↗ For Sales Pros July 17, 2025

What every won deal had (that the lost ones didn't).

An exercise for any IC: pull your last twelve closed deals: six won, six lost. The patterns that emerge are usually the ones you weren't tracking.

BY RYAN MATHEWS UPDATED · AUG 2026 6 MIN READ FILED · FOR SALES PROS
The short answer

Pull your last twelve closed deals, six won and six lost, and for each write down three things: the first meaningful conversation, the middle moment where it turned toward close or stall, and the closing condition, or what was not true for the losses. An hour of work surfaces three kinds of pattern: behavioral (a discovery, multi-threading, or objection move the won deals share and the lost ones miss), contextual (a buyer condition like an org change, budget-cycle alignment, or a sponsor with skin in the game), and timing (won deals keep the sequence of discovery before demo, multi-threading before procurement, executive engagement before contract). The reps whose trajectory compounds keep running this quarterly.

This is a short article because the exercise is short. Run it before reading anything else this quarter.

The exercise.

Pull your last twelve closed deals. Six won, six lost. (If you don't have twelve yet, do it with what you have.) For each deal, write down three things:

  1. The first meaningful conversation. Who was on the call, what did they tell you, what did you ask.
  2. The middle moment. The specific point where the deal either turned toward close or turned toward stall. There is almost always one.
  3. The closing condition. What specifically had to be true for the deal to land (or, for the lost deals, what wasn't true).

An hour of work. Some of it from memory. Some of it from notes you'll have to dig for. The deals where you can't remember any of these three things are themselves data: those deals closed or lost despite your process, not because of it.

What you'll find.

Three categories of pattern emerge for almost everyone who runs the exercise honestly:

Behavioral. Moves you made, or didn't make. The won deals usually share a specific discovery move, a specific multi-threading move, or a specific objection pattern. The lost deals are missing one of them.

Contextual. Conditions that were true. The won deals usually share a buyer condition: a recent organizational change, a budget-cycle alignment, an executive sponsor with skin in the game. The lost deals are missing one.

Timing. When things happened. The won deals usually share a sequence: discovery before demo, multi-threading before procurement, executive engagement before contract. The lost deals broke the sequence.

The signal is in the data. You just have to look.

Most reps run this exercise once, find three moves they didn't know they were running, and stop running it. The reps whose trajectory compounds (the ones who turn one good quarter into a career) keep running it. Quarterly, at minimum. After every cycle, ideally.

The exercise is not the point. The discipline of looking at your own deals with the same honesty you'd bring to someone else's is the point.

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Common questions

How can I find the patterns in my own deals?

Pull your last twelve closed deals, six won and six lost. For each, write the first meaningful conversation, the middle moment where it turned, and the closing condition. An hour of honest review surfaces the moves you did not know you were running.

What patterns separate won deals from lost ones?

Three kinds. Behavioral: a specific discovery, multi-threading, or objection move present in wins and missing in losses. Contextual: a buyer condition like an org change, budget alignment, or a sponsor with skin in the game. Timing: won deals keep the sequence of discovery before demo, multi-threading before procurement, executive engagement before contract.

How often should I run the won/lost review?

At least quarterly, ideally after every cycle. Most reps run it once and stop; the ones whose careers compound keep looking at their own deals with the same honesty they would bring to someone else's.