The assessment framework

22 dimensions.
One honest score.

Built from knowledge contributed by senior sales leaders with decades of experience in complex enterprise pursuits. Every dimension tests something that genuinely predicts whether you win — not a generic methodology checkbox.

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6
assessment groups
22
winnability dimensions
3
deal stages adapt questions
The 6 groups

Every group tests a
different failure mode.

The 6 groups were designed by senior sales leaders who’ve seen deals die in each of these ways. Weak groups point to specific, actionable problems — not vague aggregate scores.

A
Opportunity Fundamentals
Is this a real, fundable, time-bound opportunity worth pursuing? Group A exposes deals that look like opportunities but aren’t — bad budgets, unclear timelines, or no genuine pain.
Active: All stages
Dim 1
Strategic fit
“Is this opportunity genuinely aligned to our core capability and target market?”
Dim 2
Funded need
“Is there confirmed budget — or a credible path to budget — attached to this initiative?”
Dim 3
Compelling event
“Is there a specific business event creating urgency to act now rather than defer?”
Dim 4
Pursuit worthiness
“Does the expected return justify the cost of pursuit at this stage?”
B
Stakeholder Landscape
Do we understand and have access to the people who will decide? Group B exposes the most common deal failure mode — strong relationships with the wrong people.
Active: Qualification onward
Dim 5
Economic buyer access
“Do we have a direct, substantive relationship with the person who will sign off the spend?”
Dim 6
Champion quality
“Do we have an internal advocate who has both influence and genuine motivation to see us win?”
Dim 7
Stakeholder mapping completeness
“Have we identified all roles in the decision — including those who can block?”
Dim 8
Buying group alignment
“Are the key stakeholders aligned on the need, direction, and timeline — or are there fault lines?”
Dim 9
Political landscape
“Do we understand the internal dynamics, agendas, and loyalties that will influence the decision?”
C
Buying Process Control
Do we understand and influence how the decision will actually be made? Group C catches deals where sellers win hearts but lose the procurement gauntlet.
Active: Mid-stage onward
Dim 10
Evaluation criteria visibility
“Do we know the formal and informal criteria the buyer is using to evaluate options?”
Dim 11
Process control
“Are we influencing the evaluation process, or just responding to it?”
Dim 12
Competition awareness
“Do we know who we are truly competing against — including the do-nothing option?”
Dim 13
Decision timeline control
“Do we understand the real decision timeline and are we managing to it?”
D
Competitive & Strategic Positioning
Are we set up to win against the alternatives — including do-nothing? Dimensions 14–16 test whether our differentiation is real or assumed.
Active: Qualification onward · 3 dimensions
E
Solution & Commercial Structure
Have we shaped a solution and commercial offer the buyer will choose? Dimensions 17–19 test whether the solution is buyer-shaped or seller-shaped.
Active: Proposal stage · 3 dimensions
F
Pursuit Execution & Visible Commitment
How well are we running this pursuit — and what does the buyer see? Dimensions 20–22 catch strong strategy executed poorly.
Active: All stages · 3 dimensions
How scoring works

Scores that tell you what to do,
not just where you stand

Each dimension is scored 0–100 based on your answers. Scores aggregate to group scores and an overall winnability score. The framework uses weighted scoring contributed by senior practitioners — not all dimensions carry equal weight at every stage.

Every score below 60 triggers AI coaching — drawing on knowledge contributed by senior sales leaders who’ve dealt with that specific weakness. Every score below 40 flags as a critical deal risk requiring immediate attention.

75–100
Strong
Well-positioned. Maintain and monitor.
50–74
Developing
Real gaps. Coaching triggered. Action needed.
0–49
Critical
Deal at risk. Priority coaching. Address immediately.
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