Stop Guessing And Start Asking

We don't misunderstand our customers because we lack intuition. We misunderstand because we don't ask. You might feel like you know your audience well enough to understand how they think, what they want, and how they make decisions. You don't. Did you know that people in relationships who assumed they already understood someone were no more accurate than strangers at decoding ambiguous statements? The relationship didn't increase accuracy, but it increased confidence. Let's allow that to percolate for a moment.

The people who thought they knew best were as wrong as everyone else, and were just more certain about being wrong. I wonder how many campaigns you launched with complete confidence in your buyer personas, only to watch them fall flat. I'm guilty of that and have learned that asking works better than guessing.

It's obvious once you hear it, and yet, how many times have you assumed what your customer wants instead of asking them, guessed at messaging that would resonate instead of testing it with real people, built a feature roadmap based on internal assumptions instead of customer conversations, and created buyer personas from demographic data instead of actual dialogue?

Instead of assuming, we could just ask them.

We know we should ask. So why don't we? Likely because it is easy to get data that tells you what people do, and the far more time-consuming practice of asking tells you why they do it (they might very well lie to you, but let's err on the side of truthfulness).

For example, Basecamp famously asks customers during cancellation: "What's the one thing that would have kept you?" Not ten things, no NPS bullshit, just one thing. They've shaped their entire product roadmap from these conversations. This isn't a fluke. It's a natural result of replacing assumptions with questions.

Here are three questions that you can use if you want or not.

1. "What's the most valuable thing we do for you?" Not what you think is valuable. What they think is valuable. Ask this during onboarding calls, quarterly check-ins, and post-purchase follow-ups.

2. "Where are the friction points right now?" Don't ask "Are you happy?" Happy doesn't buy or stay. Ask about friction because friction is specific and points to real problems you can solve. This is where your next campaign idea lives. Ask this during support interactions, cancellation flows, and after any failed conversion event.

3. "How would you explain what we do to a friend?"
This is pure gold, Jerry. Customers will tell you, in their own words, what problem you solve and why it matters. Use their language, metaphors, and pain points, not yours. This is basically getting your messaging handed to you.
Ask this during case study interviews, testimonial requests, and user research sessions.

Stop guessing. Start asking.