Take the Big Custom Deal?

The first 10 questions

This is where the conversation starts. Each answer shapes what gets asked next.

1. 01What's the deal — who's the customer, what do they want built or changed, how much are they offering, and on what timeline?
2. 02Where's the business today — revenue, runway, team — and how big is this deal relative to everything else you make?
3. 03How did this come about — did they find you, did you pitch them? Have you done custom work for anyone before, and how did it go?
4. 04How far is what they want from your roadmap — your product configured, your product plus a feature others would want, or effectively a different product?
5. 05What's the real cost to deliver — engineering time, support, maintenance forever after? Price that honestly: does the deal still look big?
6. 06What does saying yes displace — which roadmap items slip, which customers wait, and what does that cost you in six months?
7. 07Is this ONE customer's need, or the first instance of a segment? What evidence says others would pay for the same thing?
8. 08What happens after delivery — ongoing dependence on this customer, maintenance obligations, renewal leverage on their side? Could they become half your revenue, and what does that do to your decisions?
9. 09Can you reshape the deal instead of answering yes/no — narrower scope, higher price, a productized version, paid discovery first, or a 'no, but here's a partner'?
10. 10Whichever way you're deciding — what's the strongest argument for the other answer, and can you honestly refute it?

+ 2 more questions across discovery, validation, and the creative brief — each one adapting to what you've already said.

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