Sales Leadership Unscripted Episode 2: Why Reps Aren’t Closing Deals

This interview has been edited for clarity and length.

Chris Turner:One of the reasons you’ve been so successful is that you’ve adopted some pretty unconventional approaches in sales. Once you get an opportunity into pipeline, what do you think sellers typically get wrong in their sales process? And what should they be doing differently? What’s worked for you and your clients?

Samantha McKenna:I’ll give you one of the easiest ones—I always think of discovery calls like a first date. Imagine showing up and immediately asking, “What’s your FICO score? What’s in your bank account? How’s your relationship with your parents?” That would be way too aggressive. You’d be out of there. And rightfully so.

But when sellers run discovery calls solely focused on checking their own boxes—budget, authority, timing—they’re solving their needs, not the buyer’s. Instead, flip the perspective. Show up to solve, not sell.

I don’t need to know your budget to help you. I need to know why you have a problem, why it matters, and who else it impacts. I can spend 28 minutes uncovering that, then say, “We’re perfect for you. Let’s book a demo.” Or, “We’re not the right fit, but here’s a recommendation.”

What some might see as a waste of time early on actually helped me build deep buyer relationships. Another unconventional approach? How we handle lost deals.

Every time we lose a competitive deal after multiple proposals and calls, we send a handwritten thank-you note to everyone involved. Simple. It says, “We appreciate your time. We wish things had gone differently. If we can ever be a resource, let us know.”

And here’s the mic-drop moment—the competitor who won? They’re probably not sending anything, let alone a handwritten note. It’s a classy way to say, “Call us if things don’t work out.”

Chris Turner:I’ve never heard of sending a thank-you note after losing a deal, but I love that. Let’s shift gears—if you have a team that’s struggling tactically, what’s the first step to improving performance across the board?

Samantha McKenna:Almost every company we talk to right now is struggling with where to start. When you’re missing numbers badly, you have to go back to the foundation.

Look at the things that happen hundreds of times a day—prospecting efforts, email quality, discovery call conversions. Before bringing in social selling experts or negotiation training, fix the basics.

Are reps self-sourcing enough? Are they sending too many bad emails that damage the brand? Are discovery calls actually converting? I was on a call with a massive financial services company, and when I asked about their discovery call conversion rates, they had no idea what good looked like.

The truth? If fewer than 60-70% of your first calls move to a second call, something is broken. If you’re at 30%, your house is on fire. But too many leaders don’t even track this.

Chris Turner:The best sales leaders I’ve worked with are total data nerds. They know their business inside and out. That brings me to another topic—your recent, controversial post about fiscal year-end.

Samantha McKenna:Ah, fiscal year-end.

Chris Turner:What are some of the biggest mistakes sales teams make at the end of the year?

Samantha McKenna:I’ve sat in so many forecast calls—my own teams, peers, clients—and the most obvious questions about deals just aren’t being asked. Even highly experienced sellers sometimes get emotionally tied to deals instead of thinking strategically.

One of the biggest mistakes? Not planning early enough. If a deal takes months to close, don’t wait until December to figure out the approval process.

I recently helped a client with a year-end deal. They were banking on a December 8 board meeting for approval—but they didn’t know what was actually happening in that meeting. Was it a request for spend? A final sign-off? No one had asked.

We also hadn’t identified potential objections, prepped procurement, or started paperwork. These are critical things that can push a deal into next year if not handled early.

Sales teams often put too much trust in their buyers. It’s not us vs. them—it’s a partnership. The goal is to equip your champion with everything they need to get the deal done.

Chris Turner:That’s such an important mindset shift. A lot of deals don’t close because sellers aren’t coaching their champions on how to navigate internal approvals.

Samantha McKenna:Exactly. If a deal has legs and you’ve built trust, asking these questions isn’t pushy—it’s necessary. And yet, how many times have we asked reps, “Does your contact have buying authority?” only to hear, “I’m not sure.”

Meanwhile, that deal is sitting at 90% in the CRM. That’s when leaders blow a gasket.

Chris Turner:This has been an incredible conversation. If you had to leave people with one big takeaway, what would it be?

Samantha McKenna:Get back to basics. High-quality outreach, genuine investment in your buyers, and actually showing you care—those are the things that will win. AI is great, but the sellers who combine AI with authentic, human connection will be the ones who stand out.

Chris Turner: Love it. Buying is human. Thanks, Sam.