I see a lot of posts like this these days…

This is Tyler Denk, the CEO of Beehiiv (the platform I’m using to send this newsletter). No, I’m not a paid sponsor. Yes, I do respect Tyler. I think Beehiiv is a great product, and from an outsider’s perspective, Tyler seems like a strong CEO.

But this particular LinkedIn post gave me pause. Why? Not because I like meetings, that’s for sure. Because of the (likely unintentional) message it sends to other founders.

Old way of operating bad.
My way of operating good.

Are weekly one-on-ones absurd? Is two all-hands per week the way to go? Maybe. Maybe not. This may work for Tyler, but it won’t necessarily work for you.

If you didn’t know, I work directly with 100+ CEOs in Highland, ranging in revenue from $1M to $100M – from AI, to retail, to sports. I don’t see everything, but I do see a lot.

Here’s how I coach Highland CEOs on designing their own operating rhythm…

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One Rhythm to Rule Them All?

LIKE TYLER, LOTS of CEOs are questioning the old way of doing things right now. And for good reason. The adrenaline shot of AI is reason enough to flip the table. After all, most of modern management was shaped by a bunch of old dudes, like Drucker and Grove, who wrote their books decades ago (btw, I like them both, but come on). Then you have the “operating system” crowd, like EOS, which claims to have found the Holy Grail of business formulas (just sign right here on the dotted line!).

Guys, here’s the reality. Talk to any experienced operator and they will tell you this:

There’s no such thing as a one-size-fits-all operating rhythm.

The activities might be the same — leadership meetings, one-on-ones, all-hands, etc. — but the way they flow across your calendar should be tailored to your company, not someone else’s.

And, unlike a classic song that stands the test of time (I’m looking at you Good Vibrations), an operating rhythm should constantly evolve based on three core factors:

• Stage: Where you are in your journey. A 5-person company is going to look totally different than a 50-person, 500-person, and 5,000-person company.

• Style: How you want to shape the culture. One CEO might want a highly autonomous, distributed team. Another might see in-person meetings as their secret sauce for innovation.

• Systems: How well your systems share information, and how far someone can get without asking for permission. Meetings multiply when people don’t understand direction and progress, or how to start a solution without permission.

Let’s go back to Tyler’s post and add this context:

• Stage: Beehiiv has around 130 people and $40M in ARR. This is a real scale company, not an early-stage startup.

• Style: Tyler wants people building-first, not talking-first. He seems to prefer high autonomy and isn’t worried about early mistakes.

• Systems: His systems are set up to enable his style. AI allows for prototyping without all the pre-planning. Slack etc. allow for a high degree of async communication.

This gives us a much better idea of why Tyler chose the rhythm he did. The context is essential before hitting “copy” and “paste” for your own company.

(although it still doesn’t explain the 2x all-hands per week. more on that below)

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Creating Your Company’s Rhythm

An operating rhythm is the flow of your operations over time. If everything was ad hoc and meeting-less, it would be too chaotic. If everything was recurring and pre-planned, it would be too rigid. Your goal as the CEO is to get the mix right for your stage, style and systems.

But don’t worry, you don’t have to reinvent the wheel. You can treat existing advice or systems as your “default setting”, then customize from there. Just make sure you’re vetting the source for experience and stage-fit. Jensen Huang (CEO of Nvidia) sure has a lot of experience, but he runs a $5.5 trillion company. Just because he has 60 direct reports doesn’t mean you should too.

In Highland we give our CEOs default settings by company stage. This is the default Northstar Operating Rhythm for small teams with 10-50 people.

This doesn’t mean it’s perfect for every company with 10 to 50 people. But, it’s a great jumping-off point. Then you customize it from there.

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Three Calendar Concept

IF YOU BROKE apart the example I gave above, you’d see three distinct calendars — Monthly, Quarterly, Annual — that fit neatly on top of each other. Each one has a specific purpose. Monthly is all about high-caliber execution. Quarterly is about reflection and calibration. Annual is about connecting the vision and strategy to annual priorities.

I call this the ‘three calendar concept’ to remind Highland CEOs that an operating rhythm is not rocket science. It’s really just three stacked calendars that fit together like a puzzle. Then, the activities you place in each calendar (meetings, reviews, updates) reinforce the specific purpose of that calendar.

For example, you don’t spend hours redoing your annual financial plan in your weekly leadership team meetings. Nor do you obsess over monthly targets when you’re trying to refresh your longer-range vision and strategy.

Your rhythm doesn’t just give people a flow, it helps them understand the altitude and focus of each activity.

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Make it Your Own

Once you have your default settings by stage, with three cohesive calendars, you’re ready to give it your own unique spin. I wouldn’t reinvent the dials, but as CEO, you can adjust the settings as you wish.

If weekly one-on-ones crush your soul, then dial them down. If all-hands meetings are part of your secret sauce, dial them up. That’s what Tyler did, without saying these exact words. Clearly he sees some magic in his all-hands meetings. So instead of doing them monthly, like most companies his size, he’s doing them twice per week. The second one he picks “a few people at random to talk about what they got done.” Most CEOs would call this a status update in disguise. But look at the word “random”. Everyone knows they might be called on. So they better have something good to share.

So how do you decide on your own unique mix (frequency and duration)?

We go back to your style and your systems.

Classy was deliberately an in-office, people-first culture. This was our style. Even when companies like 37signals, Automattic, and GitHub were making remote cool, we resisted. There was something special happening at Classy and we didn’t want to fuck it up by copying someone else. This decision drove the operating rhythm we chose. We preferred less frequent, but longer duration meetings in general. But if you’re on Zoom and Slack all day, you might want the opposite. Neither one is better or worse.

Yet, Classy’s systems were prehistoric compared to what’s possible today (and this was only a few years ago!). A lot of what was covered in our daily stand-ups, team meetings, even board meetings, can be automated today. But be careful. If I were still running Classy, I wouldn’t kill these meetings because our systems got better. I would reinvent their content — away from status updates, and towards higher levels of collaboration and accountability (exactly like I suspect Tyler is doing). Once I saw how that worked, I may decide to adjust frequency too.

⁂

Learn from everyone. Copy no one. Someone else’s rhythm might be a good jumping-off point (including my own). But there’s work to do from there. Make it your own.

Till next time,

Never say die 🏴‍☠️

Scot

→ scotchisholm.com
→ highlandacademy.com