Are you asking the right questions?

I spent YEARS asking some of the wrong questions about my business.

"How do we lower our CAC?"

"How do we improve our ads?"

“Which features should we build next?" 

These questions felt productive. But they were actually a trap.

Here's why:

When our growth slowed and friction increased, I instinctively looked for tactical fixes. But surface-level questions only led to surface-level solutions.

The real breakthroughs came when I started asking strategic questions:

• Why do our best customers actually buy from us?

• What problem are we really solving?

• Who needs this problem solved most urgently?

At Clearfit, I was obsessed with improving our trial-to-conversion rate. We spent months trying to optimize it.

But when we finally stepped back and asked "Why do our best customers buy?", we discovered something surprising:

Customers didn't care about 80% of our product - what we were showing in the trial. 

The solution wasn't a better pitch. It was clearer positioning.

After realigning our message with our customers' actual needs, trial-to-conversion rate doubled in 2 weeks.

The lesson? You can't optimize your way to the right positioning. But you can question your way there.

Having made all these mistakes myself and spent 17 years learning how to overcome them, I now help other founders ask the right strategic questions to unlock their growth.

Are you sure you’re asking the right strategic questions about your business?