5 questions for a $200K decision-maker you can't reach

I was on a group call last week with about 30 MSP sellers when Bradley got blunt:

"I'm almost at the point where I won't even meet with them if I can't get in front of the decision maker."

He'd been burning hours on deals where the owner, CFO, or business partner never showed up. An office manager runs the process. An IT contact collects the quotes. Somebody promises to bring it back to the team or overstates how much authority they have in the decision-making process.

And the deals die. The way they always do.

I get a version of this question almost every week now — from the reps I coach and from the owners trying to decide whether those deals are even worth chasing.

So let's talk about what's actually going wrong. Because it's not what most people think.

When you can't get to the decision maker, here's what's actually happening.

You can't find their real pain — because the person who feels it isn't in the room. The contact running the process or collecting quotes isn't necessarily the one losing sleep over downtime or a security gap. They aren't even paying the bill in many cases.

This is a task on their list, not a problem they own.

So you can't build a proposal around what's actually driving the decision. You build it around what the middleman told you, which is surface-level by definition.

And without their pain to anchor to, you've got nowhere to position your company. No way to show how you're different. There's no problem deep enough to make your value matter.

Which means you're just a number. The decision maker you never met looks at three proposals that all read about the same, and picks on the one variable left: price.

You didn't lose that deal in the proposal phase. You lost it the moment you accepted you'd never talk to the person with the pain, and didn't adjust your process to compromise.

This is where most go wrong. You try to force the prospect to throw their buying process out the window in order to adhere to your selling process.

But that's in your best interest as a seller. Most buyers recognize that, and almost nobody wants to be forced to change the way they buy in order to make being sold easier. Particularly if they don't understand how it benefits them.

Your best move isn't forcing people to change the way they buy in order to conform to the way you sell. It's respecting their buying process, and selling them on why getting more involved actually serves them — not you.

Look, I'm a business owner. And if there's a meeting I can skip, I skip it. I've got people who are more than capable of finding out what our options are, comparing options, and presenting them to me to make a decision. So when you tell me I "need" to be on a call, my honest reaction is: why? Why can't somebody else get you (and me) what's needed to make a decision here?

As a seller, you have to answer that.

Show me how being in the room saves me time, saves me money, or gets me a better decision. Having my input means a quote that doesn't pile in services I'll never use.

It means less back-and-forth after the proposals land, because you built it right the first time. It means services tailored to the problems that actually keep me up at night — not the ones your assessment happened to flag. And it means you can shape the whole thing around the best return, or the lowest cost, depending on what I care about most.

That's the pitch. Not "I need you there to sell my stuff." It's "you'll get a better outcome if you are."

The second it feels like you're doing this for your benefit instead of mine, you've lost me. Get that right, and the resistance frequently drops.

But sometimes it doesn't. Sometimes the answer is still no.

And here's the mistake most reps make when they hit that wall: they treat it as binary.

Decision maker in the room, or the deal's dead. It isn't. You don't need them in the room — you need their input. And there's more than one way to get it.

I worked through exactly this with Brandon last week, one of the reps on my fractional team's roster.

He had a solid opportunity. A sizable company moving off internal IT for the first time, looking at a serious monthly investment. His contact, Jason, had been there 20 years and was running point. Brandon asked to get the president and CFO into a meeting.

Jason's answer, more or less: "I probably could, but they're just going to defer back to me. I've had pretty thorough conversations with both of them."

It was a polite no. And Brandon did a great job of positioning why it'd be in their best interest to have them there, to no avail.

So we didn't keep pushing. We respected the process and built a workaround.

We helped Jason understand why their input was necessary, then asked if he'd put a few questions in front of the president and CFO to help us help them.

Not a survey. Not a form. A handful of questions designed to do four things at once: pull out the information Brandon needed, get to the real motivation behind a six-figure decision, set Brandon apart from everyone else in the running, and not sound like sales questions.

Here's what we landed on:

Read those again and notice what they're not. They're not "what's your budget" and "what's your timeline and urgency." They're the questions of someone trying to understand the business, not someone trying to win a quote.

That fourth one especially — cost to manage down versus an investment that returns something — tells you almost everything about how a CFO weighs the decision. And nobody else in that process is asking it.

And the fifth does work too. If they answer it with something you were already planning to deliver, now you know it's top of mind. If they go long on it, you've found something that matters. Either way it's an opportunity for a real signal.

The framing to Jason was simple: don't have them spend more than ten minutes on this, it's not an essay. Easy to say yes to.

And here's the part that matters even if the answers come back thin — the questions change how those decision makers think before they ever compare proposals. The fact that you asked is already half the battle.

Same spot everyone else is stuck in. Completely different position in the deal.

There is a legitimate version of "no decision maker, no deal." It's just narrower than people use it.

There's a direct correlation between close rates and the decision maker's actual involvement in the process. When they're fully engaged from the start, your close rates are higher. When they're absent, the close rate plummets. That's why getting some involvement — even asynchronously, with the questions above — helps a lot.

But low close probability isn't the same as no probability.

So whether you walk comes down to opportunity cost.

If you've got a full pipeline of high-probability deals you can't get to because you're bogged down in these no-decision-maker deals — cut and run.

But if your choice is a lower-probability deal with limited decision-maker involvement, or going to hit the streets and pound the phones for cold traffic? I'd take the lower-probability deal you're already talking to.

And candidly, most businesses aren't so overwhelmed with qualified, high-intent deals that they can't afford to work the ones with limited decision-maker involvement.

So most of the time, the answer isn't to walk. It's to get them as involved as you can. And when they won't come to you, find another way to get what you need.

Adios,

Ray