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Meet Like A Boss — The 411 On 1:1s 2 | 9

Meet Like A Boss — The 411 On 1:1s 2 | 9

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If you're a boss, 1:1 meetings with your direct reports are a must-do. The purpose of a 1:1 meeting is to listen and clarify — to understand what direction each person working for you wants to head in, and what is blocking them. These meetings are 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. On this episode of the Radical Candor podcast, Kim, Amy and Jason spill the tea about how to have effective 1:1s, even when you can't be together in person, and Kim sings a few notes from the Hall & Oates song "One On One."

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These 1:1 meetings also provide an opportunity to get to know your direct reports — to move up on the Care Personally dimension of the Radical Candor framework. This episode of The Radical Candor podcast features expanded show notes that give you extra advice from Kim's book, Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity, to help you do just that.

Read chapter 8 for more information about 1:1 meetings. Save on the 2nd edition of the book on Amazon (all tips below are by Kim Scott).

1. Manage Your Mindset

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Your mindset will go a long way in determining how well the 1:1 meetings go. I found that when I quit thinking of them as meetings and began treating them as if I were having lunch or coffee with somebody I was eager to get to know better, they ended up yielding much better conversations.

If scheduling them over a meal helps, make them periodic lunches. If you and your direct report like to walk and there’s a good place to take a walk near the office, make them walking meetings. If you are a morning person, schedule them in the morning. If you are a person who has an energy dip at 2 p.m., don’t schedule them at 2 p.m.

You have a lot of meetings, so you can optimize the 1:1 time and location for your energy. Just don’t be a jerk about it. You may like to wake up at 5 a.m. and go to the gym. Don’t expect the people who work for you to meet you there.

2. Find the Right Frequency

Time doesn’t scale, but it’s also vital to relationships. 1:1s should be a natural bottleneck that determines how many direct reports a boss can have. I like to meet with each person who works directly for me for 50 minutes a week. But I can’t bear more than about five hours of 1:1 time in my calendar. Listening is hard work, and I don’t have an endless capacity for it every day. So I like to limit myself to five direct reports.

When people are remote, I make sure that those conversations happen over video conference, and I try to supplement them with more frequent quick check-ins. This is not realistic for a lot of companies — including some of the ones where I’ve worked. If you have 10 direct reports, I’d shift 1:1s to 25 minutes a week.

Plenty of people I know have 20 direct reports, and there’s nothing they can do about it. It’s just the nature of the way their companies are managed. If you’re in that situation, I recommend 25 minutes every other week with each direct report.

Also, see if you can create some leadership opportunities for the people who work for you and reduce the number of direct reports you have. Finally, to avoid meeting proliferation, I recommend that managers use the 1:1 time to have “career conversations” and, if relevant, to do formal performance reviews.

3.  Show up!

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Probably the most important advice for 1:1s is just to show up. In an ideal world, you have less than 10 direct reports so that you can have a weekly 1:1 with each of them. Even in that ideal world, between your travel schedule, the fact that you will inevitably get sick sometimes, and the occasional vacation, you will have to cancel at least two or three out of 13 scheduled 1:1s.

If you reserve some of those slots for special 1:1s (i.e., performance reviews, soliciting feedback, “career conversations”), you will have only seven or eight “regular” 1:1s per quarter.

And if your world is not ideal and you have more than 10 direct reports, you prob ably have 1:1s every other week. That means you’re having three or four 1:1s with each of your direct reports per quarter.

So, no matter what fires erupt in your day, do not cancel your 1:1s.

4. Your direct report’s agenda, not yours, runs the 1:1

When your direct reports own and set the agenda for their 1:1s, they’re more productive, because they allow you to listen to what matters to them.

However, I recommend setting basic expectations for the agenda and how it’s delivered. Do you even want a structured agenda? If you do, and you want to see it in advance, say so. If you don’t, and you won’t even look at it in advance, set expectations accordingly. Are you OK if they come in with a set of bulleted items jotted on a napkin, or do you prefer they keep it in a shared document so you can refer back to it?

Whether you want a structured agenda or you prefer a more free- flowing meeting, the agenda itself should be directed by your direct report, not you. Your job is to hold people accountable when they come unprepared — or to decide that it’s fine to have an agenda-less 1:1 from time to time.

5. Signs you’ll get from 1:1s that you’re failing as a boss

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1:1s are valuable meetings for your direct reports to share their thinking with you and to decide what direction to proceed with their work. They are also valuable meetings for you, because these meetings are where you’ll get your first early warning signs that you are failing as a boss. Here are some sure signals:

  • Cancellations: If people who report to you cancel 1:1s too often, it’s a sign your partnership is not fruitful for them, or that you’re using it inappropriately to dispose of criticism you’ve been stockpiling.
  • Updates: If people just give you updates that could simply be emailed to you, encourage them to use the time more constructively.
  • Good news only: If you hear only good news, it’s a sign people don’t feel comfortable coming to you with their problems, or they think you won’t or can’t help. In these cases, you need to ask explicitly for the bad news. Don’t let the issue drop till you hear some.
  • No criticism: If they never criticize you, you’re not good enough at getting guidance from your team. Remember that phrase: “What could I do or stop doing that would make it easier to work with me?”
  • No agenda: If they consistently come with no topics to discuss, it might mean that they are overwhelmed, that they don’t understand the purpose of the meeting, or that they don’t consider it useful. Be direct but polite: “This is your time, but you don’t seem to come with much to talk about. Can you tell me why?”

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Key Questions Covered

What is the purpose of a 1:1 meeting with a direct report?

The purpose of a 1:1 meeting is to listen and clarify. As a boss, you want to understand what direction each person wants to head in and what is blocking them. It's your single best opportunity to really hear your team members' perspectives on what's working and what's not — and to move up on the Care Personally dimension of the Radical Candor framework by genuinely getting to know them.

How often should I have 1:1 meetings with my direct reports?

Frequency depends on how many direct reports you have. Ideally, aim for 50 minutes per week per person, but cap yourself at about five hours of 1:1 time weekly. With up to 10 direct reports, 25 minutes a week works. If you have 20 direct reports, try 25 minutes every other week. The key is to be consistent — don't cancel. Most managers end up with only seven or eight substantive 1:1s per quarter per person once travel and illness are factored in.

Who should set the agenda for a 1:1 meeting?

Your direct report should own and set the agenda — not you. When team members drive the agenda, 1:1s are more productive because you hear what actually matters to them. You can set basic expectations about format (shared doc, bullet points, etc.), but the content should come from them. If someone consistently shows up unprepared or with no topics, address it directly: ask them why and clarify the meeting's purpose.

What are the warning signs that my 1:1s are failing?

Kim Scott identifies five red flags to watch for in 1:1s:

  • Frequent cancellations — your direct report doesn't find the meetings valuable.
  • Status updates only — they're not using the time meaningfully.
  • Only good news — people don't feel safe bringing you problems.
  • No criticism of you — you're not creating space for upward feedback.
  • No agenda — they may feel overwhelmed or unclear on the meeting's purpose.

Each signal points to a specific trust or communication gap you need to address.

How should I manage my mindset going into 1:1 meetings?

Stop thinking of 1:1s as meetings and start treating them like coffee or lunch with someone you genuinely want to know better. That mindset shift leads to far better conversations. Optimize the time and location for your energy — morning meetings if you're a morning person, walking meetings if that suits you both — but don't impose your preferences in ways that inconvenience your team. The goal is a relaxed, open exchange, not a formal check-in.

How do I handle 1:1s with remote direct reports?

For remote team members, always hold 1:1s over video conference rather than just a phone call. In addition, try to supplement scheduled 1:1s with more frequent, shorter check-ins to compensate for the lack of in-person interaction. The same principles apply — let your direct report set the agenda, show up consistently, and actively listen. Don't let physical distance become an excuse to deprioritize these conversations.

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