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Discovery Questions That Drive Real Insight
Unlocking Conversations That Reveal What Really Matters Post #15
Mort Greenberg
September 14, 2025
Hi,
Great sellers don’t just ask questions, they ask the right questions. Discovery isn’t about ticking boxes on a call sheet; it’s about earning the right to deeper answers. In today’s competitive market, customers are overloaded with surface-level pitches.
What separates the average from the exceptional is the ability to uncover true motivations, hidden roadblocks, and unspoken goals. Insight doesn’t come from asking more questions; it comes from asking better questions.
When you master discovery questions that drive real insight, you position yourself not as a vendor, but as a trusted partner who “gets it” faster and better than the competition.
This workshop is designed to elevate how you approach conversations. Whether you’re a seller, a sales manager, or a business owner, you’ll learn how to go beyond generic questions and create a dialogue that reveals the real decision-making drivers.
By the end, you’ll have a discovery framework you can use in any industry, with any customer, and at any stage of the sales cycle.
WHY THIS WORKSHOP MATTERS
The quality of your discovery shapes the quality of your sale. Poor discovery leads to chasing unqualified prospects, misaligned proposals, and stalled deals. Great discovery shortens sales cycles, increases close rates, and improves customer satisfaction. Mastering this skill means building trust faster, qualifying smarter, and finding opportunities others miss.
Turn to Best View Tables Below
DO’S AND DON’TS
WHAT TO DO | WHAT NOT TO DO |
Prepare before the meeting with relevant research. | Don’t make it an interrogation, keep it conversational. |
Listen actively, don’t just wait to talk. | Don’t jump to pitching before you fully understand the need. |
Layer your questions, start broad, then drill deeper. | Don’t rely only on “checklist” questions from a script. |
Mirror the customer’s language to build rapport. |
THE 3 WORKSHOP STEPS
Step | Description | How to Execute |
1. Prepare with Purpose | Research the customer’s market, company, and role before you meet. | Use LinkedIn, news, and earnings reports to find triggers and potential needs. Identify 3 areas you want clarity on. |
2. Layer Your Questions | Start broad, then move to specifics, then to implications. | Broad: “What’s your top priority this quarter?” Specific: “What’s preventing you from hitting that target?” Implication: “If this continues, what will it cost the business?” |
3. Listen, Confirm, Expand | Show you understand by paraphrasing, then explore further. | “So what I’m hearing is that speed-to-market is critical. Could you walk me through how delays are impacting your customers?” |
3 ITEMS TO FOCUS ON FOR MAXIMUM IMPACT
Focus Area | Tip | Example |
Ask One Question at a Time | Overloading customers with multiple questions can derail depth. | Instead of “What’s your budget and timing?” ask “What’s your ideal timeline?” and then “How is budget allocated for this type of project?” |
Follow the Emotional Breadcrumbs | Listen for tone, hesitation, or passion—they signal where to dig deeper. | If a customer sighs when discussing vendors, follow up: “Sounds like past partnerships have been frustrating—what happened?” |
Make the Customer the Hero | Frame questions so the customer sees themselves as the solution’s driver. | “If you could solve this challenge tomorrow, what would that win look like for your team?” |
3 ACTIONS TO TAKE AFTER THE WORKSHOP
Build a layered discovery plan that adapts to any client conversation.
Identify and explore emotional drivers behind buying decisions.
Use customer language to position solutions more persuasively.
READING LIST
Title | Author | Year | Publisher |
The Lost Art of Closing: Winning the Ten Commitments That Drive Sales | Anthony Iannarino | 2017 | Portfolio Penguin |
Daniel H. Pink | 2012 | Riverhead Books | |
The Sales Tactician: Spycraft Techniques For Revenue Success | Mort Greenberg | 2025 | digitalCORE Publishing |
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The Revenue Workshop isn’t theory. It’s a field-tested system used by real leaders, in real markets, under real pressure.
Each newsletter is based on one of over 300 workshops and worksheets found in the eight books of the RevenueVsSales.com and TheFocusedSeller.com book series.
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Thank you for your time!
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