Mistake #18: He had already tried to fix it. I never asked why it didn't work.
If your demo gets compared on price, you skipped a step in discovery: the autopsy.
Every buyer has already tried to fix the problem. The fix failed. If you don't know why, you demo the same fix with a nicer screen.
Every retailer who asked me for tracking already had a tracking email. I demoed a nicer tracking email. He compared the two on price.
Here's what I missed:
A roadblock is not what he lacks. It's why what he already tried didn't work.
Prospects give you roadblocks as nouns:
"Tracking."
"Reporting."
"Onboarding."
"Customer experience."
A noun is what he already has. You can't sell against a noun.
If the roadblock sounds like a noun, it's too vague. Make it a mechanism.
Solution: The autopsy. 2 questions, every time.
"What have you tried?"
"Why hasn't that fixed it?"
Then write the roadblock in 1 line, as a mechanism.
Example:
Prospect: "Our reporting is a mess."
Me, before: "Got it, reporting. Let me show you our dashboards." (demo, then silence)
Me, after: "What have you tried?"
Prospect: "We built a dashboard in Google Sheets. Someone updates it every Monday."
Me: "Why hasn't that fixed it?"
Prospect: "By Tuesday it's out of date. Nobody trusts the numbers, so they ask me in Slack instead."
Before, I heard "reporting" and demoed a dashboard he already had.
After, I had:
The fix: a Sheets dashboard, updated by hand.
Why it failed: stale by Tuesday, so nobody trusts it.
The cost: every number question lands on the founder.
The feeling: he is the reporting system, and he's tired of it.
Now the roadblock, as a mechanism:
"Reporting is updated by hand, so the numbers get outdated fast and nobody trusts them. And if the person responsible is missing, nobody can update the numbers at all."
Why it matters:
The roadblock is the old way. Your solution is the new way.
Old way: numbers updated by hand, outdated by Tuesday, nobody trusts them, and it all depends on 1 person. He hates it. He just doesn't know a better way yet.
New way: the opposite. Numbers that update themselves, so they are never outdated, everybody trusts them, and nobody has to be in the office for it. With proof that it works.
Kill the old way. Install the new one.
What you're looking for:
The failed fix: what they tried, in their words.
The mechanism: the exact point where it breaks.
The consequence: hours, money, trust, dependencies.
The person: who carries it, and how it feels.
Secret Sauce: Do the autopsy before the demo.
The roadblock is the old way. Sell the new way, with proof.
Best,
Virgil
PS: Mistake #19: I sold relief. He was buying the whole climb.