Move Beyond Dashboards, Start Developing Thinkers

In my role at the Sales Center of Excellence, I look at deals from two sides: the technical precision of an engineer and the psychological lens of a coach. After reviewing the data of hundreds of sales calls, listening to hours of sales conversations, talking to individual contributors, and researching the latest trends, I started to see a pattern: We are obsessed with metrics and 'activity,' but we often overlook the cognitive side, how people actually process complex situations in real-time. This has a dramatic effect: we manage the pipeline, but we don't develop the thinker.

Compared to the time when I was a sales engineer, it seems like selling has gotten much more complex. Buyers today are well-informed, they have strong opinions, and often, they don’t even agree with each other internally. Gartner recently pointed out that the skill gaps in sales are growing and there is a lot of pressure to change how we look at performance in a sales organization. (Gartner, 2025)

In this article, I'll share my observations, a little story, and my coaching perspective.

To get this out of the way right away: the problem isn't that our people aren't working hard enough. They are. The real bottleneck is that their thinking has become 'autopilot.' It has been boxed in by the very processes, procedures, and behaviors we taught them through checklists, cheat sheets, metrics, dashboards, and standardized questionnaires. Ironically, at a time when technology has made execution easier, faster, and more scalable than ever, execution itself is no longer the most challenging constraint. In complex B2B sales environments, the new constraint is the quality of thinking applied to ambiguous, high-stakes situations.

Let me give you an example based on a real story I heard.

On paper, everything looked perfect.

The Account Executive was doing a great job with the activities: he had the meetings, the technical proof was done, and the proposal was out. If you looked at the MEDDPICC checklist, every box was ticked. He had the Economic Buyer identified, he knew the Decision Criteria, the Paper Work was clear, everything.

When the sales leader asked, "What’s the status? Who is the boss there? When do we sign?", the answers sounded very solid. So, they kept the deal in the forecast.

Three weeks later, however, the deal came to a complete halt.

It wasn't the seller's fault because he was lazy or forgot an important step in the methodology. They stopped being curious about how the buyer was thinking about the situation. It was a small risk that the client mentioned early on but which was never actually addressed. The hidden tension between Finance and IT was overlooked and eventually became a deal breaker.

Looking back, the problem wasn't the discipline or the process. It was the quality of the thinking in a convoluted situation.

So, the question is, "When a deal in your team gets stuck, do you actually find a new way to think about it, or do you just ask for more 'activities'?"

For years, sales has been managed by looking mostly backwards at the numbers to predict the future: the forecast, the pipeline, how many calls the team is making, and how many touchpoints they had with the prospect. But don't get me wrong, these things are still important. But they only help the sales team to run faster; they don't tell them if they are heading in the direction they ought to run. They optimize the process, but they don't improve the actual decisions people make in the heat of a deal.

This is, where I believe, coaching can make a difference.

If you look at the data from places like CSO Insights or the RAIN Group, it says: coaching is the biggest lever to win more deals by helping sales teams to elevate the quality of the deal conversations. It’s the difference between a 'middle-of-the-pack' seller and a top performer. (CSO Insights, 2019 / RAIN Group, 2023)

And even the science backs this up. Experts like Kahneman and Tetlock have shown that making good judgments is a skill you can train. It’s not something you’re just 'born with.'

I’m not saying every sales manager or seller has to become a professional coach. But I am saying that we need a systematic way to help sales teams think and stay curious, not just act.

Shifting into Sense-Making

In their sales enablement framework, Gartner uses the term "sense-making" to describe a seller’s competency to help buyers navigate overwhelming amounts of information. In a sales coaching environment, this means moving away from 'if-then' checklists and instead teaching sellers to listen on different levels to identify patterns in buyer behavior and information gaps. (Gartner 2025)

However, this is somewhat contradictory to the usual sales mentality of speed. When things get tough, most teams just push harder to keep the momentum or even accelerate. But in tense moments at a high pace, chances are likely that the team misses the forest for the trees. Doing the opposite in such situations, slowing things down, can help to avoid this pitfall.

Here is how the above story continued because the sales leader shifted the approach to slow down the seller's thinking.

In the next deal review, the seller framed the problem simply:

“The CFO keeps asking for more risk analysis. I think she’s trying to delay the decision.”

The sales leader didn’t argue with him. He just paused and asked a different kind of question.

“What do you think the CFO is trying to protect right now?”

The seller answered quickly. “Budget.”

“That’s the surface,” the sales leader said. “What would make approving this deal personally risky for her?”

The seller paused. Then reframed: “If this initiative fails, she owns the downside, but not the upside.”

Suddenly, the whole deal flipped. They stopped sending more data and started talking about real things, like who takes the blame if this fails.

This is where coaching comes in. Rather than giving them the answer, coaching helps them read the room, question their assumptions, and explore new perspectives. The intervention of the sales leader helped the seller to open up their mind to what has already slipped off the radar screen.

Building the 'Thinking Muscle'

Instead of just telling people what to do, we need to support them in how to process what’s happening in a deal. I refer to this as building the thinking muscle. It is less about correcting behavior in the moment and more about strengthening the underlying cognitive habits sellers rely on when situations become ambiguous. At its core, this comes down to three capabilities:

• Connecting the dots: Strong sellers don’t just listen to what buyers say; they notice patterns across interactions. They pay attention to inconsistencies between words and behavior, shifts in tone, repeated questions, or sudden requests for reassurance. Coaching at this level helps sellers move from isolated observations to informed hypotheses. Instead of reacting to the last meeting, they learn to ask: What pattern is emerging here, and what might it tell me about how this organization is deciding?
• Creating a feedback loop: Most deals move fast, but learning doesn’t happen at the same pace. Building the thinking muscle requires intentional pauses for reflection. After a customer conversation, the question is not just “What’s next?” but “What did we learn?” What assumptions held up? Which signals did we miss? Over time, this structured reflection trains sellers to self-correct earlier, rather than waiting for a deal to stall before rethinking their approach.
• Seeing the bigger system: Complex B2B deals rarely hinge on a single stakeholder. A “yes” from IT may create downstream implications for Finance, Legal, or Operations. Coaching that develops systems thinking helps sellers anticipate second- and third-order effects inside the customer organization. Instead of treating objections as isolated resistance, sellers learn to see them as signals of misalignment within a broader decision ecosystem.

Taken together, these practices don’t just improve individual deals. They develop sellers who can navigate complexity with capabilities that scale far better than any checklist ever could.

Where Frameworks Help and Where They Stop

Frameworks such as MEDDPICC remain valuable. They bring structure to complexity, create a shared language across teams, and help surface gaps in a deal. Used well, they prevent obvious blind spots and improve execution discipline.

But frameworks were never designed to do the thinking for us.

In the story described earlier, MEDDPICC was followed correctly. Metrics were defined. The Economic Buyer was identified. Decision criteria and process were documented. On paper, the deal was sound. What the framework could not reveal, however, was how those elements interacted once internal tensions surfaced. It did not explain why the CFO’s repeated requests for risk analysis carried more weight than expected, or why alignment between IT and Finance eroded late in the process.

Frameworks tell sellers what to look for. Thinking skills determine how to interpret what they see. Without that distinction, reviews risk turning into box-checking exercises. They are accurate, but shallow. Sellers may be compliant without being insightful.

When coaching focuses on developing thinking, MEDDPICC becomes a starting point rather than an endpoint. Instead of asking, “Do we have an Economic Buyer?” the conversation shifts to, “How is this Economic Buyer balancing personal risk, political pressure, and organizational incentives?” Instead of confirming decision criteria, leaders explore how those criteria might change once different stakeholders feel the downstream impact.

In other words, structure supports execution. Thinking enables judgment.

Sales organizations that understand this distinction stop using frameworks as control mechanisms and start using them as foundations for better reasoning. That mindset shift is subtle, and it is (initially) not about the sellers but how sales leaders see themselves being in service for their teams.

A Quick Outlook: Empathy Over Algorithms

Most recent research also highlights a significant shift in sales coaching due to emerging technologies. This shift moves the focus from traditional oversight to AI-augmented enablement and human-centric "mentalizing."

As we head further into the era of AI, sales managers will increasingly rely on technology as a teammate. (Gartner, 2025)

AI is great at the boring stuff, such as forecasting, logging calls, and checking data. But the 'art' of selling? That’s still on us. While a machine can give you a checklist, it can’t sit in a room and 'feel' the tension between two stakeholders. Understanding the context of complex sales situations still needs a curious human who can listen between the lines, show empathy, and use their intuition.

In 2026, AI may tell you what happened in a deal, but who helps your team understand why it mattered to the buyer? (...maybe it is a human coach!)

Conclusion

Sales leaders will always be measured by results: growing the pipeline and closing the pipeline. That won’t change. What is changing is how those results are achieved. In complex sales environments, sustainable growth increasingly depends on leaders who leverage systematic development of thinking in their teams.