Last summer, I facilitated over a dozen workshops during a global tour that took me across 12 cities, 10 countries, and 5 continents. I trained 630 executives, and while the markets varied, I discovered a shocking reality that should alarm every sales leader:
72% of participants didn’t know the real reasons why customers buy from them.
They were consistently ignoring the 3 whys of MEDDIC which are the three foundational pillars of MEDDPICC® : Why Anything, Why Us, and Why Now.
- Why Anything? (The Business Pain)
- Why Us? (The Differentiators & Decision Criteria)
- Why Now? (The Metrics & ROI)
When these three questions are left unanswered, a rep isn’t truly selling—they are just taking orders.
The Breakthrough: Watching the Lightbulbs Turn On
The good news? The talent is there and the appetite for growth is massive. In every session, the energy was electric. The most rewarding part of the tour wasn’t the travel; it was watching the lightbulbs turn on. In every session, we made huge progress by helping these executives step into difficult conversations around Metrics and uncover “True Pain.” We watched them shift from a “vendor” mindset to a purposeful role—one where they bring real value to the client and, as a result, find more fulfillment in their work.
The 3 Whys of MEDDIC / MEDDPICC
Why Anything? (The Business Pain)
This is the foundational “why” in MEDDPICC®: why should the customer do anything at all? If there’s no meaningful business problem, there is no real deal—only curiosity. “Why Anything?” means you’ve identified a concrete pain tied to the company’s priorities: wasted time on specific tasks, long time-to-market, low revenue, high cost, high risk, customer retention, security, compliance, operational efficiency, etc. It’s not a vague complaint; it’s a business-impact problem that matters enough to justify change, mobilize stakeholders, and survive internal scrutiny.
Why Us? (The Differentiators & Decision Criteria)
Once the customer agrees there’s a problem worth solving, the next question becomes: why should they solve it with you? “Why Us?” is where MEDDPICC® turns preference into a defensible choice. You align your differentiators directly to their Decision Criteria—the “shopping list” they’ll use to evaluate vendors—and you prove you meet it better than alternatives. This includes capabilities, implementation approach, time to value, support model, security posture, integration fit, and credibility from similar wins. If your differentiators aren’t clearly mapped to their criteria, you’ll be compared on price or familiarity, and you’ll lose deals you thought were “in the bag.”
Why Now? (Urgency, The Metrics & ROI)
Even when the customer wants to solve the problem and likes your approach, deals stall unless the timing is financially undeniable. “Why Now?” is driven by Metrics and ROI: quantified impact, measurable outcomes, and the cost of delay. You translate the pain into numbers (lost dollars, wasted hours, defect rates, churn, risk exposure) and connect your solution to a clear return, payback period, and business case that leadership can approve. This “why” is what turns agreement into action because it gives the Economic Buyer and the broader decision team a rational, provable reason to prioritize your project this quarter, not “sometime later.” It’s the Why that creates urgency, even when there is no compelling event.
3 Discoveries for Your SKO Agenda
As we head into Sales Kickoff (SKO) season, leaders are at a crossroads. Before you finalize your slides, consider these three discoveries from the field:
1. The Real Cost of Time
Taking 100 reps off the field for two days represents millions of dollars in potential revenue. If your SKO is just a “celebration” or a series of product updates, the ROI is negative. Every session must be a deliberate investment in better execution.
2. The Retention Gap
The “Lecture Model” is a budget killer. Research shows 85% of lecture-based content is forgotten within 30 days. To make the message stick, you must move from telling to doing. Use workshops where participants “do the work” on their actual deals to ensure the training survives past February.
3. Building Belief
To sell like an A-player, a seller needs to believe in their product. But how do leaders create belief in their teams?
I share methods and techniques in our Infinite Sales Leadership courses. One of them is about understanding the reasons why customers buy from us. If sellers don’t know why customers choose them, and why they choose now, they can’t believe in their own solution.
Building a High-Impact SKO
The difference between a “good” SKO and a “transformative” one is the focus on purpose over process. Is your agenda designed to build order-takers, or to build believers?
Turning the Tide
The most rewarding part of my tour wasn’t the travel; it was watching the lightbulb turn on. We helped these leaders move away from features and toward value, pain, and purpose. They didn’t just leave as better sellers; they left as happier, more confident professionals.
Is your SKO agenda designed to build order-takers or value-creators?
Because the client has identified real pain points to remedy—problems that are costly, risky, or blocking priorities. If there’s no meaningful pain, there’s no real reason to act.
Because the client has established decision criteria that reveal your differentiators prominently.
Because the client has built a business case using Metrics and ROI, proving urgency and priority. They can quantify the cost of delay; meaning every day they wait, they lose quantified money