August 9, 2026

Your company strategy is missing this template:

Scot Chisholm

written By
Scot Chisholm

Scot Chisholm

written By
Scot Chisholm

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Your company strategy is missing this template:

My board member pulled me aside after a meeting. 

He asked why my CFO and CRO had pitched two conflicting strategies in the same day. I said I’d look into it, but I already knew the answer.

I called Rob that afternoon.

“Why did you tell the board something different than Aaron?”

“Because he’s wrong.”

“But we agreed on it last week.”

“We talked about it. I didn’t agree.”

“So you just decided to force my hand in front of the Board?”

“Come on. The Board loved it.”

He wasn’t wrong. The Board now favored his approach and asked me to pursue it.

A few days later I sat in my office waiting for our leadership meeting to begin. I emailed the team about the strategy change the night before.

Aaron came in first and handed me a letter.

“What’s this?”

“My resignation.”

“Wait, why—”

Rob walked in. Then the team.
No one spoke a word.

I started going through the slides Rob had presented to the Board a few days before. My presentation wasn’t great. I hardly believed the new direction myself.

It took six months to know for sure, but it was the wrong strategy. Aaron was long gone by then. Rob and the Board blamed execution. No one else had the courage to defend our original decision.

But the worst part of it all?
I let it get to this point as CEO.

After the shit show, I knew we had to change the way we aligned on strategy.

In a recent newsletter I shared this mid-year offsite agenda and strategy exercise.

Today, I’m sharing another critical resource to help you go even further: the Core Bet Charter template.

This simple document defines every strategic bet your company considers. It gives the team the appropriate level of context to digest, debate and then decide what to pursue…together, as a team.

Till next time,

Never say die 🏴‍☠️

Scot

scotchisholm.com
highlandacademy.com

~~~

P.S. Core Bets are a critical part of the Northstar OS strategy framework called Strategic AIM. It stands for:

  1. Approach – your unique approach to achieve your 3-yr vision

  2. Impact – the measurable impact of achieving your 3-yr vision

  3. Market – who you’re targeting (primary, secondary, tertiary)

You can copy the Strategic AIM template here (for free). But please credit Highland’s Northstar OS when you use and share with others. Enjoy!

🐐🏔️