April 12, 2026
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I looked at my calendar.
Four out of five meetings were scheduled by someone else. Dropped there like a personal attack.
There goes another day, I thought.
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“What were our goals again?”
The rest of the team laughed.
They knew. We never do what we say we will. We have goals, but we never follow through. We have meetings, but they have no teeth. We have targets, but no one thinks they’re realistic. Then we make jokes about it.
And it never gets better.
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“Won’t Jake feel left out?”
“It doesn’t matter,” my advisor said.
“You need to draw the line between your leadership team and the rest of the company.”
He was right. The lines were blurring. The “leadership team” had grown to almost 20 people. People didn’t know who should be in what meetings, or why. It was all bleeding together.
We needed a hard reset.
THREE scenarios. Same problem. A company with too many people and too little structure.
A company without an operating rhythm.
An operating rhythm is the flow of your company’s operations.
Think of a rowing crew. If one person is off rhythm, the whole boat slows down.
Your rhythm is made up of two things: planning and checkpoints.
Planning sets the guardrails. At the start of the year, you align on:
Strategy
Goals
Metrics
Roadmap
Checkpoints are for inspection. You place them throughout the year to hold the team accountable to what it committed to.
A leadership team meeting is a checkpoint for your functional leaders. An all-hands is a checkpoint for the entire company.
Three questions drive every checkpoint: Are we doing what we said we would? What’s standing in the way? How do we remove blockers?
That’s how you build a system that pumps accountability.
Here’s how I build a company operating rhythm.
Imagine three calendars:
Annual calendar
Quarterly calendar
Monthly calendar
Each one has its own set of planning activities and checkpoints:
drafting goals
finalizing financial plan
all-hands meetings
leadership meetings
I create each calendar first. Then I stack them together to create one cohesive schedule.
Every meeting, every review, every update lines up. Each one makes sense for where you are in the year. Each one moves the company forward.
Your rhythm is this question on repeat:
Are we doing what we said we were going to do?
See an example of what I put on each calendar:
→ Three Calendar Example (Google Slides)
A company without an operating rhythm is chaos. But too much structure can slow you down.
Reed Hastings, the founder of Netflix, calls it operating on the “edge of chaos.” Enough structure to stay coordinated. Not so much that you kill the speed that got you here.
The best operating rhythms live in that sweet spot. Enough checkpoints to keep the team honest. Few enough that people can still move fast.
When you’re small (under 50 people), you want a lean version. For example, you don’t need Quarterly Business Reviews (QBRs) right away. You’ll handle most of that through your leadership meeting and all-hands.
But as you scale (50, 150, 500+ people), you need more checkpoints to avoid drift and crappy performance. At these sizes, adding QBRs makes sense because you can go deeper than you’d want to in front of the entire company. But with a broader audience than just your leadership team (which has narrowed to executives at this point).
You should reevaluate your operating rhythm at least annually. What’s working and what’s not? Is it time for an upgraded set up? On a journey from $0 to $100M+, the typical transition points are:
20 people
50 people
150 people
300 people
500 people
But AI is allowing teams to do more with less people. So, you may have a smaller team for longer, with a more consistent operating rhythm and less need for these transitions.
You also need to continuously evaluate who should be involved with each checkpoint. Just because someone was part of the leadership team at the company’s founding does not make it a permanent position.
At 100 people you might define certain checkpoints like this:
Leadership meeting (executive team)
All-hands (entire company)
1-on-1s (manager and individual)
QBRs (managers and above)
Offsites (executive team plus key leaders selected by CEO)
These types of decisions are hard for leaders to make, but it’s imperative for keeping the operating rhythm sharp and effective.
Every year your company makes fresh commitments for the next 12-months:
strategic priorities
financial targets
It starts in Q3 and launches at your company kickoff in Q1. Your operating rhythm becomes the vehicle to execute these new priorities and targets.
Strategic priorities are your company’s annual goals. I teach a system called WhyGos because EOS and OKRs broke when I was scaling Classy.
Every checkpoint in your operating rhythm should evaluate progress against your annual goals – especially your leadership team meeting.
This is your most important checkpoint because it ripples through the rest of the organization.
The key is discipline and focus. It’s wild how many companies completely forget what their priorities are mid way through the year. They chase the next shiny object. It doesn’t mean you can’t be flexible. But changing a strategic priority should be the exception not the rule.
See how I refresh my company’s goals and Northstar each year:
→ Northstar OS Template (Google Slides)
The operating rhythm only works if people are honest about progress.
Things will go off track. Goals will turn yellow and red. That’s not a failure. It’s the reality of ambition.
Average teams start pointing fingers. Great teams ask one question: how do we get back to green?
“Get to Green” is the ethos behind your whole operating rhythm. You don’t blame. You don’t skirt responsibility. You jump in and solve it together.
This happens at every checkpoint. The team comes together, looks at reality, and figures out what it takes to get back on track.
The CEO sets the tone. If your top priorities are off-pace, what could be more important than fixing them?
That’s the operating rhythm.
Plan it. Inspect it. Get to green.
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TAKE THIS HOME with you.
Now you have the framework to build an operating rhythm at your own company.
Design your three calendars
Put the right people in the right rooms
Build a culture that ‘gets to green’
Do this and you’ll be amazed at what you can accomplish.
Till next time,
Never say die 🏴☠️
Scot
→ scotchisholm.com
→ highlandacademy.com
~~~
P.S. I launched a new article since my last newsletter!
→ Why I started a coaching program for CEOs (and their teams)
Most founders inherit the CEO title before they understand the role.
Highland combines expert CEO coaching, a structured curriculum, a company-wide operating system (Northstar OS), and a community of peers scaling alongside you.
If you’re interested in joining Highland, you can apply here (takes 1 min).