The Unexpected Question

Pitch Side Stories

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Martin Tanner, 10th September 2025

Who's been here? Juggling a hot coffee and a Cornish pasty the temperature of molten lava on the train home. And, of course, you're replaying the moment. You should've seen it coming. You should've had the slide.

Up to that point, it had all been ticking along nicely. The deck had landed. The team was in rhythm. You were halfway through the story.

Then it came. A question. Not combative. Not irrelevant. Just… not what you expected.

  • "How does this scale across regions?"
  • "What happens if we don't have that data?"
  • "How does that align with existing projects?"

And just like that, the meeting took a turn. It wasn't a derailment. It was a reveal. You realised what they were actually thinking. And now you were pitching a different story.

We've all had one. The curveball that changed the pitch. It was the moment the script faded, the deck became background, and the real conversation began.

So here's one for the pitch teams: What's the most unexpected question that changed your pitch on the spot?

I would be delighted to hear your stories… especially the ones where you wished you could conjure a slide from your back pocket - just to make the room nod and the story land.

Enjoy this article? Why not try:

The Slide of Regret

First Day Back

The Cab Ride

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