you can encourage your direct reports to add any ‘random thoughts’ and questions that come up throughout the week to your one-on-one document. This will not only save you time by reducing the number of interruptions you get during the week but will let your reports know that they should feel comfortable to ask you any type of questions during your one-on-one meetings.

The best part about collaborating on a meeting agenda ahead of time is that neither you nor your report will be surprised by the questions that get asked at the one-on-one. If you add talking points throughout the week, you’ll be able to review them 15 minutes prior to the meeting. This will eliminate the stress and uncertainty of wondering what the other person is going to ask and will fuel much better conversations between you and your fellow teammates.

3 Get in the right mindset

Sometimes you need to remind yourself that one-on-ones are not like other meetings. This should be a time when you build trust and rapport with your employees.

It’s essential to recognize that most of the time, your report sees this meeting as valuable face time with their manager – and they’ve probably been looking forward to it all week. Make sure to be present and engaged in the conversation in order to make them feel that you care. (We’ve got you covered with active listening tips in chapter 4!)

As Kim Scott argues in Radical Candor, your mindset will go a long way in determining how well your one-on-ones go:

“I found that when I quit thinking of them as meetings and began treating them as if I were having lunch or coffee with somebody I was eager to get to know better, they ended up yielding much better conversations,” says Kim Scott. 4

Try it out! Next time you have a one-on-one with a direct report, don’t treat your meeting like one more thing to check off the to-do list. Instead, use this valuable time to learn something new and improve your relationship with that person.

Action Item: Maintain a shared document with notes and takeaways from your one-on-ones with each employee. Review your notes and collaborate on talking points before every meeting. Fellow can help with this!

3.1 Three powerful templates for effective one-on-one meetings

We analyzed the habits and practices of the world’s best managers and created three research-backed one-on-one meeting templates that you can alternate depending on each employee’s preference:

The 90/10 format

Most management experts argue that one-on-ones are the direct report’s meeting. This means that your employees should get to decide how they want to use this time and what kind of topics they’d like to discuss.

As Ben Horowitz, former CEO of Opsware and co-founder of the venture capital firm Andreessen Horowitz argues:

“The key to a good one-on-one meeting is the understanding that it is the employee’s meeting rather than the manager’s meeting. This is the free-form meeting for all the pressing issues, brilliant ideas and chronic frustrations that do not fit neatly into status reports, email and other less personal and intimate mechanisms.” 10

Based on this idea, you can structure your one-on-ones by splitting them into two sections: your talking points and your employee’s. Bear in mind that your report’s talking points, questions and concerns should always be addressed first.

Here’s how the 90/10 template looks in

So why are we calling this the 90/10 format? Because 90 percent of the talking points should be your direct report’s, and only 10 percent should be yours.

“During the meeting, since it’s the employee’s meeting, the manager should do 10% of the talking and 90% of the listening,” says Horowitz. 10

The 90/10 style works well for managers and reports who prefer a flexible format and tend to bring a lot of talking points to their meetings. It reminds managers that the employee’s questions should always go first and occupy 90 percent of the time.

The 8 key areas approach

There’s another format we recommend if you’d like a bit more structure and reminders of the topics you should be covering: let’s call it the key areas approach.

The second option for structuring your one-on-ones is to create a template with topics that you’d like to discuss on a regular basis. Crafting a list of headings that can be populated with questions will save you time and ensure that your one-on-ones cover topics that might get overlooked otherwise.

Here are eight key areas or headings we recommend. Remember that some headings might not get talking points every week – and that’s ok!

  1. Top of mind
  2. Things that went well
  3. Learnings
  4. Priorities
  5. Challenges and concerns
  6. Team dynamics
  7. Feedback
  8. Career development

Here’s how the 8 key areas template looks in

1 Top of Mind

Start every one-on-one discussing the things that are top of mind for your direct report. These could be all the ‘random questions’ that they wrote throughout the week, important updates, or personal news.

This is also the perfect moment to ask rapport-building questions about your direct report’s hobbies, level of engagement/happiness and life outside of work.

2 Things that went well

There’s a very specific reason why you should include this heading (which could also be called Wins or Highlights) in your one-on-one template:

Leadership coaches such as Sally Helgesen argue that some people (notably women) don’t bring up milestones and important things they experience at work with their managers because they assume that:

Having a section where your direct report describes the things that went well during their week will foster some great conversations about their strengths and accomplishments. On one hand, it will increase your direct report’s self-awareness and ability to reflect on their wins. On the other, it will help you recognize them for their good work and stay in the loop about their contributions to the team.

3 Learnings

Sydney Finkelstein, the author of The Superbosses Playbook, has studied world-class leaders for more than a decade. One of his biggest takeaways is that great leaders are also great teachers:

“Star managers emphasize ongoing, intensive one-on-one tutoring of their direct reports, either in person or virtually, in the course of daily work,” says Finkelstein. 11

Inquiring about your direct report’s learnings (or having a heading that encourages them to write their learnings every week) will help you coach them on their work and most importantly, promote a growth mindset across your team.

4 Priorities

One of your main responsibilities as a manager is making sure that your team is allocating their time wisely and working towards the same vision. You can do this by asking your direct reports to list their priorities in the one-on-one document.

“What are the one, two, or three most critical outcomes for your report and how can you help her tackle these challenges?” asks Julie Zhuo. 2

Having a priorities heading will remind you to spend some time reviewing and reorganizing your direct report’s projects, and finding ways to help them be more productive. It’s also a great segue to talk about roadblocks.

5 Challenges and concerns

Ask your employees about the roadblocks that stand in their way. This will help you identify team and organizational problems, such as processes that are not working well or internal issues that are slowing your team down.

You can also ask your direct reports about the parts of their job that annoyed or frustrated them in the past week. This will help you understand what each employee dislikes and find ways to help with those aspects of their job (perhaps by delegating those tasks to someone else or finding ways to automate them).

6 Team dynamics

In this section, you can ask employees about their relationships with their fellow teammates.

How is the team doing? Do they have any suggestions on the way the team works together? Are co-workers exchanging enough feedback, or would they like to hear more feedback from other people on the team?

Those are some of the questions you can ask to measure your team culture.

In Radical Candor, Kim Scott argues that a team’s culture has an enormous impact on its results. That’s why great managers ask about team dynamics and look for ways to foster positive relationships amongst their reports:

“One of your core responsibilities as a boss is to build a cohesive team,” says Scott. 1

Asking employees about their relationships with other team members helps you understand if everyone feels comfortable and enjoys going to work. As an added bonus, it empowers you to solve issues before they become big problems affecting the entire team or the organization as a whole.

Quick reminder: Even though part of your job as a manager is to uncover issues that might be affecting the team, you should never encourage “backstabbing.” As Kim Scott argues:

“Never let one person on your team talk to you about another behind their back. It feels like you’re being empathetic to listen, but actually you’re just stirring the political pot. Instead, insist that they talk directly to each other, without you,” says Scott. 1

7 Feedback

Creating a culture of ongoing feedback should start with your one-on-ones. Use this section to ask for feedback, recognize your employees for their great work, and share recommendations on how they can improve.

8 Career development

One last thing you can do during your one-on-ones is revisiting your direct report’s professional development plan.

We give you all the tips on how to exchange feedback and structure professional development conversations with your team in chapter 5!

Now that we’ve discussed the 90/10 format and the 8 key areas approach, here’s one last template you can use to structure your one-on-ones with direct reports:

The chronological style

Instead of structuring your meeting based on topics, you can plan your one-on-one by focusing on past wins and challenges, present priorities, and future opportunities. Let’s call this the chronological one-on-one format.

Here’s how the chronological one-on-one template looks in

Kelly Riggs, a leadership coach and author of the book 1-on-1 Management, argues that you should always start your one-on-one by asking your direct reports about their most recent challenges.

“My one-on-one meetings for 30 years have started with one very simple phrase: Tell me about last week. I know it sounds ridiculously simplistic on the surface, but trust me, there is a lot behind the curtain,” says Riggs. 12

Another great way to start the meeting is by asking your employee about something they mentioned in your previous one-on-one. For instance, if they said that they were frustrated about something, make sure to bring it up again and ask them if there’s any progress with that. This will show your reports that you take these conversations seriously, are actively listening, and want to help them as much as you can.

After addressing what happened in the previous week, you can move on to the present one. Your agenda can include questions like ‘what projects and goals are you currently working on?’ and ‘is there anything I can do this week to help you achieve that?’.

Last but not least, talk about the future, the goals and things that your direct report might be feeling anxious about or looking forward to. Ask questions like ‘what’s on your to-do list this coming week?’, ‘what areas of development are you planning to work on?’ and ‘what resources can I provide for you between now and the next time we meet?’.

This is a simple format that allows you to focus on past challenges, present priorities and future opportunities.

Now that you know three meeting formats that have been working for the most successful managers, you can alternate between them, combine your favourite things about each one, or add questions that align with your leadership style.

Whether you decide to use the 90/10 format, divide your one-on-one based on our eight suggested topics, or structure the meeting in chronological order – the most important thing is to schedule these meetings on a regular basis and acknowledge the power they give you to coach and support your employees.

3 things to keep in mind:

  1. Always start with rapport building questions (or an informal catch-up).
  2. Even when you’re using a template for your one-on-one meetings with direct reports, let the conversation flow naturally. You can revisit outstanding talking points at your next meeting.
  3. No matter what template you end up using, make sure to finish your one-on-one by going over action items and takeaways. (Check out chapter 4 for tips on how to write them).
Action Item: Try out the three one-on-one templates (90/10 format, 8 key areas approach, and chronological style) and see what works best for each one of your direct reports.

3.2 One-on-one meeting questions

Even if you have an amazing one-on-one meeting agenda template, you need a set of great questions to ensure that you’re getting the most out of these conversations.

The questions that you ask employees during your one-on-one meetings will have an enormous impact on your team’s future performance. They’ll help you understand your direct report’s perspective and coach them on their priorities and goals. By asking the right questions, you’ll make the transition from boss to coach!

What is the definition of coaching?

According to Lara Hogan, coaching is the act of asking open questions to help your teammates reflect and introspect, rather than sharing your own opinions or quickly solving their problems. In Resilient Management, she argues that asking open-ended questions is one of the best coaching techniques a manager can apply during their one-on-ones:

“Open questions often start with who, what, when, where, why, and how,” says Hogan. “Questions that start with why tend to make the other person feel judged, and questions that start with how tend to go into problem solving mode—both of which we want to avoid while in coaching mode.” 3

We want you to leverage the power of one-on-one meetings and become a coach for your team. It’s no coincidence that the majority of questions you’ll find in this section will be open-ended, and start with what.

Here are the 9 categories we’ll cover:

  1. Getting to know your employees and setting expectations
  2. Checking-in weekly or bi-weekly
  3. Helping employees organize their priorities and boost productivity
  4. Addressing roadblocks and concerns
  5. Employee engagement / General happiness
  6. Getting feedback
  7. Giving feedback
  8. Career development
  9. Team dynamics and culture

One last tip before we jump into the list: Remember to let the conversation flow naturally, and practice your intonation to make sure that your questions actually sound curious and open.

“Open questions asked from a place of genuine curiosity help people feel seen and heard,” says Lara Hogan. “However, if the way you ask your questions comes across as judgy or like you’ve already made some assumptions, then your questions aren’t truly open (and your teammate can smell this on you!).” 3

Without further ado… we present to you the list of top questions great managers ask during their one-on-one meetings with employees. You can come back to this list any time you need some inspiration – or check out this post with 121+ one-on-one meeting questions if you are looking for other categories!

1 Questions to get to know your employees and set expectations

2 Questions to check-in weekly or bi-weekly with direct reports

3 Questions to help your employees organize their priorities and boost productivity

4 Questions to address roadblocks and concerns

5 Questions to ensure that your employees are engaged and happy at work

6 Questions to get feedback from your employees

7 Questions about giving feedback

8 Questions about career development

9 Questions about team dynamics and culture

Action Item: Practice using open-ended [what] questions in your one-on-one meetings with direct reports – and come back to this list any time you need some inspiration!

Chapter 3 covered the templates and questions that will help you have more meaningful conversations. If you’ve read this far, you’re already more knowledgeable on the subject of one-on-one meetings than the vast majority of managers. Now, it’s time to level-up!

Let’s talk about the two skills that will turn you into a Supermanager – and make all your meetings (not only one-on-ones!) ten times more effective:

4.1 Mastering the art of active listening

How many times have you missed the opportunity to have an enriching conversation with your direct report just because you got distracted, didn’t follow-up on their ideas, or answered a couple of emails during the meeting?

We often hear that leaders should be confident and willing to speak up. While these can be great traits when managing a group of people, there’s one skill that can make or break your team’s success: the ability to sit down and listen up.

Listening is the most important ingredient for building healthy relationships, cohesive teams, and thriving organizations. In this section, we’ll show you four techniques that will help you master this scarce leadership skill.

The four techniques are:

  1. Using body language intentionally.
  2. Avoiding the three most common forms of distraction.
  3. Leaving your ego at the door.
  4. Following-up.

1 Using body language intentionally

The most common greeting amongst members of the Zulu tribe in South Africa is Sawubona. It means “I see you, you are important to me and I value you.”

Interestingly enough, the term was brought to the world’s attention by Peter Senge, a senior lecturer at the MIT Sloan School of Management and the author of The Fifth Discipline Fieldbook. In the book, Senge argues that this simple word explains a lot about human interactions and relationships:

“If you are a member of the tribe, you might reply by saying ‘sikhona’ or ‘I am here.’ The order of the exchange is important: until you see me, I do not exist. It’s as if, when you see me, you bring me to existence,” explains Senge. 14

It’s an interesting term, right? But how is it relevant to your one-on-one interactions with employees?

Senge’s story and the “Sawubona” expression highlight one basic principle of human nature: we feel acknowledged and important when we receive someone’s attention. This means that whenever you’re meeting with a direct report, you should use body language to “bring them into existence.”

The first thing you can do is polish up on your eye contact skills. This might sound obvious, and you might have heard a lot about the importance of ‘eye contact’ already, but it’s something we forget to practice in our day-to-day lives.

Think for a moment about the kind of attention you bring to your conversations. While someone is talking, do you look at them the entire time, or do your eyes roam around the room and scan your phone once in a while?

Maintaining eye contact is one of the easiest and most powerful ways to make your colleagues feel understood and validated during your one-on-one meetings. Besides, it’s a management tool that will help you get messages and ideas across in a more efficient way. Why do we say so? Studies show that people remember what you said for a longer time if you maintain good eye contact during your conversations with them.

Pro Tip

Eye contact is great, but we all know it can be off-putting when someone does it unnaturally – staring at you for too long. In order to avoid this from happening to you, just break eye contact every five seconds or so. And instead of looking down, just look to the side as if you’re remembering something. This skill will become more and more natural as you practice it!

We spent a lot of time talking about eye contact in this section. However, this technique wouldn’t be as effective without some of the following body language techniques. Make sure to apply them during your next meeting:

2 Avoiding the three most common forms of distraction

Can you guess the three most common ways in which managers get distracted during their one-on-one meetings?

Multitasking on your laptop or phone

You probably guessed the first one: checking your phone to read emails, texts, or social media posts! The problem is, even if we think we can multitask, finish an email, or read through our Twitter feed while listening to someone, research shows that we really can’t.

Here’s something you can do to avoid these distractions during your one-on-ones: just set your devices to ‘do not disturb’ mode.

This will let you focus on the conversation and write down notes in your shared meeting agenda – without getting a bunch of notifications that will ultimately pull your attention away from what the other person has to say.

Internal listening

The second (and less obvious form of distraction) is something Lara Hogan calls Internal Listening. It’s the process of getting distracted in your own head – processing the information that your report gives you and thinking about how you’ll react to it:

“Often, when we’ve asked a question and another person is responding, we are processing in our brain and getting ready to say the next thing: ask a follow up question, or provide some direction,” says Hogan. “This isn’t really listening. But we do it all the time!” 15

Next time you catch yourself preparing your following argument while your direct report is speaking, take a deep breath and focus on what they’re saying – the overall message they’re trying to communicate. Listen to hear, don’t listen to respond.

“If your brain starts winding up while they’re talking, say to yourself—wait! They’re not done yet,” says Hogan. “Focus on their words, their body language, and how they might be feeling. Take in all of this information as data, and practice waiting til they’re done talking before you process it.” 15

Filling the silent gaps

We rarely think about this as a form of distraction, but we do it very frequently. Filling the silent gaps can mean responding quickly with little or no thought, or using a quiet moment in the conversation to change the topic entirely just because the silence makes us feel awkward or uncomfortable.

A silent gap is not the sign of a bad conversation – it is a signal that the speaker is thoughtfully crafting their next point. If you want to develop the listening skills of a great leader, you need to get comfortable with silence.

Where can you start?

Don’t bring up a new topic and get distracted just because the other person takes a five-second break to rethink what they are trying to say. Instead, encourage your reports to ask for a pause whenever they need to clarify their ideas.

“As you practice the skill of creating silence, watch for the effects it has on the people you’re talking to,” suggests Hogan. “What additional information do they end up providing? What questions do they start asking? How much further do you get in your conversation? Remember: silence is a powerful tool in your toolbox, and can do a lot of work for you!” 15

Multitasking, internal listening, and filling the silent gaps – make sure you avoid these three forms of distraction during your one-on-ones.

3 Leaving your ego at the door

A common experience you’ve probably had is having a conversation that begins with your story, but somehow ends up with the other person saying “I know exactly what you’re talking about, let me tell you what happened to me…” – Isn’t that annoying? And the worst part is we do it all the time because we naturally like to talk about our personal experiences.

However, this is a behaviour you must avoid at your one-on-one meetings. As we mentioned in chapter 3, you should do 10% of the talking and 90% of the listening. But it isn’t as easy as it sounds. It requires leaving your ego at the door.

Susan Scott is a workplace communication expert and the author of Fierce Conversations. In the book, she argues that one of the greatest gifts you can give your direct reports is your undivided attention:

“Don’t take the conversations away from the other person and fill the air with your stories,” says Scott. “Leave your expert, storyteller, fixer, fix-it hat at the door. Come into the conversation with empty hands.” 16

We’re not saying that you shouldn’t share your stories and advice during your one-on-ones. In fact, sharing personal stories can help you build trust with employees and help them learn more about the company. However, even if your stories or comments are relevant to your direct report’s growth, make sure you don’t tell them until they have finished elaborating their argument or point of view.

“Your job as a manager isn’t to dole out advice or ‘save the day’ – it’s to empower your report to find the answer herself. Let her lead the 1:1 while you listen and probe,” says Julie Zhuo. 2

4 Following-up

The last practice that you should adopt to become an active listening expert is following-up: during and after your one-on-ones.

Following-up during the conversation

One of the best ways to let your reports know that you’re listening is repeating back or paraphrasing what they say. An occasional question or comment to recap their argument communicates that you are listening and understanding the message.

In order to do this, you can reflect back on what has been said by saying things like “what I’m hearing is…” or “sounds like you are saying…”. On the other hand, you can ask questions to clarify certain points. For instance: “what did you mean when you said…?”

Reflecting your direct report’s message gives focus to the situation and ensures that you fully understand what they have to say.

Following-up after the one-on-one meeting

Following up on previous discussion points is a crucial step to ensure that your employees feel heard and appreciated.

Christine Riordan, a leadership speaker and the president of Adelphi University, argues that the ability and willingness to listen with empathy is often what sets great leaders apart:

“Follow-up is an important step to ensure that others understand that true listening has occurred,” says Riordan. “This assurance may come in the form of incorporating feedback and making changes, following through on promises made in meetings, summarizing the meeting through notes, or if the leader is not incorporating the feedback, explaining why he or she made other decisions.” 17

There you go! Four techniques that will help you level-up to become an active listening master: Using body language intentionally, avoiding the most common forms of distraction, leaving your ego at the door, and following-up on your employee’s ideas and talking points.

Speaking of following up… Let’s move on to the next section – where you’ll learn how to write and follow up on your meetings’ action items and takeaways like a pro.

Action Item: Practice the four techniques that will help you master active listening (using body language intentionally, avoiding distractions, leaving your ego at the door, and following-up).

4.2 Writing impactful action items – and following up on them

You’ve probably attended meetings that felt like circular discussions. Meetings where you left wondering what the conclusion was, and who was supposed to do what. There might have been a ton of great ideas floating around the room, but nobody took the initiative to record next steps or own those great suggestions.

Studies show that every year, businesses in the U.S. waste 37 billion dollars on ineffective meetings. Do you know what makes most of those meetings so scarily unproductive? A lack of action items and takeaways.

In this section, you’ll learn how managers in high-performing companies promote a culture of accountability and productivity in their meetings.

What is a meeting action item?

An action item is a task that gets assigned to one or more meeting attendees. It’s an essential part of making sure that all your meetings involve new decisions and ideas – and aren’t just scheduled to exchange project updates (which should ideally happen via email or chat).

Action items should be recorded in your meeting agenda. This will allow you to track what was agreed in previous discussions and easily follow up so nothing falls through the cracks.

Here’s what action items look like in

3 reasons why you should write action items during your one-on-ones

1 Foster accountability

According to Andy Grove, many issues in a one-on-one lead to action required from both the manager and the employee. He emphasizes the importance of writing down notes and action items in High Output Management:

“When the report takes a note immediately following the supervisor’s suggestion, the act implies a commitment, like a handshake, that something will be done,” says Grove. 4

Encouraging your direct reports to write action items during your one-on-ones will ensure that you’re both on the same page about what was agreed in the meeting. This written commitment increases accountability.

2 Generate progress between meetings

Your one-on-one meetings should be like a spinning flywheel. This means that all your conversations should be interconnected, feed from each other, and flow naturally.

Even if you meet with a direct report every two weeks, you should be able to follow up on the ideas and decisions that were discussed in your previous one-on-one meetings. If you lose your notes or forget what the takeaways were, the flywheel will lose its momentum. But if you write clear and concise action items, following up on previous decisions and ensuring that there’s progress made between meetings won’t be an issue.

Paul Axtell, a personal effectiveness consultant and the author of Meetings Matter, argues that meetings are just a series of conversations – and if you always end those conversations well, your relationship with employees will improve significantly:

“Getting firm, clear commitments is the primary way to ensure progress between meetings. In order for a conversation to lead to action, specific commitments must be made. Progress depends on clearly stating what you will do by when and asking others to do the same,” says Axtell. 18

3 Give every meeting a clear purpose

One of the most common complaints from managers is that they spend too much time meeting with other people and don’t see a lot of results coming out of these discussions. Documenting commitments and assigning specific tasks will help you ensure that every meeting has a sharp focus.

It’s important to note that once in a while, some one-on-one meetings might not generate action items – especially if you’re using this time to catch-up or simply build rapport with an employee. However, it’s important to build the habit, and teach your direct reports that an action item could be as simple as “Read this book” or “Start writing a list of professional goals,” which means that even the most informal meetings can have takeaways.

4 tips to write action items like a pro

Charlie Gilkey, a business strategist and productivity coach, says writing great action items takes time and practice. However, much more time is wasted by poorly formulated takeaways – or even worse: meetings that have no action items at all!

Would you like to write impactful action items that help your team spur into action? Just follow these four tips:

1 Write action items as the meeting evolves

Something that can make your meetings 10x more effective is writing tasks as the conversation goes, and not just at the end of the meeting – since you might forget a couple of things!

For instance, you can write an action item under each talking point in your meeting agenda. That way, you’ll make sure that there are next steps for every topic that gets covered.

2 Start with a verb

There’s a big difference between these two action items:

While the first one reminds you that something needs to get done, the second one is specific and empowers you to start tackling the task immediately. Why? Because it starts with a verb!

“A verb-noun construct tells you what needs to be done to what; it automatically spurs action, which is what we want,” says Gilkey. 19

3 Be specific – imagine you’re writing for someone else

Unclear action items require you to look through different documents trying to remember what the task was actually about. The best action items are clear enough that once you read them in your to-do list, you’ll know exactly what you need to start doing and when the task is due.

“I’ve found that when people write the items as if they were writing them to someone else, they write them the right way,” says Gilkey. “That means their lives are easier in the future when they get to those action items, as well as in the now when they see the items and don’t have to do a bunch of guessing about what needs to be done.” 19

4 Assign ownership of the task

Creating a list of ‘next steps’ during your meeting isn’t enough if nobody is held accountable for them. In order to make your one-on-ones more effective, always assign action items to yourself or your employee. Reviewing the list of action items at the end of the meeting will be easier if you established specific owners or assignees.

You can assign action items using

What happens after the meeting?

  1. End your one-on-one with a recap of the action items that were assigned.
  2. Send the meeting notes and takeaways via email or Slack. (If you use a one-on-one meeting app like Fellow, you can skip this step and save some time).
  3. Don’t forget to check-in on those action items at your next one-on-one.
Action Item: Write action items during all your one-on-ones. Make sure they start with a verb, are specific, and get assigned to you or your direct report. (Don’t forget to follow up!)

5.1 The career conversation framework that will boost employee engagement across your organization.

The world’s best managers care about their direct reports’ development and professional growth. They know what motivates each person on their team and use this information to assign projects that align with each employee’s interests and goals.

“To understand a person’s growth trajectory, it’s important to have career conversations in which you get to know each of your direct reports better, learn what their aspirations are, and plan how to help them achieve those dreams,” says Kim Scott. 1

Career development conversations help you boost employee engagement, foster self-awareness, and develop trusting relationships. They’re one of the best ways to leverage each employee’s strengths and encourage the top performers in your team.

In fact, studies show that 82% of employees would feel more engaged at work if their manager showed greater interest in their career progression. That’s why (if you haven’t yet), you should start scheduling regular career conversations.

“Employees used to expect to work for a boss. Now, they’re looking for a coach,” says a study by Gallup. “Because they don’t just want to be satisfied with their role or their job. Your employees want personal and professional development, immediately and for the future.” 20

We know this sounds like a lot of work (and you might be thinking that you’ll have to add more things to your calendar), but there’s no need to worry! These professional development conversations are just one more component of your regularly scheduled one-on-one meetings.

How can you structure career development conversations with employees?

During his time as a Director of Sales at Google, Russ Laraway developed a three-step career conversation framework that led to a 10-point bump in engagement scores across the organization. If you’re trying career conversations for the first time, following this model is a great way to start.

First, book three one-on-one sessions to talk about career development with each employee. Then, cover the following three topics in each one of those meetings:

1 The life story one-on-one

According to Laraway, managers must understand the past and the employee’s plan for the future in order to help them grow. That’s why he suggests starting your first professional development conversation with this simple opening question:

“Starting with kindergarten, tell me about your life.”

This will help you understand the life events and stories that have shaped your direct report’s dreams and aspirations. Laraway’s main advice? Focus on changes that people have made and understand why they’ve made those decisions.

“It’s amazing what you can learn from a person’s life story if you pay close attention to and ask about their major pivots and transitions. Why did they make them? What did those transitions teach them about what they love and hate about their work?” says Laraway. 21

For instance, learning that your direct report has always enjoyed competitive sports will be helpful to understand what type of environments motivate them. Since they are highly competitive, you could come up with targets and ideas to make their work more exciting. If someone says they quit running and started playing soccer because they liked being on a team, you might write down that being part of a team is a motivator for this person.

2 Dreams one-on-one

Your second career conversation will focus on dreams and aspirations. Laraway recommends starting this meeting with one simple question:

“What do you want the pinnacle of your career to look like?”

This is a hard question for many of us. That’s why he suggests asking your employees to come up with three to five different ideas. You can give them some time to think about those ‘dream jobs’ by sharing your meeting agenda ahead of time.

After going over those 3-5 options, you can collaborate on a list of skills that could help your direct report achieve their goal:

“Now, your job as the boss is to help them think about how they can acquire those skills. What are the projects you can put them on, whom can you introduce them to, what are the options for education?” says Kim Scott. 1

3 The 18-month career action plan

Now that you have an understanding of your direct report’s past and future goals, you can build a relevant and thoughtful action plan for the next 18-months.

You can divide the plan into three different sections:

Following up on your direct report’s career goals

Once you’ve had these three conversations, one of the most important things you can do is following up on those short, medium, and long-term goals.

Some managers book 10-15 minutes of each one-on-one to check-in on their direct report’s progress, while others prefer to block specific one-on-one meetings to talk about professional development every three, four, or six months.

As Marcus Buckingham argues in the book First, break all the rules, the art of management involves being able to adapt your style to each direct report:

“However you choose to handle these conversations – and each will be unique, according to the potential and the performance of the individual employee – you need to ensure that, over time, two things happen. First, the employee needs to become increasingly clear about his skills, knowledge and talents (…) Second, he needs to understand, in detail, what this next step could entail and why he thinks he would excel at it.” 22

Career conversations will take time – but as Kim Scott, Russ Laraway, and many other great leaders argue, they will generate some of the most enjoyable conversations you have as a manager.

Helping people clarify their values and dreams and then aligning them to their work will help you build a strong team and retain highly engaged employees.

Action Item: Schedule career conversations where you talk about each direct report’s life story, professional aspirations, and 18-month career action plan.

5.2 How great managers give and get feedback

A study quoted in the book First, break all the rules says that the world’s best managers share three characteristics:

All during one-on-one meetings!

If you want to master the art of giving and getting continuous feedback, this section is for you.

3 Secret tips to get more feedback from your employees

Here’s one thing you might not have considered. Before giving any feedback to your direct reports, you should always ask for it first. That’s what experts such as Kim Scott say:

“There are several reasons why it makes sense to begin building a culture of Radical Candor by asking people to criticize you,” says Scott. “First, it’s the best way to show that you are aware that you are often wrong, and that you want to hear about it when you are.” 1

Here are three things you must consider when asking employees to give you feedback:

1 Acknowledge your weaknesses and ask employees to call you out on them

One way to encourage your teammates to give you feedback is letting them know about the things you normally struggle with, and asking them to call you out on them. Here’s an example: In an HBR article, Ron Carucchi describes a manager who became “painfully verbose” whenever he felt anxious during meetings or presentations.

“One of the ways he worked to improve was to acknowledge to his team that he was aware he did it (which they greatly appreciated) and he asked them to simply hold up their hands when they felt he’d gone on too long,” says Carucchi. “Self-aware leaders know their triggers, and let others name them.” 23

Kim Scott gives a similar example in Radical Candor:

“My cofounder Russ once complained that I interrupted him. It was true; I am an inveterate interrupter,” says Scott. “So I said, ‘I know, it’s a problem. Can I ask you to help me stop interrupting?’ I pulled a fat, blue rubber band out of my drawer and put it around my wrist. I asked him to snap the rubber band every time I interrupted him. Russ thought it was funny, and I agreed.” 1

As Scott says in the book, the additional snapping helped her start interrupting less. However, the most important part was that it sent a strong signal: she was taking action to apply her team’s feedback.

You don’t have to ask every employee to snap you with a rubber band. However, you can start by telling them what you want to improve. Letting your team know that you’re aware of your weaknesses makes you a more approachable boss. It not only makes you look more human, but also works as a good incentive to work continuously on your personal growth.

2 Ask specific questions

Put yourself in your employee’s shoes. If your manager asked you for feedback without being specific, it would be hard to come up with a response on the spot. This is why asking “Do you have any feedback for me?” is good… but not the way to get the best possible responses.

Instead, you can use open-ended questions to fuel better conversations! Here are some examples:

When you’re the boss, asking your direct reports to tell you frankly what they think of your performance can feel awkward. But remember: it’s even more awkward for them than it is for you.

That’s why Kim Scott adopted a ‘go-to question’ to kick things off. If you’re struggling to ask your direct reports for feedback, you can start by asking this too:

“If those words don’t fall easily off your tongue, find words that do,” says Scott. “Of course, you’re not really just looking for one thing: that opening question is just designed to get things moving.” 1

3 Reward feedback in order to get more of it

Once you’ve asked the question and understood the criticism, it’s important to follow up by showing that you really did welcome it. In Scott’s words: you have to reward the candor to get more of it.

If your employees say something about your leadership style, the first crucial step is to thank them for their honesty.

“If you agree with the criticism, make a change as soon as possible,” says Scott. “If the necessary change will take time, do something visible to show you’re trying.” 1

But what should you do when you disagree with your employee’s feedback?

Even if you disagree with the feedback, it’s important to thank your direct report for having the courage to criticize you.

Tell them you’ll take some time to think about their comments and try to find some aspect of the feedback that you agree with. Once you’ve taken the time to reflect on it, schedule a meeting to give a thoughtful explanation on why you disagree. This conversation could help you understand your report’s perspective and clarify any misunderstandings. In the end, you should always show appreciation and try to work together to find and commit to a course of action.

“Even if you don’t agree with what’s said, receive it graciously and recognize that it took effort to give. If others find you defensive, you’ll get less feedback in the future, which will only hurt your growth,” says Julie Zhuo. 2

Now you know. If you want to lead by example and exchange ongoing feedback, you must let employees criticize you first. Asking for feedback about yourself shows that you’re invested in becoming a better boss and working on your own flaws, which will make it easier to give employees feedback when there’s something they can improve.

6 Steps to give feedback effectively

1 Know your people and ask for permission

In The Manager’s Path, Camille Fournier argues that the first step to successfully giving continuous feedback is a basic understanding of your reports’ strengths and weaknesses. Ask yourself:

“Good managers have a knack for identifying talents and helping people draw more out of their strengths,” says Fournier. “Yes, you’ll also want to look for weaknesses and areas of improvement, but if you spend most of your time trying to get people to correct weaknesses you’ll end up with a style that feels more like continuous criticism.” 7

Another important component of knowing your direct reports is understanding if it’s the right time to offer them feedback. Whenever you recognize an issue, make sure to always ask for permission:

2 Don’t wait!

Talk about the things that don’t seem to be going well as soon as you notice them. Remember: The best feedback is timely ⏰.

Did someone say “uuhmm” a lot during a presentation? Find some time (right after their talk) to let them know your thoughts and offer some advice. Did a team member make a mistake at work? Let them know during that week’s one-on-one meeting and not four months later, at a performance review.

“This also goes for getting praise. A great manager will notice some of the little things you’re doing well in your day-to-day, and recognize you for them,” says Camille Fournier. 7

3 Praise in public, criticize in private

If it’s time to give someone on your team constructive feedback because they did something that needs improvement, make sure to give them that piece of feedback in person and in private. Don’t send them an email or call them out at a team meeting. If your intention is to help that person grow, you should find a quiet space to offer your advice face-to-face.

“The purpose of feedback is to help each individual understand and build on his natural talents. You cannot do this in a group setting,” says Marcus Buckingham. 22

Giving constructive feedback in person can also help you avoid misunderstandings:

“The clarity of your guidance gets measured at the other person’s ear, not at your own,” says Scott. “That’s why it’s best to deliver guidance in person.” 1

On the other hand, praise can be shared publicly — as long as your report is comfortable with it.

“Public praise tends to lend more weight on the praise, and it encourages others to emulate whatever was great,” says Scott. 1

4 Don’t personalize

Feedback should never be directed at the person, but at the action or habit they should work on.

For instance, if someone has been late to your team meetings several times, you must never say things such as “you’re irresponsible” or “you don’t care about other people’s time.” Instead, you can describe the specific events and the ways in which that person’s tardiness affected everyone else on the team.

As Kim Scott argues, radically candid criticism is about the work, not the person:

“There is a big difference between caring personally and personalizing when giving praise and criticism. Caring personally is good. Personalizing is bad,” says Scott. 1

If you’re still wondering how to make your feedback less “personal,” you can use what Lara Hogan calls the feedback equation:

“If you structure all of your feedback this way—not just big, important feedback, but even tiny little pieces of feedback that you might casually have throughout your day—you’ll find it’s really easy to give successful feedback that people will actually hear,” says Hogan. 3

5 Focus on the future

While the first part of your discussion may focus on the employee’s actions, the majority of time should be devoted to what Marcus Buckingham calls “the truly creative work” — which means, figuring out next steps and ways in which you could help:

“Great managers focus on the future: They want to discuss what could be rather than allowing the conversation to descend into recriminations and postmortems that lead nowhere,” says Buckingham. 22

If your goal is to be a helpful manager, telling people that they did something wrong is not enough. You should offer resources, ideas and guidance to help them accelerate their growth.

Ask questions like “is there anything I can do to help you?” or “what are the next steps you’ll take to change this behaviour?” — focus more on the future, and less on what happened before.

“Ultimately, continuous feedback works best when you, as a manager, pair that feedback with coaching,” says Camille Fournier. 7

6 Last but not least: Record the feedback

Recording the feedback and next steps ensures that none of you will forget that this conversation took place. It will help you follow up on the discussion and analyze emerging themes and behaviours from previous feedback sessions.

“When you zoom out and look at many examples of task-specific feedback for a report, what themes emerge?” asks Julie Zhuo. “By connecting the dots across multiple examples, you can help people understand how their unique interests, personalities, and habits affect their ability to have an impact.” 2

Giving feedback — both when things are going well and when they aren’t — is one of the most important responsibilities of a manager. Bring out the best in your team and show them that you care about their growth by providing positive and constructive comments as soon as you notice something!

“Feedback is a gift. It costs time and effort to share, but when we have it, we’re better off. So let’s give it generously,” says Zhuo. 2

Action Item: Ask your employees for feedback about yourself. Then, practice the “feedback equation” to give effective feedback and praise.

6.1 It’s not working!?! Troubleshooting: The most common obstacles with one-on-ones – and how you can overcome them.

We know that turning your one-on-one meetings into effective growth machines comes with its challenges. As with any other skill or habit, putting the theory into practice isn’t always as easy as it sounds.

There are many obstacles that you won’t be able to anticipate. For instance, having a direct report who doesn’t like one-on-one meetings… or the need to have a difficult conversation on the spot.

Some of the obstacles you might face in the process of implementing regular one-on-ones include:

If you ever face any of these challenges, don’t worry. You’re not alone! Let’s go through some tips and tricks you can use to overcome them.

Employees question the new meeting

If your team has never held one-on-ones, these meetings might come as a surprise to some of your direct reports. In order to avoid feelings of uncertainty and confusion, try to explain the outcomes you hope to achieve as clearly and confidently as possible. Send out an email (like the one we included in chapter 2) or use a team meeting to explain the value that employees can get from their one-on-ones with you.

The meeting feels awkward or forced

… either because you or your report aren’t naturally extroverted, there are communication roadblocks hindering mutual understanding, or simply not enough things to talk about.

First, make sure to include a list of questions on the agenda and prompt your employees to add their own. Having talking points ready before the meeting is the best way to avoid awkward silences.

However, you must remember that silence doesn’t have to feel awkward. It’s not uncommon that people need time to think before replying. If you ask a deep or difficult question, tell your direct reports it’s ok to take a few seconds if they need to.

Finally, if you think that your relationship with your report could use a bit more trust, try going out for coffee or lunch with them. Your first one-on-ones can be casual conversations where you learn about their hobbies and life outside of work.

“To get to know your teammates as individuals, start from a place of genuine curiosity and authenticity,” says Lara Hogan. 3

The one-on-one turns into a gossip-session

In contrast, if your direct report feels very comfortable around you (or you’re transitioning from being their peer into being their manager), it can be easy to turn the one-on-one meeting into a venting session about other team members.

Instead of fueling the gossip machine with questions and complaints about other people, coach your direct report on ways they can address the conflict and deliver feedback to their peers.

“Start by coaching your teammate (with open questions and reflections) about what it would look like to share their feedback directly,” says Hogan. “Then, in mentoring mode, walk them through the feedback equation and help them craft some good words and phrases for each of the three parts. Help your teammate ensure that their observations are just the facts, without judgment or opinions seeping in.” 3

You feel overwhelmed by too many meetings

Keeping track of all your work interactions and conversations can be stressful. Here are three tips to avoid this feeling:

First: Try using a one-on-one app or shared document to track all your talking points and action items in one place. You won’t have to worry about losing notes or having to store a pile of notebooks with observations for each direct report. One-on-ones don’t have to be overwhelming, and is here to help.

Second: If you manage a team of more than ten people, try creating more leadership opportunities for your teammates by reducing your number of direct reports.

Third: Use one-on-ones to talk about career development, share feedback, and ask for your employee’s thoughts on new initiatives – you don’t have to schedule new meetings to do these things.

“To avoid meeting proliferation, I recommend that managers use the 1:1 time to have career conversations and if relevant, to do performance reviews,” says Kim Scott. 1

You’ll have some difficult conversations

It’s hard not to get emotionally involved when you’re having a tense conversation. Whether it’s time to give an employee critical feedback or talk about a disagreement you had, it’s important to remember that we all have core needs that affect how we react to threatening situations.

According to coach Paloma Medina, learning about humans’ core needs at work can help you better understand why people react in different ways during difficult conversations. The six core needs (also quoted in Lara Hogan’s Resilient Management) are: belonging, improvement, choice, equality, predictability, and significance.

“When coaching two people through a conflict, I like to describe this model and ask them which of these core needs (if any) felt relevant to why they reacted the way they did,” says Lara Hogan. “Understand each other’s core need can be tremendously helpful in de-escalating that amygdala hijacking and returning to a place of empathy.” 3

Other tips that can help you manage emotions and empathize with employees include:

You might not have all the answers (and that’s ok)

Becoming a manager doesn’t mean that you need to be the best and brightest in the room. One of the challenges you might face is not having the answers to your direct report’s questions – and that’s fine! You can always support them by finding resources and mentors.

Another similar challenge faced by managers is trying to give out all the answers, instead of coaching employees to come up with their own ideas and solutions through open-ended questions.

“A coach’s best tool for understanding what’s going on is to ask,” says Julie Zhuo. “Don’t presume you know what the problem or solution is. Too often, attempts to ‘help’ aren’t actually helpful, even when served with the best of intentions.” 2

6.2 Am I doing it wrong? Top 10 mistakes managers make during their one-on-one meetings.

Some of the most common mistakes that managers make during their one-on-one meetings can be prevented by seeking mentorship and following the advice from other great leaders. Here’s a list of the ten mistakes that – after reading this guide – we hope you’ll be able to avoid!

1 Not collaborating on a meeting agenda prior to the meeting

… Which results in blank stares, awkward silences, and the typical “I don’t have much to talk about” from employees.

⭐️ Pro tip: Use a shared document or a one-on-one app to build your meeting agendas and prompt the other person to add talking points ahead of time.

2 Doing most of the talking

You’ll probably have updates to give and feedback to offer. However, if you’re the one doing most of the talking, you’re missing a critical opportunity to learn more about your employee.

Remember to let them speak for 90% of the time. You never know what you might learn!

⭐️ Pro tip: Move your direct report’s talking points to the top of the agenda so they kick-start the conversation.

3 Not inquiring about your employee’s overall well-being

Studies show that managers that are empathetic and compassionate have the greatest impact on organizational profitability and productivity. It’s important to remember that the employee has (or should have) a life outside of the office where they might be struggling with something.

⭐️ Pro tip: Once in a while, remember to zoom out and ask about your direct report’s level of engagement and general state of mind.

4 Making it a status update meeting

The purpose of one-on-one meetings is to listen and clarify so you can understand how your direct reports are feeling, and the direction which each person wants to head in. It is not a project focused meeting.

If people just give you updates that could simply be emailed to you, encourage them to use the time more constructively.

⭐️ Pro tip: Use a meeting template with headings that remind you to steer away from status updates. Headings such as Wins – Learnings – Priorities – Challenges – Team dynamics – Feedback – Career development.

5 Allowing distractions

Mindful leaders don’t just hear conversations. They listen and engage in the dialogue, take note of what’s being said and how people are saying it, and make continuous eye contact to ensure the person sitting on the other side of the table feels heard.

⭐️ Pro tip: Be an active listener. Start by setting your phone and laptop to ‘do not disturb’ mode, and focus on establishing eye contact with your direct report.

6 Not following up on action items

If your one-on-one meeting generates action items, make sure to follow through on them. This will not only make your meetings more productive but also make it easier for you to track each direct report’s progress.

⭐️ Pro tip: Encourage your employees to write action items as the meeting evolves. Then, use a tool like Fellow to track what was promised and follow up with each direct report.

7 Rushing or cancelling the meeting

If your employee has prepared an agenda and is looking forward to their weekly check-in with you, you don’t want them to feel that you don’t value this time. That’s why you shouldn’t be in a rush or cancel your one-on-ones.

⭐️ Pro tip: Don’t schedule between back-to-back meetings so you come late and have to cut out on the dot. And instead of cancelling the meeting, just reschedule it to another day in the same week when you’re both available.

8 Always meeting in the office

We know that life gets busy and coming up with creative locations for your one-on-ones isn’t always realistic. However, research shows that sometimes, you should take your meetings outside.

⭐️ Pro tip: If you’re planning to have a difficult conversation, try going for a walk. Walking and looking in the same direction feels more collaborative than sitting across a table.

9 Assuming your one-on-ones are effective

Have you ever asked your employees for feedback about your one-on-ones? Do they feel like these meetings are a good use of their time? Is there a different format that they’d like to try?

One of the most common mistakes managers make is assuming that their direct reports are benefiting from their meetings, instead of asking how they feel about them.

⭐️ Pro tip: Ask employees for feedback on your one-on-one meetings. You can get some help by using Fellow’s feedback templates!

10 Scheduling monthly one-on-ones

If you meet with a direct report for 30 minutes every month, you’re only spending six hours a year getting to know them personally.

In fact, a study by Manager Tools shows that direct reports are more likely to dislike one-on-ones when they’re scheduled monthly (perhaps as a way to rebel against a boss that doesn’t spend much time helping and getting to know them).

Besides, nobody remembers what their challenges, learnings, and concerns were 30 days before a meeting.

⭐️ Pro tip: Schedule weekly or biweekly one-on-one meetings with each one of your direct reports.

The worst mistake of all!

Let’s be real. The worst mistake some managers make is not scheduling any sort of one-on-one meeting. In fact, some managers wait for quarterly (or yearly!) performance reviews to exchange feedback and have career conversations with their direct reports.

If one-on-one meetings were once a challenge for you, they shouldn’t be anymore. You’re now fully equipped to avoid all these mistakes and have one-on-ones that will foster a culture of guidance and trust!

Action Item: Come back to chapter 6 anytime you feel like your one-on-ones are not going well. It might help you realize what might need a change!

7.1 One-on-one tools and resources to turbocharge your management career

Technology can be a great ally when it comes to holding and tracking great one-on-ones. These are the four tools we recommend using if you want to make the most out of these meetings while saving some time!

1 Use a calendar tool (such as Google Calendar or Office 365) to schedule recurring meetings with each direct report.

2 Use a meeting agenda app like Fellow to collaborate on talking points, record feedback, and track action items from all your conversations.

3 If your team works from different locations (or you manage remote employees), you might want to use a video conferencing tool like Zoom, Skype, or Google Hangouts to see the other person’s body language and facial expressions.

4 If your company uses an internal communication tool like Slack, you can use the Fellow bot to add Slack messages as meeting talking points and send agendas without interrupting your workflow!

One-on-one resources and books quoted in this guide

We recommend checking out these management resources if you’re looking for more inspiration!

  1. Radical Candor (Kim Scott)
  2. The Making of a Manager (Julie Zhuo)
  3. Resilient Management (Lara Hogan)
  4. High Output Management (Andy Grove)
  5. Reduce interruptions with 1:1 meetings (Dave Crenshaw)
  6. State of the American Manager (Gallup)
  7. The Manager’s Path (Camille Fournier)
  8. What are the advantages of a walking 1:1 meeting? (Avi Arfin) 
  9. How to Have Effective 1:1s (Russ Laraway) 
  10. One on one (Ben Horowitz)
  11. The best leaders are great teachers (Sydney Finkelstein) 
  12. 11 Questions to Ask Your Employees in One on One Meetings (Kelly Riggs) 
  13. Managers Tools podcast (Michael Auzenne and Mark Horstman)
  14. The Fifth Discipline Fieldbook (Peter Senge)
  15. Active Listening (Lara Hogan)
  16. Fierce Conversations (Susan Scott)
  17. Three ways leaders can listen with more empathy (Christine M. Riordan)
  18. The right way to end a meeting (Paul Axtell)
  19. 7 ways to write better action items (Charlie Gilkey) 
  20. 3 reasons why performance development wins in the workplace (Bryant Ott)
  21. The problem with career conversations today (Russ Laraway)
  22. First, Break All The Rules (Marcus Buckingham)
  23. 4 ways to get honest, critical feedback from your employees (Ron Carucci)

7.2 The ultimate one-on-one action item list

Action item: Open your calendar and schedule recurring one-on-one meetings with all your direct reports.
Action item: Let your team know that you’ll be scheduling regular one-on-ones and explain the benefits that the team will get out of them.
Action item: Ask your direct reports if they’d like to have their next one-on-one over coffee, lunch, or a nice walk in the park.
Action item: Maintain a shared document with notes and takeaways from your one-on-ones with each employee. Review your notes and collaborate on talking points before every meeting. Fellow can help with this!
Action item: Try out the three one-on-one templates (90/10 format, 8 key areas approach, and chronological style) and see what works best for each one of your direct reports.
Action item: Practice using open-ended [what] questions in your one-on-one meetings with direct reports – and come back to this list any time you need some inspiration!
Action item: Practice the four techniques that will help you master active listening (using body language intentionally, avoiding distractions, leaving your ego at the door, and following-up).
Action item: Write action items during all your one-on-ones. Make sure they start with a verb, are specific, and get assigned to you or your direct report. (Don’t forget to follow up!)
Action item: Schedule career conversations where you talk about each direct report’s life story, professional aspirations, and 18-month career action plan.
Action item: Ask your employees for feedback about yourself. Then, practice the “feedback equation” to give effective feedback and praise.
Action item: Come back to chapter 6 anytime you feel like your one-on-ones are not going well. It might help you realize what might need a change!