How to prepare for a one-on-one meeting as a manager

The 4 things you should do to make the most out of your next one-on-one meeting.

You’re not prepared. Or at least that’s what employees think when it comes to one-on-one meetings. In a recent survey we conducted of 1,182 managers and 838 employees, we found 36% of employees believe their manager is only “somewhat prepared” – and 40% of employees think their manager is “not prepared” or “not prepared at all.”

That’s almost half of employees thinking that their managers aren’t as prepared for one-on-one meetings as they could be.

Managers seem to agree. Twenty-four percent of managers we surveyed said their biggest frustration with one-on-one meetings is they’re never sure how to prepare or what to ask.

Fortunately, preparing for a one-on-one meeting is neither hard nor time-consuming. Before your next one-on-one, here are the four things you can do (and each takes 10 minutes or less):

#1: Get up-to-speed.

You waste time when you’re not up-to-speed. When you walk into a one-on-one meeting not knowing what the person has been working on for the past month, you squander 10–15 minutes to get caught up on old information. That’s 10–15 minutes that could’ve been spent discovering and discussing new information. Instead, spend a few minutes getting up to speed before the meeting rather than during it. Specifically:

  • Review status updates ahead of time. You’ll save time by not rehashing “What’s the latest on X?” And you’ll better orient yourself on what the focus of the one-on-one meeting should be.
  • Revisit notes from the last one-on-one meeting. You’ll realize there’s an important topic you need to circle back on, or an action item you need to complete. These notes can also help inform the questions you want to ask for this upcoming meeting.

#2: Ask your direct report to create an agenda.

Ask the employee to create an agenda ahead of time with what might be on her mind. You can say or write something like: “Mind kicking-off the first draft of the agenda for our one-on-one meeting? I want to focus on what you want to talk about, first. And then I’m happy to take a pass and add anything else to it.”

By letting her take the lead and initiate the agenda, you demonstrate to her that it’s her priorities that you want to address first. She’s in the driver’s seat, not you.

Then, of course, you’ll want to review the agenda before the meeting, and offer any additions for what you want to talk about.

#3: Clearly define for yourself: What do you want to know?

Yes, you’re asking the employee to write the agenda — but you also want to think for yourself what you want to know. Is there a concern you have about this person’s ability to work well with others? Are you wondering if they feel challenged enough by the work itself? If nothing specific comes to mind, consider these four areas of focus for a one-on-one meeting:

  • Concerns and issues. What potential problems might be bubbling up that you don’t know about, but should?
  • Feedback about work performance. What does your direct report need to be doing differently? How can you improve your own management style?
  • Career direction. How can you help support this person progress toward their career goals? Are you both on the same page for what progress looks like?
  • Personal connection. What outside of work in their life is going on that you want to know more about?

Reflect on these four areas to generate ideas for questions you should be asking, or topics you think should be covered during the one-on-one meeting.

I’d recommend picking one or two of these focus areas, and then brainstorming at least 3–7 questions for each area. You may not ask all the questions (or any!), but they are helpful to have in your back pocket should the conversation lag or veer off-topic.

To help you get started, here are some examples for one-on-one meeting questions in each focus area:

Questions that uncover concerns / issues…

  • “When have you felt most motivated about the work you’ve been doing?”
  • “Is anything holding you back from doing the best work you can do right now?”

Questions that elicit feedback about work performance…

  • “Would you like more or less feedback on your work? Why/why not?”
  • “What’s a recent situation you wish you handled differently? What would you change?”

Questions that help provide career direction…

  • “What’s one thing we could do today to help you with your long term goals?”
  • “Is there an area outside your current role where you feel you could be contributing?”

Questions that foster a sense of personal connection…

  • “Been anywhere recently for the first time?”
  • “What have you been excited about lately?”

I always try to ask at least one question focused on personal connection, and use that question to open up the meeting. This helps break the ice at the beginning of your meeting, and builds rapport with your employee. Without this sense of rapport, your employee won’t feel comfortable divulging anything meaningful — nor will she find the conversation much fun.

For more ideas for questions to ask during a one-on-one meeting, you can visit here. (We also give you hundreds of question ideas and four meeting templates to use in Know Your Team.)

#4: Calibrate your mindset.

Take a minute to remind yourself: This meeting is not like other meetings. You aren’t running it. Your primary job is to absorb the information being shared with you, poke holes to figure out how an employee is actually feeling, let things marinate, and then figure out when you need to do. You shouldn’t be talking. You should be listening and scanning for the truth.

These four steps takes 15 minutes, maybe 30 minutes at most, to complete in total. That’s 15 minutes — 30 minutes of preparation that ensures your hour-long one-on-one meeting is not an hour wasted. Invest in preparing for your one-on-one to get the most out of this time together.


P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

Announcing: A Guide to One-on-One Meetings for Managers and Employees

Based on data from 2,000+ people, I wrote a guide to one-on-one meetings for managers and employees — and it’s finally live! 🙂

Dear manager or employee who cares about their team’s success,

You hold one-on-one meetings. But are they working?

Over the past four years, I noticed how almost every person I talked to did not know the answer to that question. They held one-on-ones — but felt in the dark if their one-on-ones could be run better (or, if they were working at all).

So I surveyed hundreds of managers and employees. I spoke and wrote to hundreds of Know Your Team customers and Watercooler members. And from the data, insights, and conversations, I put together two guides: One for managers, one for employees.

In these guides, you’ll learn…

  • The purpose of one-on-one meetings: What’s the point?
  • How long, how often, and with who to hold one-on-ones with
  • How to prepare for a one-on-one meeting
  • The best 8 questions to ask during a one-on-one
  • What to put on your one-on-one meeting agenda (with 4 agenda templates)
  • How to get honest insights from your one-on-one
  • Best practices for writing notes during a one-on-one meeting
A lil’ preview inside the guides

Here’s what people have been already saying so far…

“It’s gold! The guides provide clear, consistent and actionable steps to make 1:1s…dare I say fun? Claire dives right into the meat of how to remove the “awkward” from what should be a success driver for everyone.” — Morgan Legge, HR Champion at Convert

“My direct reports are already telling me our 1:1s are much better after using these templates! Thank you!” — Matt Born, Product Design Manager at Sprout Social

“The information is succinct, fresh and without fluff.” — Ali Merchant, Founder at Marin Software

“An evergreen, relevant guide that focuses on the essentials and immediate results. I’ll be sure to put some of Claire’s advices into practice on my next one-on-one!” — Éric Leblond, Vice President at Sigmund

“Claire and her Know Your Company colleagues continue to exceed my elevated expectations and these latest one-to-one meeting guides keep that streak going. You’ll laugh, you’ll cry (okay, that’s hyperbole) and you’ll be incredibly grateful that somebody took the time to do this work and share it.” — Paul Kanarek, Managing Partner at Collegewise

“I loved this. Thanks so much for distilling this info into such an easy to use guide — it’s an instabuy!” — Brady Kent

“Claire’s guide to one-on-one’s for managers came just at the right time for me — her suggestions helped me to get the most out of the meeting.” — Zoe Cunningham, Managing Director at Softwire

To get access to the Guide to One-on-One Meetings, you’ll want to check out Know Your Team — our software to help you become a better leader.

In our software, Know Your Team, we include this guide, plus six other guides, tools, and an online community.

👉 Try Know Your Team today.

Enjoy the guides, and look forward to hearing from you!

P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew).

What’s the best way to run an effective all-hands meeting?

There’s no one-size-fits-all solution — but there are best practices. Here are 5 recommendations from leaders all over the world on how to hold a well-run company-wide meeting.

“Does my team think this is a waste of time?” The thought slips into your mind as your prepare for your all-hands meeting. Whether it’s the first all-hands you’ve prepared for or your fiftieth, the question inevitably creeps up.

You need to get everyone in your company on the same page. And so, like most leaders, you decided to hold an all-hands meeting.

But, you wonder if the energy in the room will be flat. Are the topics being covered repetitive? Will folks be sitting there, dying to do just anything else than attend the all-hands?

To figure out how to hold an effective all-hands meeting — one that employees don’t dread or feel apathetic about — I posed the question to The Watercooler, our online community of 1,000+ leaders from all over the world: What do they do to make sure their all-hands meeting is not a waste of time?

The answers I received were from companies as small as 10 employees to companies as big as 260, with ideas as varied as their company size.

However, they did agree on these five recommendations for an effective all-hands meeting:

#1: Never shut up about your mission, vision, values, and goals.

Whatever you choose to talk about, tie it back to the bigger picture of what the company is trying to accomplish. Progress motivates employees— so sharing how their progress fits into the company’s progress gives them energy. One Watercooler member remarked: “Because my business partner and I talk about this stuff (mission/vision/values) all the time, it feels like old news to me. But a big part of our jobs as leaders is to never shut up about this stuff.

#2: Pull back the curtain.

Reveal something in the company that is opaque. Unlike status update meetings or quarterly emails, the all-hands meeting is a rare opportunity to shine a light on something most people in the company find confusing or “off limits” to talk about. For example, some companies will walk through their financials at a high-level. Other companies have the CEO share her thoughts on the vision for the company over the next year.

#3: Mix it up, keep it fresh.

Yawn. Watercooler members admitted that all-hands meetings can become, well, boring. Pass around the mic and avoid the potential of CEOs droning on (myself included!). Delegating speaking roles will get everyone involved, and give folks who best know their domain a chance to shine. Consider also mixing up the meeting format each time, as well. You could invite an outside speaker for one meeting, or ask a team to give a presentation for another. When you vary the format, you can better keep your team’s attention.

#4: Don’t make them mandatory.

The minute you make something required, people resent it. Don’t twist employees’ arms or cajole them into showing up to an all-hands meeting. Instead, make it clear what benefits of attending are, and make it optional. Watercooler members noticed that they saw the greatest engagement during their all-hands meetings when they didn’t force everyone on their team to attend.

#5: Invite critical questions.

It can feel daunting to open yourself up for questions to a room full of 80 people. But your vulnerability has an upside: You show your employees you’re open. And, you source insights that you typically might not get. If your team tends to be resistant to asking tough questions, offer a few questions to your team to get the back rolling. For example you could ask:

  • Who in the company has done great work here that’s gone unnoticed?
  • Is there anything we’re behind the curve on as a company?
  • Have you seen a competitor do anything recently that made you think, “I wish we’d done that?”
  • What red tape do you think we can cut at the company?
  • What’s one thing we could do to improve these all-hands meetings?

Ask these questions, and you’ll inspire someone in the room to ask a critical question of their own.

How many of these things are you already doing during your all-hands meeting? If you have yet to try one, give it a shot. Even implementing one of these best practices can be the difference between your all-hands being a waste of time or a good use of it.

P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew.)

One-on-ones 101: With whom and how often?

As a busy leader, you may be wondering how to fit one-on-ones into an already packed schedule. Here are some best practices selected from The Watercooler, our online community for leaders.

A frequent question I receive when it comes to having one-on-ones with employees is: With whom and how often? Everyone? Direct reports? A cross-section of employees from different departments? Once a week? Once a month? Bi-weekly? Quarterly? Once a year?

One-on-one meetings can be notably time-consuming — especially if you’ve got more than 50 employees. So figuring out how who you’re talking with and the right cadence of conversations is crucial.

To get a sense of what other successful leaders have implemented at their companies, I posed the question of one-on-one frequency and structure to The Watercooler, our online community in Know Your Team with 1,000+ leaders, managers and executives from around the world.

Here’s some of their best advice about one-on-ones:

  • With more than 100 employees, this content strategy leader can’t have one-on-ones with everyone. She holds one-on-ones with direct reports every two weeks, and she meets with peers and stakeholders in different teams and departments across the company every one-to-three months.
  • One leader of a 50-person-plus organization said she conducts one-on-ones with six managers and four or five employees selected at random. This gives her a good understanding of what’s going on in the company — and not just from a manager’s perspective. The frequency is one a month.
  • With a company of about 25 people, one leader said she meets with four direct reports weekly for 30 minutes, and twice each week for an hour with two different employees. This ensures that everyone has the opportunity to voice long-range items.
  • Another leader of a small team of about 10 people said she can still conduct one-on-ones with everyone. But rather than load up everyone’s calendars with meetings, she tries to be more present and aware about what’s happening in terms of attitudes and behaviors across the team, which allows her to actively react by scheduling more one-on-ones with those who may need it most.

How often do you hold your one-on-ones, and with whom? Share your experience in the comments below, or join us in The Watercooler and read what leaders from around the globe are discussing when it comes to leadership and employee engagement. Look forward to hearing from you!