Before You Sign Any Check

Every expensive technology mistake I’ve seen started the same way: someone signed a check they couldn’t evaluate.

Not because they were careless. Because they were moving fast, the decision felt urgent, and the person across the table spoke with more confidence than they had context. That’s not a failure of intelligence. It’s a failure of leverage.

Over the past few weeks I’ve written about specific versions of this: hiring agencies, choosing cloud providers, agreeing to rewrites, making your first senior engineering hire. Different decisions, different price tags. But the same underlying pattern.

A founder without a technical partner is negotiating with one hand behind their back. Not because they’re not smart enough. Because the person selling the solution understands the details in a way the person buying it doesn’t. That asymmetry is where the expensive mistakes live.

Three questions cut through it every time.

What does this decision look like if I’m wrong? If the cost of reversing course is low, move fast. If unwinding this choice takes months and money, slow down.

Who benefits most from this recommendation? Me or the person making it? This isn’t about assuming bad intent. It’s about recognizing that incentives shape advice, and the best advisors make their incentives visible.

Can I get a second opinion from someone who doesn’t profit from the answer? The most valuable perspective often comes from someone with nothing to sell. Someone who’s been on your side of the table and knows what the view looks like from there.

You don’t need to become technical. You need someone technical in your corner. Not to make the decisions for you, but to make sure you understand what you’re signing.

What’s the most expensive technical decision you’ve had to make without a technical partner?

#BeforeYouSign #StartupTech #FractionalCTO