What commercial judgement still lives in one person?

The founder’s answer is less valuable than how they reached it.

Consider the question ‘Is this account a fit?’ An ICP checklist may say yes, while the founder says no because a previous buyer in the same segment had an impossible implementation timeline. That exception contains more useful learning than another checkbox.

Listen for recurring judgements about buyer readiness, objections, pricing concessions and promises the delivery team can actually keep. These are the moments where personal experience influences the commercial path.

Use live deals to make the decision logic visible.

Choose a small set of won, lost and disqualified opportunities. For each one, record the starting hypothesis, signals that confirmed or contradicted it, alternatives considered and the reason for the eventual next step.

A short annotated example is often more useful than a long playbook of ideal behaviour. It shows what the team should notice in the imperfect situations they actually encounter.

Turn principles into questions the team can ask.

Rather than writing ‘the founder handles pricing’, identify the conditions that make pricing flexible, the trade-offs that must be discussed and the boundary at which approval is required. Rather than saying ‘target the right accounts’, describe the customer problem and evidence of urgency that make an account worth attention.

Store the reasoning alongside account context in the CRM, and use deal reviews to compare the team’s interpretation with the founder’s. The aim is not to copy a personality; it is to develop shared standards for deciding.

“Documenting judgement is not about prescribing every answer. It is about giving the next person a better question.”De Grijff · Commercial operating principle

Test one decision in the team before expanding the playbook.

Pick a repeated decision, such as whether to progress an early-stage opportunity. Let a colleague explain their assessment before hearing the founder’s view. Compare the evidence each used, then update one shared decision principle.

Repeat across several opportunities. If the team can make the choice consistently and explain why, that piece of judgement has begun to travel. Only then widen the scope to more complex negotiations or strategic accounts.