"Just stop,” spat the COO from across the table.

“I don’t have time for this generic line of questioning.”

I was two years into my first tech sales job, thinking I was doing everything right.

I asked open-ended questions to unearth pain.

Just like the sales books told me to do.

Yet this COO kicked my teeth in, leaving me and his ops manager twiddling our thumbs.

“I’m as confused as you,” uttered the ops manager after the COO stormed out.

“We teach our reps to ask the exact same questions.”

Have You Ever Been There?

If you’re in sales, you’ve probably felt that before.

In this post, we’ll unpack how to prevent that from happening.

The COO in my story wasn’t simply cranky.

He wasn’t “having a bad day.”

No.

Here’s why he jerked me around and stormed out:

Open-Ended Discovery BACKFIRES With the C-SUITE

A few years ago while I was at Gong, I led an analysis of 39,105 deals.

The Zoom calls were analyzed with AI to find successful and unsuccessful selling behaviors.

This study revealed a counterintuitive insight.

Asking discovery questions to C-SUITE EXECUTIVES decreases your win rate.

Here’s a chart that showcased the data:

Once you’ve asked a small handful of questions to a c-suite exec, every additional question decreases your odds of success.

In fact, successful meeting with the c-suite involve only four sales questions on average.

Unsuccessful meetings have eight.

It’s worth emphasizing a point I skimmed over:

This data was based on sales calls where an SVP or C-SUITE buyer was present on the call.

Senior Executives Have “Discovery Fatigue”

This takes us back to our opening story.

The COO — a senior decision maker — felt like he was being interrogated.

He had probably been through the "discovery dance" with 2-3 other sellers already.

It probably felt taxing to answer all those questions.

But it’s not just him.

Senior decision makers in general are becoming fatigued by salespeople’s questions.

When Questions Feel Like Pickaxes

Senior decision makers in general are fatigued by salespeople’s questions.

So what do we do about that?

When every sales book on the planet tells us to ask MORE, not fewer questions… where do we turn to close more deals when we have to sell to the C-SUITE?

Well.

That answer is not to stop asking them questions.

My interpretation of the data?

It’s not that C-SUITE execs hate being asked questions.

It’s that they hate being asked DUMB questions. Questions that you should have asked someone else. They don’t want to be your research assistant.

The answer?

Asking them context-led questions. 

Context-Led Questions: The Ultimate C-Suite Technique

Here’s what I mean:

In other words, these are targeted questions.

They are specific questions.

They are questions that show an exec “I’ve done my homework. I’m not here to waste your time.”

Want to see an example?

In his podcast, The Tim Ferriss Show, Tim does an amazing job asking these.

Here’s a transcript from the interview he did with Lebron James, and James’ personal trainer:

Notice that the question is frontloaded with a ton of rich context and relevant insight.

If you ever listened to that podcast episode, you’ll notice that Mike went on an AT-LENGTH answer.

That’s exactly what you want from your buyers.

Now imagine a different situation.

Imagine if Tim tritely asked:

“So Mike. What’s your recovery process like for Lebron?”

After taking a deep, irritated sigh, he’d probably give as short an answer as he could.

Context-led questions trigger your buyers to WANT to speak at length.

That includes execs.

Because when you do this well?

You show them that you know their world.

Here’s the Bad News

Using context-led questions is like playing with fire.

It’s nuanced.

There are many more wrong ways to do it than there are right ways.

And if you get it wrong, you’ll get kicked in the teeth (and embarrass yourself).

Plus…

Context-led questions have to fit within a great selling system.

Otherwise, you’re just using ‘random acts of tactics.’

If you want to close more deals consistently…

You have to know how to uncover pain.

You have to know how to uncover the ‘need behind the need.’

You have to know how to diagnose the root cause to favor YOUR product.

You have to know how to build the cost of inaction.

You have to know how to co-create a compelling future vision with your buyer.

That is exactly what we cover in the SaaS Discovery Masterclass inside the pclub.io Platinum Passport.

You’ll learn how to create high-urgency conversations with senior executives, step by step.

I’ll show you two real-life examples.

I’ll show you hands-on exercises.

You’re going to get GOOD at this stuff.

You’ll also learn what to avoid so you don’t get delegated to a lower level (or worse, walked out on).

So.

If you want to learn how to find business pain that MONEY follows.

If you want to learn how to create urgency from thin air.

If you want to learn how to close more deals and sell in an economic downturn.

And yes, if you want to learn how to master the art of asking context-led questions (so you can sell to the C-Suite)...

Learn more about the Platinum Passport right here.