THE SECRET QUESTIONS ONLY THE BEST ASK...

5 Aug 2026 · 52 min
The Brutal Truth about Sales and Selling - We interview the world's best B2B Enterprise salespeople.

5 Aug 2026 · 52 min

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In this episode of the Sales Leadership Show, host Brian Burns interviews veteran enterprise software salesperson Dean Wiener, who has spent over 20 years selling the same technology to CIOs and other senior executives. Dean shares hard‑learned lessons about how large, top‑down deals are won and why most salespeople waste time on low‑value activity. He emphasizes a problem‑centric approach—selling the business need rather than product features—using “TED” questions (Tell me, Explain, Describe) to uncover fear, need, or envy driving a buyer. Dean outlines his ABC account‑prioritization system, devoting three‑quarters of his effort to A‑accounts while still nurturing B and C accounts. He stresses quality over quantity, the importance of performance (the execution of calls, demos, and conversations) versus mere activity counts, and the necessity of rigorous debriefs after wins and losses. Trust and relationship building are portrayed as a family‑like bond with customers, reinforced by 24‑hour availability and personal branding. The conversation also covers industry shifts toward line‑of‑business and cloud‑driven solutions, the move from perpetual licensing to subscription models, and the growing role of partners and solution consultants. Dean’s “super‑power” is trust, built through consistent follow‑through and empathy. Throughout, he shares personal anecdotes that illustrate judgment, focus, and the motivational drivers of fear and winning, offering actionable advice for sales professionals seeking to close multi‑seven‑figure deals.

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