Mistake #17: I accepted vague answers and moved on.
Every discovery call with a retailer started the same way.
"What's going on with shipping?"
"Customers complain, support is drowning, we need something better."
I agreed with the "that sucks indeed" nod and moved on to the demo.
I never found out what was happening, what it cost, or what it meant for his business as well as for him as a person.
Here's what I missed:
Pain motivates purchases better than pressure. And a vague answer has no pain in it.
"Support is drowning" sounded like a problem.
It was a feeling, and you can't put a feeling in a proposal.
Every answer was vague, incomplete, or confusing, and never with a number in it.
What I needed was their current reality.
Not the tool he asked for, not the problem he named.
What was actually happening, and why he needed it fixed now.
Solution: I started asking deeper questions!
After every call, I wrote out their current reality in 5 lines.
Example:
Prospect: "Too much of this is manual."
Me, before: "Got it, manual work. Let me show you how we automate that." (demo, then silence)
Me, after: "What's happening right now that makes it feel urgent?"
Prospect: "The team is drowning, and customers are waiting on us."
Me: "Tell me what actually happens. What does your team do?"
Prospect: "A customer asks for a status update. Someone opens 3 systems, copies the status into an email, and replies. About 20 minutes each."
Me: "Who else gets interrupted when this happens, and how often?"
Prospect: "My ops manager, when the customer is already angry. About 127 times a week."
Before, I had "manual" and a demo.
After, I had:
The actual work: 3 systems, copy, email, 1 by 1.
127 times a week, 20 minutes each.
A manager pulled in when the customer is angry.
If they can't walk you through what actually happens, you don't know their current reality yet.
Then write out the 5 lines.
1. Experienced problems: What are they stuck with, in their words?
After each call I wrote out their problem, as they said it.
Today you can pull it from call transcripts or emails with AI.
Keep at least 15, as "I" statements:
"I'm answering the same customer question 50 times a week."
"I find out about a problem after the customer is already angry."
"I rebuild the same report by hand every Monday."
If it does not cause frustration, stress, fear, or confusion, it does not count.
If you struggle to get past 7, you don't know your customer well enough yet.
2. The workaround: How are they solving, avoiding, or absorbing it? (the logical reason)
Usually 1 of 3:
Solving it: a manual process.
Avoiding it: "we have this issue, but we just do X."
Absorbing it: "it's part of doing business at this point."
Pro tip! Not "it's a manual process." Which systems they open, what they copy, who they email.
3. Price: What does it cost in time and money?
Requests a week × minutes per request = hours.
Hours × hourly rate = money.
From the example:
127 requests × 20 minutes = 42 hours of somebody's time, every week.
42 hours × $30 an hour = $1,270 a week.
Most of them didn't know their number, so we found it together.
4. If it's not fixed: What happens next, and how does it grow?
More requests and more hours, every month.
Slower answers, more refunds, more apologies.
And it grows with the business.
5. Meaning: So what does this really mean for the business, and for him? (the emotional reason)
His customers: mad, waiting, losing trust, and writing bad reviews.
His team: exhausted, low morale, and the good ones want to quit.
Him: stuck dealing with this instead of growing the business, and if it doesn't grow, the problems get bigger.
That's what "too much of this is manual" meant.
Why it matters:
The 5 lines do 2 jobs.
On sales calls: the validation guideline for your team. This is what a real answer sounds like, keep digging until you hear it.
In marketing: the messaging. The reader sees his own week on your page, lifts his hand and says, "that's us."
A real answer has a number in it, a feeling in it, what they already tried, and what happens if nothing changes.
Specific pain closes itself.
Vague pain asks for a discount.
Secret Sauce: Sell to specific problems.
Pain motivates purchases better than pressure, and it hides in the details.
Best,
Virgil
PS: Mistake #18: He had already tried to fix it. I never asked why it didn't work.