The Danger of Falling in Love With Your Own Pitch

The Sales Code - #18

There’s a curious thing I’ve noticed over the years—whether I was leading a micro-mobility revolution across Europe, courting investment funds in the Gulf, or huddled in a tiny office in Milan, trying to figure out if our marketing budget could stretch another month.

Most salespeople, founders, and even seasoned executives eventually fall into the same trap: they fall in love with their own pitch.

They become so enchanted by the elegance of their own narrative that they stop noticing when the prospect is silently edging toward the exit.

I’ve seen this happen firsthand.

I remember being in New York, during my time as CMO of Helbiz. We were negotiating a strategic partnership with a massive North American transportation player—let’s call them Company Z. My team and I had prepped a deck so beautiful it would make a designer weep. We’d rehearsed every line. We were ready.

Thirty minutes into the meeting, something felt off. Their CEO’s body language shifted: arms folded, eyes darting to the door. But instead of stopping to ask a question or check in, I plowed ahead—after all, I was sure our value proposition was self-evident.

By the end of the hour, their team thanked us politely and disappeared.

We never heard back.

That day taught me a lesson that’s stayed with me through IPO bell-ringing, venture scouting, and all the boardrooms in between:

Persuasion is never about how perfectly you present your story. It’s about how well you draw out theirs.

Too many salespeople focus on being convinced instead of being convincing. They think a polished narrative guarantees commitment. But human behavior rarely works that way.

People need to feel heard before they feel sold.

Here’s the antidote to falling in love with your own pitch:

1. Interrupt Yourself.
   When you sense the mood shift, stop. Check in. Say:
   “I’m talking a lot. What’s on your mind?”
   The pause might feel awkward. Do it anyway.

2. Use the “Reduction to the Ridiculous.”
   If price objections come up, break big numbers into small ones.
   In my Helbiz days, I once reframed a six-figure sponsorship as “the equivalent of €120 per day to be in front of millions of riders.”
   Suddenly, the CFO saw it differently.

3. Ask Questions That Lead, Not Push.
   Instead of “Do you agree?” try:
   “How would this look in your organization?”
   or
   “If you could wave a magic wand, what would you change about this?”
   Questions transform a pitch into a collaboration.

4. Be Hard of Hearing to No—but Not to Concerns.
   Some of the best deals I’ve closed started with a polite “We’re not interested.”
   It often meant, “We don’t see how this fits yet.”
   Your job is to help them see it without bulldozing their reservations.

5. Stay Stoic.
   You’ll be rejected. You’ll get ghosted. You’ll have prospects who nod and never call back.
   Smile. Refine your approach. And remember: your worth isn’t tied to their signature on the dotted line.

If you take anything from today’s letter, let it be this:

Don’t let your love for your own pitch blind you to the conversation that actually matters.

Because in the end, closing isn’t an act of performance—it’s an act of understanding.

Stay sharp, stay curious, and keep selling with integrity.

— Ruggero

P.S. If this resonated, hit reply and tell me where you’ve seen this in your own deals. I read every note.