Cracking the Code to Customer Decisions

Monica Reynolds

Welcome back to the Dayforce SKO 2026 Breakout Sessions Recap. I’m Monica Reynolds, and today we’re diving into a challenge I know is top-of-mind for every sales professional—cracking the code to customer decisions, especially when we’re up against indecision in the downmarket. Now, if you caught our recent episode on building trust and leveraging relationships, you probably remember we touched on the buyer experience tipping the scales in every deal. Today’s focus—well, it’s what happens when a prospect gets stuck and just... does nothing.

Monica Reynolds

So, let’s get real for a second. Challenger’s recent research—yeah, that’s 2.5 million sales calls, not a typo—found that somewhere north of 40–60% of all lost deals don’t go to a competitor. They end in... no decision. Which is, honestly, pretty brutal. You spend all this time and effort moving a deal forward and then boom: radio silence, or a polite "we’re going to hold off for now." Why does this happen? Buyers are overwhelmed—by choices, by information, and, maybe most of all, by the fear of making the wrong decision. The fear of failure. There’s actually a framework I like: pain of change versus pain of same. Sometimes that new option sounds riskier than just doing nothing at all.

Monica Reynolds

That’s where the Challenger techniques come in. They aren’t new if you’ve followed the last few episodes, but I want to break them down for overcoming indecision specifically. First up: teaching for differentiation. This is about delivering real insight—something the customer isn’t getting anywhere else—and using it to reframe how they see their problem. You can’t just pitch features; you need to give them a new lens entirely. Then, tailoring—the art of resonance. Now, that means you speak to the buyer’s world, their goals, their risk factors. The difference is night and day when a message lands personally. There’s also creating what we call constructive tension. I love this—because it’s not about making people uncomfortable for the sake of it. It’s about shifting how they see the risk, so not changing actually feels riskier than moving forward. And finally, taking control. This is guiding them through the buying journey step by step, not just hoping momentum keeps you on the path.

Monica Reynolds

I’ll give you a quick example. I once worked with a mid-market client—they were shopping for HR software, and I swear they had a spreadsheet that looked like a NASA flight plan. Ten platforms, different features, demos piling up. They were totally paralyzed. So, I hit pause and switched gears, using what Challenger calls Commercial Teaching. Instead of comparing products, I walked them through a scenario—what would life look like if nothing changed? Where were they losing time and money? Only then did we talk about one or two features that actually mattered for their business. Funny enough, the lightbulb went on. We moved past the status quo and suddenly, a decision didn’t feel so impossible.

Monica Reynolds

I might be oversimplifying—every deal is different—but that unsure, overwhelmed buyer? They’re everywhere in the downmarket. If you focus first on their source of indecision, and then bring the right Challenger moves, that’s when deals start making it over the finish line.

Monica Reynolds

Now, let’s shift gears and head upmarket—where it’s not just indecision, but complexity, that’s the killer. Larger buying groups... I mean, it used to be five or six decision makers, right? Now it’s often north of 6, sometimes 11 people in the room, each with their own agenda. And the data shows the more people you have, the less likely you are to actually reach a purchase. The likelihood drops off fast. So, the challenge in upmarket sales is clear: how do you build consensus when you’ve got a roomful of competing priorities?

Monica Reynolds

Challenger lays out a three-step approach that’s become my north star here. First, optimize your group. Honestly, a lot of sellers just invite everyone they can—more the merrier, right? Wrong. You need the right mix—what Challenger calls Choosers, Users, and Buyers. That means folks with skin in the game, either on business outcomes, implementation, or budget, not just whoever has an office calendar open.

Monica Reynolds

Second step: plan for collective learning. This part trips up a lot of people. You don’t just deliver a canned presentation. You map out conversation points—what’s the root business pain everyone cares about, and who owns which piece? Prompting questions, bounding questions—these are your tools. Prompting opens the floor, bounding focuses back when the discussion goes off on a tangent. And trust me, it always does. I’ve literally lost count of how many meetings I’ve seen derailed by one stakeholder going deep on an edge case no one else actually cares about.

Monica Reynolds

Third, and this is crucial: drive to your outcome. The meeting isn’t a brainstorming session; you’re there to get agreement and forward momentum. That means summarizing—“Here’s what I’m hearing from the group”—and then making a strong ask. “Can we align on next steps?” or, at the very least, “What’s missing before we can?”

Monica Reynolds

Just last quarter, I facilitated an enterprise sales meeting with eight stakeholders. It started to unravel halfway through—two people were on entirely different wavelengths, pulling the discussion toward technical nuances that didn’t align with the core business drivers. I had to pull out what Challenger calls bounding questions: “Can we tie this back to the impact we discussed at the beginning? What would success look like for each of you if this goes right?” It wasn’t smooth sailing—frankly, it never is—but we got back on track and left with clear, agreed next steps across the group.

Monica Reynolds

Honestly, for anyone in upmarket sales, mastering this facilitation role is non-negotiable now. The win goes to whoever can navigate stakeholder complexity, keep the room focused on shared business pain, and nudge everyone toward true consensus—even with a few would-be derailers in the mix.

Monica Reynolds

Building on that—once you’re in with a client, the next step is expanding your footprint, right? But here's the catch: not every internal supporter is created equal. This comes up all the time in base expansion. If you’ve been following Challenger’s buyer profiles, you already know the difference between Mobilizers, Talkers, and Blockers. Mobilizers are the magic ingredient—these are the folks who don’t just like your message or take your calls. They actually drive action inside their company. And here’s a fun fact: research shows there’s no reliable link between being a Mobilizer and having a fancy title or C-level role. Title or no title, you’ve gotta identify the real movers.

Monica Reynolds

So how do you spot a Mobilizer? There’s a couple of classic tells. Healthy skepticism is a big one—they’ll question your assumptions, poke holes, suggest risks, but in a productive way. If someone instantly agrees with everything you say? Maybe not a Mobilizer, just a friendly “Talker.” Mobilizers focus on what’s best for the greater good—they use “we” language, volunteer for cross-functional projects, and aren’t shy about challenging the status quo if it’s right for the organization.

Monica Reynolds

And, of course, there are tests—straight from Challenger’s playbook. Commitment tests, like asking them to run a diagnostic or present your solution to a wider group. Influence tests, too—ask if they can arrange for other key stakeholders to join a meeting. If most of those folks show up? You’ve probably found your Mobilizer.

Monica Reynolds

I’ll share a recent example from my own pipeline. At a longstanding customer, I started picking up signs from a payroll manager—she was asking critical questions, poking at gaps in our proposed solution, and was quick to loop in her peers when she spotted an issue. I suspected she was a Mobilizer, so I ran an influence test, asking if she could get counterparts from finance and compliance into a working session. Sure enough, we had a room full of new stakeholders and an open dialogue. That meeting kickstarted a cross-departmental project and, within the quarter, accelerated a sizable upsell that probably would’ve dragged on for months otherwise.

Monica Reynolds

So, next time you’re working a base expansion or cross-sell? Don’t just aim for the friendliest face or the most senior title in the room. Take the time to diagnose who’s asking the right questions, who’s pushing for tangible outcomes, and who actually has the sway to bring people together. Mobilizers are the ones who help you break through internal inertia and turn a “maybe” into a “we’re on board.”

Monica Reynolds

Alright, that’s all for today’s episode. Remember, whether you’re battling indecision, wrangling stakeholders, or hunting for real Mobilizers, these Challenger strategies are your toolkit to drive action and build real momentum. I’ll be back soon with more SKO insights and, hopefully, even more stories from the frontlines. Thanks for listening.