Every dimension has a depth. Naming it is the first rung.

Not on the ladder

“When this is working a year from now, what number does your team report differently?”

Gets the measure in their words and their reporting cadence, not yours.

Next rung · quantified

“What is that number today, roughly, what does it need to be, and where do those figures come from?”

Gets a baseline, a target and their source in one answer. An estimate is fine here, as long as you know whose it is.

Next rung · tied to value

“If you took that figure to your CFO tomorrow, what is the first thing they would push back on?”

Surfaces the weakness in the business case while there is still time to fix it.

Top rung

That’s the top rung. Check it against what the buyer actually said.

Not on the ladder

“When something this size gets approved here, whose signature is the last one on it?”

Asks for the approver by the approval rather than by title, so you do not name the evaluator by mistake.

Next rung · motivated

“What is [name] on the hook for this year — the number they get asked about?”

Gets the buyer’s personal measure, which is rarely the champion’s.

Next rung · engaged

“Would it help if I put the numbers in front of them directly, or would you rather take it?”

Tests access without asking for it — and a refusal is itself information about your champion.

Top rung

That’s the top rung. Check it against what the buyer actually said.

Not on the ladder

“When you compare options, what goes on the scorecard, and who wrote it?”

Gets the criteria and their author together — and the author is usually who you position with.

Next rung · positioned

“How would you rank us against the alternatives on that one today — honestly?”

Turns a named criterion into a positioned one, and an unflattering answer is the useful one.

Next rung · proven

“What would you need to see to be confident on it, and who has to see it with you?”

Names the proof and the audience for it, which are usually two different problems.

Top rung

That’s the top rung. Check it against what the buyer actually said.

Not on the ladder

“Walk me through what happens after you decide you want this — who sees it, and in what order?”

Gets the sequence in their words, including the steps that never appear in an RFP.

Next rung · owned

“Who carries each of those steps — a name, not a team?”

A step with no named owner is a step nobody is doing.

Next rung · dated

“Working back from when you want this live, when does each of those steps need to start?”

Turns the sequence into dates the customer set, which is what a close date can stand on.

Top rung

That’s the top rung. Check it against what the buyer actually said.

Not on the ladder

“Which reviews does a purchase like this go through here — legal, security, procurement, anything else?”

Gets the full list in one question, before any of it is urgent.

Next rung · owned

“Who runs security review here, and what do they need from us to start?”

Turns the review most likely to stall the deal into a task with an owner and a start date.

Next rung · dated

“Once the decision is made — how long did the paperwork take the last time you bought something this size?”

Gets a real duration from a real precedent, rather than an optimistic guess about this one.

Top rung

That’s the top rung. Check it against what the buyer actually said.

Not on the ladder

“What made you take this call now, rather than six months ago?”

Gets the problem in their words, with a hint of what changed.

Next rung · contextualized

“Who feels that day to day, and what do they do instead right now?”

Moves a stated problem into context by finding the workaround, which is where the cost lives.

Next rung · quantified

“How many hours a week does the workaround take, and whose hours are they?”

Builds the number from the workaround you already found, in units they can check.

Top rung

That’s the top rung. Check it against what the buyer actually said.

Not on the ladder

“Who on your side is closest to this problem, and would want a hand in fixing it?”

Finds the candidate by the problem, not by who was friendliest on the call.

Next rung · motivated

“What does a win here look like for you personally?”

Finds the motivation, or finds that there isn’t one — both are worth knowing in month two.

Next rung · influential

“If you were putting this in front of your leadership without me, what is the version that lands — and what is the bit they push back on?”

Tests whether they have rehearsed the internal case, which is the first evidence of a real champion.

Next rung · tested

“Who else needs to be comfortable with this, and would you be willing to bring them in?”

A small, safe test of whether they will actually spend standing on this deal.

Top rung

That’s the top rung. Check it against what the buyer actually said.

Not on the ladder

“What happens if you do nothing for another two quarters?”

Puts the real competitor — the status quo — on the table where it can be argued with.

Next rung · positioned

“What do you like about the way they do it?”

Gets an honest read on the rival’s strength, which a defensive question never will.

Next rung · trap set

“When you look at them next, would you ask how they handle [the step you do best]?”

Sets a trap: a question that keeps working in a meeting you are not in.

Top rung

That’s the top rung. Check it against what the buyer actually said.

Not on the ladder

“What is driving the timing on this — why this quarter rather than next?”

Finds whether a real event exists, or whether the date is your forecast wearing a disguise.

Next rung · dated

“Is there a date on that — and whose date is it?”

A date the customer holds survives; a date you proposed moves.

Next rung · consequenced

“What happens on your side if that date passes?”

Tests whether the event has a consequence, which is what separates a deadline from a wish.

Top rung

That’s the top rung. Check it against what the buyer actually said.

Not on the ladder

“What does it have to do for this to count as fixed — in jobs, not features?”

Gets the list in the customer’s language, which is the language they will score you in.

Next rung · tied to value

“Of everything on that list, which one, if we got it wrong, would make the whole thing not worth doing?”

Sorts a flat feature list into the one capability the decision actually turns on.

Next rung · evidenced

“What would you want to try yourself before you believed it?”

Names the evidence they would accept, so the proof step is designed rather than guessed.

Top rung

That’s the top rung. Check it against what the buyer actually said.