The emotional cost of unpredictable sales

📣 Big Announcement
This Wednesday, I’m hosting a 90-minute live session on how to run discovery calls that convert. Readers know I’m adamant that 80% of deals are won or lost here.

Nail it, and your sales process becomes predictable. Miss it, and you’ll feel it downstream.

We’ll break down the exact framework we coach founders on how to close revenue predictably, including how to qualify with precision, ask questions that uncover genuine pain points, and guide conversations that drive momentum forward.

I’ll walk you through it step by step, with live role-play, real examples, live Q&A, and frameworks you can copy instantly.

🎁 Bonus: Every attendee will get a free copy of our Discovery Call Talk Track.

👉 Register Here For The Discovery Call Training 👈

Title: The Emotional Cost of Unpredictable Sales

Read time: 3 min

Today, I’ll discuss something that feels especially relevant, given the live training I’m running on Wednesday on how to run discovery calls that actually convert.

Because here’s what I see over and over again: founders and sellers work incredibly hard. They built a great product. They generate a pipeline. They put in the time to craft a compelling pitch. And yet, their deals still stall out.

They’re not getting hard rejections. They’re not hearing “no.” The deals just don’t close when they should.

And that can be unbelievably frustrating. I still feel it sometimes myself, especially when I know I’ve done everything right when the product/service is a no-brainer. When the call went well, when you know it should have closed.

I talk to founders all the time who share the same story. There was interest. The discovery call felt solid. The demo landed, and they seemed engaged, but then nothing.

And now, you’re waiting. You’re following up. You’re trying to stay top of mind. And you’re left wondering what went wrong.

So today, I want to talk about why this keeps happening, and more importantly, what you can start thinking about now to make sure it doesn’t keep happening.

You Don’t Rise to The Occasion; You Fall to The Level of Your Training.

~ Archilocus

Why This Is a Bigger Problem Than You Think

Because you didn’t lose the deal at the end, you lost it at the beginning. Closing is a byproduct of a well-executed qualification.

Deals are sometimes lost within the first 30 minutes of the sales process.

The part most people call discovery. The part that seems somewhat simple and like it’s going fine.

But the moment when trust is built, pain is uncovered, urgency is created, and qualification is established, is where the majority of sales momentum is either generated or destroyed.

If you don't get that right, the rest of the deal becomes a slow, painful uphill climb.

What Most People Are Doing Instead

The trap I see people fall into, and I say this from experience, both as a coach and someone who's been in those exact shoes.

They show up to the discovery call ready to have a good conversation.

They ask what they believe to be the right types of questions:

• “What are you currently using?”

• “What’s your biggest challenge right now?”

• “What are you hoping to improve?”

The buyer answers. You take notes. Perhaps you have a story or two to share. You both leave feeling like it was productive. But then... the deal drags. Next steps are fuzzy. The buyer loses steam, and you're wondering what went wrong.

Here’s What Went Wrong

You didn’t go deep enough. There are certain questions that you have to ask and understand deeply; otherwise, you get more or less service-level answers.

You heard pain, but you didn’t uncover urgency. You qualified the problem, but not the stakes. You identified a need, but not a priority.

In short, the buyer felt heard, but not moved.

Understanding the nuances of these things is critical.

For example, there are two questions you should always ask.
1. What are some reservations or concerns with technology like ours?
2. What do you need to see and validate with us to feel confident moving forward?

These two questions will flesh out 90% of the blockers that prevent the deal from closing downstream.

In B2B sales, inertia and not giving your prospect a clear reason to act are your biggest competitors.

The Real Confusing Part

The worst discovery call isn’t the one that goes poorly. It’s the one that feels good, feels like you nailed it, but gives you nothing you can actually sell on.

This is what leaves you wondering what the f**k, I thought it went so well.

I’ve been selling at a high level for a long time. I’ve listened to over 7k sales calls, and have been on a few thousand myself. Here is the part that will take a very long time to figure out when you’re building.

• Buyers will sound interested and still disappear.

• They’ll discuss “challenges” without any genuine pain.

• They’ll say the timing is good, and then not reply for 4 weeks.

• They won’t move forward and give you no reason why.

It doesn’t mean they’re flaky; it means your discovery call didn’t get to the truth. Most buyers don’t open up naturally. You have to guide them with intention. With skill. With structure.

It’s a process of peeling back the onion.

And like any great diagnosis, it’s not about throwing out a bunch of questions and hoping one hits. It’s about leading someone to clarity they didn’t have before.

Once they see the real problem and feel the cost of not solving it, the decision becomes obvious.

But if your discovery call doesn’t do that, no matter how good your solution is, it won’t land.

Where Discovery Breaks Down, Quietly

Let’s break down a few common failure points in most discovery calls.

1. Too much rapport, not enough direction
Everybody wants to be likable, but Steve Jobs famously said, If you want to be liked, get into the business of selling ice cream. Because being liked doesn’t build urgency. A ten-minute intro and bio warmup kills momentum before the call even starts.

2. Accepting vague pain as real pain
When a buyer says, “Yeah, we’re looking to improve our process,” that’s not pain; it’s them being cordial. It sounds like progress, but it doesn’t move the deal. Real pain has stakes, urgency, and emotion. You have to dig for it.

3. Skipping the “Why now?”
Urgency isn’t created by accident. If you don’t help the buyer articulate why this matters today, they’ll default to someday.

4. Letting the buyer control the flow
They’re coming to you because they believe you’re the expert, and if you’re not conveying that throughout the process. When you're not leading, they stay surface-level. Real discovery requires structure, not just curiosity.

Sneak Peek Into Wednesday’s Call

My focus for the upcoming training on Wednesday will show you exactly how to fix this. It’ll be 90 minutes long, so we’re going deep.

We’ll dive headfirst into:

• The discovery call structure that creates urgency from minute one

• How to qualify in a way that drives momentum instead of stalls

• The questions you should never ask (and what to ask instead)

• The psychology of buyer resistance, and how to disarm it

• Real role plays + examples so you can see what “great” sounds like

And afterwards, I’ll share with you the full Discovery Call Talk Track that you can copy, customize, and use immediately.

Here’s what I’ll say in advance:

The fix is rarely about asking more questions. It’s about asking the right ones, in the correct order, to unlock something most buyers don’t even know how to say out loud.

That’s the skill. That’s the shift. And that’s what I’ll be walking you through live.

Join us this Wednesday

If deals are stalling or ghosting somewhere in the funnel, and you don’t have clear visibility into why, even when everything seems to be going right, you don’t want to miss this session. Feel free to share the invitation with Founder friends. This is for you, the community, and the readers. Join us! 💪

🎉 Event: Live Discovery Call Training

📆 When: November 5, 2025, 12-1:30 PM EST

📍 Where: Zoom

🎁 Bonus: Free copy of the Discovery Call Talk Track for attendees only

👉 Register: Click here to register

I hope to see you all there!

Darren

P.S. If you’re a venture-backed startup looking to level up your sales and distribution, book a call here.