#034 | If They're Asking, You're Winning
I used to think the best pitch was one where no one had anything left to ask.
No questions = nailed it.
But over the years - and after coaching thousands of pitches - I’ve realized the exact opposite is true.
If your pitch leaves no room for curiosity, you’ve missed the point.
You’ve explained instead of inspired. You’ve informed instead of intrigued.
And the cost of doing that?
-
The story becomes a checklist.
-
The pitch keeps growing longer and longer.
-
And suddenly, there’s no time left for the part where the magic happens - Q&A.
Here’s the big mindset shift:
A question from your audience is not a problem to solve in advance. It’s a sign that your pitch worked.
If someone asks a question, it means they’re interested. They care. They want more.
That’s not something you fix.
It’s something you celebrate.
The “Stuff Everything In” Trap
I see this all the time with founders I coach.
They get a question during Q&A, and their first instinct is:
"Next time, I’ll add that to the pitch."
But what happens when you do?
- The pitch keeps getting longer.
- The story falls apart.
- The emotional thread breaks.
Just the other day, a founder told me:
"People always ask me about my second product. So, should I just put it in the pitch?"
So we tried it.
And guess what? The flow was gone. The focus disappeared. The story turned into a technical overview.
We want to stuff everything in because we’re scared.
Scared of leaving things unsaid.
Scared someone might not “get it.”
But a pitch isn’t meant to tell everything. It’s there to hook your audience.
If you try to answer every question up front, you steal the audience's chance to lean in.
Let Curiosity Work For You
Here’s what to do instead:
-
Keep the pitch focused on the emotional hook, not every technical detail. (Instead of "explaining everything up front.")
-
Anticipate likely questions and prepare sharp answers for Q&A. (Instead of "preemptively stuffing it into the pitch.")
-
Use Q&A as a second act of the pitch, where you shine with clarity and depth. (Instead of "overloading the first act.")
Your pitch opens the door.
The Q&A invites them to walk through it.
I’ve seen this approach work time and time again:
-
Founders stay within the time limit- and still feel like they said enough. (What worked)
-
Their message is clear, memorable, and human. (Why it worked)
-
Investors and judges ask exactly the questions they expected - and founders shine answering them. (Direct connection to this approach)
The real win:
Founders leave the stage with momentum, not just a finished script.
If your pitch doesn’t leave them with questions, you probably played it too safe.
The best pitches light a spark - and then let the Q&A turn it into a real conversation.
Because a pitch is about creating interest, not covering every bullet point.
Next time you pitch, don’t aim to finish with silence.
Aim to finish with energy.
Your goal isn’t to answer everything. It’s to make them want to ask for more.
That's all for today. I hope you enjoyed it.
See you next Thursday.