Last week, I committed to a little experiment – listening more, talking less. It’s been eye-opening, especially when it comes to how founders (including yours truly, back in the day) sabotage their own success with too much pitching.
- The “Always Be Closing” Trap: We get told hustle matters, that we need to be constantly selling our vision. But sometimes, the smartest move is to ask a few good questions, then sit back and let the potential customer talk themselves into needing you.
- Mistaking Interest for Intent: A prospect nodding along, saying “that’s interesting,” is NOT the same as them signing a contract. I’ve wasted far too much time chasing lukewarm leads because my ego wouldn’t accept a polite “maybe”.
- The Demo Disaster: Look, I get that you’re proud of that sleek interface. But if you jump straight into showing off features without establishing whether I even HAVE the problem your product solves, it just comes across as tone-deaf.
Case Study: The Accidental Close
One of my most successful early deals happened almost by mistake. I took a meeting as a favor to a friend, not expecting much. Instead of my usual pitch deck, I spent most of the time asking about their biggest operational headache. Turns out, I had a half-baked side project that, with minor tweaks, was the perfect solution. They were sold because I focused on THEIR needs, not pushing my own agenda.
Turning Questions into Revenue
Founders, try this counterintuitive approach, especially in early sales conversations:
- “What’s your current biggest pain point with [X]?” (Open-ended, gets them talking)
- “How are you dealing with that problem right now?” (Reveals workarounds, signals budget)
- “If you had a magic wand, what would the ideal solution look like?” (Uncovers priorities, lets them visualize the value)
Bonus Tip for Corporate Leaders: This applies to internal meetings too! Instead of jumping straight to your solution, ask your team to articulate the problem in detail. You might be surprised at the fresh ideas that emerge.
Sometimes the best sales pitch is no pitch at all. True persuasion starts with understanding what the other person actually needs.
