The Tool Desk
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1. Start with the problem and the motivation
Momentum can make a decision feel obvious before the team has agreed on what it is trying to solve. Jessup’s foundation questions bring the conversation back to the purpose:
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- “What problem are we solving?”
- “What are you excited about?”
The first question tests whether the group has defined a problem rather than simply rallied around an idea. The second helps reveal what is driving people’s interest, which can clarify whether their enthusiasm is grounded in the same goal.
2. Check what is known about execution
Once the problem is clear, practical questions can expose gaps between a promising idea and what the team has actually learned or built. Ask:
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- “Where are you in the build?”
- “Do you have a minimum viable product?”
- “What does your market actually look like?”
- “Have you talked to any potential customers yet?”
These prompts focus the discussion on build progress, market understanding and customer conversations. They help distinguish evidence the team has gathered from assumptions it may be treating as facts before committing resources.
3. Invite the information you may have missed
A founder or team leader cannot be expected to see every implication alone. Ask the group, “What are we missing?” or “What else should we be thinking about?” Then leave room for answers that challenge the current plan.
In Jessup’s account, a team member raised the need for an investor performance dashboard. The example illustrates how an open-ended prompt can bring an overlooked requirement into view; it is an anecdote, not independent evidence that the question will always surface a blind spot.
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Before settling a consequential decision, ask: “Where are you on this decision: yes, no or hold? Why?” Hearing both a person’s position and the reason behind it can reveal concerns that a quick vote would miss. Jessup argues that this exchange can change a decision and build shared ownership; that is his stated experience, not a measured outcome.
Use the question in meetings, one-to-ones and major decisions. The value is in listening to the reasoning, not collecting a yes-or-no tally.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Put the questions together in a meeting
For a decision that needs discussion, move from defining the problem to checking evidence, inviting missing perspectives and hearing individual positions:
- Clarify the problem and what motivates the team.
- Ask what has been built, what is known about the market and whether potential customers have been spoken to.
- Ask what the team may be missing, and listen without steering toward a preferred answer.
- Ask each person whether they are at yes, no or hold, and why.
A short recurring set captures the sequence: “What problem are we solving?”, “Where are we really on this?”, “What are we missing?” and “Where are you on this decision, and why?” The longer practical prompts still matter when build, market or customer evidence is central to the choice.
Jessup’s advice is to ask questions and listen; it does not establish that following a fixed sequence guarantees better decisions. No named statistic or quantitative study is offered to measure its effect on founder outcomes.
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