Two Tall Guys Talking Sales

Hosted by Kevin Lawson and Sean O'Shaughnessey

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Oct 2026

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"Two Tall Guys Talking Sales," where Sean O'Shaughnessey and Kevin Lawson discuss a single sales topic. Kevin and Sean together have about 60 years of experience in professional selling. This podcast helps people in sales, sales leadership, and business leadership or company owners realize the maximum value of their company by improving their revenue generation capability. This podcast is designed to help those people enhance their companies' sales management practices, methodologies, processes, teams, and messaging. Sean O'Shaughnessey and Kevin Lawson are Fractional Vice Presidents of Sales. They operate their own companies separately but have partnered for this podcast to advise salespeople and SMB companies on successful strategies and methodologies. Kevin is the CEO of Lighthouse Sales Advisors. Lighthouse Sales Advisors is a sales leadership solution provider for small businesses. Lighthouse helps business owners navigate the potential pitfalls around sales growth, sales turnaround, or scaling up by leveraging sales acumen and decades of experience to build effective sales teams. https://www.lighthousesalesadvisors.com/ Sean is the CEO of New Sales Expert. He helps company owners realize the maximum value of their company by improving their revenue generation capability. He helps owners enhance their sales management, methodologies, processes, teams, and messaging.

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October 20, 2026Episode 21116 min

Find the Real Decision-Makers With Smarter Sales Discovery Questions

Discovery calls can determine whether a B2B sales opportunity advances or stalls, but too many salespeople rely on generic questions that reveal little about the prospect's business. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey explore how to build a discovery question bank that uncovers business challenges, identifies decision-makers, and positions salespeople as credible business advisors. From hypothesis-driven questioning and the PESTEL framework to understanding financial pressures and navigating the buying committee, Kevin and Sean share practical sales strategies that can make your very next discovery meeting more productive. Whether you're an individual salesperson looking to improve your sales success or a sales leader strengthening your team's sales processes, this episode delivers questions you can put to work immediately. Key Topics Discussed (00:00) Building a Discovery Question Bank That Improves Sales Performance: Kevin introduces the discovery question bank as a practical sales enablement resource, similar to battle cards but focused on the early stages of the buyer journey. Sean explains how individual salespeople can use it to sharpen their skills, while sales managers can develop a shared question bank during team meetings to improve discovery consistency and effectiveness. (03:41) Demonstrating Business Acumen Instead of Pitching Products: Sean challenges salespeople to stop asking questions that could be answered by visiting the prospect's website. Instead, ask how the company goes to market, acquires customers, and generates revenue. These conversations expose organizational challenges, internal dynamics, and opportunities for value selling while establishing the salesperson as a business partner rather than another vendor. (05:35) Using Hypothesis-Driven Discovery and the PESTEL Framework: Kevin explains how researching industry pressures, company priorities, and market conditions helps salespeople formulate intelligent hypotheses before meeting a prospect. Using an example involving professional services and financial compliance, he shows how carefully crafted questions can uncover real business needs. Even when a hypothesis proves incorrect, the discovery process can reveal opportunities that generic questioning would miss. (09:09) Identifying Decision-Makers and Navigating the Buying Committee: What happens when your initial contact cannot answer an important business question? Sean explains why that knowledge gap may be your best opportunity to reach additional stakeholders. By asking who else in the organization understands a particular issue, salespeople can expand their relationships, identify decision-makers, and better navigate complex B2B buying decisions. (11:00) Understanding How Prospects Lose Money and Where You Can Create Value: Sean encourages salespeople to investigate the economic pressures affecting their prospects, including supply chain disruptions, tariffs, and changing operating costs. Understanding where a company loses money creates opportunities to connect solutions to meaningful financial outcomes. These conversations help shift discovery toward business value, profitability, and potential ROI. (12:42) Practical Discovery Questions You Can Use in Your Next Sales Meeting: Kevin closes with a collection of questions covering success metrics, budget authority, decision criteria, consequences of inaction, previous solutions, and internal stakeholders. Learn how questions such as "What happens if you don't solve this problem in the next six to 12 months?" help reveal urgency, establish priorities, and improve the quality of your sales opportunities. Key Quotes Kevin Lawson (02:45): "It's gotta be effective, not just efficient." Sean O'Shaughnessey (04:00): "I try to talk about business, because I want to be perceived as being a business partner." Kevin Lawson (08:46): "You've actually gotten them to tell you what their pain point is, what their goal is, and how you can help them solve it." Sean O'Shaughnessey (09:40): "When the customer doesn't know the answer to your discovery question, that allows you to say, 'Is there somebody else in the organization that might know the answer to that question'" Sean O'Shaughnessey (12:33): "Because when a CFO finds out that you can stop them from losing money, life will be better for you." Additional Resources The hosts reference several frameworks and sales enablement resources that can help structure more effective discovery conversations: PESTEL Framework: A strategic analysis approach for identifying political, economic, social, technological, environmental, and legal factors affecting a prospect's industry. Kevin explains how this type of research helps salespeople develop hypotheses and prepare better discovery questions. Sales Battle Cards: Sales enablement tools that organize competitive positioning, messaging, and product information. Kevin compares these resources to the discovery question bank discussed in the episode. Product FAQs and Company Websites: Existing sources of customer and product information that salespeople should review before discovery meetings, so they can focus on insights not found through basic research. A Significant Actionable Item from this Podcast Create a Five-Question Discovery Bank Before Your Next Prospect Meeting Before your next discovery conversation with a new prospect, research the company's website, business model, and the external pressures affecting its industry. Develop a hypothesis about a business challenge your solution might address. Then prepare five questions that explore different dimensions of the opportunity: Business performance: "How are you measuring success today, and what KPIs are you accountable for?" Financial consequences: "What happens if you don't solve this problem in the next six to 12 months?" Decision authority: "Who ultimately signs off on the budget for this type of initiative?" Evaluation process: "When you have evaluated solutions before, what criteria mattered most to the decision team or you?" Previous attempts: "Have you ever tried to solve this before? Have you tried any other solutions? How did that work?" Adapt these questions to your prospect's business rather than reading them mechanically. Listen for answers that challenge your assumptions, reveal additional stakeholders, or expose a financial problem worth investigating further. If you lead a sales team, turn this into a collaborative sales management exercise. Ask each salesperson to contribute questions that have produced meaningful discoveries, then assemble a shared question bank your team can refine over time. The objective is to leave every discovery meeting knowing something important about the prospect's business that you did not know when you entered. Summary Great discovery is about understanding the prospect's business, not simply collecting enough information to prepare a proposal. In this practical episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey demonstrate how thoughtful research, strong business acumen, and a well-constructed discovery question bank can transform early sales conversations. You'll hear how to test assumptions, uncover financial pressures, expand relationships within the buying committee, and ask questions that separate competent salespeople from trusted business advisors. Best of all, Kevin shares specific discovery questions that you can adapt and use immediately. If you want more productive discovery calls, stronger B2B sales opportunities, and a better understanding of what motivates prospects to buy, this is an episode worth adding to your playlist before your next customer meeting. 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/

October 13, 2026Episode 21016 min

Stop Automating Bad Sales: Use AI to Win More B2B Deals

Artificial intelligence is changing B2B sales, but using AI to send more automated emails or accelerate ineffective sales processes misses the real opportunity. What if AI could help you understand your customers more deeply, identify hidden opportunities in your pipeline, and deliver the kind of personalized attention that once defined great customer relationships? In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey explore how AI is transforming sales research, account planning, and customer engagement. From analyzing CRM data to creating customer-specific presentations and uncovering revenue opportunities, Kevin and Sean share practical sales strategies that help salespeople work smarter, strengthen relationships, and win more business without sacrificing the human connection that drives sales success. Key Topics Discussed 00:00 – AI as a Sales Assistant, Not an Automated Salesperson: Kevin explains why the greatest value of artificial intelligence comes from helping salespeople research, analyze, and make better decisions. Discover why automating ineffective outreach with AI just creates more noise, while human-in-the-loop automation can improve customer engagement and sales effectiveness. 01:43 – Bringing Back Personalized Selling with AI: Sean draws a fascinating parallel between the neighborhood general stores of the early 1900s and today's AI-enabled sales environment. Learn how generative AI lets you recreate highly personalized customer relationships at scale, tailoring messaging, presentations, and conversations to each buyer's specific needs and business challenges. 05:46 – Using AI and CRM Data to Find Hidden Sales Opportunities: Kevin shares real-world examples from HubSpot, Zoho, and Pipedrive that demonstrate how AI can identify qualification gaps, analyze historical wins and losses, and reveal overlooked opportunities. These insights improve sales management, sharpen pipeline prioritization, and help salespeople spend their limited customer-facing time on activities that actually produce revenue. 08:36 – Turning Annual Reports into Powerful Sales Intelligence: Sean demonstrates how B2B sales professionals can use AI tools such as ChatGPT, Claude, and Gemini to analyze corporate 10-K reports and SEC filings. Discover how to identify a prospect's business priorities, uncover challenges relevant to your solution, and develop compelling, customer-specific presentations that emphasize value selling rather than generic product pitches. 11:46 – AI-Powered Account Planning for Smaller Businesses: You don't need Fortune 500 customers to benefit from AI-driven sales strategies. Kevin explains how analyzing 24 months of internal sales data can uncover product trends, pricing pressures, growth opportunities, and customer risks. Learn how to turn ordinary quarterly business reviews into strategic conversations that strengthen relationships, boost revenue, and differentiate your company from competitors. Key Quotes Kevin Lawson (01:35): "This is you getting more out of your selling day by using AI as a tool, not as a silver bullet." Sean O'Shaughnessey (04:12): "Because you have this amazing sidekick sitting beside you all the time, keeping track of all the details, keeping track of all the wisdom, researching every single thing that's going on in the company." Kevin Lawson (07:38): "This is effectiveness over efficiency." Sean O'Shaughnessey (11:26): "It's gonna be about how you are going to help your customer solve their problems." Kevin Lawson (13:29): "So when you're thinking about using AI, think about the story you're gonna tell about the insight that you've derived with your AI-assisted sales enablement." Additional Resources The following tools and information sources are discussed in the episode: ChatGPT, Claude, and Google Gemini: Generative AI platforms that can assist with customer research, document analysis, account planning, and personalized sales presentations. HubSpot, Zoho, and Pipedrive: CRM platforms discussed as examples of how AI can help salespeople analyze opportunities, identify qualification gaps, and improve sales processes. SEC Form 10-K and Form 8-K: Public company filings that provide information about business performance, strategic priorities, financial risks, and significant corporate developments. A Significant Actionable Item from this Podcast Use AI to uncover five actionable insights about one important customer before your next sales conversation. Choose an active customer or prospect with an upcoming meeting. If the company is publicly traded, obtain its latest 10-K and relevant recent SEC filings. If you're working with a smaller, privately held customer, consider your company's internal sales history for that account, including purchasing patterns, product mix, and pricing trends. Use an appropriate AI tool to analyze the information and identify five insights that could influence the customer's business decisions. Look for growth opportunities, emerging risks, changes in purchasing behavior, or problems your company might help solve. Keep confidential information within approved systems, and verify the AI's findings against the source data. Select the most compelling insight and incorporate it into your next customer conversation. Instead of delivering your usual product presentation, lead with a relevant business observation and a thoughtful question that encourages discussion. The objective is to demonstrate that you understand the customer's business, not simply that you know how to use AI. One well-researched observation can open a more valuable conversation than another generic sales presentation. Summary AI is creating an extraordinary opportunity for B2B salespeople to combine the personal attention of traditional relationship selling with the analytical capabilities of modern technology. But the competitive advantage won't come from generating more emails, creating more presentations, or automating every stage of the sales process. It will come from using better information to make smarter decisions, deliver more relevant messaging, and create meaningful customer value. In this episode, Kevin Lawson and Sean O'Shaughnessey move beyond the AI hype to share practical techniques you can implement immediately, whether you're managing complex enterprise deals or growing accounts with smaller businesses. If you want to improve sales productivity, uncover opportunities your competitors are missing, and turn AI-assisted research into stronger customer relationships and measurable revenue growth, this episode of Two Tall Guys Talking Sales deserves a place on your playlist. 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/

October 6, 2026Episode 20916 min

Your Sales Comp Plan May Be Killing Revenue Growth

What happens when your best salesperson hits quota in October? A poorly designed compensation plan may quietly tell them to slow down. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey examine why sales compensation accelerators can be one of the most profitable tools available to a sales leader. They break down the economics behind above-quota sales, explain why fixed costs make incremental revenue especially valuable, and challenge the common fear that high-performing salespeople can somehow be "paid too much." For CEOs, CFOs, sales managers, and any VP of Sales preparing next year's compensation plan, this conversation connects sales management, revenue management, sales motivation, and business valuation in a very practical way. Key Topics Discussed Why Sales Compensation Plans Need Accelerators — 00:49 Sean opens the discussion with a simple problem: once a salesperson reaches quota, what reason have you given them to keep selling? A flat commission structure can unintentionally create a ceiling. Properly designed accelerators reverse that incentive, giving salespeople a financial reason to keep pushing beyond 100% rather than protecting deals for the next compensation period. Incentivize the Outcomes the Business Actually Needs — 03:08 Kevin argues that compensation should do more than reward revenue. It should reinforce the sales strategies that matter to the business. If existing customers will continue buying with relatively little selling effort, paying disproportionately for those transactions may not produce the growth the company needs. Sales processes and compensation design can deliberately incorporate net-new logos, incremental growth, renewals, or other strategic outcomes. Why Above-Quota Revenue Can Be Exceptionally Profitable — 05:24 Sean explains the financial logic behind accelerators. By the time the company reaches its planned revenue target, much of its fixed-cost structure—base salaries, benefits, rent, and other operating expenses—has already been covered. In businesses with low incremental delivery costs, additional revenue can therefore carry significantly higher margins. Paying a salesperson a higher commission rate on that additional business can still generate substantially more profit for the company. Using Compensation Tiers to Drive Sales Success — 07:08 Salespeople tend to be competitive and goal-oriented. Sean describes how graduated accelerators at levels such as 80%, 100%, 120%, and even 140% of quota give sellers another target to pursue. Instead of compensation becoming static once quota has been achieved, the plan creates another scoreboard. That makes the compensation plan part of the company's broader Sales Enablement system, not merely an accounting mechanism. Stop Worrying That Top Salespeople Are Making "Too Much" — 08:27 Kevin challenges one of the most persistent assumptions in sales management: that a high commission check means the company is overpaying the salesperson. If the compensation structure is properly modeled, exceptional variable compensation should indicate exceptional company performance. The more important questions are whether the seller is generating profitable revenue, whether the plan rewards the right behaviors, and whether the economics work for the business. Better Sales Systems Can Increase Enterprise Value — 10:14 Compensation design does not exist in isolation. Kevin connects the comp plan to the sales playbook, marketing, company objectives, customer acquisition costs, customer lifetime value, and the larger operating model. A more intentional and predictable selling system can create a more efficient company—and potentially a more valuable one. Key Quotes Kevin Lawson — 03:08 "Incentivize the outcomes you want." That may be the episode's central principle. Compensation is not simply how a company divides up the money after a sale. It is a management system that tells sellers which results matter most. Sean O'Shaughnessey — 07:08 "You can actually afford to pay more money on your variable compensation…because it's going straight to your bottom line." Sean's point reframes accelerators as an investment in profitable incremental revenue rather than simply an additional sales expense. Kevin Lawson — 04:43 "If there's no additional trophy case winnings for going over quota, they'll stop." The language is colorful, but the management lesson is serious: once the economic incentive disappears, leaders should not be surprised when discretionary selling effort disappears with it. Sean O'Shaughnessey — 07:30 "They want to achieve the next goal. They want to make the next score." An effective compensation plan gives high performers somewhere else to go after they reach quota. Additional Resources Sean references several pieces of research supporting the use of sales accelerators and the risks associated with flat commission structures: Do Bonuses Enhance Sales Productivity? A Dynamic Structural Analysis of Bonus-Based Compensation Plans - https://pubsonline.informs.org/doi/10.1287/mksc.2013.0815 Kinks as Goals: Accelerating Commissions and the Performance of Sales Teams - https://ideas.repec.org/a/inm/ormnsc/v71y2025i6p4622-4642.html Motivating Salespeople: What Really Works - https://store.hbr.org/product/motivating-salespeople-what-really-works/R1207D Sean also invites listeners who are working through compensation plans, revenue generation challenges, and related B2B sales management questions to continue the discussion in the B2B Sales Lab at b2b-sales-lab.com. A Significant Actionable Item from this Podcast Before finalizing your next sales compensation plan, examine what happens economically and behaviorally when an AE reaches 100% of quota. Do not stop at asking whether the commission percentage seems reasonable. Model what happens to company gross profit on the next dollar of revenue after the planned fixed costs have already been covered. Then ask what behavior your existing plan encourages at 100%, 120%, and 140% attainment. If the salesperson receives essentially the same economic reward for the next deal after reaching quota—or worse, has a reason to push that deal into the following year—you have built a sales management problem into the compensation plan. Consider creating meaningful acceleration tiers above quota and tying selected incentives to the outcomes the company actually needs: net-new logos, incremental revenue, profitable growth, renewals, or another strategically important result. Compensation should align the salesperson's preferred behavior with the company's preferred outcome. Summary Sales compensation is not simply an HR exercise or a spreadsheet owned by finance. It is one of the most direct ways a company communicates its priorities to the sales organization. In this episode, Kevin and Sean explain why well-designed accelerators can improve Sales success while simultaneously increasing profitability, strengthening sales culture, and encouraging top performers to keep producing after quota has been reached. They also dismantle the assumption that a large commission check is inherently bad for the company. When the economics are designed correctly, the opposite should be true: the salesperson makes substantially more money because the business is making substantially more money. If you are a CEO, CFO, sales manager, or VP of Sales responsible for B2B revenue generation, this episode offers a valuable framework for evaluating your next compensation plan. And if you are an AE wondering why your incentive plan seems to run out of ambition the moment you hit quota, you may want to send this episode to your boss.

September 29, 2026Episode 20817 min

Find Hidden Revenue in Existing Accounts: White-Space Analysis for B2B Sales

Most sales organizations are surrounded by useful customer data, but too often, they only examine it after something goes wrong. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey explore a more proactive approach to B2B sales management: using white-space analysis, customer segmentation, executive relationships, and disciplined account reviews to uncover untapped revenue generation opportunities. From identifying products an existing customer should buy to building stronger connections across the buying committee, Kevin and Sean show how better business acumen and smarter sales processes can turn ordinary account management into a repeatable sales success strategy. They also discuss how AI and workflow automation can capture customer conversations, distribute action items, and help the entire company contribute to value selling. Key Topics Discussed Why Sales Leaders Need Data to Find Them — 00:00 A VP of Sales cannot possibly know every detail about every active account, customer, and opportunity. Kevin explains why effective sales management requires systems that surface meaningful insights rather than forcing leaders to continually hunt through spreadsheets, CRM records, and individual deals to discover what has changed. Using White-Space Analysis to Increase Wallet Share — 01:59 Kevin walks through a practical method for comparing the purchasing behavior of an ideal client against similar customers. If strong customers consistently allocate a predictable percentage of their purchases across several product lines, those patterns can expose missing revenue opportunities. The zeroes—and unusually small percentages—are often where the opportunity begins. Finding Revenue Beyond Your Core Offering — 04:06 White space does not have to mean simply selling more of the existing catalog. Kevin shares an example in which becoming proficient at sourcing difficult-to-find products helped a supplier become a vendor of choice. The customer reduced the complexity of managing multiple vendors, while the seller created additional revenue and potentially higher-margin business. Segmenting Customers and Creating an Executive QBR Strategy — 05:20 Sean recommends categorizing customers into A, B, and C groups based on their available revenue potential—not merely what they currently purchase. The largest and most strategic accounts should have relationships extending beyond the AE or account owner. CEOs and other executives should engage top-tier customers, while the VP of Sales and salespeople systematically build relationships with the next tiers. Turn Customer Reviews Into a Program, Then Use AI to Capture the Learning — 09:23 A customer review should not be an occasional sales tactic. Sean argues that it should become an institutional sales process, reviewed by executive leadership and supported across the company. Record the meetings, use AI to produce transcripts, extract action items, and route those insights to sales, marketing, supply chain, operations, or anyone else who can improve the customer relationship. This is workflow automation applied directly to sales enablement and customer retention. Map the Relationship White Space Inside Complex Accounts — 11:54 Product white space is only one dimension of account growth. Kevin recommends analyzing relationship white space as well: Who is above your current contact? Who reports to them? Who could be promoted, transferred, or become part of the future buying committee? In enterprise sales and other complex deals, understanding those relationships creates augmented sales intelligence that can protect an account and uncover additional opportunities. Key Quotes Kevin Lawson — 03:36 "Insights is what we're after here." That sentence captures the larger point of the episode. Data alone has limited value. Sales success comes from turning customer information into insight that changes the next conversation, next question, or next sales strategy. Sean O'Shaughnessey — 09:23 "This needs to be a program, not a project, not a one-off." Sean's distinction matters because customer intimacy cannot depend on individual initiative. QBRs, account development, relationship building, and follow-through need to become part of the operating rhythm of the company. Kevin Lawson — 11:54 "Do the white space analysis on what they're not buying." The most useful sales opportunities may already exist inside your customer base. Instead of immediately searching for another prospect, examine where existing customers are underpenetrated—and determine whether there is a legitimate value-based reason to expand the relationship. Additional Resources Ideal Client Profile Analysis — Use your strongest representative customer as a benchmark for understanding expected purchasing patterns across products, services, locations, units, or other meaningful customer dimensions. White-Space Analysis — Compare what customers currently purchase against what similarly situated customers could reasonably purchase. Extend the analysis beyond products to services and relationships. Quarterly Business Reviews (QBRs) — Use structured customer reviews to evaluate performance, surface concerns, discuss future requirements, and identify opportunities to create additional value. EOS L10 Meetings — Sean references incorporating the customer-review program into the executive leadership operating cadence so meetings, findings, commitments, and follow-through remain visible. A Significant Actionable Item from this Podcast Choose one strategically important B customer this week—an account that has the potential to become an A customer—and conduct a simple white-space analysis. Start by comparing that customer's purchasing mix against one of your strongest ideal-client relationships. Where are the obvious zeroes? Which products or services are dramatically underrepresented? Then add a second dimension: relationships. Identify the people you know today and the people you should know throughout the organization. Do not turn the output immediately into a sales pitch. Use it to create questions for a customer review. Schedule a QBR or strategic account conversation and ask what has changed, where the customer is experiencing friction, what they are buying elsewhere, and what additional problems they would trust your organization to solve. Record the discussion—with appropriate permission—and use AI to create the transcript, summarize the insights, and distribute concrete action items. That combines data analysis, value selling, human-in-the-loop automation, and disciplined sales management into one repeatable process for growing existing B2B accounts. Summary Your next meaningful revenue opportunity may not require another prospect. It may already be sitting inside an existing account. In this episode, Kevin Lawson and Sean O'Shaughnessey demonstrate how disciplined white-space analysis can reveal missing product revenue, how structured QBRs can expose new customer needs, and why executive relationships matter when navigating multi-stakeholder deals. They also argue that customer knowledge shouldn't stay trapped in the salesperson's head: AI, transcripts, workflow automation, and company-wide action items can turn individual customer conversations into organizational intelligence. For salespeople, sales leaders, CEOs, and anyone responsible for B2B revenue generation, this episode offers a practical framework for increasing wallet share without defaulting to price competition. If your sales strategy calls for deeper customer relationships, better account penetration, and more predictable growth from customers you have already earned the right to serve, this is an episode worth hearing. 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/

September 22, 2026Episode 20717 min

Stop Chasing More Leads: Turn Your Quote Backlog Into Revenue

Sales organizations often assume that revenue growth starts with finding more leads. Kevin Lawson and Sean O'Shaughnessey challenge that assumption in this episode of Two Tall Guys Talking Sales. For manufacturers, distributors, and other B2B companies that generate a high volume of quotes, substantial revenue may already sit in the existing pipeline—buried under unanswered proposals, unclosed opportunities, and customers whose buying behavior has never been analyzed. Kevin and Sean break down how disciplined sales management, internal service-level agreements, quote follow-up, and wallet-share analysis can turn an overlooked quote backlog into a practical revenue generation strategy. Key Topics Discussed Sometimes You Don't Need More Leads—You Need to Manage the Ones You Have — 01:01 Before spending more money on lead generation, examine the opportunities already sitting inside the business. Existing customers and prospects have already raised their hands, requested pricing, or engaged with the sales process. Sean explains why even modest improvements in follow-up and wallet share can create meaningful sales success without adding another prospect to the top of the funnel. The issue may not be lead volume. It may be sales process discipline. Sending a Quote vs. Presenting a Quote — 02:21 Not every quote deserves the same sales strategy. A simple transactional request may warrant sending pricing and establishing a follow-up reminder. A larger opportunity involving a buying committee, multiple stakeholders, or a more complex decision should be handled very differently. Sean argues that sellers should present significant proposals rather than merely emailing them, using the conversation to reinforce value selling, business impact, and the reasons the customer should choose their company. Most importantly, the AE should leave that conversation with the next meeting already scheduled. Build Internal SLAs Around Quote Response and Follow-Up — 05:09 Kevin challenges sales leaders to establish clear internal service-level agreements for quote handling. How quickly should an inbound request be acknowledged? When should the salesperson respond? At what dollar value does a quote require a presentation instead of an email? When should operations, delivery, or finance become involved? These rules create measurable sales processes instead of relying on individual habits. With CRM, email, and phone activity connected through the sales tech stack, leaders can measure response time, conversion, staffing requirements, pipeline velocity, and coaching opportunities rather than managing by anecdote. Stop Being a Quote Factory: Measure the Cost of Customers Who Rarely Buy — 08:43 One of Kevin's favorite measurements exposes a hidden revenue management problem: customers who consume enormous quoting resources but rarely purchase. He describes a client whose supposedly valuable customer requested roughly 30 quotes per day, each requiring about 15 minutes of work, while converting only a tiny percentage into orders. That data changed the conversation. Instead of assuming the account was valuable because it was active, leadership could see the administrative burden it created and ask the customer how the supplier could become a stronger vendor partner. This is exactly the kind of analysis that can expose opportunities to reduce non-selling activities while improving revenue. Use Quote Win Rates to Estimate Wallet Share and Find Growth Opportunities — 10:52 Many companies cannot answer a basic account-management question: what percentage of the customer's category spend do we actually receive? Sean builds on Kevin's example to show how quote activity can provide an important clue. If a customer asks for dozens of quotes but awards very few orders, competitors are probably capturing much of that spend. At the opposite extreme, if the company wins nearly every opportunity it receives but is never invited to quote other product categories, that can signal another kind of growth opportunity. Both conditions deserve deliberate account strategy from the VP of Sales or sales leader. Turn Quote Data Into Better Sales Leadership Decisions — 12:20 The objective isn't merely cleaner CRM data. Quote conversion patterns can tell a sales leader where coaching is needed, which customers deserve more attention, which accounts consume disproportionate resources, and where cross-sell opportunities may exist. That creates a more informed approach to enterprise sales and account development: identify the anomaly, understand why it exists, and decide what the sales team should do differently. Key Quotes Kevin Lawson — 01:01 "Sometimes you don't need any more leads. Let that sink in. Sometimes you don't need more leads. Sometimes you need to do a better job of managing the ones you have." Sean O'Shaughnessey — 02:44 "There's a big difference between sending a quote and presenting a quote." Sean O'Shaughnessey — 03:42 "You do not leave until you say, 'Can you open your calendar and check when I can see you next to follow up on this?'" Kevin Lawson — 08:43 "My favorite metric bar none…for my existing customers, who's using me as a quote factory and consuming a lot of my resources versus who's actually buying from me?" Sean O'Shaughnessey — 12:20 "You as the sales leader, as the company owner, owe it to your salespeople, your sales team to guide them to say, 'This client needs more of our attention.'" Additional Resources B2B Sales Lab — 13:32 Sean discusses the B2B Sales Lab as a community where salespeople and sales leaders can bring real sales challenges, participate in office hours, learn from Sean and Kevin, and hear how sales professionals from other companies and industries have handled similar situations. Learn more at b2b-sales-lab.com. The episode also points listeners to a resource they already have in their sales tech stack: open opportunities and quote history in their CRM or ERP. Rather than treating those records as administrative clutter, sales leaders can use them to analyze quote volume, win rates, customer behavior, wallet share, follow-up discipline, and opportunities for additional revenue generation. A Significant Actionable Item from this Podcast Run an open-quote analysis and create an internal quote SLA. Set aside 60 minutes this week with the people responsible for sales, operations, and quote fulfillment. Pull every open quote or opportunity that has not been marked closed-won or closed-lost. Don't begin by debating whether the CRM data is perfect; the messy data is part of the problem you are trying to expose. Segment those opportunities by age, dollar value, customer, salesperson, and status. Then establish a simple set of internal rules: how quickly every quote request must be acknowledged, how quickly a complete response must be delivered, how often an outstanding quote must be followed up, and the threshold at which a salesperson must present the proposal rather than simply send it. Then look one level deeper. Calculate quote-to-order conversion by customer. Accounts requesting large numbers of quotes while awarding very little business deserve investigation. So do customers where you win nearly everything you quote but receive opportunities for only a narrow portion of what you could sell them. Those two extremes can reveal overlooked wallet-share opportunities, unnecessary administrative burden, and very different conversations your sales team should be having. This is basic workflow automation and sales enablement at its most useful: not adding technology for its own sake, but using your existing CRM, ERP, and sales processes to make the next action visible and measurable. Summary Before you ask marketing for another campaign, hire another SDR, or pour more money into prospecting, look closely at the business already sitting in your quote file. Kevin and Sean make the case that one of the fastest paths to stronger B2B sales pipeline predictability may be hiding among customers who already know you, opportunities your team already quoted, and follow-ups that never happened. This episode of Two Tall Guys Talking Sales is especially valuable for sales leaders in manufacturing, distribution, services, and other quote-intensive businesses where hundreds—or even thousands—of opportunities can accumulate without a disciplined process for resolving them. You'll hear how to distinguish transactional quotes from complex deals, establish internal SLAs, prevent ghosting by scheduling the next conversation before the current one ends, identify customers who are turning your team into a quote factory, and use conversion data as a practical proxy for wallet share. The bigger lesson is about sales management discipline. More leads will not repair weak follow-up, inconsistent sales processes, or accounts whose economics nobody has examined. Better data will not help if nobody acts on it. But when sales leaders combine clear operating rules with thoughtful analysis of customer behavior, an ordinary quote backlog can become a map showing where revenue, efficiency, and account-growth opportunities have been hiding.

September 15, 2026Episode 20618 min

Why Qualified B2B Deals Still Fall Apart: MEDDPICC, Economic Buyers, and Buying Committees

Filling every box in MEDDPICC does not mean you actually understand the deal. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey dig into one of the most dangerous problems in B2B sales: confidently believing you have identified the economic buyer, decision process, decision criteria, and business impact—only to discover late in the cycle that your assumptions were wrong. From complex deals and buying committees to stalled proposals and hidden influencers, Sean and Kevin explain why qualification is not a CRM exercise. It is an ongoing discipline that demands business acumen, better questions, and the willingness to challenge what you think you know. Key Topics Discussed MEDDPICC Is Only as Good as the Answers You Put Into It — 00:23 Sean explains why qualification frameworks such as MEDDPICCC, BANT, and SPICED can create false confidence. Completing the fields is not the same as validating them. In Enterprise Sales and other complex deals, getting one critical assumption wrong—especially the economic buyer or decision process—can derail the entire opportunity. The Economic Buyer vs. the Person Managing the Budget — 04:59 Kevin explores the distinction between someone who manages a budget and someone who can actually authorize a purchase. Using examples ranging from fleet fuel to professional services, he shows why strong sales strategies require follow-up questions about authority, contracting, procurement, and how decisions actually get made. Discovery Does Not End When the CRM Stage Changes — 08:20 Sean challenges the conventional sales process assumption that discovery is an early-stage activity. Effective salespeople keep testing their assumptions throughout the opportunity. The goal is to continually verify that the information remains accurate as the buying committee and deal evolve. Follow the Business Impact to Find the Real Power — 08:58 The economic buyer may control the money, but the executive or department receiving the business benefit can have enormous influence over the purchase. Sean explains how metrics such as reduced selling time, increased deal size, lower supply-chain costs, or stronger ROI can show which stakeholders need to join the conversation. This is where value selling and business acumen become essential. When the Deal Stalls, Reopen Qualification — 12:05 A proposal has been sent. A week passes. Then another. Silence. Kevin explains why being ghosted should trigger a review of the opportunity rather than another generic follow-up email. Reassess the person, the impact, and the decision process—and have the courage to admit that you may have missed something. Getting Better Sales Coaching Outside the Forecast Call — 13:11 Sean discusses the value of having experienced salespeople and sales leaders available to challenge assumptions before a deal falls apart. For AEs, sales managers, and VPs of Sales, stronger coaching can improve qualification discipline, pipeline velocity, and ultimately sales success. Key Quotes Sean O'Shaughnessey — 01:16 "If you know the correct answer, you almost always will know if you can win the deal, if you will win the deal, and also if you shouldn't win the deal because you're not a good fit." Kevin Lawson — 07:41 "Mastering it can take a lifetime." Kevin compares professional selling to golf: the basic mechanics are easy to understand, but consistently executing the right sales processes and asking the next question takes years of disciplined practice. Sean O'Shaughnessey — 08:20 "Discovery happens throughout the sales process." That distinction matters. Discovery is not something you complete and leave behind. In complex B2B opportunities, every new stakeholder, metric, objection, and approval step can change your understanding of the deal. Kevin Lawson — 13:05 "Take the 30 seconds of courage and ask the question." Sometimes deal acceleration does not require another sales tool or a more sophisticated message. It requires asking the uncomfortable question that exposes what you missed. Additional Resources MEDDPICCC — A qualification methodology frequently used in Enterprise Sales and complex deals to examine metrics, the economic buyer, decision criteria, decision process, pain, champions, competition, and other critical elements of an opportunity. BANT — A simpler qualification framework focused on budget, authority, need, and timing. SPICED — Another structured approach to understanding customer situations, pain, impact, critical events, and decision-making. B2B Sales Lab — A community where sales professionals and sales leaders can discuss real opportunities, sales management challenges, sales strategies, and execution issues with other practitioners. Visit b2b-sales-lab.com. September 22 B2B Sales Lab Office Hours — Sean and Kevin invite listeners to attend this session without becoming a member, giving salespeople and sales leaders an opportunity to bring real questions into the discussion. You can join at https://b2b-sales-lab.circle.so/c/live-events-w-two-tall-guys/sean-kevin-office-hours-bring-your-challenge-and-let-s-work-on-it-6-23-26-820b44-56a8a6-1bbbaa-e6a739-92888c-7cd4d454-33e8-44fd-a8a6-f43b8196c5f9 A Significant Actionable Item from this Podcast Take one meaningful opportunity in your pipeline and conduct a qualification audit without looking at the answers already entered in your CRM. For each major qualification point, ask yourself: What evidence do I actually have that this is true? Pay particular attention to three questions: Do I know who can actually authorize the purchase? Do I understand every meaningful step between my proposal and a signed agreement? Do I know which executive or department owns the business result my solution is supposed to improve? If any answer rests primarily on assumption, reopen discovery. Ask the additional question now—before the opportunity becomes another mysteriously stalled deal in the forecast. Summary Strong qualification is not about completing MEDDPICC, BANT, SPICED, or any other sales methodology. It is about knowing whether the information behind those fields is actually true. Sean and Kevin show how experienced B2B sellers keep testing their assumptions, map the real buying committee, connect business impact to organizational power, and recognize when a stalled opportunity is signaling a deeper qualification problem. If you sell complex deals, manage an Enterprise Sales team, or simply want more confidence in what is really sitting in your pipeline, download this episode of Two Tall Guys Talking Sales. It may cause you to look at a few "qualified" opportunities very differently.

September 8, 2026Episode 20516 min

Hit 120% of Quota: Manage Your Sales Territory Like a Business

What if the biggest obstacle to hitting your sales quota isn't your territory, your product, or even your competition, but the way you manage yourself? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey challenge sales professionals to stop thinking only like employees and start managing their territories like businesses. They break down the numbers every seller should know, explain why CRM discipline directly affects sales success, and show how average deal size, selling effort, close rates, and opportunity quality should drive daily decisions. For B2B sellers who want stronger business acumen, better sales processes, faster pipeline velocity, and more predictable revenue, this episode offers a practical framework for becoming the manager your territory needs. Key Topics Discussed Being Your Own Sales Manager — Not Just Your Own Boss (00:00) Kevin and Sean draw an important distinction between thinking like a business owner and actually managing yourself like one. Sean introduces the idea of treating your sales territory as your own franchise: the company provides the products and infrastructure, but you are responsible for how effectively that territory produces revenue. That mindset changes sales management from something your VP of Sales does to you into something you actively do for yourself. Define What a Successful Day Looks Like Before It Starts (02:48) Before the first call, email, meeting, or prospecting activity, Sean argues that a salesperson should know exactly what must happen for the day to count as successful. Sometimes that means completing an important proposal or responding to customer questions. Other days require prospecting, building pipeline, or starting new conversations. Effective sales strategies start with consciously allocating limited time and attention to the activities that matter most. Know Your Numbers—and Manage Beyond 100% of Quota (03:56) Kevin connects strong sales management to systems and controls: the system determines how the work gets done, while the controls tell you whether it is working. Sellers should know their quota, compensation structure, average deal size, close rate, customer concentration, territory concentration, and other performance metrics. More importantly, Kevin makes the case for planning toward 120% of quota rather than 100%, because salespeople can't fully control when complex deals close. That buffer is risk management, not optimism. Understand the True Cost of Winning a Deal (07:01) Sean goes beyond average deal size and introduces the idea of the "average transaction"—the total selling effort necessary to create that deal. How many meetings were required? How much time did those meetings consume? Did the opportunity begin through a referral, inbound inquiry, networking connection, or cold prospecting? When sellers understand the actual investment required to generate revenue, they can begin making better ROI decisions about where their selling time belongs. If the current activity model mathematically cannot produce quota attainment, working harder is not the answer. The assumptions or sales processes need to change. CRM Data Hygiene as a Competitive Advantage (10:41) CRM administration is often treated as an annoying non-selling activity. Kevin challenges that assumption directly. Good CRM data helps sellers understand where deals stall, where they lose, how often opportunities convert from particular stages, and whether the next step actually advances the buying process. Better information creates better coaching, stronger opportunity qualification, and potentially significant sales productivity gains. In that sense, reducing sales administrative burden should never mean eliminating the information needed to manage the business intelligently. The Next Step Must Describe Progress—not Just Another Meeting (13:22) "Schedule another meeting" is not a meaningful next-step opportunity. A legitimate next step describes what needs to be accomplished: confirm several requirements before preparing a proposal, identify the economic buyer, re-scope the solution, or determine whether a proof of concept makes sense. That level of specificity creates accountability and helps sellers manage complex deals based on evidence, not enthusiasm. Key Quotes Kevin Lawson (00:00): "Being your own manager is not the same as being your own boss." Sean O'Shaughnessey (02:12): "You are a franchisee of your territory, selling those products… You own it. You need to run it." Kevin Lawson (05:50): "You should always be planning to exceed your quota, not just hit it, 'cause you're managing risk." Sean O'Shaughnessey (09:23): "If you cannot make your number by working hard and doing all the things correctly… then you gotta change some of those assumptions." Kevin Lawson (11:16): "If you're in the camp of saying, 'I don't wanna put information in my CRM,' you're gonna get outsold by your competition." Additional Resources B2B Sales Lab — 14:00 Kevin invites listeners who want help calculating and applying the metrics discussed in the episode to join the B2B Sales Lab at b2b-sales-lab.com. Members can bring their own selling situations to office hours and work through tactical and strategic questions with Sean and Kevin. The episode also highlights the value already sitting inside your CRM. With clean historical data, sellers can analyze conversion rates, opportunity stages, deal progression, losses, and required next steps rather than relying on intuition alone. Even relatively simple AI tools can make that analysis easier—but only when the underlying sales data is worth analyzing. A Significant Actionable Item from this Podcast Build the math behind your quota before doing more activity. Take 30 minutes and write down your quota, average deal size, historical close rate, and the approximate number of selling interactions required to close an average deal. Then work backward. How many wins must you produce to reach 120% of quota? How many legitimate opportunities must enter your pipeline to create those wins? How much sales capacity does each opportunity consume? Now compare those requirements with your current pipeline and available time. If the numbers do not work, do not simply conclude that you need to "work harder." Determine what must change: larger deals, better qualification, improved conversion rates, fewer wasted meetings, greater prospecting volume, or faster movement through the sales process. That is the difference between hoping for sales success and actively managing toward it. Summary Great sellers do not surrender responsibility for their performance simply because someone else carries the title of sales manager. They understand the economics of their territory, know what activities actually produce revenue, maintain the data necessary to make intelligent decisions, and recognize when a deal is consuming resources without creating progress. In this episode, Kevin and Sean turn sales management inward and give B2B sellers a practical way to evaluate their own time, talent, pipeline, and sales processes. If you want greater pipeline predictability, stronger business acumen, better CRM discipline, and a clearer path toward quota attainment, this episode of Two Tall Guys Talking Sales deserves a place in your queue.

September 1, 2026Episode 20417 min

Stop Chasing More Pipeline: How to Win More B2B Sales Deals

Most salespeople do not lose because they cannot make the spectacular play. They lose because they miss the layups. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey challenge the conventional wisdom that sales success requires ever-larger pipelines and more activity. Instead, they make the case for disciplined sales processes, tighter qualification, faster follow-up, stronger business acumen, and a relentless focus on the opportunities you should actually win. If your sales management system assumes that closing 20% or 30% of your pipeline is normal, this conversation may force you to rethink the math. Key Topics Discussed 00:25 – Stop Missing the Sales "Gimmes" Sean uses basketball free throws and layups to illustrate one of the simplest—and most expensive—problems in B2B sales: failing to execute the obvious fundamentals. Responding quickly to a prospect, writing a compelling follow-up email, providing requested information, and introducing the right customer reference are not advanced sales strategies. They are basic execution. Consistently missing them creates unnecessary friction, slows pipeline velocity, and costs revenue generation. 03:04 – Build Your Pipeline Around High-Probability Opportunities Kevin introduces an 80%, 90%, and 95% framework for thinking about ICP fit and opportunity quality. Salespeople often become enamored with "whale" opportunities that resemble half-court shots while neglecting the prospects with strong product-market fit, clear buying signals, and obvious need. Whether you are an AE, SDR, VP of Sales, or working inside RevOps, the question is the same: how much of your pipeline consists of deals you genuinely have a right to win? 06:27 – Rationalize the Pipeline and Get Out of Bad Deals Pipeline management should not be an exercise in protecting inflated opportunity counts. Kevin argues for something more disciplined: determine whether you belong in each deal. Do you understand the economic buyer, the decision process, the decision criteria, the goals, and the fit? If not, either develop that understanding or leave the opportunity. Better sales management means removing bad deals rather than pretending weak opportunities will somehow convert. 08:28 – Why 3X, 4X, and 5X Pipeline Coverage Can Hide a Bigger Problem Sean challenges one of the most common assumptions in revenue management: that every salesperson needs three, four, or even five times quota sitting in the pipeline. Five-times coverage implies an expected close rate of roughly 20%. Instead of celebrating pipeline volume, sales leaders should ask why such a low conversion rate is considered acceptable. Better qualification, value selling, messaging, and ICP discipline can create a smaller but dramatically more productive pipeline. 11:26 – A 90% Close Rate Is Not Fantasy—If You Measure It Correctly Kevin draws an important distinction: the close-rate calculation should begin after meaningful discovery and qualification. A prospect should not move into proposal or scoping simply because someone wants a quote. If you do not understand the economic buyer, business goal, impact, and buying conditions, the deal has not earned advancement. This is where sales enablement and process discipline become more valuable than simply increasing activity. 12:40 – Improve Your Close Rate Before Lunch Tomorrow The episode finishes with highly practical execution. Define the next step. Prepare properly for the next meeting. Document customer goals. Brief internal participants. Send the buyer an agenda. Clarify what must happen next. In complex deals involving a buying committee or an Enterprise Sales environment, seemingly small actions build trust, surface weak opportunities earlier, reduce non-selling activities later, and improve B2B sales pipeline predictability. Key Quotes Sean O'Shaughnessey – 02:25 "Are you doing the simple things well?" That question cuts through a tremendous amount of sales-tech noise. Artificial intelligence, workflow automation, conversational intelligence, predictive analytics, and an increasingly complicated sales tech stack can improve sales productivity—but none of them compensate for poor execution of the fundamentals. Kevin Lawson – 06:27 "Am I in the right deals or am I in the wrong deals?" That may be one of the most important questions in pipeline management. Better revenue management begins by distinguishing real opportunities from deals that merely make the CRM look healthy. Sean O'Shaughnessey – 08:28 "I like lazy salespeople." Sean's point is deliberately provocative: great salespeople should not have to brute-force their way to quota. They know what they sell, who should buy it, the value it creates, and which opportunities deserve their time. That clarity creates a better ROI from every hour sold. Kevin Lawson – 12:02 "What we're talking about here is discipline to the selling process, not trying to rush to the quote." That distinction separates professional sales processes from quote generation. Discovery should determine whether the buyer and seller are sufficiently aligned to justify the next stage. Additional Resources B2B Sales Lab Kevin and Sean discuss the B2B Sales Lab as a place where salespeople and sales leaders can bring real questions about close rates, qualification, messaging, pipeline conversion, and quota performance to experienced peers. The community includes office hours and an open forum designed to extend the practical conversations that begin on Two Tall Guys Talking Sales. A Significant Actionable Item from this Podcast Audit every qualified opportunity in your pipeline and assign it a probability based on actual deal quality—not the stage currently displayed in your CRM. For each opportunity, ask whether you clearly understand the customer's goal, economic buyer, decision process, decision criteria, next step, timing, and reason to change. Then make a decision. Advance the opportunities where you have earned the right to win. Develop the gaps that can realistically be closed. Remove the deals that should never have survived discovery. Do not measure the success of this exercise by how much pipeline remains. Measure it by how much confidence you gain in the opportunities that remain. For sales leaders, this can completely change pipeline conversations. Instead of asking, "Do we have 3X coverage?" ask, "What percentage of these deals should we actually win?" That is a far more useful question for forecasting, coaching, sales enablement, RevOps, and revenue generation. Summary More pipeline is not automatically better pipeline. More activity is not necessarily more productivity. And a heroic pursuit of Complex Deals does not compensate for missing the layups sitting directly in front of you. In this episode, Sean and Kevin challenge salespeople and sales leaders to reconsider the assumptions behind pipeline coverage, close rates, qualification, and sales management. The result is a practical argument for disciplined selling: choose the right customers, qualify hard, execute the fundamentals, prepare for every conversation, define meaningful next steps, and stop spending valuable selling time on opportunities you have little chance of winning. Artificial intelligence and Generative AI may eventually give sellers extraordinary capabilities—from AI-powered sales coaching and augmented sales intelligence to AI relationship intelligence, mapping the buying committee with AI, scaling ABM with AI, intent data personalization, hyper-personalized outbound sales, and warm outreach at scale. But technology cannot rescue a salesperson who consistently misses the easy shots. Before you add another deal acceleration tool, workflow automation platform, or RevOps AI deployment to your stack, listen to this episode. You may discover that one of the fastest paths to sales success is not doing more. It is becoming much better at the things that should already be routine. 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/

August 25, 2026Episode 20317 min

When to Walk Away From a Sales Deal: Stop Wasting Time on Bad Opportunities

There is a hidden cost in every sales pipeline: the deals that consume time, attention, and internal resources without a compelling reason to remain there. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey challenge B2B salespeople to stop treating every opportunity as something that deserves to be won. They examine how strong sales management starts with deciding where your time creates the greatest return, recognizing opportunities outside your "deal box," and knowing when walking away can actually improve revenue generation and pipeline velocity. If you are an AE, SDR, VP of Sales, or sales leader trying to improve sales productivity and B2B sales pipeline predictability, this conversation provides a disciplined way to distinguish a difficult deal worth fighting for from a bad deal that should never have been in the pipeline. Key Topics Discussed 01:46 – Your Prospects Must Earn the Right to Be in Your Pipeline Kevin introduces a powerful reversal of the traditional sales mindset: salespeople are trying to earn a buyer's business, but prospects must also earn the seller's time investment. A large opportunity is not automatically a good opportunity. Strong sales strategies require evaluating whether the potential customer fits the company's capabilities, economics, customer mix, and broader revenue management priorities. 03:02 – Understanding Your "Deal Box" Not every revenue-generating opportunity fits the business. Kevin describes the "deal box"—the characteristics that define the opportunities your company is best positioned to win, serve, and grow. An account buying only a peripheral product may appear attractive because of margin, but if maintaining that customer consumes disproportionate resources or offers little expansion potential, the ROI may be poor. Effective sales processes require looking beyond the initial transaction. 05:32 – Evaluate the Account, Not Just the Current Opportunity Sean expands the discussion from deal planning to account planning. Is this a company with which you want a long-term relationship? Can the account support additional revenue generation? Does pursuing this opportunity advance your territory strategy, or is it simply consuming time that could be better spent on higher-value prospects? Business acumen and value selling require evaluating both the immediate deal and the economic potential of the relationship behind it. 07:51 – Use the One-on-One Sales Meeting for Deal Decisions A salesperson should not quietly abandon a questionable opportunity. Sean explains why these situations belong in a one-on-one sales management conversation. Bring the evidence to your manager, explain why the opportunity may no longer justify the investment, and ask whether you are missing any strategic information or coaching. A strong VP of Sales or sales manager may confirm that the opportunity deserves more resources—or agree that those resources should be redirected elsewhere. 08:47 – How to Withdraw Without Burning the Relationship Walking away does not require an adversarial conversation. Sean describes a direct approach: tell the buyer you are questioning whether your company is truly the best fit and invite them to explain why you should remain involved. That creates an unusual moment of honesty. The prospect may confirm that you should exit—or reveal information about the buying committee, competitive position, internal priorities, or stalled decision process that changes your understanding of the opportunity. 11:14 – Divide Your Pipeline Into Three Categories Kevin closes with a practical pipeline exercise. Identify the deals you most want to win, the deals you want but have the lowest probability of winning, and the opportunities that have no legitimate reason to remain in your pipeline. Those groups require three different responses: deal planning, sales coaching, and an exit strategy. That discipline improves pipeline velocity, sales productivity, and ultimately sales success. Key Quotes Kevin Lawson – 01:46 "Your prospects need to earn the right to be in your pipeline." That statement reframes pipeline management. Opportunity volume is not the objective; productive allocation of selling resources is. Sean O'Shaughnessey – 06:33 "Your job as a salesperson is to maximize the revenue coming from your territory, however you define your territory." That means evaluating opportunity cost, not merely asking whether a particular deal could eventually close. Sean O'Shaughnessey – 08:47 "I'm not sure that we're a perfect fit for what you're trying to accomplish." Sometimes the most effective messaging is a willingness to disqualify yourself. The buyer's reaction can expose information that months of conventional follow-up failed to uncover. Kevin Lawson – 11:33 "Which of these do I most want to win? And which of these deals do I think are least likely for me to win?" Those are different questions, and confusing them leads to poor pipeline decisions. Additional Resources B2B Sales Lab – Kevin and Sean discuss the B2B Sales Lab as a place where sales professionals and sales leaders can bring real opportunities, difficult sales situations, and questions about complex deals to a practitioner-led community. Members can post questions, learn from other experienced sellers, and participate in office hours directly with Kevin and Sean. Visit b2b-sales-lab.com. A Significant Actionable Item from this Podcast Open your pipeline and force every active opportunity into one of three categories: Deals you most want to win. These deserve a documented deal plan, clear next steps, and deliberate attention to the people, competition, value proposition, and buying process required to win. Deals you want to win but are least likely to win. Take these into your next one-on-one sales meeting. Do not simply work harder. Ask for coaching and determine specifically what would have to change to move from third place—or fifteenth place—to first. Deals that should not be in your pipeline. Develop an exit strategy. Determine how much additional time the opportunity warrants and how you can withdraw professionally while preserving the relationship. The important distinction is between a hard deal and a bad deal. Difficult enterprise sales and complex deals may justify substantial investment when the strategic fit and potential return are strong. A bad opportunity does not become better simply because an AE has already spent six months pursuing it. That is sunk-cost thinking masquerading as persistence. This exercise is also where AI and modern sales enablement can eventually help. Conversational intelligence, augmented sales intelligence, predictive analytics, AI-powered sales coaching, and human-in-the-loop automation can surface risk and reduce administrative burden, but no Sales Tech Stack can substitute for the fundamental management decision: Is this opportunity worth more of our time? Summary Great salespeople do not merely know how to advance opportunities. They know which opportunities deserve to be advanced at all. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey provide a practical framework for examining deal quality, account potential, opportunity cost, sales management coaching, and the difficult decision to walk away. The result is a cleaner pipeline, better allocation of selling time, stronger B2B sales pipeline predictability, and more attention available for the opportunities most likely to create meaningful revenue. If your pipeline contains deals that have been sitting there because nobody wants to declare them dead—or opportunities you continue pursuing simply because you have already invested so much time in them—this episode will make you look at those deals differently. Listen before your next pipeline review or one-on-one sales meeting. You may discover that one of the best sales decisions you make this week is deciding what not to sell. 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/

August 18, 2026Episode 20217 min

How to Run a One-on-One Sales Meeting That Actually Improves Sales Performance

A one-on-one sales meeting should not be a passive status report where the salesperson waits for the manager to ask questions. Done correctly, it becomes one of the most valuable tools for improving sales performance, removing obstacles, strengthening skills, and accelerating revenue generation. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey explain how salespeople can take greater ownership of these conversations—even when their sales manager has not created an effective structure. From forecasting the deals you expect to close to asking for resources, coaching, and candid feedback, Sean and Kevin lay out a practical framework for turning recurring one-on-ones into working sessions that support better sales processes, stronger sales management, and ultimately greater sales success. Key Topics Discussed Take Ownership of Your One-on-One Sales Meeting — 01:18 The salesperson should arrive prepared rather than treating the meeting as something the manager owns. Know the details of your opportunities, understand where you need help, and be ready to direct attention toward the issues that could materially affect your results. Kevin describes the meeting as an enablement resource: your job is to own the deal, while your sales leader can help mobilize marketing, technical, consulting, or other internal resources needed to win it. Start With the Scoreboard: Dollars, Deals, and Obstacles — 03:23 Sean recommends beginning with a clear statement of what you expect to close during the relevant sales period—whether that is the week, month, quarter, or another cadence appropriate to the business. Then identify the concerns surrounding those opportunities. Where is the deal blocked? What support is missing? What could prevent the projected revenue from becoming real revenue? This moves the discussion beyond vague pipeline updates and toward concrete decisions that can improve Pipeline Velocity and deal execution. Use the Meeting to Close the Loop on Commitments — 06:32 Kevin breaks the meeting into a scoreboard followed by the outstanding to-do items from prior conversations. That accountability runs in both directions. Salespeople should report on what they committed to doing, but they should also appropriately "lead up" by asking managers about resources, introductions, or assistance that was previously promised. Doing this prevents half-completed initiatives from accumulating and ensures the AE or salesperson receives the Sales Enablement support needed to move Complex Deals forward. Your Pipeline Is Not the Entire Meeting — 08:28 Pipeline matters, but Kevin warns against allowing pipeline inspection to consume the entire conversation. A productive one-on-one should also address problems, resources, execution, and development. A sales management system that does nothing more than repeatedly ask, "When is this deal closing?" leaves enormous value on the table. The meeting should help the salesperson improve the business, not merely describe it. Run Your Territory Like a Business—and Ask to Be Coached — 09:11 Sean suggests thinking of yourself as the CEO of your territory, with your sales leader serving as the chair of your board. You are responsible for the performance of that business, but you should also expect the leadership team to provide resources and guidance. That includes skills development. Ask your manager to review recorded calls, presentations, and customer conversations and provide specific coaching about what could have been done better. Demand Useful Feedback, Not Empty Praise — 11:01 Sean tells the story of challenging a newly promoted VP of Sales who accompanied him on customer calls but initially offered nothing beyond praise. Sean had already identified five things he could have done better and pushed his manager to provide equally substantive feedback. The lesson is not to imitate Sean's rather dramatic airport maneuver; rather, experienced salespeople still need coaching, and leaders have an obligation to help them improve. Key Quotes Sean O'Shaughnessey — 01:18 "You should have the philosophy of this is your meeting." Salespeople who take responsibility for the preparation, agenda, and desired outcomes of their one-on-one put themselves in a far stronger position to get the resources and coaching they need. Kevin Lawson — 02:47 "Your name's on the deal, and so it's up to you to figure out how you're going to win the deal and reach your quota." The manager can provide resources, coaching, and organizational support, but ownership of the opportunity remains with the salesperson. Kevin Lawson — 08:52 "Pipeline is not the only content for a pipeline meeting." Forecasting matters, but simply reviewing opportunity stages and expected close dates does little to develop the salesperson or remove the problems preventing deals from advancing. Sean O'Shaughnessey — 13:09 "You need your leadership to help you get better, and you need to demand it if they're not doing it." Strong salespeople do not outgrow coaching. They become more intentional about seeking useful feedback rather than accepting generic reassurance. Additional Resources B2B Sales Lab — Sean and Kevin invite listeners who want to go deeper into structuring effective one-on-one sales meetings to join the B2B Sales Lab and bring their specific challenges to office hours. The discussion can be tailored to the organization's particular sales process, sales cycle, and management environment. b2b-sales-lab.com A Significant Actionable Item from this Podcast Before your next one-on-one, create a simple, standardized agenda that begins with three things: the deals and revenue you expect to close, the specific risks or obstacles that threaten those deals, and the help you need from your sales leader. Then add outstanding commitments from the previous meeting and at least one skill you want your manager to help you improve. Do not wait for your VP of Sales, manager, or company to design the perfect process for you. Take ownership of the meeting yourself. Over the course of 50 or more meetings each year, improving the quality of these conversations can lead to meaningful gains in sales productivity, better resource allocation, stronger sales strategies, and more predictable revenue. Summary Most salespeople spend far too little of their week actually speaking with customers, which makes poorly structured internal meetings particularly expensive. In this episode, Kevin and Sean challenge both salespeople and sales leaders to stop treating the one-on-one as just another routine pipeline inspection and to start using it as a serious business management session. You will learn how to arrive with a clear scoreboard, surface the barriers threatening important opportunities, hold both sides accountable for commitments, secure the resources necessary to move deals forward, and make coaching an expected part of the conversation. If you want better sales management, sharper execution, stronger business acumen, and one-on-one meetings that actually contribute to B2B sales success, this episode gives you a framework you can put to work before your next meeting. 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/