How Can I Tell If a Deal Is Real?
Curiosity fills your pipeline. Intent moves budget. Three ways to tell which one you’re in.
Every founder I talk to has a pipeline full of deals that feel real.
Good calls. Nice people. “This is exactly what we need.”
And then nothing.
The problem isn’t that founders can’t sell. It’s that they can’t tell the difference between curiosity and intent. Curiosity gets you a second meeting. Intent moves budget. They feel the same on the call. They are not the same.
I wrote about this in Harvard Business Review with Vincent Onyemah — mistaking curiosity for intent is one of the ways founders misread product-market fit and build a pipeline that looks healthy and isn’t. This post is the practical version. How do you tell them apart in a live deal?
I look for three things.
1. What changed?
Buyers don’t act because a problem exists.
The problem existed last quarter. It existed last year. If the problem alone were enough, they’d have already bought something.
Buyers act because something changed. A new exec. A new mandate. A number that got missed. A tool that broke. A competitor that moved.
If you can’t name what changed, you’re not in a deal. You’re in a conversation.
So ask it directly. Why now? What’s different this month than three months ago? If the answer is vague, the deal is vague.
2. What exec is on the hot seat?
Deals don’t get funded because the work is annoying.
Annoying gets nodded at and tolerated. Somebody says “yeah, that’s a pain” and moves on with their day.
Deals get funded when a specific executive has a specific problem they’re being measured on. When there’s a name attached. When someone in that org is going to have a hard conversation with their boss if this doesn’t get solved.
So find the name. Who feels this the most? Whose number is exposed? Who has to explain it upward?
If the pain doesn’t have a face, it doesn’t have a budget.
3. When does it need to be solved by?
This is the one founders skip.
You ask a buyer when they need this solved and they say “yesterday.” Or “soon.” Or “this year.”
They’re not lying to you. They just don’t have a date. And if they don’t have a date, they don’t have urgency, and if they don’t have urgency, you don’t have a deal. You have a maybe.
Your job is to extract a real date. Not because you’re being pushy. Because a date is the difference between a deal that closes and a deal that drifts.
How I get to the date
“Yesterday” is what buyers say. It’s your job to get something better.
Here’s the move.
When they say “soon,” you don’t accept it. You give them two anchors and let them place themselves between them.
“Is this something that has to be live by end of the month, or are we really talking about Q3?”
That’s hotter, colder. Almost every buyer can tell you which end they’re closer to, even when they can’t give you a date cold. Then you narrow. “Closer to end of month or the middle?” And you keep going until you have something exact.
Because Q1 means nothing. February 15 means something.
And once you have February 15, you work backwards. If it has to be live February 15, when does the contract need to be signed? When does procurement need to start? When does the exec need to be bought in? Suddenly the timeline is real, the steps are real, and you know whether the buyer’s stated urgency survives contact with a calendar.
And the calendar is less generous than buyers think. Ask anyone who’s tried to close in December. Half the month is gone to holidays. Decision-makers are out, procurement is out, the exec you need in the room is on a beach somewhere. A “December close” is usually a first-week-of-December close or it’s a January close, and most people don’t realize that until they’ve mapped it. Work backwards and the dead weeks show up. That’s the point. You want them showing up now, not the week you were counting on a signature.
Most of the time it doesn’t. That’s not bad news. That’s the deal telling you the truth early, instead of six months from now.
A real deal has all three. Something changed. Someone’s on the hook. And there’s a date that survives when you work backwards from it.
Two out of three isn’t a deal. It’s a nice call you’ll remember and they won’t.
If your pipeline is full of deals that feel real but don’t close, the problem usually isn’t the deals. It’s what’s underneath them. The three signals here are the front edge of a bigger framework — SPRINT — that I laid out in Harvard Business Review. In five days I can give you a clear approach to what’s actually holding you back. Set up a call to discuss here: daverubinstein.com.