Ask these in passing at a first meeting and the answers usually settle which side he's on:
1. "When did you last replace a tool you were using?" — an organisation that hasn't changed anything in three years is almost certainly not an early adopter, so stop pitching like it is.
2. "If this moves forward, who signs it off?" — early adopters can often decide alone; a mainstream buyer recites a list of names. The longer the list, the more he needs evidence that others have done this, not evidence that it's advanced.
3. "Who in your industry is doing something similar?" — if he names people instantly, he's carrying a mental list of peers. If your references aren't on that list, you effectively have none.
A reverse warning: don't file the mainstream buyer under "conservative, doesn't get it." Predictability is as rational a thing to buy as novelty. If he seems slow, it's usually that you don't hold the kind of evidence he buys on.
Mechanism: people decide whether information deserves belief by asking how much like them the source is — not by weighing the information itself. So a reference's power doesn't depend on how impressive the referee is, it depends on whether the listener will file himself and the referee in the same category. No category match, and even a beautiful case study is just somebody else's story.
Boundary: these categories apply to a category of product, not to a person's personality. The same individual can be an eager early adopter of tools and deeply conservative about anything touching money or compliance. Don't label the customer; work out which side he's on for this particular thing.
He asks "is this going to work?" Don't answer "don't worry." Answer:
"Let me name three things that could go wrong. One, we've never connected to your {legacy system}; worst case that adds two or three weeks, and I won't charge for that stretch. Two, in the first month your {role} will find it more annoying than what they do now — that's real; it pays back from about week three. Three, if {some precondition} doesn't hold, you shouldn't do this at all, and I'll tell you so directly."
Why that beats any guarantee: someone willing to say where it breaks has weight when he says a thing won't break. And you've turned three unknowables into three budgetable costs — he can now repeat that paragraph to his own boss.
Pair it with an exit: "Run it in one department for three months; if it isn't working, stop and we hand back all your data." Reversibility is the cheapest ambiguity-reducer there is. He'll almost certainly never use the clause, but without it he won't start.
Mechanism: risk with known odds and uncertainty with unknown odds don't run on the same circuitry, and they don't yield to the same sentence. Saying "don't worry" only repackages the ambiguity; a number, a person he can phone, and an exit clause actually convert it into risk he can price.
Boundary and red line: this only works when he genuinely faces uncertainty. If his hesitation is really "I don't want to change," reducing ambiguity does nothing — go back to pricing the cost of not changing, where the quantification method from the digging-for-pain piece beats any reassurance. The red line: the ugly parts have to be genuinely ugly. Inventing two harmless flaws to buy trust is a performance, and it survives exactly one detection.
Mechanism: word of mouth only travels between people who are both similar and actually in contact. Concentrating on one niche artificially raises the density of that conduction network — you spend the same effort, but every deal now paves the way for the next instead of ending where it landed.
Boundary: too narrow really can strand you — the test is whether you can name the two adjacent squares. And the whole approach assumes word of mouth genuinely matters in your category. Where buyers don't talk to each other and decide independently (much low-price impulse consumer buying), concentration pays far less, and choosing an audience by channel efficiency makes more sense than choosing one by network.
Write out every step between signature and "he actually has the result," one square per step. Not your features — the things he has to do.
Fill three things into each square: who does it · how long · who's on the hook if it goes wrong. The squares you can't fill are where your chasm currently is.
The right answer is not "all of them, by us": you fill the ones that standardise and get reused (migration scripts, a go-live checklist); a partner fills the ones needing credentials, bodies or localisation; he fills some himself — but only if it's confirmed to his face, written into the plan and assigned to a named person, because "he'll handle it" and "nobody's handling it" look identical in meeting notes. The difference is whether there's a name.
One counter-intuitive trade: every square you fill counts for this niche only. So don't generalise it to widen your addressable market — a generic whole product can never be finished. Narrow is what makes it finishable; finishing it is what lets you roll into the next square.
Mechanism: the comparison in a buyer's head is never "you vs the competitor," it's "change vs don't." And the total cost of changing includes every gap — any square he has to figure out himself gets priced at worst case, because he doesn't know what might happen there. Writing a name in it compresses an unknown into a specific number.
Labelled honestly: the framework layer here — whole product, ownership tables — is an experience system, not a tested theory. I've seen no clean controlled study quantifying how much filling gaps lifts conversion. What is empirically supported is the mechanisms underneath (ambiguity aversion, status quo bias, self-selection). Use it as a checklist, not a law, and after filling the table watch whether your own win rate moves.
Two hours on whichever line is most stuck right now — whether you sell a product, a service, or yourself.