In this hard‑hitting discussion, Steve Gielda reveals how hidden assumptions can quietly sabotage your sales success. Drawing on rigorous win‑loss analysis, Steve highlights three critical areas where sales reps consistently misjudge opportunities, derailing deals.
1. Misreading Business Metrics
Salespeople often think they understand which business metrics matter most to a prospect. In reality, superficial measures frequently overshadow deeper, more strategic indicators. Steve stresses the importance of going beyond surface metrics by asking, “What are the 2–3 business metrics you’re held accountable for?” This simple yet powerful question exposes the real value levers driving buyers’ decisions—all too often overlooked in typical sales conversations.
2. Incomplete Stakeholder Mapping
Another common pitfall is the assumption that sales reps are engaging with all relevant decision-makers. Steve points out that overlooked influencers can hold the key to winning an opportunity—especially when competitors cultivate relations the rep doesn’t even see. A revealing probe like, “Who is our competition speaking with that we aren’t?” helps uncover these hidden players and ensures your approach includes all stakeholders.
3. Price as the Excuse, Not the Cause
When deals fall apart, salespeople often default to blaming price. Yet Steve’s data shows that pricing is rarely the primary deal-breaker. The real culprits lie elsewhere—perhaps in perceived product fit, implementation concerns, or internal dynamics. To uncover these, Steve advises asking, “Besides price, what criteria will you use to make your choice?” This question forces buyers to articulate their true decision factors, exposing the real barriers to closing.
How to Break the Cycle of Assumptions
Steve advocates building a culture of critical inquiry through peer challenge. Before critical meetings, reps should rehearse with a colleague or manager willing to play “devil’s advocate”—not to grill them, but to purposefully test and uncover flawed assumptions. Sales managers play a crucial role here, too: stepping beyond administrative tasks to engage in coaching that stretches strategic thinking, rather than simply reviewing CRM data.
The episode closes with a practical method: select one or two high-priority deals and unpack every assumption—step by step—with a peer. Doing so transforms unconscious biases into deliberate, evidence-backed plans, and builds invaluable habits. Over time, these habits produce more insightful questions, stronger alignment with buyer needs, and ultimately a healthier sales pipeline.
Bottom line: Unchecked assumptions erode credibility, stall pipelines, and ultimately sabotage your sales success. By pausing to question metrics, stakeholder coverage, decision criteria—and by routinely challenging internal assumptions—sales teams can sharpen their approach and sell more effectively.