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Your Playbook Is Missing the Work

Your best rep is running a sales process that never made it into the playbook... and your managers may be coaching the wrong work.

4-minute read below. Hit reply and let me know what you are seeing on your side.

I have watched this happen inside more sales teams than I can count... one rep is sitting at three times quota, the rest of the team is somewhere around average, and the sales leader is getting pressure from the CEO and the board to explain the gap.

So they pull the top rep into the next team meeting and ask them to teach everyone what they are doing. The rep walks through discovery, demos, follow-up, multithreading, all the usual stuff; everyone nods along, and two weeks later nothing has changed because none of that explained the gap in the first place.

This week, Dale and I sat down with Jack Siney, a seven-time entrepreneur with five exits and the co-founder of FrontRace, and he put a useful frame around the problem. The difference between the top rep and the median rep is often “20 small things”... the order of the touches, the timing between them, the channel they use, the way they follow up, and the moments they decide to leave the buyer alone.

YOUR PROCESS MAP IS FICTION

When I ask a leadership team to show me its sales process, I usually get a clean slide with 20 or 30 boxes. Discovery happens here, the demo happens there, pricing comes next, procurement comes later, and every arrow makes the whole thing look far more orderly than any deal I have ever been part of.

An actual deal may have twice as many steps, sometimes three times as many, because the rep is doing work that never becomes a stage change or a required field. They send the text after the buyer's team wins, wait an extra day before following up, answer a question at night, pull another person into the thread, or change channels when the email goes quiet... and none of that shows up when the manager opens the dashboard on Monday.

That is how a leadership team ends up saying Susan is “more personable” or has a “better demo.” Those are not explanations; they are guesses, and guesses are hard to coach.

YOUR BEST REP CANNOT TEACH IT

The frustrating part is that the top rep probably is not hiding anything. They have repeated these choices so many times that the work feels obvious to them, which is why asking them to run a training session usually produces a tour of the official process instead of an explanation of what they really do.

Remote work made this harder. A new rep cannot sit beside the best seller for three days and quietly watch the small moves, and a manager looking across the CRM, call recordings, email, text, and Slack is trying to reconstruct a deal from pieces that were never meant to tell one story.

If you want to see the missing work, compare one top rep and one median rep across five similar deals, then look at:

• Every buyer touch, including calls, emails, texts, and meetings

• The order of those touches

• The time between each touch

• Any channel switch before the buyer re-engaged

• The point where more contact started hurting the deal

THE SEVENTH TEXT

On this week's podcast, Jack shared an example from a company that tracked its text activity and found that, after the seventh text, the team did not win the deal. The rep was not trying to annoy the buyer... they were doing what many of us have coached people to do for years, which is keep following up until you get an answer.

Seven is not a universal rule, and I would not take that number into your next sales meeting as if it applies to your buyers. The useful part is that a small behavior, one extra text, carried more weight than the activity total or pipeline coverage number the manager had been watching.

This is why I would look at losing patterns first. Winning can be messy, and two reps may get there in very different ways, but the moment a specific behavior keeps showing up before a deal dies, you have something concrete to question.

COACH BEHAVIOR, NOT PERSONALITY

This is where managers tend to make the next mistake... they find something the top rep does, turn it into a rule for the whole team, and assume the behavior transfers cleanly. It may not. Adam can be blunt on a call and win, while another rep can use the same words, with the same buyer, and damage the relationship because the tone and trust are different.

The job is to separate the behavior from the personality. Pick one behavior, connect it to a set of wins or losses, and test it with one other rep for two weeks while keeping that rep's voice intact. Then look at what changed, decide whether the behavior belongs in the playbook, and move to the next one... because trying to roll out 20 new rules at once is how the team ends up ignoring all 20.

ON THE AIR

Jack Siney is a seven-time entrepreneur with five exits and the co-founder of FrontRace. He joined Dale and me to talk through the small behaviors that separate top reps from the rest of the team, why managers struggle to see them, and why adding AI on top of a broken process usually gives you a faster version of the same problem.

Some key themes that came up:

• Why CRM activity and call recordings cannot explain performance gaps on their own

• The “20 small things” behind a deal: order, timing, gaps, channel, tone, and follow-through

• Why asking a top rep to train the team misses the work they do without thinking

• How losing patterns, such as one contact too many, can be easier to spot than winning patterns

• Why companies should clean up their process and source records before adding another AI tool

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