September 7, 2025
How did this happen?
1 on 1 meetings filled my entire calendar. I had no space for actual priorities.
A decision all managers face.
“1 on 1’s are killing our company”, I said to our head of people.
I’m cancelling all of mine.
True. Most people were stuck in endless 1-on-1s in the name of alignment and accountability. We were strangling ourselves with a million individual meetings.
I was convinced. 1-on-1’s weren’t making us any better.
But was my move too extreme? Are 1-on-1’s really dead?
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The formal 1-on-1 meeting was popularized in the 80’s by the legendary CEO of Intel, Andy Grove.
Grove advocated for weekly 1-on-1 meetings as a critical tool for staying aligned, coaching and catching issues early.
Forty years later, 1-on-1s dominate corporate culture.
Ben Horowitz, parter at Andreessen Horowitz, and author of Hard Things About Hard Things, has been one of the most vocal advocates.
And everyone from famous CEO coach, Matt Mochary, to organizational psychologist, Steven Rogelberg, agrees: 1-on-1s are here to stay.
But recently there’s been pushback.
Brian Halligan, the founder and former CEO of Hubspot chimed in on a post by long-time Amazon Executive Ethan Evans.
Twitter tweet
The most public statement was from the polarizing CEO of Airbnb, Brian Chesky, who called 1-on-1’s a therapy session.
So what’s the deal?
The conflicting guidance is confusing. I’ve had more founders ask me about 1-on-1s this year than ever before.
Are 1-on-1 meetings helpful or hurtful?
Here’s my (updated) take…
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1-on-1 meetings are high risk, high reward.
Get them right and they can deliver on many of their early promises.
But done wrong, they’re not just bad, they’re disastrous for your organization’s productivity. They create more noise, more drama and more confusion than without them.
It’s a VERY fine line.
Twitter tweet
Three types of behavior (or people) turn 1-on-1 meetings into a cultural nightmare. You must eliminate all three.
1. The Rambler
This person talks in circles (or complains in circles). Going on so many tangents the 1 on 1 meeting becomes useless.
Priorities and progress aren’t discussed. They only bring forward low-level, low priority items.
Companies that let individuals fully control the agenda (advice fed by Horowitz, Mochary, etc.) create this problem. This is outdated advice.
My advice: Stop letting individuals fully own the agenda. Follow a structured agenda that both the individual and manager contribute to. Progress against individual goals should always be the priority. Manager’s role is to coach the person through blockers.
2. The Procreator
This person (usually a manager) sets up 1-on-1s with as many people in the company as possible. Well beyond their direct reports.
They justify it as “staying in synch” cross functionally. But all they do is create communication silos.
Ultimately this behavior leads to a 1-on-1 arms race. Whoever has the most 1 on 1s, has the most information, and therefore, has the biggest personal advantage within the organization. It’s a downward spiral from there.
My advice: Always prioritize group meetings – like your leadership meeting – over 1- on-1 meetings. This breaks down silos and lets information flow freely. Vary your 1-on-1 frequency and length based on the person’s performance. If the person is new, or struggling, the 1-on-1 meeting remains a great management tool.
3. The Seed Planter
The toughest to spot, but the most dangerous culturally.
This person injects a dissenting idea into their 1-on-1 meetings.
For example, an executive who disagrees with a leadership decision, then tries to influence others to side with their position.
In this case, the 1 on 1 meeting acts like a vessel for toxicity. Hidden from the leadership team. But spreading person by person nonetheless.
My advice: Advanced situation, but happens more than people realize. You must stay “tight at the top”. Ensure leadership alignment around final decisions, even if some people disagree initially. Formalize a communication plan that rolls down to the rest of the organization. Don’t let the executives wing the message.
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Eventually I came around. I just became more selective on how and when I did 1-on 1-meetings.
A 1-on-1 meeting, done right, can be high leverage. It helps someone make optimal decisions for weeks, if not months, without you in the room.
This especially helps new employees or under-performers who need more coaching.
Here are my three golden rules for 1 on 1 meetings:
Select the duration & frequency by person
Follow the same agenda framework every time
Never let 1 on 1’s turn into a rambling bitch-fest 😬
I start with weekly 1-on-1’s if the person is brand new. Then I’ll move to every other week by month 3 or 4. By year 2 I’ll drop the frequency to monthly if the person’s performance stays up.
My goal is to get everyone to monthly. This takes the least tax on your schedule, but retains all the benefits.
If someone’s performance starts to dip, you move them back to weekly, or every-other-week until sorted. Never keep under-performers on a monthly cadence. That’s a recipe for disaster!
Here’s an example of how I would do a 1-on-1 meeting with someone in a weekly cadence:
Weekly 1-on-1 Details:
Same agenda structure every time
Both the individual & manager contribute
But the individual leads the meeting
45 minutes total
Example agenda for weekly 1 on 1 meeting
The structure stays the same for other frequencies, the duration just gets longer:
Weekly: 45 minutes long
Every-other-week: 60 minutes long
Monthly: 90 minutes long
For details on each agenda section, visit my full article here:
How to Crush your 1-on-1 Meetings
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1-on-1’s aren’t dead. But they need to be smarter.
If you keep open agendas and treat every 1-on-1 the same you’re going to F your productivity.
Till next time,
Never say die 🏴☠️
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