1. One-On-One-Meeting Mindset
Your mindset will go a long way in determining how well your one-on-one 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 one-on-one 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. One-On-One-Meeting Frequency
Time doesn’t scale, but it’s also vital to relationships. Your one-on-one meetings 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 one-on-one time on 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 one-on-ones 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 one-on-one time to have Career Conversations, and if relevant, to do formal performance reviews (see the bonus chapter of Radical Candor for more information about performance reviews).
3. Show up for your One-On-One-Meetings
Probably the most important advice for one-on-one meetings is just to show up. In an ideal world, you have less than 10 direct reports so that you can have a weekly one-on-one meeting 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 one-on-ones.
If you reserve some of those slots for special one-on-ones (i.e., performance reviews, soliciting feedback, Career Conversations), you will have only seven or eight “regular” one-on-ones per quarter.
And if your world is not ideal and you have more than 10 direct reports, you probably have one-on-ones every other week. That means you’re having three or four one-on-ones with each of your direct reports per quarter.
So, no matter what fires erupt in your day, do not cancel your one-on-ones.
4. One-On-One-Meeting are for Your direct report’s agenda, not yours
When your direct reports own and set the agenda for their one-on-one meetings, 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 prefer a more free-flowing meeting, the agenda 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 one-on-one from time to time.
5. Follow-up questions to ask during One-On-One-Meetings
Here are some follow-up questions you can ask to show not only that you are listening but that you care and want to help, and to identify the gaps between what people are doing, what they think they ought to be doing, and what they want to be doing:“Why?”
“How can I help?”
“What can I do or stop doing that would make this easier?”
“What wakes you up at night?”
“What are you working on that you don’t want to work on?”
“Do you not want to work on it because you aren’t interested or because you think it’s not important?”
“What can you do to stop working on it?”
“What are you not working on that you do want to work on?”
“Why are you not working on it?”
“What can you do to start working on it?”
“How do you feel about the priorities of the teams you’re dependent on?”
“What are they working on that seems unimportant or even counterproductive?”
“What are they not doing that you wish they would do?”
“Have you talked to these other teams directly about your concerns? If not, why not?” (Important note: the goal here is to encourage the people to raise the issue directly with each other, not to solve the problem for them.)
6. Encourage new ideas in one-on-one Meetings
It’s worth keeping Jony Ive’s quote, “new ideas are fragile,” top of mind before a one-on-one.
This meeting should be a safe place for people to nurture new ideas before they are submitted to the rough and tumble of debate.
Help them clarify both their thinking about these ideas and their understanding of the people to whom they need to communicate these ideas.
The ideas may need to be described in one way for an engineer and another for a salesperson.
Here are some questions that you can use to nurture new ideas by pushing people to be clearer:“What do you need to develop that idea further so that it’s ready to discuss with the broader team? How can I help?”
“I think you’re on to something, but it’s still not clear to me. Can you try explaining it again?”
“Let’s wrestle some more with it, OK?”
“I understand what you mean, but I don’t think others will. How can you explain it so it will be easier for them to understand?”
“I don’t think ‘so-and-so’ will understand this. Can you explain it again to make it clearer specifically for them?”
“Is the problem really that they are too stupid to understand, or is it that you are not explaining it clearly enough?”
7. Signs you’ll get from one-on-one meetings that you’re failing as a boss
One-on-one meetings 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 one-on-ones 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?”
Now that you’ve got the 411 on one-on-ones, go forth and meet like a boss!
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