June 11, 2026
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In 2026, 1 on 1 meetings are on the hot seat. CEOs like Brian Chesky, Jensen Huang and Jack Dorsey have all spoken out against them.
But 1 on 1 meetings aren’t completely dead, they’ve just changed. CEOs use them less, lower-level managers use them more.
In all cases, the frequency, duration and structure matter a lot. It’s the difference between 1 on 1’s killing productivity and unleashing it.
Strong dashboards + AI handle status updates. So, 1 on 1 meetings in 2026 focus more on coaching, course-correcting and problem solving.
I still have meeting PTSD from the early days at Classy (acquired by GoFundMe in 2022) where I ran all my meetings wrong, especially the recurring 1-on-1 between manager and individual.
They felt like an inconvenience any time I saw one on my calendar. Can’t this person handle their own shit without meeting with me every week?!?
But once I fixed my 1-on-1 structure, I started to see the light. A 1-on-1 meeting, done right, can be massively beneficial for both the leader and the individual. But most leaders do them wrong. They’re just not productive enough. And the cumulative effect of a negative 1-on-1 culture is a massive time suck across the organization.
I first wrote this article a few years ago when 1-on-1’s were standard management fare. My structural advice hasn’t changed, in fact the points below have only gotten more important in 2026. Famous CEOs are trashing the 1-on-1, AI is automating some of it, and young CEOs are asking whether the meeting should exist at all.
This article is my answer. A deep dive into 1-on-1 meetings – my recommended format, frequency, duration and agenda – after 20 years of leading teams as a CEO. Below you’ll find highly actionable advice for both the manager and the individual, so you never dread another 1-on-1 again!
Let’s dive in…
I created a Leadership Kit that helps you implement everything in this blog post into your company’s One-on-One Meetings. Get access HERE.
The 1 on 1 meeting is one of the most powerful tools in a leader’s toolkit. In a short amount of time someone, you can:
But most people get these meetings wrong. It’s very common to see 1 on 1 meetings with no clear agenda, no connection to goals, and an unreliable cadence. This makes people dread their 1 on 1 meetings and view them as a waste of time. But as you’ll see in the rest of this article, to turn wasteful 1 on 1’s into a productivity power house.
Since I first published this article, 1 on 1 meetings picked up some powerful enemies.
Brian Chesky doesn’t do them. “I don’t believe in one-on-ones, and almost no great CEO in history has ever done them,” he told Fortune. His complaint: the recurring meeting where the employee owns the agenda turns you into their therapist. Jensen Huang skips them too. He wants every conversation in a room where the whole team hears the reasoning. And Jack Dorsey wants to go further than killing the meeting. He wants to kill the management layer entirely. That one deserves its own article, and it’s coming next week.
Now read Chesky’s complaint again. A recurring meeting the employee owns. No structure. Low-priority items. Therapy. He’s not describing 1 on 1s. He’s describing bad 1 on 1s. The exact version I tell you to kill later in this article. I agree with every word of his diagnosis. We just disagree on the prescription. He canceled the meeting. I fixed the agenda.
And before you take a podcast quote as permission to cancel yours, consider Brian Halligan. In the early days of HubSpot, he skipped the weekly 1 on 1 too. Big group meetings, everything in the open, very Jensen. Then as the company scaled, he brought them back. Weekly. He ran the experiment most people only tweet about, on the way to building a $25 billion company, and he landed where I did.
One more thing, and this is the part that matters if you’re the CEO. When Chesky talks about skipping 1 on 1s, he’s talking about his executives. People with their own forums, their own staff meetings, and access to him whenever they want it. But that’s not what your company hears. Your company hears that the CEO of Airbnb just gave every manager permission to cancel the one meeting where people tell the truth. You’re not picking a personal meeting style. You’re setting the operating system for every manager in your company. Choose like it.
But I’ll be honest – for a long time I didn’t understand the point of 1 on 1 meetings. But that’s because the meeting was too free-form. I was allowing rambling conversation, low-priority items and complaining into the meeting. Sound familiar? These are 1 on 1 productivity killers. Now imagine this across your entire organization. Dozens, if not hundreds, if not thousands or unproductive meetings happening every single month. Yikes. 😳
Eventually I realized that the difference between a ‘good’ and a ‘bad’ 1 on 1 meeting was massive. A 1 on 1 meeting can be super high leverage – helping someone make optimal decisions for weeks, if not months, without you in the room. But a really bad 1 on 1 creates negative leverage (yes, NEGATIVE). It’s not only unproductive, it actually creates more noise, more drama, more confusion than before.
So how do you make sure you get your 1 on 1 meetings right? Here’s how I did it:
Yes, I did say that (we’ve all been there). But it’s important to call out, because your 1 on 1 meetings should never become a continuous stream of complaints (especially about other co-workers). This is a 1 on 1 meeting at its worst, and indeed, a waste of time. Conflict must be dealt with as a team, or at minimum, with both parties present.
The other thing to watch out for is the “open agenda”. You’ll often here business guru’s tell you that a 1 on 1 meeting is “their meeting” — meaning the agenda should be 100% owned by the individual, not the manager. Not true. I followed this advice for a while too, but the meetings weren’t nearly effective enough. The employee would typically show up with lower-level items to fill the agenda and avoid the really hard, thorny issues that actually needed discussion.
This is human nature of course – to choose the path of least resistance. But it doesn’t drive high performance. So what did I do instead? Find out below 👇
As a manager, the 1 on 1 meeting is your chance to unlock each person’s true potential. It also serves as your early warning system for issues and under-performance. Apply these 3 simple rules to go from a weak 1 on 1 meeting to a winning one.
Instead of handing an open agenda to the individual, the manager should set the overarching structure of for the 1 on 1 that both sides understand and agree to. Here’s an example of my battle-tested 1 on 1 agenda that I’ve been using for many years.
Weekly 1 on 1 Meeting Details:
Weekly 1 on 1 Meeting Agenda:
This example is for a weekly 1-on 1-cadence. But the structure of the agenda is the same for every-other-week and monthly frequencies. The duration just gets longer:
Now let’s dive into each section of the agenda:
Agenda Section 1: Settle In
For the first 5 minutes you both settle into the meeting. Ask if the person had a nice weekend. Ask how things are going generally. Keep it human, break the ice.
For the next 20 minutes, the individual gives the manager an update on how they are doing against their goals. I use a simple green, yellow, and red light status system. Regardless of what you choose, make sure that progress is communicated clearly and issues are raised early. This is your early detection system.
If the individual doesn’t have goals, you should start there. Have them create annual goals that align with the company’s. Then break them into quarters and/or months to track progress.
For the next 20 minutes, you let the individual bring their own agenda items to the table. This empowers them to raise important issues or blockers to their progress. But there are two key things to keep in mind with this:
This section is short because the meeting is already set up to be coaching-heavy. But I love to find something to reinforce or praise. It’s a great way to end each meeting on a positive note, while maintaining a culture of feedback.
It’s unbelievably important to remain consistent with your 1 on 1 meeting schedule, and be present during the 1 on 1 meeting itself. The fastest way to destroy the relationship between you (the manager) and the individual is doing these three things:
These three things say: “My other priorities are more important than you.” Yet, so many managers do exactly that. 🤦🏻♂️
How to be consistent with your 1 on 1 meetings:
Consistent doesn’t mean more frequent. You don’t want 1 on 1 meetings to overrun your calendar. Instead, I select frequency based on person’s experience-level and their time at the company.
Here’s a simple table that explains how I think about it:
As you can see, the frequency of my 1 on 1’s depends on the person’s performance and time in their role. If a person’s performance is low, then you want to meet more frequently. If the person’s performance is high, then you gradually move from more-frequent to less-frequent as trust is established. If the person is new to the organization, you start more-frequent for the first 90 days, then depending on performance, you gradually move to less-frequent.
It’s important to note that no position on this table is permanent. If the person starts under-performing, you always move to higher-frequency 1 on 1s in order to increase the level of coaching. This is the same 1 on 1 philosophy for any level of experience or role in the company.
How to be present in your 1 on 1s:
It feels funny even writing this section, but it deserves a strong reminder. And I used to be a culprit myself as a new manager. Too many times I’d catch myself checking slack or my phone during a 1 on 1 meeting. This is a definite no-no. You must be 100% present to establish mutual respect and trust with the other person. The person on the other side of the table will never give you their best if you’re not willing to first.
1 on 1 meetings are the perfect forum for candid, supportive dialogue about growth areas. Take notes between meetings on:
Then, use the last 15 minutes to give both – praise and feedback. You won’t always have something to coach them on, but you should aim for at least 50% of the meetings.
And don’t forget this part: you’ll also want to get honest feedback on how you’re doing as a manager. Ask questions like:
You are there to help them remove blockers and coach them towards goal achievement. So, the last thing you want is to become the blocker yourself! But sometimes the manager doesn’t realize they are holding things up, and the individual feels awkward about raising it. So asking these questions on a regular basis opens up the conversation in a comfortable way.
Now 3 rules for the individual in the 1×1 (one-on-one) meeting…
While the manager sets the agenda structure, the individual should take the lead on the majority of the meeting (first two sections). Use these 3 rules to get the most out of your 1 on 1 meeting with your manager. Or, if you’re a manager, you can give these tips to all of your direct reports.
A 1 on 1 meeting is a great time for you, as the individual, to showcase your leadership skills and future potential. Coming to every meeting prepared is key.
You should:
Think of your agenda time (section 2) as a space to collaborate and problem solve with your manager. That said, you should still come with a well-thought through agenda, raise important discussion points, or present something for feedback to make the best use your manager’s time.
Avoid using large chunks of the agenda for small admin-type items, unless you really can’t get the answer elsewhere. If you do have these types of questions, batch them into a 10-minute block and ask them rapid fire to your manager. Don’t spend too much time on discussion. Get an answer and move on to bigger items.
Want the 1:1 Meeting Kit? You’ll get access to a 1-hour masterclass, step-by-step guide, implementation plan, agenda, checklist, and more. Get access HERE.
Asking for help shows self-awareness, not weakness. If you’re giving your manager an update on your goals, it’ll become natural to talk about your blockers and ask your manager for help where applicable.
But be clear about what you’re asking for:
The third one will happen now and again, but make the first two the norm. You don’t want to be throwing all your problems at your manager for them to figure out for you. Think of your manager like your “editor” not your “writer”. You’re letting them know there’s a problem, giving status on where you’re at and asking them for help as applicable.
Don’t be afraid to add personal development items to the 1 on 1 agenda, especially if you’re on pace to hit your goals (since you’ll need less time on that section). If you’re manager is doing these meetings correctly, you have their undivided attention – take advantage!
Here’s a few ideas:
This is time well spent. A great manager will embrace the chance to help you develop personally. Just enter this conversation with an open mind and an “always be learning” mindset!
Here are a few final tips to make your 1 on 1’s epic:
I wrote about the extended 1 on 1’s here: The Annual Meeting is Dead. Here’s what I do instead:
Remember – 1 on 1s can either be a total pain in the ass, or a productivity machine. It just comes down to consistency, structure and how both sides show up. When used effectively, 1 on 1’s can single-handedly boost team performance more than almost anything else a manager can do. And as an individual, this is time with your manager you don’t want to waste! Use it to help achieve your goals and develop as a professional.
Now, get out there and start crushing your 1 on 1’s!
Every week I tackle management, operations & startup topics that are helping 300,000+ people become better leaders.
Written Weekly by Scot Chisholm
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