What good looks like was never written down

A 10-minute test for your enablement program, and the two pages that fix it

Your new AE is in week 3. Sit in on one of their calls and you’ll hear the playbook from their last company, run start to finish, on your deal, with your buyer.

It happens for a boring reason. That playbook is the only one they have in writing.

Your onboarding covered the product, the systems, the territory, the comp plan, the security training and the org chart. What it did not cover is what a good discovery call sounds like at your company, on your deals, with your buyers.

That knowledge exists. It lives in the heads of your three best reps. And none of them have six hours to write it down, because they’re your three best reps and they’re busy closing.

There’s a second problem underneath that one. When you do get an hour with a top performer, they describe outcomes rather than moves. Ask how they run discovery and you get “I just make sure I really understand their business.” Great. Useless. The move they actually made was a second-order question about a number the buyer had already mentioned, and they don’t know they did it, because for them it’s reflex. Getting that out of somebody takes a specific question, asked about a specific deal.

The Airspeed team puts the underlying problem plainly in their own material: ramp takes months because the knowledge is in people’s heads. That’s the whole thing. And it makes this a documentation problem before it’s a training problem, which is a slightly awkward sentence for me to write given what we sell.

Where your selling knowledge actually lives

Four stages. The test in the next section tells you which one you’re in, and it usually comes back one stage lower than expected.

Stage 1. In your top reps’ heads. Knowledge moves by shadowing and proximity. Ramp time depends on whether the new rep happens to sit near the right person, which in a distributed team means whether they happen to get invited to the right calls.

Stage 2. In a deck somebody built in 2023. Accurate about the product. Silent about the deals. Forty slides, read once, never opened again.

Stage 3. In a searchable record. Calls recorded, notes logged, closed-won tagged. The answer is in there, and a motivated rep can find it if they already know which question to ask.

Stage 4. On the deal in front of the rep. The relevant prior win shows up without anybody going to look for it. This is where Airspeed’s coaching agent sits, and it’s the right end state whether you get there with software or with a very disciplined frontline manager.

What makes stage four different

The first three stages are storage. Stage four is a loop.

Storage means the knowledge sits somewhere and waits for somebody to come and get it. A loop means every call, every closed-won deal, every objection that got handled well feeds back in, so the next rep working the next deal starts from a slightly better answer than the last one had.

The Airspeed team describes the end state as the system learning what works and applying it to the next deal, which is the right description, with an implication people skip past. A loop only compounds if the inputs keep arriving. A system that learns from your deals is exactly as good as what your team puts into it, which is why most of this post is about a 10-minute ritual instead of a purchase order.

Every company already runs a version of this loop. At a lot of them it runs through one long-tenured manager who remembers everything, and it stops working the week that person takes another job.

The 10-minute test

Ask a rep to find out how your team handled a specific objection last quarter. Pick a real one. Time them.

Under 10 minutes, you’re at stage three. Over 10 minutes, you’re at stage two, whatever the stack cost.

It’s one Slack message, and it will tell you more about your enablement program than every completion rate in your LMS.

Page one: what good looks like

One page per stage of your sales process. Five fields, and the fields matter more than the format.

The three questions our best reps ask here that others skip. Not the standard discovery list. The three your top performers ask and your middle performers don’t. Getting them takes one conversation with each of your best three reps, 20 minutes each, and you should run those conversations yourself.

What a real answer sounds like, quoted verbatim off a call. This is the field people skip and it’s the one that does the work, because a paraphrase teaches almost nothing. Transcribe the words the buyer actually used. That teaches a new rep what a real answer sounds like and, more usefully, what a polite dodge sounds like when it’s coming at them live.

The disqualifier we keep ignoring. Every process has one. Write it down and your reps will start using it, which will shrink your pipeline number and improve your win rate at the same time. Get ready for that conversation before you have it.

The proof we use here, and the one we’ve worn out. Reps repeat whichever case study they heard most recently. Name the one that lands at this stage and name the one that’s gotten tired, because somebody is still opening with it.

How we know this stage is done, written as evidence. “The buyer is engaged” is a feeling. “The buyer sent us their security questionnaire” is evidence. Only the second kind belongs in this field.

Page two: the win capture

Getting those pages filled is the actual problem, and most attempts die the same way. A six-hour offsite to document the sales process is not going to happen. If it does, the document will be beautiful, and wrong within a quarter.

So capture it as it happens instead. This is the loop from a few sections up, run by hand: five questions, asked by the AE within 48 hours of a closed-won deal, 10 minutes, logged in one place.

1. Who signed, and who actually decided. Those are different people far more often than your CRM suggests.
2. What they were doing instead of buying, and what changed. The status quo is the competitor you lose to most and the one that never gets logged. This question is the only place you find out what beat it.
3. The objection that almost stopped it, and the words that got past it. Verbatim again. This field is where your objection handling doc comes from, and it will be better than anything a vendor sells you, because it happened at your company to your buyer.
4. What we would have lost on if the buyer had pushed once more. The hardest question on the list. It’s also the one that predicts your next loss.
5. The one thing we’d tell a rep starting this deal over. Ask it last, while they’re still in the deal emotionally.

The loss version is the same five questions, run by the manager rather than the rep. Reps don’t write honest loss notes about themselves and it’s unfair to ask them to. Run it about 10 days out, once the story has stopped being about who let them down.

One thing on ownership, because this is where these efforts stall. Enablement should write the page, and a named rep should sign off on it. Written by enablement alone, reps read it and privately decide it’s not how the job really works. Handed entirely to a rep, it never gets written, and that’s a fair trade on their part. The signature is what makes the page survive contact with the floor.

I’ll point out what’s slightly ridiculous about me writing any of this. I hand every new hire at Sales Assembly a 4-page document called “A Teammate’s Guide to Working with Matt.” How I communicate, how I make decisions, what drains me, how to get a fast answer out of me. Four pages. On me. (Like most good ideas around here, I stole the format from someone I worked with years ago.)

So I have thoroughly documented myself. Worth asking how many companies have done the same for the thing they actually sell.

What to measure

Three numbers, and none of them are course completions.

• Time to answer. The 10-minute test, run once a quarter with a different rep and a different objection each time.
• Capture rate. The percentage of closed-won deals with a capture logged. Under 50% and the ritual didn’t take, so go find out which manager isn’t asking for it.
• The week-3 check. Sit in on one call per new hire in their third week and count how many of your plays show up. This is the number that tells you whether any of the rest of it worked.

That third one is the only measure of enablement I’ve ever fully trusted, and the one that never makes a board deck, because it takes 30 minutes and produces a number you can’t round up.

Where to start