Better questions build better companiesUS founders · Pre-seed to Series A
Section 01 of 12 / Understand the decision

Direct questions

Straight answers to the choices that consume runway, equity and focus.

13Research pages
10Sources cited
28 Oct 2026Last updated
Founders reviewing documents around a meeting table

The first questions to ask.

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01

Should I pivot my startup with six months of runway?

Don't decide from runway alone: calculate the cash and time available to test the current hypothesis, then compare it with a narrower repositioning or a genuinely different market.

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02

How do I tell whether a founder adviser will challenge me instead of agreeing?

Ask the person for evidence of a time they disagreed with a client, what disconfirmed their first impression and how the eventual decision was documented.

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03

Executive coach, startup mentor or strategic adviser: which do I need?

Choose based on the output you require.

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04

How much should a startup strategic adviser cost?

There is no defensible US-wide published median for an independent founder decision review .

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05

Can I compare two SAFE offers using only the valuation caps?

No.

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06

When should I hire my first VP of Sales?

Hire for a proven management and scaling requirement, not as a remedy for a founder who has not validated a repeatable sales motion.

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07

Is investor-paid founder coaching confidential?

Only to the extent spelled out in the agreement and applicable law.

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08

Can ChatGPT or another AI replace a human decision adviser?

For organising options, finding missing questions and drafting pre-mortems, an AI tool can be an inexpensive first pass.

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09

How do I ask for a genuinely independent second opinion on a funding offer?

Give the adviser a decision-focused, bounded scope before asking for an introduction to investors.

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10

What will a good decision review leave behind?

Expect a brief decision statement, an evidence register, credible alternatives, a pre-mortem, explicit conflicts and a record of why the founder chose a path.

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Research quality

Editorial self-assessment
Not independently validated

10/10Buyer fit
9/10Depth
10/10Question coverage
9/10Source support