Good questions to ask your employees during a one-on-one

Ghina Fahs
March 8, 2023
Good questions to ask your employees during a one-on-one
People management

Management isn’t just about providing order and consistency to organizations; there are many factors that make a great manager, such as empathy, curiosity, being an empowering mentor, inclusivity, and so on. But here’s one of the key ingredients: having excellent interpersonal relationships with the people you manage. To cultivate this, spending quality one-on-one time with your team members is paramount. You’ll want to make sure you’re dedicating time and effort to nurture the relationships with your employees, because one-on-one time can significantly improve employee engagement.

As reported in Harvard Business Review, "perhaps unsurprisingly, employees who got little to no one-on-one time with their manager were more likely to be disengaged. On the flip side, those who get twice the number of one-on-ones with their manager relative to their peers are 67% less likely to be disengaged."

Whether the meetings happen weekly, biweekly, or monthly, one-on-ones create a safe space for managers and their team members to promote open communication, get to know each other better, exchange honest feedback, build trust, get into a harmonious rhythm, and check in with one another. One-on-ones are also a great way to nip problems in the bud before they become larger issues further down the line.

Ultimately, your aim should be to make your team members feel heard and supported, get to know them on a personal level, and take time to acknowledge and appreciate them. Meanwhile, you’ll be helping them actively work towards reaching their greatest potential, and along the way, they’ll help you unlock yours, too. In the words of Asana’s co-founder, Justin Rosenstein, “you spend so much time finding great people, it’s worth it to help them grow to be the best they can be.”

It’s important to keep in mind that carving out the time to do this is only half the battle—leading the conversation the right way is equally important in getting the most out of your one-on-one sessions. So, go ahead and suggest a nice cafe to meet your employee over lunch and head over there with this set of 13 questions that can create momentum for you to achieve exactly that:

  1. How are you? How is life outside of work?
  2. How is your overall health? Are there any issues that you need help with?
  3. How are you feeling about your work at the moment? How satisfied are you?
  4. How do you feel your work-life balance is right now?
  5. What can I do to better support you?
  6. Are there some specific areas you want to improve, develop, progress?
  7. Are there any events or training you'd like to attend to help you grow your skills?
  8. Do you feel like you need more frequent feedback on your work?
  9. How do you prefer to receive feedback?
  10. What's one thing we could change about work for you that would improve your personal life?
  11. What is something I could do better? What is some corrective feedback that you have for me?
  12. What is one book you think everyone should read?
  13. Ask a question of your choice that helps you get to know them better

How are you? How is life outside of work? Are there any issues you need help with?

Don’t jump into a formal conversation from the get-go; start by asking your colleague about their life outside of work, as in setting the “professional” aspect aside and hang out with your friend for a moment. "Informal chats between managers and employees are key to engagement and productivity,” says Carlos Castelán, MD of business management consulting firm The Navio Group.

We all lead personal lives that are in constant flux and it can sometimes feel like we’re living our personal lives in an entirely different universe from our work lives. Check in on their mental, physical, and emotional health, and remind them that they’re not alone.

You’re both human after all, and sharing your struggles can be relatable, whether it’s anxiety, asthma, or just those funny little nuisances and pet peeves that can feel all too familiar. This can enable you to deepen your relationship, which is great for morale, work loyalty, and dedication.

How are you feeling about work at the moment? How satisfied are you?

Moving on, start bringing work into the conversation, ensuring that you’ve created a comfortable environment for them to be transparent and honest about their thoughts on their role, the work environment, and how they see themselves moving forward.

At this point the employee may start opening up, and if something important gets revealed take the time to fully unpack it and make sure they feel heard. In other words, don't jump straight to the next question. Alternatively, they may give a very simple answer like "fine" or  "not bad," in which case continuing to ask more questions can help you dig deeper.

How do you feel about your work-life balance right now?

Having a healthy work-life balance is one of the most important factors that come into play for people to function at their highest potential. Not only does it significantly limit burnout, health problems, and absences, but it also increases employee retention, engagement, productivity, and wellbeing.

I'd love to share some feedback with you. Can we talk about what's going well and what I'd like you to work on improving?

Now would be a good time to open up the door for giving feedback. Highlighting your employee’s strengths and letting them know how well they’re doing is often a great way to boost their self confidence and motivation, while making them aware of what needs improvement can give them a better sense of direction as they move forward.

What can I do to better support you?

Follow up the last question with an offer of support, whether they feel like they have a healthy work-life balance or not quite, even just the act of asking if there’s a way you can support them can provide them with the comfort of knowing they’re cared for. This alone can go a long way.

Are there some specific areas you want to develop, improve or progress?

As the conversation progresses, get more specific about their role and the direction they want to be going in. This will help you better understand their goals and how to ensure they’ll be satisfied with the work they’re doing, as opposed to finding themselves in a place or position they didn’t intend to be in.

At this point, it’s a good time to get a better understanding of what the employee perceives their own strengths to be, as well as what they would personally like to work on, learn, or improve. This helps for them to remember that they’re heard and seen, and it gives them some autonomy over their career growth, reminding them to stay inspired and motivated to go after what they want.

Are there any events or training you'd like to attend to help you grow your skills?

After getting clear on what they’re interested in developing, let them know there are options to make these things happen. Suggest a course of action such as a workshop, online course, event, or book.

This is also a good opportunity to agree on what you would like them to have done between now and the next check-in so it doesn’t remain open-ended. Moreso, decide on the most suitable way for both sides to track progress and follow up with each other.

Guy sitting on the table talking business with another man while drinking coffee

Do you feel like you need more frequent feedback on your work?

Receiving feedback can be a great driver to reignite productivity and motivation, whether it’s about a job well done or about something that could be improved. Knowing where they stand and what they need to focus on is a lot less anxiety-inducing than the ambiguity of not knowing at all. Everything is a learning process and it’s important to be getting ongoing feedback on the journey.

To add to that, employees that are on the shy side might be a little hesitant to ask for feedback when they really need it. Instead, they just might wait for you to take the lead.

How do you prefer to receive feedback?

Whether it’s weekly or monthly, delivered in real-time or periodically in one go, conducted online over a Zoom call, typed out in an email, or communicated in person over a cup of coffee—accommodating their preferred way of sharing feedback is one way to let them know you’re mindful of their boundaries and preferences at work.

What’s one thing we could change about work for you that would improve your personal life?

We all work in order to cultivate a better quality of life; as the saying goes, we work to live, we don’t live to work. But unfortunately, there are a lot of people in the workforce that tend to forget that. Let your employees know that you recognize how work can impact their lives and that you want to make sure their work adds to their lives instead of taking from it.

What is something I could do better? What is some corrective feedback you have for me?

At some point during the meeting, you’ll want to start shifting the conversation around and ask for upward feedback from your team members. Again, ensure that they feel safe enough to be transparent and honest. One-on-ones are not only for the manager to assess the employee, but they’re also for the employee to assess the manager—ideally, you’re both pouring into each other’s cups!

What is one book you think everyone should read?

Books are the best teachers, and there’s always something to learn from every person on your team. Asking them to recommend a book is a great way to tap into their depth and complexity, something that’s always there but most times hidden under the surface or overlooked. It can also show that you value their opinion and see them as a source of insight that you can learn from, not just the other way around.

Share your recommendations, as well.

Ask a question of your choice that helps you get to know them better

This could be anything really; ask what their favorite dessert is, their favorite color, their favorite animal, or their dream destination. This will also be a fun and effective way to know exactly what to gift them when their next birthday comes around!

That’s it for now!

Anyone can carry the title of a manager, but not every manager seems to be stepping into their role most effectively—in other words, not every manager is a great leader, but every great leader is a great manager.

If you’re an employee looking for questions to ask your manager, head over to this blog post where we cover the other side of the conversation!

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