Top 10 Questions Great Managers Ask During Their One-on-Ones [Free Template]

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Great managers make it a priority to check in with their direct reports 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.

As Julie Zhuo, VP of Product Design at Facebook argues in The Making of a Manager, one-on-one meetings let you discuss important topics that would never come up otherwise:

“The most precious resource you have 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.”

If you’re looking for some inspiration to improve the quality of your meetings, this post is for you. Here are the top ten questions great managers ask to have productive meetings and highly engaged employees:

1 How’s life outside of work?

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

That’s one of our favourite quotes from Kim Scott’s Radical Candor. It shows that in order to have a highly engaged and productive team, you must develop positive relationships with your employees.

But relationships can’t be built from one day to the next. 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 direct reports 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 perfect way for managers to build better relationships with employees.

So why is asking your employees about their life outside of work the best way to start these check-in meetings? It shows that you care about who they are as a person, and not just as a number in your employee list.

“What caring means,” says Julie Zhuo, “is understanding that we are not separate people at work and at home — sometimes the personal blends into the professional, and that’s ok.”

While it may be obvious, many leaders forget to ask employees about their family and hobbies outside of work. 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.”

If your goal is to become a great manager, start your one-on-ones by showing employees that you’re interested in them. Remember Dale Carnegie’s quote in How to make friends and influence people:

“You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.”

2 What are your top priorities this week?

One of your main responsibilities as a manager is to coach your direct reports on their priorities, and one-on-one meetings are the perfect scenario to do this.

“The ideal 1:1 leaves your report feeling that it was useful for her,” says Julie Zhuo. “Remember your job is to be a multiplier for your people. If you can remove a barrier, provide a valuable new perspective, or increase their confidence, then you’re enabling them to be more succesful.”

Jeremey DuVall, a leadership blogger and support lead at Automattic, argues that making decisions about what to work on is a skill that everyone should develop and master. As he writes in this post, the art of prioritizing 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. That’s why you should ask your direct reports to write down their priorities and help them rank those in order of importance. This will empower them to be more productive— and as a consequence, you’ll have a high-performing team.

3 What’s one recent win… and one recent situation you wish you handled differently?

One-on-one meetings are all about helping your direct reports 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 that experience.

As Grayson Lafrenz, CEO at Power Digital Marketing argues, asking about recent wins can help you understand what matters to each of your employees 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.

 On the other hand, you should also inquire about learnings or situations that could’ve been handled differently:

“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.

4 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, he suggests a simple antidote for this issue: regular one-on-one meetings.

“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 do their best work.

Better 1-on-1s and team meetings

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

In 2016, Russ Laraway spoke about the concept of Servant Leadership in the First Round CEO Summit:

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

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

Along with this line of thinking, managers are responsible for coaching employees on the skills they’re interested in and helping them find different opportunities for growth.

For example, if your direct report says they’re interested in public speaking, you could help them find a great book, a workshop, or a mentor that can teach them what they’re looking for.

When you ask employees about the skills they want to develop, you help them create clear and attainable short-term goals.

“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 Dan McCarthy — author of the Great Leadership blog.

6 How do you find working with the team? Is there anything we can do to improve team culture/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 amongst their reports:

“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.

If you’re interested in learning other ways to nurture a great team culture, you should check out this article— where we summarize our main takeaways from Julie Zhuo’s new book.

7 Are our meetings a good use of your time? What can we do to improve them? 

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.

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.”

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

Of course, we use the Fellow feedback feature 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.

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.

8 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 learn new skills.

As Julie Zhuo argues in this post, employees that have a growth mindset crave feedback from their managers, because they know it’s the fastest way to 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.

9 What’s 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.

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 feedback.

On the other hand, you may agree with the criticism or think it’s useful to improve your management style. If you agree with the feedback they give you, go ahead and find ways to fix it. Applying your direct reports’ feedback will make you seem like a more approachable boss.

10 What are your long-term professional goals? 

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

In fact, a recent study by Right Management found that 82 per cent of employees would be more engaged in their work if they had career conversations with their manager. Similarly, 75 per cent said they would be more likely to stay at their current company if they received ongoing professional development coaching.

Coaching employees on their professional development not only helps you create an engaged team but is a great way to foster positive relationships and assign tasks that are relevant to each employee.

 This is why Kim Scott argues that you should have career conversations with each person who reports directly to you:

“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 Scott.

Should you ask your employee about their professional goals during every one-on-one? The answer is no. There are other things to talk about, such as weekly challenges, team dynamics, and strategies to help your direct-report on their day-to-day work.

However, leaders like Sourov De, co-founder and president of Stryve, argue that you should have these conversations at least twice a year:

“It works pretty well. We haven’t had a full-time employee leave in the 9 years we’ve been in business. That’s a 100% retention rate for our full-time employees. It’s something we’re really proud of,” he says.

. . .

Great! You made it through the list 👏 If you’ve read this far, we can tell you’re very committed to being a great manager — and we 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. What are your top priorities this week? + What can I do to help?
  3. What’s one recent win and one recent situation you wish you handled differently?
  4. Would you like more or less direction from me? 
  5. Are there any skills that you’d like to acquire in the short term?
  6. How do you find working with the team? Is there anything we can do to improve team culture/dynamics?
  7. Are our meetings a good use of your time? Is there anything we can do to improve them?
  8. Do I give you enough feedback?
  9. What’s something I should consider changing or start doing?
  10. What are your long-term professional goals?

. . .

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