One on One Meeting Questions Great Managers Ask Their Employees

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Great managers make it a priority to check in with their direct-reports on a regular basis to ensure they are on track, feel engaged, and have the resources they need to do their job well.

The benefits of one-on-one meetings are vast: they help you enhance team productivity, foster positive work relationships, and set clear expectations with your fellow teammates.

In fact, Gallup’s State of the American Manager report shows that employees who have regular meetings with their managers are almost three times as likely to be engaged as employees who don’t.

With statistics like this one, it’s not surprising to see forward-thinking companies around the world establishing weekly and bi-weekly one-on-ones between managers and reports as the norm.

The topics you cover during your one-on-one meetings (and the importance that you give them) can make or break your team’s success. That’s why you should always come prepared with two things: a meeting agenda 📝 and the willingness to listen actively to what your employees have to say.

We know being a manager gets busy, and sometimes can be hard. That’s why we curated a list of the top 10 questions that great managers ask employees during their one-on-ones:

1) How’s life outside of work?

Employees who feel personally cared for by their managers are more likely to feel happy and engaged at work.

That’s why — as Jeremey DuVall argues in this post — it’s important to get to know your teammates on an individual level by meeting regularly with them:

“In my mind, caring personally breaks down into three main bullet points:
- Do I understand what drives and motivates this person?
- Do I understand what type of work this person naturally excels at?
- Have I invested in learning about this person on an individual level?”

Asking your direct-reports about their family, hobbies, and personal interests helps you build positive relationships and a highly engaged team. As Mark Horstman, host of the Manager Tools podcast argues:

“The most common mistake of first-time managers is not developing relationships with their direct employees, and focusing too much on individual work instead of their team.”

While it may be obvious, many leaders forget to ask employees about their family and hobbies outside of work. However, great managers understand what each person’s priorities are when they’re not inside the office.

As Kim Scott argues in Radical Candor:

“At the very heart of being a good boss is a good relationship.”

2) Would you like more or less direction from me?

This is one of the most important questions you can ask during your one-on-one meetings. It will help you find out if your employees are feeling micromanaged, or lost figuring out how to do their job.

If you tend to be a micromanager, ask your employees if they’d like more opportunities to take the lead on projects or implement their own ideas. On the other hand, if your style is more hands-off, make sure to ask your employees if they’d like more direction and support from you.

Being a manager is a hard balance between not obsessing about details (micromanaging) and not letting your teammates feel alone (under-managing). As Victor Lipman, a management trainer and author of The Type B Manager argues:

“Micromanagement gets most of the attention, but under-management may be just as big a problem.”

In a study conducted by RainmakerThinking, Bruce Tulgan argues that the “under-management epidemic” brings huge costs to employers, managers, and employees — with only one in ten managers exhibiting the qualities of a good leader.

However, Tulgan suggests a simple antidote for this issue: regular one-on-one meetings between managers and direct-reports.

“Like clockwork, productivity and quality improve almost immediately when leaders, managers, and supervisors begin spending time daily in one-on-one dialogues with their direct-reports to provide management basics,” says Tulgan.

Most managers don’t spend enough time setting goals and clear expectations with their employees. However, when you ask your direct-reports if they’d like more direction from you and meet regularly to set those priorities, you empower your team to be more productive.

3) Do I give you enough feedback?

When was the last time you gave your direct-report specific praise about something they did well, or constructive feedback after they did something that could be improved? Was it months ago… during your last performance review?

Asking employees if you give them enough feedback will help you understand if they’d like more guidance or praise on their work.

The answer is, if you’re not giving employees timely feedback (immediately after things happen), you are not doing it enough. As Kim Scott argues, the best feedback is timely — and shouldn’t only be given during stated cycles:

“The benefits of feedback deteriorate quickly. If you wait to tell somebody for a week or a quarter, the incident is so far in the past that they can’t fix the problem or build on the triumph,” says Scott.

On the other hand, asking employees if they’d like to get more feedback will help you promote a growth mindset and a culture where everyone is constantly looking for ways to improve.

As Julie Zhuo, VP of product design at Facebook and author of The Making of a Manager argues in this post, employees that have a growth mindset crave feedback from their managers, because they know it’s the fastest way to learn and improve:

“A growth mindset presumes that no matter where you are now, you can improve. If you believe that, then whenever someone tells you, ‘Hey, this thing you did isn’t great,’ you think, Okay, that feedback was useful and it’ll help me do better next time,” says Zhuo.

If your employees have a growth mindset, they’ll probably want to get more feedback about their work. You can use a tool like Fellow.app to exchange ongoing feedback and keep a portfolio of the interactions you have with each direct-report.

4) What are your top priorities this week?

Part of your responsibility as a manager is to coach your direct-reports on their priorities.

When you ask employees about their weekly projects and plans, you help them organize whatever’s on their to-do list and better manage their time.

Jeremey DuVall argues that making key decisions about what to work on is a skill that everyone should develop and master. As he writes in this post, “being able to see what matters” can be broken down into three main steps:

“-Knowing which projects will have the biggest impact on your bottom line.
-Knowing where your time is best spent, which projects you should be working on.
-Knowing when to shut a project down and shift focus to something else.”

However, not all employees are great at prioritizing their time or have the experience necessary to understand what will bring the highest ROI.

As Victor Lipman argues, you wouldn’t have much to do as a manager if everyone around you had exceptional talent and knew exactly what to do all the time:

“It wouldn’t be management. It would be sitting around doing little while legions of highly motivated people worked happily and diligently.”

Your job as a leader is to set clear priorities and goals for people on your team. That’s why you should ask your direct-reports to write down their priorities, and coach them in the process of ranking them in order of importance during your one-on-one meetings.

You’ll enhance team productivity and avoid having overwhelmed employees.

5) What’s one recent win, and one recent situation you wish you handled differently?

One-on-one meetings are all about helping your fellow teammates grow. By asking about their wins and their learnings, you help them celebrate their successes and figure out what’s working and what’s not.

For instance, if your direct-report tells you that something went well last week, you can help them take a step back and analyze why their efforts were successful, and what they learned from them.

As Grayson Lafrenz, CEO at Power Digital Marketing argues, asking employees about their recent wins can help you understand what matters to each of them, and what types of things they enjoy doing:

“Armed with this knowledge, you can work together to find ways to expand their responsibilities into more of those areas or projects. Doing so can offer new challenges and keep your employee motivated which, in turn, can lead to increased happiness and success,” says Lafrenz.

Apart from asking about recent wins, you should also inquire about situations that could’ve been handled differently. Asking these sorts of questions is another good way to foster a growth mindset.

As Lafrenz argues, great managers ask their employees about their obstacles and challenges:

“This will help you both identify the employee’s weaknesses which could use development or other organizational problems such as processes that are not working well or internal issues that could bring the team down,” says Lafrenz.

6) Are there any skills that you’d like to acquire in the short term?

Have you ever heard about the concept of service leadership? Here’s a quote from Russ Laraway’s talk at the 2016 First Round CEO Summit that does a great job at summarizing it:

“One way to know if you’re exhibiting service leadership is if the people under you are growing and developing.”

When applied to management, servant leadership is all about helping your direct-reports learn new skills, improve at their job, and eventually get their dream position or role.

Along this line of thinking, managers are responsible for coaching employees on their interests, and helping them find opportunities for growth.

Dan McCarthy, a leadership consultant and writer of the Great Leadership blog, argues that investing in the development of employees is the most important and rewarding thing a manager can do:

“Developing employee skills also helps with recruiting and retaining the best employees, and it allows you to delegate so you can focus on your other roles as a manager,” says McCarthy.

When you ask employees about the skills they want to develop, you help them create short-term goals and become more ambitious. The important thing is being as helpful as possible —by helping them find books, workshops, resources, and mentors that could help them with this goal.

7) How do you find working with the team? Is there anything we can do to improve team dynamics?

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 between members of their team:

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

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

So what should you do when one person brings up a problem or conflict they have with another team member?

First of all, insist that they talk directly to each other and coach your employees on ways to address the situation.

“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.

If trying to talk things through doesn’t work for your teammates, offer to have a three-way conversation where you act as a mediator. This might seem like a lot of work, but it’s better to solve an issue quickly than to have a negative sentiment spread across the entire team.

“Open, fair, and fast conflict resolution is one of the services you owe to your direct reports,” says Scott.

8) Are our meetings a good use of your time?

Have you ever asked your direct-reports for feedback about the meetings you organize?

An article published in the journal Current Directions in Psychological Science shows that the value of meetings is often questioned by employees. According to the study, employees spend an average of six hours a week in meetings, while managers spend an average of 23. (That’s a lot of time!)

If you’re already spending several hours a week in meetings, you should ask employees if they’re getting any value from them. As Muriel Vega argues:

“The most effective meeting leaders regularly gather feedback on the quality of their meetings from attendees — an easy path to improvement that’s too often overlooked or avoided.”

It’s important to understand how your direct-reports are spending their time. That’s why another question you can ask is: What percentage of your time is spent in meetings vs. doing work?

If they seem to be spending most of the day in unproductive meetings, you know there’s something you need to do about that.

At Fellow.app, we’ve developed the habit of asking for meeting feedback all the time.

Of course, we use the Fellow feedback app for that.

It’s an awesome way to understand how people feel about the meetings you organize and gather suggestions on how to make those meetings better for everyone.

One of the most common mistakes managers make is assuming that their direct-reports are benefitting from their one-on-ones. You could be having weekly or bi-weekly meetings (and that’s great!) but they won’t be very productive if your employees are not getting anything from them.

Next time you meet with one of your direct-reports, ask them for feedback or suggestions on how to improve your recurring meetings. This will empower both of you to take ownership of your time.

9) What are your long-term professional goals?

Having career conversations is an essential part of being a great manager.

As we explain in this post, coaching your employees on their professional development helps you develop positive relationships and assign tasks that are relevant to each employee’s dream job.

For instance, if your direct-report tells you that one of their career goals is to become a manager, you can start assigning more tasks that will help them develop leadership and management skills. You can also suggest books, podcasts, and resources that can guide them in the process of becoming a team lead.

As Amy Gallo, author of the HBR Guide to Dealing with Conflict argues, the key to coaching employees on their professional growth is to be hands-on, while giving them the necessary room to succeed on their own:

“Once a goal is set, ask your employee to explain how they plan to meet it,” says Gallo. “Have them break goals down into tasks and set interim objectives, especially if it’s a large or long-term project.”

10) What is something I should consider changing or start doing?

If you want to be a great boss, you need to ask your team for feedback about your leadership style — even if it feels a bit awkward.

Asking for feedback not only helps you become a better manager, but shows your team that you genuinely care about what they think.

“You also set an ideal for the team as a whole: everyone should embrace criticism that helps us do our jobs better,” says Kim Scott.

As we mention in this article, some of the best practices to ask employees for feedback include asking specific questions, encouraging employees to call you out on specific weaknesses, and rewarding employees publicly when they give you constructive criticism.

If you’ve already asked, there’s a really good chance that you’ve gotten responses like “everything’s fine” or “I can’t think of anything right now.” However, the best thing you can do is count to six, and wait for your direct-reports to come up with a response.

The goal isn’t to make your employee feel nervous or uncomfortable, but to get them to say what’s been on their mind — even if it’s the most minimal suggestion.

Whatever they say, don’t dismiss it.

In some cases, you may disagree with the criticism. If that happens, you can thank your direct-report for their honesty, let them know that you’ll think about it, and schedule a time to talk about it again. You can use that time to come up with a thoughtful and respectful explanation of why you disagree with their criticism.

On the other hand, you may agree with the criticism or think it’s useful most of the time. If you agree with the feedback they give you, go ahead and find ways to fix it.

As Ron Carucci, author of Rising to Power argues, applying your direct-report’s feedback will make you seem like a more approachable boss:

“Self-aware leaders know their triggers, and let others name them,” says Carucchi.

Great! You made it through the list of 10 questions. If you’ve read this far, I can tell you’re very committed to improve the quality of your one-on-one meetings — and I congratulate you for that!

Here’s a recap of the 10 questions in case you want to use them for your next meeting agenda:

  1. How’s life outside of work?
  2. Would you like more or less direction from me?
  3. Do I give you enough feedback?
  4. What are your top priorities this week?
  5. What’s one recent win, and one recent situation you wish you handled differently?
  6. Are there any skills that you’d like to acquire in the short term?
  7. How do you find working with the team? Is there anything we can do to improve team dynamics?
  8. Are our meetings a good use of your time? What percentage of your time is spent in meetings vs. doing work?
  9. What are your long-term professional goals?
  10. What is something I should consider changing or start doing?

I’d love to know if you use any of these questions in your upcoming meetings, and if they spark any good conversations with your teammates!


Enjoyed reading this article? Make sure you click the 👏 button so other managers can benefit from it — and click here if you’d like to get early access to Fellow.app: the tool that helps managers have better 1:1s and team meetings, track goals and exchange feedback — all in one place!

…Oh and it integrates with the tools you already use like Calendar and Slack 😁

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