where would you rather fail?

When I joined CrossChx a year ago, I joined in a business development role. I expected to learn a lot about sales and customer development, and I was right.

My team hit the streets cold-calling to push a product that was still under active development. Every day, we rapidly iterated on our messaging based upon how our customers reacted.

We would exchange best practices for what was working to get past the gatekeeper, what was our best way of phrasing our ask, and how we could succinctly describe the product before we were shooed away.

Our VP of Sales got us into a habit of role playing at 7:30am every morning before we left the office. It was as awkward as it sounds – pitching a product to your coworker who knew the product very well, but was instead pretending to be a middle-aged woman.

“Fail with your friends so you can win with your customers,” the VP would say.

And he was completely right. Every interaction we had with a customer was a valuable first impression. If we botched it, that lead was sunk before it ever got started.

By role playing, we shook out early jitters and got into a rhythm without sacrificing any potential leads. Not only that, but we honed our message to get into the correct rhythm.

Fast forward to today, and this advice is still just as relevant.

For the last few weeks, I’ve been helping my friend David to launch a podcast. We’ve learned the process together and it’s been a constant feedback loop on every aspect: the format, the topics, the structure, the artwork, the intro music, and more.

This weekend, David sent me a text message about the value of that feedback.

Just five minutes after talking about feedback did David ask for more feedback.I wrote a few days ago about the danger of personal blind spots and the value of friends who help you to locate yours. It’s equally valuable to get feedback on your work.

This week, I’ve been asking for constant feedback on ideas, assumptions, and assets I’ve created for Unreal Collective. I am my own biggest critic, and it’s hard to ask for that feedback. If something satisfies me, but then someone else calls my baby ugly, it’s a hard pill to swallow.

But the reality is, you get very close to the work and it’s easy to miss something. Would you rather fail in front of a friend and someone you trust, or the person you truly want to impress or sell to?


Hey, can I have your email address? I will only send you more articles like this one.