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The five things your buyers ask that your reps cannot answer, and how to drill them until they can.
JOSH DEMPSEY
STAGEONEGTM.COM
FOR
Sales leaders whose team loses on the technical call
PAIRS WITH
The Ramp Plan
TIME TO RUN
One week to harvest, fifteen minutes a week after
01
The question was never a request for information.
A rep is on a call with a serious buyer. Rapport is real. Then the buyer asks something specific, and the rep says: great question, let me get you an answer on that.
Twenty years ago that was a good response. It bought a follow-up, which bought another meeting, which was the point. The rep was the door, and information lived behind it.
Now that same buyer typed the question into a language model before the call and got a confident answer in nine seconds. They did not ask because they needed the information. They asked to find out whether your rep knew it. And your rep just told them.
The charm did not stop working. The toll booth got removed.
02
WHAT CHANGED
Not your reps. The information asymmetry they were being paid to hold.
02
Do not announce it as an assessment. Just do it in a team meeting.
Pick your five hardest real customer questions. Not objections. Questions, of the kind that come from someone who has done their homework and is probing the edges. Ask each rep to answer on the spot, no notes, no deck.
| SCORE | WHAT IT SOUNDS LIKE | WHAT IT MEANS |
|---|---|---|
| PASS | A buyer could act on it. Specific, includes the caveat, reasons from mechanism. | Fluent. Can handle a question nobody anticipated. |
| PARTIAL | Correct but generic. Restates the feature, pivots to a benefit. | Memorised. Holds until the question is unexpected. |
| FAIL | Offers to follow up. Loops in an engineer. Changes the subject. | Not fluent, and the buyer now knows it. |
BENCHMARK
In most organizations I have audited, between one and three reps in ten pass. That gap is not motivation. Those reps work hard. Nobody built the system that would make them fluent.
03
SCORE ON ONE THING
Could a competent buyer act on this answer, or would they go look it up themselves?
03
Five is the number because a team can hold five and will ignore fifteen.
WHERE THEY
ALREADY ARE
Call recordings. Search for “let me get back to you” and its variants. Every hit is a candidate.
Closed-lost notes. The question that preceded a deal going quiet is usually the one nobody could answer.
Your solutions engineer. Ask what they get pulled into most. That is the fluency gap, expressed as a calendar.
Support tickets from new customers. Anything asked in the first thirty days should have been answerable during the sale.
The competitor question. There is always one comparison your reps handle badly.
Rank by frequency times damage and take the top five.
WHAT SEPARATES A FLUENT ANSWER
Mechanism, not outcome
Why the product produces the result, so a rep can reason forward when a buyer describes something nobody anticipated.
The edge
Where it does not work and who should not buy. The strongest trust signal available, and nearly impossible to fake.
Teachable
The rep leaves the buyer smarter about their own business whether or not a deal happens.
04
THE TELL
If your solutions engineer is in every late-stage call, that is not coverage. That is the gap on a calendar.
WHY RANDOM SELECTION
Ask for a volunteer and you will hear from the rep who is already fluent. The point is to find out about everyone else.
05
04
Harvest this week. Drill next week. Do not wait until the answers are perfect.
| THE QUESTION | THE ANSWER, INCLUDING THE EDGE | |
|---|---|---|
| Q1 | ||
| Q2 | ||
| Q3 | ||
| Q4 | ||
| Q5 |
06
ONE RULE
If the answer does not contain a caveat or a limitation, it is not finished yet.
05
WHAT TO
DO NOW
01
Harvest five questions from the sources on page four. Do not invent them. Whatever your reps already dodge is the list.
02
Run the test in a team meeting without calling it a test. Score pass, partial or fail. Whatever number passes tells you more than any dashboard you have.
03
Write the answers with the edge included, then drill one question every week until every rep can give it without thinking.
04
One question. That is the whole first month. It sounds small, and it is the difference between a second meeting and a polite no.
NO. 04
OF 06
If you run this yourself and your reps start answering the hard question in the room, that was the point. Nothing here is held back for a paid version.
JOSH DEMPSEY · STAGEONEGTM.COM · JOSH@STAGEONEGTM.COM