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To catch blind spots before committing time or money, pause and ask four kinds of questions: what problem you are solving, what the practical evidence shows, what the team may be missing, and where each person stands. Len Jessup presents this approach as advice drawn from his experience—not as a scientifically validated decision method. Use it to make assumptions and disagreements visible, not to guarantee a better outcome.
1. Start with the problem and the motivation
Before debating a solution, establish what the team is trying to solve and why it matters. Jessup’s foundation questions are:
- “What problem are we solving?”
- “What are you excited about?”
The first question checks whether the discussion has a clear problem statement or is being carried forward by momentum. The second surfaces what is motivating people. If answers point to different problems or motivations, clarify those differences before evaluating a proposal.
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Then test what is known about execution, the market, and customers. Useful prompts include:
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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 questions help distinguish evidence from assumptions: how far the work has progressed, whether a usable early product exists, what the team knows about its market, and whether potential customers have been heard from. The answers can expose missing information or constraints while there is still an opportunity to address them.
3. Invite perspectives you may be missing
Ask the team, “What are we missing?” or “What else should we be thinking about?” Then make room for people to answer before moving on. Jessup recounts a team member raising the need for an investor performance dashboard—an example of how a colleague can bring an overlooked consideration into a decision. It is an anecdote from his account, not independent evidence that the prompt will produce a particular result.
4. Hear each person’s position and reasons
Before settling a consequential choice, ask: “Where are you on this decision: yes, no or hold? Why?” Hearing both the position and the reasoning can reveal reservations or information that changes the discussion. Jessup argues that this can build shared ownership; that is his stated view, not a measured outcome.
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Use the question in meetings, one-to-ones, or major decisions. A quick round in which each person shares a stance and reason can make disagreement easier to see than a general request for consensus.
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When time is short, Jessup’s approach can be condensed to these four prompts:
- “What problem are we solving?”
- “Where are we really on this?”
- “What are we missing?”
- “Where are you on this decision, and why?”
This short set is a reminder, not a replacement for the more specific build, market, and customer questions when those facts matter. Asking and listening can help surface blind spots, but the questions do not verify assumptions by themselves or guarantee sound decisions. Jessup’s article includes no named statistic or quantitative study establishing their effect on founder outcomes.
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