There's no possible way I can get up to speed on what a founder knows about their industry, plan, goals, or team, in just a few hours or even days. Hell, I could spend weeks on it and, hopefully, it wouldn't make a difference.
You should know way more about this than I ever could.
That's why the consistent theme among the very worst pitches I take are the ones where the entrepreneur asks me what I think--about everything. It feels as if the entrepreneur doesn't know for certain that the idea is good, and they want me to validate it.
That's not my job.
You're the one investing all your time into it.
You're going to put way more money--either directly or into opportunity cost--than I ever will. You'll need to take on the responsibility of your employee's livelihoods. It will be your reputation on the line much more than it will be mine.
So when you're asking me if an idea is good, my first thought is...
You tell me!
The most successful founders I've work with are in a position to know whether a plan is the right one. Sure, there might be some blindspots in it--and that's where outside perspective can be helpful, but the general direction isn't for me to vet.
It's for you to tell me after you've told it to yourself convincingly--because you know you've done your homework and you're in a great position to be the judge.
Don't ask me if you're raising enough money.
Tell me you are.
Don't ask me what I think of the product.
Tell me what your customers do think or will think--and why.
Don't ask me what the milestone should be.
You tell me what's really hard and what should convince a next round investor that you've accomplished amazingness after you reach it.
Most of the time, I'm pretty sure the entrepreneur pitching me lacks clarity and conviction, and they're not asking me to judge--they're asking me what they need to do to become sure.
The person they need to convince usually isn't me--it's a customer, and they probably haven't spent enough time with them, or never was one themselves.