PLAN Selling
The central methodology for navigating complex B2B buying. Everything else here is built around it.
WHEN IT RUNS · FROM THE FIRST QUALIFIED CONVERSATION TO THE SIGNATURE, AND AGAIN AT EVERY DEAL REVIEW.
I spent my first fifteen years building teams and leading people. Not just building the engine, but making sure it produced the results. And there is only one way that happens across a whole team: consistency in how you measure what good looks like.
The measuring sticks on offer never sat right. The sales-centric models grade what the seller extracted: did I identify the economic buyer, did I get my champion, did I complete my criteria. A rep can fill every box and still lose, because none of it asks whether the buyer has a problem worth solving. So PLAN got built the other way around. Every letter is a question about the buyer's reality: their problem, their priorities, their committee, their timeline. When the answers are yes, the deal closes itself politely. When they are no, you know today, not at the forecast call.
PLAN is also where the craft becomes a number. Every deal review answers the PLAN questions; answer them all or you have a lead, not a deal. The Deal Confidence Score grades deal health against PLAN, which is how the forecast stopped being a guess. Installed and inspected weekly, this system sat behind a forecast that went from 65 to 94 percent accurate and a win rate that doubled.
Every letter is a question about the buyer.
The one most pressing challenge, found with the 3 Whys: the stated problem, the business impact underneath it, and the personal or strategic priority underneath that. Most deals die because the seller stopped at the first why.
Confirm the problem is urgent and fits what the buyer is already prioritizing. A real problem that is not a current priority is a next-year deal wearing a this-quarter forecast.
Map the stakeholders, the criteria, the blockers, the process, and the timeline. The modern buying committee is six to ten people; a deal with one contact is a conversation, not a deal.
Specific, mutual, timely, valuable, achievable commitments. Every interaction ends with one. Momentum is not a feeling, it is a calendar entry both sides agreed to.
How it runs well, and how it dies.
Problem-centric before product-centric, stakeholder mapping before stakeholder hoping, business impact before feature interest, and a clear mutual commitment before anyone leaves the room.
Treating it as a checklist to fill instead of a read of where the buyer actually is. The letters are questions about the buyer's reality, not boxes about the seller's activity.
Not a definition. A standard.
Good is measurable. After every interaction, the deal gets scored one to five on each letter, against anchors everyone shares. The score is not paperwork; it is the difference between a forecast and a feeling.
“They need better pipeline visibility.”
“Their forecast is off by 40 percent each quarter and the CEO is losing confidence in the sales org. The buyer said it, and could repeat it back.”
“They said it is important.”
“It is their number two initiative this quarter; the CEO named it in the all-hands. The test: if pushing this to next quarter would be easy, it was never a priority.”
“I will follow up next week.”
“Thursday at 2pm, thirty minutes with their CFO, agenda agreed, to review the ROI model built on their numbers.”
| DIMENSION | 1 | 3 | 5 |
|---|---|---|---|
| Pinpoint | No specific problem identified yet. | We know the surface-level pain. | Root cause uncovered with the 3 Whys, and the buyer has articulated it back to us. |
| Line up | This is a nice to have. | They say it is important but have shown no proof. | Budget allocated, someone's bonus tied to solving it, and they can name what they deprioritized to make room. |
| Advance | Talking to one person. | We know who else is involved but have not engaged them. | Three or more stakeholders engaged, blockers identified, and the champion equipped to sell it internally. |
| Next steps | No specific next step scheduled. | A vague follow up next week. | Confirmed meeting with named attendees and an agenda tied to moving the deal forward. |
16 to 20 is a real deal with real momentum. 11 to 15 needs work, starting with the lowest score. 6 to 10 is not a real deal yet. Below 6: stop pretending it belongs in the pipeline.
In the deal review, five questions in thirty minutes: the problem, the company priority, the value date, the decision process, the next steps. All five answered confidently is a commit. Four is best case. Three or fewer is pipeline. And the score tells you where to coach: low P goes back to discovery, low L challenges the priority or walks away, low A starts multi-threading, low N forces the commitment or disqualifies.
Not theory. Receipts.
The framework is yours. The scorecard and the AI skill that runs it come with the subscribe.
One story a week on putting AI to work in sales, the right way. Plus the runnable playbook and skill behind PLAN Selling.