The 324-item checklist a burned founder sent me

Hi, it's Sharan.

This week I spent over two hours on calls with a founder I'm about to sign. She runs a delivery business that takes orders every single day. Her ad campaigns bring in real revenue, and she can't trust a single number in her own analytics. Tracking is broken, data flows are unstable, and at one point her previous team lost data outright. It never came back.

Her peak season starts in October. The new platform has to be live in a month and a half. That's what the wrong vendor actually leaves you with. Not a bad invoice, a business flying blind into its most important quarter.

I won't name her, but I want to tell you what she did next, because it's the smartest thing I've watched a buyer do in a long time.

She didn't open with price. She sent a checklist of 324 feature items and asked me to mark what exists today, what we can realistically build by October, and what I'd advise her to drop. She asked for an SLA with response times and escalation written into the contract, not promised on a call. She wanted the source code and licence terms in plain language so her lawyers could read them without a translator. She asked what happens if we run more than two weeks late, and whether that costs us anything or only her. And she wanted working credentials for every side of the platform, admin, restaurant, courier and customer, so she could run a real order herself instead of watching my screen share.

The easy take is that she's a difficult customer. She isn't. She's what a customer looks like after the wrong vendor. Every question on that list maps to something that already went wrong once. Broken tracking is why she insists on testing with her own hands. The lost data is why she asks who owns what, and the blown timelines are why lateness now comes with a number attached.

Nobody is born asking for penalty clauses. You learn what belongs in a contract when the first one goes wrong.

If you're choosing a vendor right now, for delivery software or anything else, borrow her list. Ask where support response times are written down, and walk if the answer is "we're always available". Ask what you keep if you part ways, meaning the code, the data, the customer list. What happens if they're late matters too, and it should cost them something, not only you. And before any money moves, test every role in the product yourself.

These questions cost you nothing. The founders who don't ask them aren't lazy, they just haven't been burned yet. Her version of this education cost her a year of bad numbers and nearly a season. Yours can cost a week of emails.

To be fair, if you're paying $50 a month for an ordering widget and doing a handful of orders a day, you won't get an SLA and you probably don't need one. This level of paperwork is for the moment the platform is the business. She's at that moment, and if you're reading this, you might be too.

For what it's worth, her questions made us sharper. The agreement I sent her has response times and escalation inside the SLA itself, the source code terms sit in their own section, and she got credentials for all four apps the same day. I'd rather win deals in writing than on charm.

If you're evaluating vendors right now, book a call and ask me her questions. Ask the uncomfortable ones. I'll answer in writing, and if what you need isn't what we sell, I'll tell you that too.