Sales and Cigars · 2026-04-21 · 8 min
Most CEOs think they have a sales hiring problem, a sales performance problem, or a pipeline problem. But often, the real issue is deeper - and harder to see. In this solo episode of Sales & Cigars , Walter Crosby breaks down one of the most expensive hidden problems in growing companies: a lack of shared sales story and positioning clarity. This is not usually a problem caused by bad salespeople. In fact, it often shows up inside experienced sales teams. Reps sound confident. Conversations seem productive. Deals appear to move forward. But underneath the surface, the team is defaulting to pitching instead of guiding buyers through a clear story. Walter explains why pitching is often a coping mechanism, how false momentum shows up in the pipeline, and why this issue compounds as companies grow.
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