April 21, 2025

The perfect leadership meeting (seriously):

Scot Chisholm

written By
Scot Chisholm

Scot Chisholm

written By
Scot Chisholm

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The perfect leadership meeting (seriously):

I should have cancelled this meeting. It’s a complete waste of time. Now this will make five terrible leadership meetings in a row. Nice job, Mr. CEO…

This time a new culprit – one of the execs came in hot and was dominating the conversation – locking horns, taking us on tangents and propping his team up like god.

Two hours of brain damage later, the team finally broke. But I just sat there staring at the wall. I knew what this meant…

Another bad leadership meeting would cause months of misalignment rippling through the organization. I had to fix these meetings fast, or we were screwed.

So I spent the next few months asking every operator I knew how to run one like a proper CEO (not the schoolboy I was playing).

It wasn’t easy at first but I eventually got things under control. Not only that, the leadership meeting became one of (if not the) most important things I managed as CEO.

My mantra for the leadership team became “tight at the top” – if we worked hard on flawless alignment through this leadership meeting, it would create the right focus and behaviors all the way down the organization.

Honestly, this made all of our jobs much easier. Nail this one 90-minute meeting and great performance followed – that’s a great deal for everyone!

So here it is – the exact playbook we used for years with great success on our way to $100M and beyond.

Stay ‘tight at the top’ my friends…

Till next week,

Never say die 🏴‍☠️

Scot

Ps. Highland is the “school” and community for founders I launched last year. It’s booming and you should join us. Learn more here: www.joinhighland.com