What are "one-on-ones"?

A one-on-one is a regularly recurring discussion between you and someone who works directly below you: if you’re running a small business, we’ll assume that’s an employee. It’s not a formal meeting or a work check-in. Instead, the idea is to give a platform for your employee to communicate with you on topics that are important to them. Every one or two weeks, at an agreed day and time, you give space (typically 30 to 45 minutes) for an employee to ask in-depth questions, highlight any issues they’re having and receive guidance on their strengths and weaknesses. Or even for them to talk about personal problems that are on their mind – it’s really up to them. This is their meeting, not yours.

How to carry out a productive one-on-one

1. Decide on the length and frequency. Work out what makes sense and is achievable for you based on your schedule and number of employees. If you have a lot of employees, a bi-weekly meeting might make more sense. Two weeks should be the maximum time between meetings, and 30 minutes should be the minimum length. Equally, junior employees might benefit more from a weekly meeting than experienced employees who are more settled. Whatever you decide upon, it needs to be something you can stick with and commit to going forward.
2. Explain what you’re doing with your team. Communicate with all of your employees in advance, focusing on why you’re doing one-on-ones and outline how they’ll actually work in practice. Make clear that this is their platform and space to use as they see fit – and not just for updates on projects and tasks. Since the onus is on them, provide a list of thought starters. That might include challenges they’ve faced or concerns they have; their current job focus and interests; roadblocks; the culture within the team; and how they’d like to grow.

3. Find a time. Secure a slot in the week that works for both you and your employee and is unlikely to get pushed back or cancelled. For example, Monday mornings aren’t usually the one, as the week’s to-do list can often dominate your thoughts. Put it as a recurring event in your calendars.
4. Find a place. Decide where you’re going to do it. The location for your one-on-one needs to be somewhere where you both feel comfortable (and is convenient for your workday in general). That might be in a public space, like a cafe; a walk and chat; a place where you have a little bit of privacy in your workplace; or done remotely. It doesn’t have to always be the same and it can be a good chance to break up the day and change things up.

5. Come prepared. Before your chat, review any previous notes you might have made about that employee, and note topics or areas you want to speak to them about. During the week, you should be jotting down bullet points or questions to ask on a document. This can then become a running summary of your meetings with the employee, where you also note takeaways and actionable to-dos at the end of each session.
6. Give them the floor. Conduct your one-on-one following the structure above, letting the employee talk first. If they talk for longer than you’d anticipated, let it happen. Be flexible with your agenda. When it comes to your turn to talk, ask what they need from you and what you can improve upon. Touch on those same overarching topics as mentioned in Step 2, and try to finish with an element of coaching where you can give them tips or feedback on how they can improve in certain areas. And always finish on a positive or affirming note.
7. Agree on some action items. At the end of the chat, make any relevant action items clear, so both you and the employee know what you’ll do before the next one. That means you won’t be starting again from scratch and the next meeting can pick up naturally from where you left off. Your doc should have an ongoing log of the major topics and points that you can constantly refer back to – and use to understand whether they’re being improved upon.  

Key takeaways
The main purpose of a one-on-one is to build a strong relationship between you and your employee – not to discuss work projects.

This is all about giving space – and a platform – to your employee to talk about the things they want to talk about, no matter what they might be.

It needs to be organized for a recurring time and loosely structured. Trying to do it ad-hoc will result in it falling by the wayside and not benefiting either party.