Founders often fail because they worked on the wrong questions for too long.
This article offers a diagnostic tool, a structured set of questions designed to surface whether your startup is actually ready to move forward.
Use it when:
- things feel stuck,
- decisions keep getting delayed,
- or execution feels heavier than it should.
How to Use This Diagnostic
Before you move to questions, it is important to note:
- Write your answers down.
- Notice where answers are vague, defensive, or circular.
- Any question you cannot answer clearly is a constraint, not a failure.
You are not looking for confidence.
You are looking for a signal.
1. Foundational Clarity
These questions expose whether you are building on assumptions or evidence.
- Who is the specific customer we are building for right now (not eventually)?
- What concrete problem are they actively trying to solve?
- What behavior change proves they care?
- What did we learn about this customer in the last 30 days that changed a decision?
- If we removed one feature, would our value still be clear?
If these answers are fuzzy, execution speed will not save you.
2. Go-to-Market Readiness
These questions surface whether demand is emerging or being imagined.
- How does our customer currently discover solutions like ours?
- What channel produced our first real signal (time, money, commitment)?
- What happens immediately after a prospect hears our value proposition?
- Can we describe our positioning in one sentence without qualifiers?
- What assumption must be true for our GTM motion to work?
If you cannot point to a signal, you do not yet have a GTM strategy—you have a hypothesis.
3. Execution Discipline
These questions reveal whether progress is being converted into learning.
- What decision did we avoid making last week?
- Which activity looks productive but produces no signal?
- Where does work consistently slow down or queue up?
- What metric do we review that never changes a decision?
- If we stopped half our initiatives, which one would still matter?
Execution without learning is just motion.
4. Runway and Decision Health
These questions expose how pressure is shaping behavior.
- What decision feels emotionally heavy right now?
- Where is founder involvement required when it shouldn’t be?
- Which decisions are being delayed “until we have more data”?
- What would we stop doing if runway were cut in half tomorrow?
- Where is pressure causing centralization instead of clarity?
Pressure does not break startups.
Unstructured pressure does.
5. Structural Constraints (Venture Physics)
These questions operate above tactics. They reveal whether your system is sound.
- What assumption are we treating as fact without proof?
- What would have to be true for our strategy to clearly fail?
- Where is uncertainty highest—and are we testing it directly?
- Can an external system (human or machine) understand our value quickly?
- What part of our motion would collapse if the founder stepped back?
These questions do not judge ambition.
They judge mechanics.
What the Answers Tell You
You do not need perfect answers.
You need honest ones.
Patterns matter more than individual responses:
- repeated vagueness = unresolved uncertainty
- repeated defensiveness = identity attachment
- repeated delays = decision bottlenecks
Those patterns are your real work.
What to Do Next
After answering:
- Identify the three weakest answers.
- Turn each into a testable hypothesis.
- Design one experiment per hypothesis.
- Time-box learning, not execution.
- Revisit this diagnostic monthly—especially under pressure.
Clarity is not a personality trait.
It is the output of a disciplined system.
References & Further Readings
- Blank, S. – Startups Are a Search, Not an Execution Machine (HBR)
- Eisenmann, T. – Why Startups Fail (HBR)
- First Round Review – The Early GTM Mistakes That Kill Momentum
- McKinsey & Company – Decision-Making Under Uncertainty
- Sequoia Capital – What to Measure at Seed Stage
- Y Combinator – How to Test Startup Ideas Quickly