Most sales discovery questions fail before the buyer even answers them. Questions such as "What keeps you up at night?" and "What challenges are you facing?" have been used so often that buyers respond almost automatically, giving sellers little useful insight. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey challenge sales professionals to replace generic scripts with informed, business-specific questions that improve discovery, uncover operational consequences, and help buyers think differently about their problems. They also explain how artificial intelligence and Generative AI can help sellers prepare deeper question paths, navigate Complex Deals, and establish themselves as trusted advisors rather than interchangeable vendors.
Key Topics Discussed
Why generic discovery questions produce generic answers — 00:00
Kevin and Sean open by dismantling familiar questions such as "What are your goals?" and "What keeps you up at night?" Buyers have heard these questions hundreds of times. Strong discovery must demonstrate Business acumen, industry knowledge, and a genuine understanding of the customer's operating environment.
Researching the customer's business before discovery — 01:51
Public information about industries, competitors, economic pressures, and business trends is readily available. Sellers should use frameworks such as PESTEL and the Business Model Canvas to understand what drives the prospect's economics, how the company creates value, and where a proposed solution might improve Revenue generation, ROI, or operational performance.
Using operational questions to expose real business problems — 03:11
Kevin illustrates how questions about month-end close procedures, manual spreadsheets, reporting delays, and disconnected Sales processes can produce a meaningful conversation. The goal is not merely to identify which system a prospect uses. It is to uncover the consequences, workarounds, handoffs, and hidden costs that make change valuable.
Using AI to create better discovery question paths — 05:58
Sean presents a practical method for using ChatGPT, Claude, Gemini, Copilot, or another AI platform to develop branching discovery questions. Instead of asking an AI tool for one generic question list, sellers can ask it to anticipate several possible buyer answers and then generate the appropriate follow-up questions for each response. This turns AI prompts for B2B sales prospecting into preparation for a real business conversation rather than superficial personalization.
Teaching the customer how to buy — 07:00
In Enterprise Sales, buyers often understand their current situation better than they understand the process of selecting and implementing a new solution. Sellers must guide the Buying Committee through workflow changes, implementation tradeoffs, user concerns, and expected outcomes. This is where Value selling becomes practical: the seller connects the solution to the customer's processes, risks, and desired business results.
Improving questions through sales management and peer coaching — 10:03
Kevin explains how a VP of Sales or sales manager can improve discovery without simply criticizing the team's existing questions. Questions should be evaluated based on whether they advance the next step, increase deal value, improve Pipeline Velocity, or strengthen the seller's competitive position. Sales Enablement can also become more effective when AEs, SDRs, and sales leaders exchange successful questions and discuss the order in which they should be asked.
Key Quotes
Kevin Lawson — 00:00
"Buyers have heard these questions hundreds of times, and they answer them on autopilot."
Sean O'Shaughnessey — 00:45
"Questions that show that you understand the business… force your customer or your prospect to have a clearer thought process."
Sean O'Shaughnessey — 09:00
"You know more about selling your product than they know about buying your product. You have to lead them through the way."
Kevin Lawson — 12:03
"Stop asking questions the buyer has already heard. Start asking the questions that get the buyer to say, 'I've never thought about that.'"
Additional Resources
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PESTEL analysis: A framework for examining the political, economic, social, technological, environmental, and legal forces influencing an industry.
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Business Model Canvas: A tool for understanding how a company creates, delivers, and captures value.
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The Challenger Sale: A sales methodology centered on teaching customers something valuable, tailoring the conversation, and leading the buying process.
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Generative AI platforms: ChatGPT, Claude, Gemini, and Microsoft Copilot can help sellers research industries, anticipate buyer responses, and develop stronger discovery questions.
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B2B Sales Lab: A community where sales professionals and sales leaders can develop their sales acumen, discuss active opportunities, and improve their approach to B2B sales.
A Significant Actionable Item from this Podcast
Create a branching discovery question bank for one customer segment or active opportunity.
Begin with five questions you currently ask during discovery. Eliminate any question the buyer could answer without thinking. Then use an AI tool to generate five plausible responses to each remaining question and develop two or three follow-up questions for every response.
Do not treat the resulting output as a script. Review it for business relevance, arrange the questions in a logical sequence, and identify which questions reveal operational impact, financial consequences, organizational resistance, and decision criteria. Then compare the question bank with a successful AE, SDR, sales manager, or industry peer.
This is a practical form of AI-powered sales coaching and human-in-the-loop automation. AI expands the seller's preparation, but the seller must still apply judgment, listen carefully, and decide which path to pursue. Done well, the exercise improves Sales success, supports B2B sales pipeline predictability, and helps accelerate Complex Deals without replacing the human conversation.
Summary
Strong discovery is not a contest to see who can ask the cleverest question. It is evidence that the seller understands the prospect's business well enough to uncover something the buyer has not fully considered. In this episode, Kevin and Sean show how better research, disciplined questioning, sales management coaching, and Generative AI can help sellers move beyond scripted conversations and into meaningful business diagnosis. For sales professionals who want to strengthen their Messaging, improve Value selling, navigate multi-stakeholder deals, and earn the position of trusted advisor, this episode offers a direct and highly practical approach. Listen before your next discovery call—and reconsider every question that allows the buyer to answer on autopilot.
B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com
You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/
You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/
You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin
You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/
