5 Key Questions Every VC Should Be Asking Founders

Despite all the diligence, data rooms, and market sizing that goes into early-stage investing, most VCs still rely heavily on instinct when it comes to evaluating the people behind the pitch. And while pattern recognition and gut feel have their place, they also introduce bias, inconsistency, and blind spots into the most critical part of the investment decision: the founder.

The truth is, most founder evaluations happen through unstructured conversations and surface-level impressions. But the factors that actually determine whether a founder can scale—resilience, adaptability, coachability, relational intelligence—rarely come through in a pitch deck or a 30-minute coffee meeting.

That’s why we built the Founder Readiness Level (FRL)℠. It’s a structured, research-backed assessment that gives investors a deeper, more objective lens on the people they’re backing. But even before using a tool like the FRL, there are better questions investors can be asking.

Here are five that every VC should be weaving into their founder diligence process:

1. How does this founder respond when things go wrong?

Every startup hits walls. The question isn’t whether challenges will come—it’s how the founder metabolizes them. Do they spiral? Do they blame? Do they retreat? Or do they regroup, learn, and adapt?

This speaks directly to executive resilience and stress adaptation—one of the six constructs measured by the FRL. Founders with high resilience don’t just survive adversity; they use it as fuel for sharper decision-making. Low resilience, on the other hand, often leads to burnout, reactive leadership, or premature pivots driven by panic rather than strategy.

Instead of asking “Tell me about a time you failed,” try: “Walk me through a moment where everything was falling apart—what did you do in the first 48 hours?”

2. Can this founder take hard feedback and actually change?

Coachability is one of the most cited traits investors look for in founders—but it’s also one of the hardest to assess in a pitch setting. Founders are trained to project confidence and certainty. But the ones who scale are the ones who can hold strong conviction and remain open to being wrong.

The FRL measures scalability mindset and coachability—the ability to shift identity, release ego, and evolve as the company demands it. A founder who can’t move from “brilliant builder” to “scale-ready CEO” becomes the bottleneck.

Ask: “Tell me about a time a mentor, advisor, or investor gave you feedback you didn’t want to hear. What did you do with it?”

3. How does this founder build and hold trust with their team?

You can have the best product and the biggest TAM—but if the founder can’t build a team that trusts and follows them, nothing scales. Relational intelligence isn’t a soft skill. It’s a force multiplier.

The FRL evaluates relational intelligence (EQ/RQ)—the founder’s ability to generate psychological safety, read group dynamics, and build high-trust environments. Founders who score well here attract better talent, retain longer, and navigate co-founder dynamics with far less friction.

Ask: “How would your team describe the culture you’ve created? What would they say about how you handle conflict?”

4. Can this founder hold complexity without simplifying too early?

Startup environments are messy, ambiguous, and fast-moving. The founders who succeed aren’t the ones who have all the answers—they’re the ones who can sit with not knowing, hold multiple contradictory truths, and still make clear-eyed decisions.

This is the domain of vertical development—the FRL’s measure of a founder’s meaning-making capacity. Founders at later stages of vertical development demonstrate sharper strategic thinking, better systems-level awareness, and a more nuanced approach to leadership under uncertainty.

Ask: “Tell me about a decision you had to make where there was no clear right answer. How did you think through it?”

5. Does this founder have the agility to pivot without losing their anchor?

Startups require constant adaptation—but agility without purpose leads to thrashing. The best founders are anchored to a deep sense of mission while remaining radically flexible in how they execute.

The FRL measures chaos adaptability and strategic agility—the ability to operate effectively in VUCA (volatile, uncertain, complex, and ambiguous) environments while staying grounded in long-term vision.

Ask: “Have you ever had to make a major pivot? What stayed the same, and what changed? How did you bring your team along?”

Why These Questions Matter

These five questions map to the core constructs behind the FRL—and they represent the dimensions of founder readiness most closely tied to success or failure in venture-backed startups. They go beyond the pitch. Beyond the pedigree. Beyond the pattern match.

But questions alone aren’t enough. The FRL provides a structured, AI-informed assessment that scores founders across all six constructs using scenario-based video responses, psychometric analysis, and expert interpretation. It gives investors a shared language, a developmental baseline, and a repeatable framework for evaluating the people behind the venture.

Let’s get founder diligence right.