When you have your first one on one meetings with your new employees, it’s exciting and full of potential. Once your company has scaled up and you have 10 reports, though, it’s a big time suck and something that many managers actively avoid.

It’s a problem I’ve faced before, leading teams of 1-40 at 18 different companies I’ve worked or consulted at. And I’ve found a secret formula to scaling one on one meetings no matter how big your team grows. 

Introducing cadences to scale one on one meetings

The way I run teams of any size relies on three cadences:

  1. Digital bullet journaling as a daily scrum
  2. A weekly sync at the end of the week. In this sync, we plan for the week to come
  3. Monthly one on one meetings with everyone in my reporting chart. That’s been up to 40 in the past, so this scales up and down quite nicely as your team does

I’m going to focus on steps 2 and 3 in this article.

Weekly meetings vs. monthly meetings

Every week I meet with my direct reports to plan out the week to come. This is a task-focused meeting that is hopefully guided by monthly or quarterly-level goals. There’s some reflection about the outcome of projects and experiments that have concluded, but this is a largely forward-looking discussion. 

Every month I ask all of the reports in my reporting chain to take a moment, step back, and think about the broader picture of how things have been going at work. This is the kind of discussion where you have people talk about interpersonal conflicts, personal problems that are getting in the way of work, and goals and aspirations that you want to help them achieve.

In my experience, as I earn my team members’ trust, this is usually about 50% strictly about work at the office and 50% about what they want to accomplish outside of work. 

Structuring one on one meetings

Monthly one on one’s might sound crazy (especially with a team of 40!) but this cadence is the single best tool I’ve found for aligning teams, identifying star performers, and helping laggards realize their potential. 

So how do I run the one on one? I find simpler processes are easier to lead and more adaptable to different people, so there are just two elements to it: Asking questions and taking notes.

Asking questions to guide the meeting

Most employees dread one on one’s and can’t really adequately prep for them. What are you gonna talk about? Will their boss be happy or will they be up for a performance improvement plan? They’re stressful as heck. 

I always ask the exact same set of questions, and I even remind the employee the day before the one on one what precisely those questions are.

Here’s the set:

  • What’s gone well this month?
  • What’s gone poorly?
  • What do you need to do better work?
  • What do you most want to accomplish in the next 30 days?
  • What do you most want to do in the next year?
  • How is this company helping you with those goals?

Why these questions matter

By asking the same questions every month and by taking notes on them (more on that in a moment), you help team members understand what you’re trying to accomplish. The result is that you help reduce the stress of a one on one. Now, I’ve had employees come into a one on one meeting and know that everything went poorly in the last month. Naturally, they’re stressed about how their performance is going to affect their career path. But on the other hand they also know that this is going to be a topic of discussion, and they’re prepared for it. 

Another important element of always asking what went poorly each month is that it normalizes the fact that sometimes you fail. If you want honest communications in your team, it’s crucial you normalize failure as a chance to learn, not a thing to be hidden.

Part of the one on one involves reflecting on performance at work and asking what the team member wants to accomplish over the next 30 days. But I’ve had team members tell me about things far outside of work, such as, “I had a fantastic time reciting poetry at a big poetry slam last week”, “I feel great about hitting my weight loss goals for the month”, “I want to prep for a marathon next month” and “I want to start seeing a psychiatrist again”. It’s good when someone feels enough trust to tell you that kind of thing. But what is most relevant to the company’s trajectory is also making sure that you guide some of that self-reflection on work-related topics.

Ideally, you’re using some kind of ranking mechanism for what’s important for your team to tackle next month and that can guide your talk as well.

Fundamentally, you’re looking to identify and record examples of what this team member succeeds at, what the person struggles at, and how well they’re aligning on the company’s goals. If the work-related things they believe went really well are irrelevant to their job and the company’s purpose (“I think I was really great at the company volleyball match last week!”), that’s a red flag that they’re not pointed the right way. 

This is especially important with junior team members, I find it’s helpful to use the self-reflection to ask questions about their KPIs and see if they have answers. If not, review them and make it clear that they’re responsible for knowing their KPIs for next month. 

Taking notes on the one on one meeting

So when I conduct a one on one meeting, I open up a document in my cloud-based text editor of choice and simply paste the above questions in. Then, as we talk, I write. It looks like this:

Example notes from a one on one meetings

This (somewhat redacted) one on one meeting notepad is not fancy at all, and as you can see there’s more than a few typos. I’m a fast typer, but not necessarily the most accurate one.

Next month, when we have our next meeting, I simply hit enter a few times at the top of that document and then do it again.

Eventually, I end up with a document that contains months or years of regular monthly one on one meetings. Each meeting only takes 30 minutes, but over time it lets me build a very sophisticated understanding of my team.

Also, I share this document with the team member. It is a record of performance and accountability that serves as a reference for both the team member and for you. 

Over time, I’ve found some of my best team members will fill out the month’s one on one the day before we have our chat, giving me time to review their accomplishments or problems and come more prepared with suggestions and next steps.  

I’ve also found that low-performance team members never open the one on one notes over the month, and come unprepared (even though they know that the questions are going to be) for the meeting each month. It’s an interesting trend to watch for on your team.

People tell you who they are based on the actions they take. Using the three cadences that I’ve used over the last decade (daily, weekly, and monthly records of what is attempted and what is accomplished), it’s easy to understand what every team member is great at and needs help at. Strengths-based leadership is the best way I know of to make your whole team high performers, and this simple tool is the most powerful one I’ve found to do it.

This post originally appeared on PulseBlueprint.


  • Stefan Palios

    Journalist and entrepreneur passionate about the people behind tech

    Stefan is an entrepreneur who has founded three businesses (one failure, one success, and his current one). He writes about diversity, innovation, and entrepreneur journeys, among other things. He's the founder of PulseBlueprint Publishing, an digital publisher focused on helping people solve workplace challenges.