One-to-One Questions for Supervision

If you are managing staff or volunteers then it’s important to carry out one-to-one meetings with them, but what questions should you ask?

On a regular basis, you should check how they are, how their work is going, what further support or training they may need, and most importantly, how can you, as their manager, help them?

One-to-one questions often vary by the manager, by the organisation, and can be specific to your organisation and the way it works. One thing is clear though is that an organisation that invests in its people – is best equipped to help others. You can’t pour from an empty cup.

There are no rules about how to structure a one-to-one meeting but we have researched the following set of one-to-one questions across multiple organisations and against our own knowledge of human behaviour to pull together a balanced set of supervision questions to help you to help your team.

We’ve explained the sections and questions below, and you can download the one-to-one questions template at the bottom of the page.

One-to-one Happiness Questions

Do you understand the strategic objectives of the organisation?

It’s a quick check to ensure that they understand what the organisation is trying to achieve at a very base level; what is the main objective of the organisation? What is the elevator pitch?

Some supervisors find that if they ask questions that are too broad then the people who report to them give ‘nod’ answers – or answers that don’t really uncover a useful answer, so another way to ask these sorts of questions are by asking what they don’t understand or what they struggle with. For example, What do understand least about what the organisation is trying to achieve?

Do you know what your part is in helping the organisation to achieve its objectives?

This is about checking that the person feels part of the organisation and understands how they directly contribute to the organisation in its work to achieve its objectives.

Are you proud to be a member of the organisation and of your team?

Going beyond happiness, we ideally want the people we work with to be advocates for our organisations. Check in with your reports to see if they have pride in their team and what they are achieving?

Do you feel that your team gives you help and support to complete your work?

Sometimes when a team’s output is high is can mask the performance of individual members of the team. Check in with your reports to see if they feel the team is pulling together as a whole and if they are supporting each other.

What are the biggest obstructions for you each week?

My previous CEO loved to say that ‘your role as a manager is to get out of the way’. I believe a less simplified view of that is that your role as a manager is to empower your reports, protect them, and enable them by removing obstructions.

A lot of the time it can be something small and otherwise unnoticed that causes a roadblock which prevents your team from achieving even more.

For example, one organisation we’ve worked with reports that it can take at least 25 minutes just to log in to the secure system that allows them to access client accounts. They changed around the structure of the day and invested more into IT support and removed that obstruction.

Another organisation found that staff were spending two hours a week looking for a parking space just to be able to come to work. It’s not something that falls within the working day or would even be a concern to most employers, but by supporting their staff to purchase long-term parking permits, they improved workplace wellbeing, performance, and start-times.

Do you have enough direction and information to do your work? Do you know who to ask if not?

There’s nothing worse than sitting in front of a piece of work, stuck, and not knowing who to speak to or who can help you to move on. By ensuring that your team have access to written help, a workplace wiki or help-centre, or that they know which team members or line-managers can provide the support needed then you are removing yet another roadblock to a more productive and happier workforce.

Is there anything we should start doing as a team, or that we should do more of?

Some of the best ideas come from the people closest to the action. Some come from a long-distance perspective, but mostly, the people doing the work have ideas about how the work could be done better, more efficiently, or more productively.

Start with the positive and see what new ideas come up or how something that you already do could be made more significant.

It could be something as simple as having more regular, shorter team catch-ups. Or it could be the creation of a team handbook that documents how the team works and how tasks are completed – a perfect introduction to a new starter. Whatever the idea is, its adoption will be easier if the team came up with the idea themselves.

How could we improve the ways our team works together?

Now have a quick canter through the negative; looking at the existing systems and processes – is there anything that could be improved here?

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

Going back to the earlier point about empowering your team and removing obstacles for them, now let’s conclude this section by being more specific and asking what, specifically, could you do to help them?

Manage expectation at this point whilst never dismissing ideas out of hand. Write down the action, ask open questions about how you might achieve it for them. Don’t just block ideas, ask them how it can be done.

One-to-one Performance Questions

When it comes to measuring anything, I’m a great believer in making sure that measurement doesn’t interfere in work wherever possible.

Evaluating something shouldn’t negatively impact on performance otherwise the results aren’t giving you a true picture of what could be achieved. Schrödinger’s Cat comes to mind.

What metrics do you think it would be useful to measure?

For employee and volunteer performance measurement, engage the team in setting the metrics. If people are responsible (with guidance) for determining what the metrics are, and then together you co-create the targets, then the sense of ownership and responsibility is there and people are more likely to strive to achieve those targets. It also helps you to understand what people think is achievable.

What achievements would you like to be recognised formally?

Make sure that you have already thought through achievements that you would like to celebrate about the team-member in case they don’t readily volunteer an answer, but use this moment to encourage them to celebrate their own achievements.

Ask what they achieved since the last supervision/one-to-one meeting that they would like to be celebrated. What project or event resulted in a positive result for the organisation that went above and beyond normal?

What concerns do you have about work?

This question gives them the opportunity to discuss anything that’s bothering them related to performance at work but beyond the specific roadblock discussed earlier.

Asking an open question here allows for discussion about the broader issues that may affect work.

Future Plans

If you don’t know where you’re going, how will you know when you’ve got there? (Although I would argue that some of the best destinations were unintentional!)

In the Future Plans section of the one-to-one questions we want to setup the conversation for the next one-to-one, looking at long-term and short-term goals and what steps need to be taken to get there.

What are your long-term goals and how can we work towards these?

The world is bigger than your team, your line management, and your organisation. And, yet another management wisdom nugget I’ve picked up along the way, your role as manager is to train them up and pass them on.

Find out what makes your reports tick. What are their passions? What are their long-term goals? If you know the answers to these questions then you can help support them to achieve their goals. Supported people are happy people are performing team members.

What are your short-term goals before next supervision?

Bring the focus back down to a more local level. What are their plans in the next two-months? These plans may or may not be related to their long-term goals but they should definitely not be conflicting. What do they want to achieve before the next supervision?

How can these be supported?

Now you know what the long-term and short-term goals are, it’s time to explore what support is needed to make them happen.

The support needed might not necessarily need to come from you or within your organisation, but by helping the person to establish what support would help them to achieve their goals, you are supporting them in achieving those goals.

Most people don’t know where to start. You may even find that your experience and professional network can help.

What learning or development would be useful that we could support?

Back to you and your organisation. What areas of personal development could you support, that are in-line with your organisational goals, that will also support your report in achieving their goals?

Supervision Questions Summary

It’s great to take brief notes throughout the one-to-one questions but try to maintain eye contact and not be looking at your notebook the whole time, or worse – typing.

As we reach the end of the supervision take a moment to summarise what you have heard and ask the most important questions – “Have I understood correctly? Is there anything that I have missed?”

Depending on their answer, you may need to revisit some of your notes to check you have understood correctly, or to make sure you have understood their personal weighting of importance on the conversation topics you’ve discussed.

On a scale of 1–10, how happy are you at work?

Personally, I hate rating scales and I never include this question, but your organisation might be different. So i’ve left it to the end so it’s answer doesn’t inadvertantly shape the rest of the supervision.

I feel different at lunchtime to how I do in the mornings most days. I’m sure I also feel different on a sunny Friday to how I do on a wet Tuesday afternoon. I’m not sure that an arbitrary number really gives us much to go on, especially when it pales so insignificantly against the rich open questions above.

Metrics from last supervision?

Check up on the metrics from the last one-to-one. Hopefully you will have discussed any problems from the questions above, but it can be useful from an administrative point of view to summarise the metrics at the end/top of the supervision notes so they are easily comparable over a longer time period and across multiple one-to-one sessions.

Next actions?

A vital part of the process is to make sure you have written down the next actions. Actions begin with a verb, so make sure that you now produce a to-do list for both you and them that lists specific verb-led actions for you to achieve.


We hope that you have found these one-to-one questions useful should you find yourself managing a team of staff or volunteers and that these questions help you to empower your workforce, co-create meaningful goals with them and ultimately to have a happier, more productive team helping more beneficiaries.