#60 Stop Trying to Hire Your Way Out of Sales

I was 8 years old when I made my first sale.

My grandparents had a small farm outside Öxabäck, between Varberg and Borås. That summer the whole family had picked enough strawberries to fill a few crates. Me, my dad, my sister, my cousins, their father. Grandad had built these wooden carriers with handles, each one holding a grid of pink strawberry boxes. We loaded them into the car and drove to Hanatorp camping, carrying them between us as we walked the site, asking people if they wanted to buy strawberries.

Simple product. Fair price. A market that wanted exactly what we were selling. A customer could imagine enjoying fresh strawberries in about thirty seconds.

Imagining how an investment in your product will lead to more sales or lower costs twelve months from now is something else entirely.

I started selling strategy and design services in the mid-90s. The first ten years were the hardest. The market wasn't ready and the product wasn't really a product, more an argument. Every meeting felt a bit like standing in front of someone you'd worked up the courage to ask out, holding your heart in your hand, waiting to hear whether you were enough.

I understand, completely, why many founders want out of that role as fast as possible.

I've watched it happen up close, more than once, in companies I've been close to over the years. A founder, tired of the nos, or starting to lose confidence, brings in someone to take over. And almost always, within six to twelve months, the results disappoint. The offer just wasn't ready to be sold by someone who didn't build it. In fact, the nos you're trying to escape are the only way to find out whether what you're selling is actually ready to be scaled up.

Every no is a data point. Every "we'll think about it" is a signal. Every meeting where you can almost see the customer getting it, but not quite, tells you something about where your offer is unclear, too expensive, too early, or aimed at the wrong person.

When the same type of customer keeps saying yes for the same reason, that's when you bring in more people. Not before.

The paradox is that the founders most eager to make that hire are often the ones who can least afford to. The discomfort of repeated rejection is real. It's much more comfortable to sit with the team and sketch out the next feature than to go back out there and get another no.

I get that. I've felt it. But unless you're selling strawberries, the discomfort is the job. You are exactly where you need to be.

Get used to it.