Why Your Deals Aren’t Closing: The Gaps Reps Won’t Tell You (Until You Coach Differently)

If deals keep stalling and the story is always “they’ve gone quiet,” the real issue usually showed up much earlier — and it often isn’t being said clearly in coaching.

This session with Steve Myers and Richard Smith gets into the actual reasons deals don’t close, and how deal coaching can surface the truth without turning into a forecast grilling.

We break down how to diagnose what’s missing in the deal, validate what’s real vs assumed, and coach reps beyond surface-level reasons into compelling, evidence-backed buying drivers.

This is for you if you're a sales leader dealing with:

• “Close” deals that never close and pipelines full of hope instead of proof
• Reps who can’t clearly articulate why a prospect will actually buy
• Stalled opportunities where next steps were never properly locked in
• A coaching culture where people tell you what sounds good, not what’s true

In this episode, you’ll hear the deal-killers hiding in plain sight:

• Reps mistaking “they want X” for a real problem worth solving
• “I think…” language replacing evidence — and nobody challenging it properly
• Surface-level pain (“save time,” “be more efficient”) with no detail behind it
• Discovery that never gets to the full three levels of pain: symptom → business impact → how people feel about it
• No clear understanding of where budget comes from, how the decision gets made, or where veto power sits
• Leaders accepting the rep’s narrative without validating what’s actually happened
• Weak upfront contracting — so next steps aren’t agreed, meetings aren’t booked, and deals drift into silence
• Repeated stalls that look like a skills issue… but are really discomfort, need for approval, or fear of being too direct
• Keeping a deal alive when the best outcome is clarity to qualify out and redirect effort elsewhere

Timestamps:

• 0:00 – 5:13 | Creating the conditions for truth: Removing agendas and power dynamics so the real issues surface
• 5:14 – 7:31 | Diagnosing what’s really going on: Buying journey context, decision process clarity, and validating the rep’s story
• 7:32 – 13:02 | The real reasons deals don’t close: Evidence vs belief, solution-language, and coaching to three levels of pain
• 13:03 – 18:10 | Repeat deal failure: Technical vs mindset problems, and why reps don’t use the skills they “know”
• 18:11 – 21:52 | Prep that prevents stalls: Meeting plans, upfront contracting, objectives, and keeping calls on track
• 21:53 – 24:05 | Outcomes that matter: Immediate next actions, strategic skill-building, confidence — and when to qualify out