How to carry out one-to-one meetings: questions managers should be asking

one to one meeting

More than a mere formality, one-to-one meetings can be a huge boost for productivity, morale and engagement. Make them matter with these essential questions.

Despite their inherent value, one-to-one meetings can often seem either rushed and unorganised, or a rigid procedure that both parties simply want to get out of the way. Or worse, they’re conducted with such infrequency that there’s little benefit to be gleaned from the discussion.

If your handling of one-to-one meetings is a little on the lacklustre side, then both you and your team are missing out on what can provide a multitude of opportunities throughout the year. When properly conducted, these face-to-face chats can do much to promote productivity and engagement in the long term, bringing a real value to both you and your direct reports’ efforts.

If one-to-ones are an area that you’ve been looking to improve upon, then we’re here to help. Below you’ll find tips and advice on how you can prepare, structure, and make the most of every one-to-one you’ll have going forward, including the questions you can ask to help improve performance and development throughout your team.

How to prepare for one-to-one meetings

Get in the right mindset

Despite the appearance of the word meeting, think of one-to-ones as more of a free-form discussion. Rather than overthinking things, the conversation should be flexible enough that you can touch on topics that are on both party’s minds. You might want to keep a shared collaborative space that allows both of you to keep track of upcoming topics to be discussed, as this can help you both prepare for a more effective conversation.

business woman talking to boss

Consider changing up the format to help keep things informal. You might like to go on a walking meeting, have a coffee, or meet up for breakfast – but me sure to bring your discussions points with you. This can help your direct report feel more at ease discussing certain topics, too.

Set a recurring schedule

To improve the efficacy of your one-to-ones, they need to be conducted with regularity. Agree with your direct report when and how often they should be held, and added as a regular meeting to each other’s calendar. This can be a huge show of your investment in both the one-to-one format and your direct report, illustrating that you’re committed to consistently making time for an individual.

And although it may be difficult to stick to the schedule, you should never cancel; do your best to reschedule. Cancelling can seem like the meeting isn’t important to you as a manager.

Set an agenda

Or, if you’d prefer to keep things more informal, prepare a few discussion points. Since you both have your own duties to attend to, the latter tends to be the more realistic option. Have your direct report do the same and when you do meet up, briefly compare the topics and decide together which you’d like to devote the most time to. This also allows you to stay on topic to a degree, anchoring the focus if the both of you end up getting distracted.

business meeting

How to conduct a one-to-one meeting

Start on a positive note

A good way to begin your meeting is by sharing a win. If there was a recent project they worked on or they gave a successful presentation, for instance, then be sure get things on the right foot by complimenting them accordingly. It creates a positive energy that helps to put your direct report at ease.

Listen actively

Rather than attempting to formulate a rote response while they’re talking, it’s crucial to listen actively to what’s being shared. Instead of just listening to be polite, it shows you’re directly supporting them, showing recognition and respect towards the context and opinions mentioned by the direct report. Such an approach means managers are more likely to strengthen their relationships with their teams.

Part of this active approach is being fully present, too. It’s a time to make a connection with the person opposite, so give them your full attention. Switch your phone off and mute or lock your computer so that you’re not distracted by any notifications you might receive. Don’t send the message that these things are more important than the person who’s talking.

business meeting

Don’t be afraid to get personal

Sharing personal anecdotes or experiences in your one-to-ones can help provide your direct report with a solution to any similar challenges that they’re facing. Such an approach lets them know they’re supported, but it also allows them to open up and share any problems they’re not sure how to overcome.

Be open-minded towards their feedback about you

Remember, one-to-ones are a two-way process. Within the face-to-face environment, set the example by showing you’re open to feedback about their own performance and development. Successful managers are ones who are willing to learn from what their team thinks of them and their management style.

Ask about both individual and team morale, and whether or not you feel it needs improving to boost camaraderie and collaboration. When you have a clearer picture of the things that work and things that don’t within your team, you can begin the process of improving your approach to management and leadership.

The questions you should be asking

Work habits

Questions about how each of your team members operate can clue you in on their processes and approaches with regards to productivity, showing your support in ways that allow them to work more efficiently. Consider the following:

business meeting

Which part of the day do you feel most and least productive? What can be done so you can get the best out of a workday?

What do you do when you get stuck on something? Who is the team member you turn to for help?

Team collaboration

Asking the right questions about the interpersonal relationships can uncover the challenges among the team that stand in the way of productivity. Ask these, for example:

• Who inspires you in the team? Whose opinions do you respect?

• Do you find it difficult working with anyone? Why?

• What do you think about the amount of feedback in our team?

• What do you think would help us work together better?

Job satisfaction

Each individual’s happiness can affect how well they work. Glean insights into each team member’s own job satisfaction with the following:

• Are you happy with your recent work? Why or why not?

• What keeps you engaged with your daily work?

• What kind of projects do you enjoy working on? Is it possible to name three things we can do to help so you can enjoy your job more?

• Do you feel appreciated for your accomplishments?

businessmen having a conversation 

Personal development

Are your team members learning and developing in the same way you are? Learn more about their motivations with the following:

• Do you feel like you are learning at work? What are the areas you want to learn about and from whom?

• Do you think that you receive enough feedback and is it helpful for your personal development?

• Would you like more coaching? What aspect of your job do you like more help and coaching on?

Manager improvement

As we mentioned earlier, knowing what your team thinks about you and your management style is important. It might be tough to hear at first, so make sure you frame your questions wisely:

• What can I do as a manager to make your work easier?

• What do you like and dislike about my management style?

• Would you prefer more or less of my own involvement in your duties?

• What is something I could have done better? When could I have helped more but didn’t?

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