Two Tall Guys Talking Sales

"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 turnaro

Two Tall Guys Talking Sales is a business podcast hosted by Kevin Lawson and Sean O'Shaughnessey, with 206 episodes on record and a Required Pod Score of 80.

Kevin Lawson and Sean O'Shaughnessey hosts Two Tall Guys Talking Sales, a business show with 206 episodes published.

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  Episode #208

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

  Sep 29, 202617 minS1

  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/

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  Episode #207

  Stop Chasing More Leads: Turn Your Quote Backlog Into Revenue

  Sep 22, 202618 minS1

  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.

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  Episode #206

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

  Sep 15, 202618 minS1

  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.

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  Episode #205

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

  Sep 8, 202617 minS1

  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.

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  Episode #204

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

  Sep 1, 202618 minS1

  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/

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