How to Start Using One-on-Ones with Your Team

What We're Going to Cover

When we did our initial set of user research for building Kommon, 90 percent of the managers we spoke to said they were scheduling one-on-one meetings with their team members.

But that’s where the consistent practice ended.  In terms of what people actually did with those meetings... well, our findings were a lot more mixed.

"It’s pretty common throughout the organisation to have a relatively regular check in with your manager so that was like a pre-established norm in my mind. Ok I have to have a weekly call with these people. The rest of it is the wild wild west."  Kommon Interview

“I certainly have had managers who… like in our weekly catch ups just wanted to gossip about the team.  You do it a few times and it’s quite fun but then you realise you actually haven’t had any guidance, or coaching or support, and you don’t know anything that’s going on.”  Kommon Interview

As the great CEO and managerial innovator Andy Grove said, meetings are just a medium.  It’s what gets done in them that actually matters.

Simply scheduling one-on-ones doesn’t make you a better manager.  But using them in the right way can help you be a great one.  

This article will help you get there.  We cover the following questions:

• Why are one-on-one meetings important anyway?

• How long should my one-on-one meetings be?

• How often should I have one-on-one meetings? 

• What should I say in one-on-one meetings?

• How do I know if I’m doing one-on-ones right?

• What if my team members don’t say much?

Let’s get started.

Why are one-on-one meetings important anyway?

When you’re busy, and particularly if you have lots of team members, making time for one-on-ones can seem a hassle.  

But they’re almost certainly the most important meetings in your calendar.  

One-on-ones offer the potential to improve the way you work, develop your team’s careers, gauge the wellbeing of your team, and build trust with your team members.  All in the space of about 30-45 mins.   

Improving Work

One-on-ones are a unique opportunity to understand and affect how your team functions in a level of detail you won’t get anywhere else.  

“One-on-ones are your must-do meetings, your single best opportunity to listen, really listen, to the people on your team to make sure you understand their perspective on what’s working and what’s not working.”   Kim Scott, Radical Candor

This level of detail enables you to make far better decisions about how to run your team, which unlocks higher performance. 

“Let’s say you have a one-on-one with your subordinate every two weeks, and it lasts one and a half hours. Ninety minutes of your time can enhance the quality of your subordinate’s work for two weeks, or for some eighty-plus hours, and also upgrade your understanding of what he’s doing.” Andy Grove, former CEO, Intel (High Output Management)

If you’re alarmed at a 90 minute one-on-one, don’t worry they don’t have to be ninety minutes.  But Grove’s point is sound.  For the sake of 45 mins of your time, you could gain insights and improve decisions which impact hours, if not days and weeks of your team’s work.  Why wouldn’t you invest that time? 

As Mike Krieger said, reflecting on his time as co-founder of Instagram:

“Once you add a management position...you realize that you were only aware of the top 5% of what needed to get done” Mike Krieger, Co-Founder, Instagram

Career Development

One-on-ones don’t just inform better decision-making about how to run your team, but also how to develop your individual team members.  

It’s through these meetings that you learn more about people’s strengths, weaknesses, career aspirations and challenges.  This is the information you will use to shape the assignments they work on, the people they meet and the skills they build.  Without one-on-ones, you’re shooting in the dark, with significant opportunity costs for your team’s progress.

Checking-In

Whilst the insights you gather in your one-on-ones will help you improve the performance of your team, it’s also where you’ll find out how your team is doing more generally.  Are they happy?  If not, where are the problems?  What can you do to fix them?  

Because of their more personal nature, it’s often only in one-on-ones that these details emerge, and only through regular one-on-ones that you can get a sense of your team’s overall wellbeing.

“The sound that surrounds a successful regimen of one-on-ones is silence. All of the listening, questioning, and discussion that happens during a one-on-one is managerial preventative maintenance. You’ll see when interest in a project begins to wane and take action before it becomes job dissatisfaction. You’ll hear about tension between two employees and moderate a discussion before it becomes a yelling match in a meeting. Your reward for a culture of healthy one-on-ones is a distinct lack of drama.” Michael Lopp, Engineering Leader, Apple

Building Trust

At the core of any great relationship between a manager and a team member is trust.  Now, trust is a famously tricky thing to establish, particularly early on.  Many new managers look to the skies and wonder how they can possibly make a start on earning it from their team.

One way to help is one-on-ones.

Showing up for your one-on-ones is one of the most concrete ways to demonstrate to your team that you’re invested in them and their progress.  And when we say ‘showing up’, we don’t just mean attending the meeting, but really engaging in it (more on this later). 

How long should my one-on-ones be?

If you go back to why one-on-ones are important, how long do you think it would take to have a meaningful conversation on these subjects?  

Generally you should schedule at least 30 mins, preferably 45.  

Any shorter generally doesn’t leave enough time if your team member wants to have a substantive conversation on a particular topic.  Worse, by rushing you’ll actually diminish the trust your team has in you. 

“In your 15-minute one-on-one, all you learn is that you don’t have time to care.” Michael Lopp, Engineering Leader, Apple

How often should I have one-on-one meetings?

In short, there’s no rule (although some companies will make one).  It depends on your individual team members, and your availability.  But they will typically end up happening on something like a weekly or fortnightly schedule. 

Your team members 

Again, think back to why one-on-ones are important: improving work, career development, checking-in, and building trust.  

One-on-ones won’t be the only time you’ll interact with your team members and get signals on these topics.  If you’re working daily with a team member, and if you have an established relationship, you both may feel an additional weekly meeting doesn’t add much value.  More experienced team members may also prefer more infrequent meetings.  Conversely, if your team member has something specific to discuss, you might put in more time.  

In short, schedule them so they’re most constructive.  

That said, the unique benefits of dedicated one-on-one time mean that most managers and team members will typically schedule them on at least a fortnightly basis. 

Your availability

By ‘your availability’ we don’t just mean ‘have you got a gap in your calendar.’  We mean whether you’ve got the availability to genuinely dedicate that portion of time to your team members.

A good one-on-one requires intense listening and understanding.  No multitasking.  No answering emails.  No playing with other apps whilst you’re on Zoom.  At least 30 mins of your undivided attention (potentially with some prep before and note-taking after).  

In an ideal world, you would be able to give that to your team members on whatever schedule they preferred.  However, if you have lots of team members, you may need to compromise to ensure you are actually ‘available’ to schedule one-on-ones. 

If you can’t find 30 mins per team member at least every two weeks, you probably have too many direct reports.

‘One-on-ones should be a natural bottleneck that determines how many direct reports a boss can have.’ Kim Scott, Radical Candor

What should I say in one-on-one meetings? 

Often, not very much. 

One-on-ones are an opportunity to learn from your team members about their work, think about how you can help them, and demonstrate your investment in their professional growth.  For these reasons they are typically led by the team member.  For managers, attentive listening is a far more vital skill for conducting an effective one-on-one than knowing what to say.

When you do speak, it’s likely to be prompts and questions to draw out some of these insights, and ensure your one-on-one doesn’t descend into silence, or worse, a status update.  Neither party learns anything from either of these.

Fortunately, by listening intently to your team members talk about their work, their success and their challenges, you’ll usually spot some detail which can be drawn out into a useful discussion.  For that reason, often managers start their one-on-ones off with an open-ended question like ‘How are you?’ or ‘How has the week been?’.

It sounds basic, but it gets the conversation flowing and gets your team member leading it.  Depending on their thoughts, you can then evolve the discussion.  You might use prompts like:

• Can you tell me more about that? 
• I know this quarter you’re focusing on (insert skill), has this helped with that?
• I know we’re trying to do more of (insert focus area) on the team, how do you think we’re doing? 
• What would you like to do more of?
• What would you like to do less of?
• Are you getting the right support from your colleagues?
• Is there anything that I can help you with?
• Can I put you in touch with anyone over the next month? 
• I know I’ve been busy this month with (insert task).  Were there times when I could have supported you better?

You’ll notice the last example includes an admission of fault on behalf of the manager.  One-on-ones should be a place where team members can offer feedback to the manager, although it can take time for people to feel comfortable doing this.

N.B. You may have read articles with titles like ‘121 questions for your next one-on-one’.  Whilst these can be useful, they can also create the unhelpful impression that you’re doing a bad job if you don’t ask this full range, which is nonsense.  Using lists like these can also come across as robotic and impersonal, when you’re meant to be demonstrating how much you care!  

That said, if you consistently find you’re not having productive one-on-ones, these lists can be useful for prompts and inspiration.  So here’s a giant list if you find these things helpful.

Using an agenda

You may see advice that all one-on-one meetings should have an agenda.   Again, there’s no hard and fast rules here.  It’s the team members’ meeting, so it should be run however is most constructive for them.

Some team members may really like the structure of an agenda.  Others may find it constraining and unhelpful.

If you haven’t tried it before though, it’s certainly something worth experimenting with.  Not least because, for complex questions, it can give the manager some time to prepare and offer better answers. 

If you’d like to try using an agenda, Kommon’s one-on-one meeting tool includes an agenda-builder which you and your team members can both add topics to.  You can also both add comments and action items to each topic to provide further detail and identify to-dos for either party.   

You can also add specific goals or feedback as agenda topics to be discussed, which are then automatically linked to in the meeting to make them easier to access.

How do I know if I’m doing one-on-one meetings right?

The eternal question for the new manager is ‘how do I know if I’m doing this job right’. 

When it comes to one-on-ones, there’s a few signals you’ll be able to spot if they’re not going well (these are nicely consolidated in this article on evaluating one-on-ones by Adrienne Lowe):

• Cancellations: pretty obvious, if your team member consistently stops showing up, it’s a fairly strong signal they don’t value the meeting!
• All smiles: ok, some good news is great.  But if you’re consistently discussing positive stories then that suggests your team member doesn’t trust you enough to discuss their real challenges, and you’re missing the key value of the meeting.
• A status update: a one-on-one is not a project management meeting, but it can be easy to slip into this, particularly if you haven’t spoken to the team member in a little while.  Status updates should be for other forums (typically emails), and are a waste of one-on-one time.

But if everyone’s showing up regularly, communication’s flowing well, and everyone’s learning, it’s probably going just fine. 

What if my team members don’t say much? 

This is a relatively common question from new managers, particularly in the early stages of building relationships with a team.  This usually indicates one of two things:

1. They’re unsure about how to use the one-on-one and what they should be discussing.
2. They don’t trust you enough yet to discuss the issues that are most important to them.

Number one can usually be solved by ensuring that your first one-on-one with a team member sets some context about how you see one-on-ones, their value, and how you hope your team member can get the most out of them.

Number two is more difficult, and can simply take time.  But you can try a few things to shorten the time frame:

• Keep showing up: keep demonstrating your commitment to them by regularly holding engaging one-on-ones, even if they’re a little reluctant to come forward at first. Don’t be disheartened!
• Tell some of your own stories: you can show some vulnerability yourself and model behaviour to a certain extent by speaking about some of the topics you’ve previously raised in one-on-ones with your manager, and how that helped you.  It might encourage your team member to open up on similar topics.
• Change the format: it may be that your team member doesn’t enjoy another Zoom call.  Consider going audio-only, or doing it on a walk.  For in-person settings (remember them?), often meeting outside the office, or over a meal/coffee, can help the flow of conversation. 
• Ask: if you’re consistently finding that your team members are unresponsive to one-on-ones, try asking them directly about it and what you could be doing differently.