My strategy exercise for leadership teams:

The question hung on the screen like a boat anchor.

We were failing. People felt it, but no one wanted to speak up.

The problem was our ambition.

We were trying to build business software for nonprofits. Think Hubspot, Shopify, Salesforce.

We were ALSO trying to build a crowdfunding site for consumers. Think GoFundMe, Kickstarter, Indiegogo.

It was a bold vision, but it was killing us slowly.

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Going from good to great

This question – What can you be best in the world at? – comes from the book Good to Great, by Jim Collins. When I first read it, I was floored. You know a book is good when you’re embarrassed reading it as the leader.

I was doing so much wrong. But my biggest sin? Lack of focus.

I was leading the team in too many directions. Our roadmap was two companies in one. How were we supposed to build all of this!?!

So I promised Jim (in my head) we’d pick just one path. Business software or consumer crowdfunding. Fifty percent less to worry about. I felt better already.

Then came the next paragraph…

Just focusing wasn’t enough. What we decide to focus ON makes all the difference in the world. Shit.

What could Classy be best in the world at?

I threw the question on the screen at the leadership offsite and hoped for the best. The team seemed relieved. Finally, someone had knocked some sense into me! Thanks Jim.

This prompt led to hours of conversation. What were we actually good at? Where did we have the biggest advantage? What could we be great at some day?

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Find what’s uniquely you

Our decision seems obvious now. Classy started by hosting fundraising events for nonprofits in San Diego. We knew this customer in a way our competitors didn’t. It was uniquely us. So we picked the nonprofit software path.

But this decision wasn’t easy. Consumer crowdfunding was exploding. It felt like a gold rush. Our competitors were launching crowdfunding and getting funded. Union Square, Andreessen Horowitz, Greylock. Even Eric Riess, the author of “The Lean Startup”, bet against us.

After that offsite, we shut down our consumer business and doubled down on nonprofit software. I’m still proud of the team for this decision.

A few years later, GoFundMe swept the crowdfunding space with their own unique focus. We became the leader in nonprofit software.

What about those well-funded competitors? They all went out of business. Tried to be great at too many things, but never even made it to good.

Then, in a full circle moment, Classy was acquired by GoFundMe in 2022 to create the largest giving platform in the world.

Our original vision came to fruition after all, just in a different way. A proven software company merging with a proven consumer company. The vision was never wrong, we just couldn’t have pulled it off alone.

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An exercise for your team

Sometimes the best strategy is knowing what not to build.

So this week I’m sharing an exercise I’ve done with leaders in Highland. The goal of this exercise is to identify what your company can be best in the world at, align on it, and pursue it relentlessly.

Click the image below to get the full google doc with detailed instructions!

I hope you find this exercise valuable. Any questions, feel free to hit reply to this newsletter. And I’m always open to new topic selections for future newsletters as well!

Till next time,

Never say die 🏴‍☠️

Scot

~~~

P.S. See that on the screen?

That’s the Northstar OS template that every member of Highland gets when they join. We use it to create absolute clarity across their organization.

• Mission

• Values

• Vision

• Goals

• Metrics

The result is almost always game changing. That’s because most leaders assume this stuff is clear to their team… but its usually not even close.

We’re approaching 100 companies in Highland and I’ll be capping it at 150. If you’re a founder or CEO, you should apply now while you still can!

Apply here (takes 1 min):
https://joinhighland.com/apply/

(then our team will reach out to assess fit)