Two Tall Guys Talking Sales

Kevin Lawson and Sean O'Shaughnessey
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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.

  1. 9h ago

    Should Sales Leaders Reset Quotas at Midyear

    Midyear exposes the truth in every sales organization. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey tackle a problem many business owners, sales leaders, and salespeople quietly face at the halfway point of the year: unclear goals, weak commission plans, soft pipeline discipline, and the temptation to reset expectations instead of fixing the sales processes that created the gap. This is a practical conversation about B2B sales management, quota accountability, revenue generation, pipeline prioritization, and the uncomfortable but necessary work required to improve sales success in the second half of the year. Key Topics Discussed Midyear goal setting when the original plan was missing or unclear — 00:00 Sean explains why some companies reach July without properly documented sales goals or commission plans. The corrective action is not complicated, but it is often avoided: write the plan down, align compensation with company priorities, and make sure salespeople know exactly how they are being measured. Why sales leaders should not casually reset the goal — 02:14 Kevin argues that adjusting the target downward can create a dangerous management precedent. If the number was the right number, the job is to solve the gap through better sales strategies, qualification, activity, referrals, and pipeline focus—not move the scoreboard. The rare exception to keeping the original quota — 06:34 Sean adds an important leadership caveat. If the CEO or executive team built the number around a product launch, acquisition, market event, or business assumption that never materialized, that is not a salesperson's problem. That is an executive planning problem, and it should be handled honestly. Pipeline rationalization and better qualification — 09:57 Kevin walks through the discipline of deciding which deals deserve time and which ones do not. Complex deals, unclear next steps, bad-fit opportunities, and stalled prospects all consume selling capacity. Better qualification improves pipeline velocity by giving salespeople time back to pursue better opportunities. Time management, delegation, and protecting prospecting time — 13:43 Sean warns against the classic sales rollercoaster: closing current business while starving future pipeline. Whether a company uses SDRs, AEs, business development resources, or full-cycle salespeople, every stage of the sales process needs dedicated time. Revenue management requires knowing where the week actually went. Key Quotes Sean O'Shaughnessey — 01:14 "You didn't get it done at the first of the year. That doesn't mean you can't do it now." Kevin Lawson — 03:40 "You never adjust the goal. Your job as a salesperson is to hit the goal or your quota." Sean O'Shaughnessey — 08:34 "Salespeople can't make their goals for things that are outside of their control." Kevin Lawson — 10:22 "You've got to figure out which deals are aligned and which ones are not aligned to what you do." Sean O'Shaughnessey — 14:03 "We were so busy selling that we forgot to sell." Additional Resources EOS implementers — referenced as part of the broader business coaching and planning conversations happening at midyear. FocalPoint and ActionCOACH — mentioned as examples of coaching organizations business owners may turn to when trying to catch up or plan ahead. Microsoft PTAP — referenced by Kevin as "plan to exceed plan," a useful framing for quota planning and sales performance management. MEDDPICCC, BANT, and SPICED-style qualification methodologies — referenced as examples of structured approaches to qualification, deal inspection, and sales process discipline. Marketing-generated digital assets — discussed as one practical source of conversation creation when salespeople are behind and need to rebuild pipeline coverage. A Significant Actionable Item from this Podcast Audit your pipeline and calendar before changing the goal. Identify every active opportunity, mark which deals have clear next steps, remove or deprioritize poor-fit opportunities, and block time this week for prospecting, referral requests, outreach to past customers, and networking. Do not rely on optimism. If an opportunity does not match your ideal customer profile, lacks buyer commitment, or requires too much customization to win, it is likely stealing time from better revenue-generating work. Summary This episode is a timely midyear inspection for any B2B salesperson, VP of Sales, business owner, or sales management leader who is trying to protect the second half of the year. Kevin and Sean make a clear argument: missed goals are not solved by pretending the number changed. They are solved by stronger qualifications, clearer commission plans, better time allocation, disciplined sales processes, and more honest pipeline review. If you are behind, ahead, or unsure where you really stand, this conversation will help you decide whether you have a quota problem, a planning problem, a pipeline problem, or a leadership problem—and what to do next.

    20 min

  2. Jun 23

    From Marine Recon to Venture Capital: Paul Claxton on Sales Strategy, AI, and Founder Readiness

    In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey sit down with Paul Anthony Claxton of Digirati Investments for a sharp conversation on venture capital, founder readiness, sales architecture, and why early-stage companies cannot hide behind product obsession or incomplete data. Paul brings a rare blend of Marine Corps reconnaissance discipline, sales leadership, investment judgment, and AI perspective to the table. The result is a fast-moving discussion about Business acumen, customer conversations, market intelligence, Sales processes, and the practical realities of Revenue generation when founders are trying to build something the market may not yet know it needs. Key Topics Discussed Founder adaptability and the path from Marine to venture capitalist — 00:20 Paul explains how adaptability, opportunity recognition, and power networking shaped his move from the Marines into venture capital. His point lands hard for anyone in sales management: the best salespeople and founders do not simply follow the plan. They adjust when the market, the customer, or life changes direction. Why investors look beyond the product — 02:19 Paul discusses what he looks for when evaluating founders and companies. Product matters, but it is not enough. Founders need to understand macroeconomics, microeconomics, contracts, deal structure, customer impact, and the broader commercial environment. That is where Business acumen becomes a serious differentiator. Inventing necessity and creating surrounding market demand — 03:24 Paul introduces Digirati Investments' phrase "inventing necessity" and explains why strong products do more than solve one isolated problem. They create adjacent needs, new sub-industries, and additional opportunities for Revenue generation. This is a useful framing for founders, sales leaders, and anyone building Sales strategies around emerging markets. The danger of product-centric founders — 04:43 Sean pushes into a critical founder question: how often do companies believe they have a market-changing product before they have validated the market? Paul's answer is direct. Too many founders are product-centric instead of people-centric. Real Sales success starts with human conversations long before the product is fully built. Data, AI, and consultative selling in modern sales ecosystems — 05:33 Paul argues that strong data flow is essential, but data alone cannot replace human interaction. He connects AI, CRM automation, customer engagement, and consultative selling to a broader point: modern Sales processes need both high-quality data and high-quality conversations. Reconnaissance, competitor intelligence, and explainable AI — 09:15 Drawing from his Marine background, Paul explains why companies must gather intelligence from both customers and competitors. AI can support that work, but leaders must understand where the data came from and whether it reflects the actual market. Bad assumptions create bad Messaging, weak qualification, and flawed Revenue management decisions. Key Quotes Paul Anthony Claxton — 00:35 "The best salespeople are the most adaptable people." Paul Anthony Claxton — 05:33 "A lot of times I'll run across founders that are product-centric instead of being people-centric." Sean O'Shaughnessey — 08:41 "How do you know that what you're doing is going to work if you don't have salespeople out pre-talking and pre-building up what that problem is?" Paul Anthony Claxton — 09:15 "If you don't have people gathering reconnaissance, it's not just talking to who you think your prospective customers are, but it's also understanding how your competitors qualify." Kevin Lawson — 11:49 "Not only do we have to know as sellers who our total addressable market is, but our service obtainable market is, but it's important to keep that data current." Additional Resources Paul Anthony Claxton — Venture capitalist, U.S. Marine, sales architecture thinker, and guest on this episode. https://www.linkedin.com/in/businessmanathletemarine/ Digirati Investments — Paul's investment firm, discussed in the episode through the lens of "inventing necessity." Explainable AI — Paul's podcast, referenced during the conversation about understanding the origin, quality, and accuracy of AI-driven data. PaulClaxton.io — Paul's personal website, where you can learn more about his work, investments, and related ventures. A Significant Actionable Item from this Podcast Before investing more time, money, or sales effort into a product, schedule direct market conversations with prospective customers and competitive intelligence reviews. Do not rely only on internal conviction, CRM data, AI summaries, or founder enthusiasm. Validate the problem, study how competitors qualify and sell, and pressure-test whether your Value selling story connects to a real business need. This one discipline improves Sales strategies, sharpens Messaging, and prevents companies from building sales motions around assumptions the market has not confirmed. Summary This episode is a compact but high-value conversation for founders, investors, sales leaders, and anyone responsible for Revenue generation in an uncertain market. Paul Anthony Claxton brings a different lens to sales and investment evaluation: part Marine reconnaissance, part venture capitalist, part sales architect. Kevin and Sean guide the discussion into the practical questions that matter most: Does the founder understand the market? Is the product creating real necessity? Is the data explainable? Are customer conversations happening early enough to shape the business before money and time are wasted? Listen to this episode of Two Tall Guys Talking Sales if you want a sharper view of founder readiness, modern sales management, AI-informed selling, and the kind of Business acumen required for durable Sales success.   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/

    16 min

  3. Jun 16

    Stop Wasting Time on Bad Deals: Sales Management Lessons for a Cleaner Pipeline

    In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey take on one of the most expensive problems in B2B selling: pipeline clutter. Sellers have limited customer-facing time, and too much of it gets wasted chasing deals that were never truly qualified, never aligned with the ideal client profile, or never likely to close. Kevin and Sean dig into the math, mindset, and sales management discipline required to protect selling time, improve forecast accuracy, and focus on the right opportunities. This conversation connects time management, Business acumen, Sales strategies, Sales processes, Value selling, Messaging, Revenue management, and Revenue generation into one practical question: Are you spending your limited sales time on deals that can actually produce Sales success? Key Topics Discussed Why seller time is the most valuable sales resource — 00:00 Kevin opens the episode by pointing out that only a fraction of a seller's week is spent directly with customers. The rest disappears into research, reporting, scoping, internal meetings, travel, and administrative drag. That makes time management a revenue issue, not a productivity slogan. How to identify deals that do not belong in your pipeline — 01:14 Sean challenges sellers to open their CRM and look honestly at the deals expected to close in the next quarter or six months. Do they fit the ideal client profile? Do they look like the kinds of customers the company wins? Or are they sitting in the pipeline because the seller hopes they might become something? Using quota math to evaluate opportunity cost — 02:45 Sean breaks the problem down to simple math: take the seller's annual working hours, divide by the quota, then adjust for actual customer-facing time. The farther a prospect is from the ideal client profile, the more time it typically consumes. That raises the real question: could the seller create more revenue by focusing on easier, better-fit deals? The danger of an aspirational pipeline — 04:12 Kevin explains how inflated pipelines create false confidence, poor forecasting, and bad leadership conversations. A pipeline full of hope does not create commissions. A pipeline full of qualified, workable, attainable deals gives sales leaders and sellers better data for decision-making. Discovery discipline and hard qualification questions — 07:07 Kevin emphasizes the importance of asking hard questions early. Budget, business pain, decision authority, and the pain of change must be tested before a deal moves too far forward. If a seller has issued a proposal to someone who cannot buy, does not control the budget, or cannot define the business problem, the sales process has already drifted. Becoming your own sales manager — 08:48 Sean pushes sellers to manage their own pipeline with the same honesty they would expect from a strong sales leader. The best salespeople ask themselves whether a deal is real, whether it is efficient, whether it has access, whether the buyer is engaged, and whether it belongs in this year's forecast at all. Key Quotes Kevin Lawson — 00:00 "As sellers, people who are chasing a quota every year, we have one thing that is so precious that it is absolutely paramount for us to pay attention to, and that's our time." Sean O'Shaughnessey — 01:14 "We all know that if we had more time to call on great customers, we'd probably make more money. So let's talk about calling on great customers." Kevin Lawson — 05:46 "Your commission is driven by your accuracy of closes, not your aspirations. Aspirational deals don't turn into commissions." Sean O'Shaughnessey — 09:09 "The best salespeople are great independent sales managers of themselves." Kevin Lawson — 12:09 "Simply quota, close rate, number of deals, average deal size. That's really all you need, and it's all stuff that's in your pipeline now." Additional Resources B2B Sales Lab — Sean mentions that sellers can use the B2B Sales Lab to pressure-test pipeline questions, get peer feedback, and discuss whether specific opportunities deserve more time and attention. Join the Lab at b2b-sales-lab.com CRM pipeline review — The episode repeatedly encourages sellers to use their CRM as the source of truth for examining deal fit, timing, stage accuracy, close probability, and forecast quality. Ideal Client Profile — Kevin and Sean reinforce the importance of understanding which prospects fit the company's best customer profile and which ones sit too far outside the target to justify the time required. Customer Interaction Hours episode — Kevin refers listeners back to a previous discussion in which Sean explained customer interaction hours and why increasing time in front of the right buyers improves the win position. Quarterly Business Reviews — Kevin notes that past customers and QBRs can help sellers and sales leaders identify strategic conversations, referral opportunities, and ways to generate more of the right pipeline. A Significant Actionable Item from this Podcast Before your next pipeline review, identify three deals in your CRM that do not clearly fit your ideal client profile, lack decision-maker access, have weak urgency, or keep slipping from one forecast period to the next. For each one, decide whether it should stay active, move to a future follow-up task, or be disqualified. Then have the direct conversation with the buyer: "It does not seem like this is a priority right now. Should we pause this and revisit it later?" That single question protects your time, improves forecast accuracy, and forces cleaner revenue management. Summary This episode is a practical reminder that sales success is not created by carrying a bigger pipeline; it is created by carrying a more honest one. Kevin and Sean show why bloated pipelines waste time, damage forecasts, and distract sellers from the deals most likely to generate revenue. The conversation is especially useful for salespeople, sales managers, and company leaders who want better sales processes, sharper qualification, stronger messaging, and more disciplined value selling. If your pipeline looks impressive but does not reliably convert, this episode will challenge you to stop admiring the number and start managing the reality. 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/

    17 min

  4. Jun 9

    Are Your Salespeople in the Wrong Roles? How to Match Talent to Revenue Growth

    Two Tall Guys Talking Sales takes a practical look at one of the most common sales management mistakes: assuming all salespeople are built for the same job. Sean O'Shaughnessey and Kevin Lawson use a basketball analogy to unpack the difference between hunters, farmers, lone wolves, challengers, relationship sellers, transactional sellers, and trappers. This episode challenges owners, sales leaders, and frontline sellers to examine whether their sales processes, compensation plans, and revenue management expectations actually match the type of salesperson required for Sales success. If your team is underperforming, the issue may not be a lack of effort. It may be role design. Key Topics Discussed 01:00 — Why Sales Roles Need Clear Definitions Sean opens with a basketball analogy: if you do not understand the positions, the game becomes harder to follow. The same is true in sales. Confusing labels like hunter, farmer, challenger, lone wolf, and trapper can create bad hiring decisions, poor coaching, and broken sales strategies. 02:50 — Do Not Confuse Seller Type with Business Model Kevin draws an important distinction between the kind of salesperson you have and the kind of business you operate. A transactional sales model, a relationship-driven sales model, and an enterprise sales model each require different selling behaviors, messaging, and support structures. 06:20 — Hunters, Farmers, and the Cost of Misalignment Sean explains why a one-time ERP-style sale usually requires a hunter, while repeat-purchase relationships often require a farmer. Asking one type of salesperson to behave like another may be possible, but it is rarely efficient. Sales leaders need Business acumen to know what role the business actually requires. 08:25 — Lone Wolves, Challengers, and Unsupported Sales Teams The discussion turns to lone wolves and challengers, especially in organizations that give salespeople little infrastructure, weak marketing, poor sales processes, or minimal sales enablement. If leadership expects sellers to "just figure it out," they may be selecting for independence while unintentionally creating risk. 09:50 — How to Reshape a Sales Team Without Blowing It Up Kevin warns against the instinct to immediately replace the team. The better move is to take an intellectually honest look at the team's structure, upskill where possible, and decide whether the business needs account managers, customer service support, hunters, or relationship-focused sellers. 12:50 — The Trapper: Building Toward Enterprise Revenue Generation Sean closes by describing the trapper: the salesperson who can hunt, farm, lead, challenge, and plan proactively for larger future opportunities. This is where Value selling becomes more than a technique. It becomes a disciplined approach to expanding from a pilot project to departmental adoption, divisional traction, and eventually enterprise-level revenue generation. Key Quotes Sean O'Shaughnessey — 01:07 "Not knowing what the roles are is a big deal. So that same kind of thing happens in a sales arena, where you may not understand what type of salesperson you have or what type of salesperson you need." Kevin Lawson — 02:51 "It's important to note that just because somebody looks like something doesn't mean that's actually what they are." Kevin Lawson — 03:51 "You, as a seller, need to understand your business model so that you know how to sell." Sean O'Shaughnessey — 08:08 "Asking one type of salesperson to be another is really difficult to do. That's like asking that point guard to be the center." Kevin Lawson — 10:39 "Change people before you have to change people." Sean O'Shaughnessey — 14:15 "How do you become proactive? How do you plan for the deal that's going to happen in nine months?" Additional Resources The Challenger Sale — Referenced during the discussion of lone wolves and challengers, especially the idea that some sellers succeed by taking control of complex customer conversations. Eliminate Your Competition by Sean O'Shaughnessey — Sean refers to the "trapper" concept from his book as the more complete sales archetype for complex, enterprise-level selling. B2B Sales Lab — Kevin mentions that this topic will be explored further in B2B Sales Lab office hours, where sellers and sales leaders can dig into the practical work of assessing team fit, role design, and sales execution. A Significant Actionable Item from this Podcast Audit your current sales team against the sales motion your business actually requires. Do not start with personality labels. Start with the business model. Are you selling once and moving on? Are you expanding accounts over years? Are your deals transactional, relationship-driven, enterprise-level, or a mix? Then map each salesperson against the role the business needs: hunter, farmer, account manager, challenger, lone wolf, or trapper. The decision that follows is the real work. Some people need coaching. Some need a different seat. Some roles need compensation redesign. Some teams need additional support around account management, customer success, prospecting, or CRM discipline. Sales success improves when the revenue management system fits the people, the process, and the customer buying motion. Summary This episode of Two Tall Guys Talking Sales is a useful listen for any owner, VP of Sales, sales manager, or seller who has ever wondered why a capable salesperson still struggles in the wrong role. Kevin Lawson and Sean O'Shaughnessey make the case that sales performance is not only about talent. It is about fit, structure, expectations, and leadership discipline. If your sales strategies are not producing the results you expected, this conversation will help you look beyond activity levels and ask the more important question: Do we have the right people in the right sales roles for how our customers actually buy? 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/

    18 min

  5. Jun 2

    When Buyers Don't Care: Stop Selling Features and Start Selling Value

    Opening a prospecting conversation with "we have 180 million contacts" may sound impressive inside the seller's company, but it often misses the buyer's reality. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey challenge salespeople and sales leaders to stop confusing features with value. They unpack why strong Messaging starts with the buyer's problem, how Value selling creates separation, and why better sales management requires sales teams to understand what customers actually buy—not just what sellers think they sell. Key Topics Discussed Why "more data" is not the value proposition — 00:00 Sean opens with a sharp critique of prospecting tools that lead with database size. A salesperson does not need 10 million contacts. They need the right four people inside the right account. That distinction is central to effective Sales strategies because activity without relevance does not generate Revenue. The buyer does not buy your product; they buy the outcome — 01:56 Kevin reframes the discussion around the "why" behind value propositions. Customers rarely wake up wanting sales infrastructure, fractional sales leadership, or backend data aggregation. They want reliability, growth, better decision-making, and improved business performance. That is where real Business acumen enters the sales conversation. The hospital cleaning example: selling safety, not cleaning supplies — 04:21 Kevin shares a memorable story about a janitorial services salesperson who understood the true value of his work. In a hospital, the outcome was not a clean room. It was a safe, sterile environment for children receiving serious care. That example lands because it shows how Value selling moves beyond product language into buyer consequence. Sean's college selection story: outcomes beat features — 07:02 Sean explains how his college won his attention not by selling class size, curriculum, or facilities, but by emphasizing employment outcomes. For a young person entering a difficult economy, "graduates get jobs" mattered more than institutional features. The lesson applies directly to modern sales processes: speak to the outcome the buyer is trying to achieve. Using PONI to uncover what customers really value — 09:33 Sean introduces PONI: Project, Old way, New way, Improvement. It is a simple but powerful way to build case studies, sharpen Messaging, and identify what your product actually does for customers. The improvement is the story. The product is only the mechanism. Stop training buyers to shop you on price — 10:52 Kevin gets practical about a common sales mistake: opening with "I can save you money." That may feel buyer-friendly, but it teaches the customer to evaluate you on price alone. Strong Revenue management depends on protecting margin, defending value, and guiding the buyer toward profit, growth, reliability, and strategic impact. Key Quotes Sean O'Shaughnessey — 00:32 "I have never needed 10 million people that I need to talk to. What I needed was the four people at that company." Kevin Lawson — 04:21 "You all have the need to sell your product, but your customer may not need to buy your product. They need what your product does for them." Sean O'Shaughnessey — 09:57 "What was the improvement? Go figure that out, and then from that point on, always talk about the improvement." Kevin Lawson — 11:13 "If all you can do is save them money, you're not adding any other value." Kevin Lawson — 13:39 "Revenue feeds ego, profit feeds family." Additional Resources B2B Sales Lab — Kevin invites listeners to join the B2B Sales Lab for office hours, peer discussion, and deeper work on real-world sales challenges. Visit b2b-sales-lab.com. PONI Framework — Sean's practical structure for turning customer stories into stronger sales conversations: Project, Old way, New way, Improvement. CIH and Metrics — Kevin references prior podcast discussions on CIH and metrics as foundational to improving sales execution, qualification, and the probability of success in major opportunities. A Significant Actionable Item from this Podcast Interview your five best customers and ask them to show you how they use your product or service. Do not ask what features they like. Ask what changed. What was harder before? What is easier now? What risk disappeared? What cost came out? What revenue opportunity opened up? Then rewrite your primary sales message around the improvement rather than the product. That single exercise will expose whether your current Messaging supports real Sales success or merely describes what you sell. Summary This episode is a direct challenge to lazy positioning. Kevin and Sean are not arguing against features, data, tools, or price discipline; they are arguing against making those things the center of the sales conversation. Buyers care about outcomes, risk, growth, profit, reliability, and internal justification. If your sales management system, Sales strategies, and sales processes do not force sellers to uncover and communicate those outcomes, your team will drift toward feature dumping and price defense. Listen to this episode if you want a sharper way to explain value, protect margin, improve Revenue generation, and turn customer outcomes into sales conversations that actually matter. 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/

    18 min

  6. May 26

    The Sales Management Metric That Reveals Whether Your Pipeline Is Real

    In complex B2B sales, the best opportunities rarely move forward because of a single perfect conversation with a single perfect buyer. They move because the seller creates enough meaningful customer interaction to uncover problems, build internal consensus, reduce the risk of being ghosted, and increase the odds of winning larger deals. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey dig into Customer Interaction Hours, or CIH. This practical sales management metric helps sellers evaluate the real quality of their meetings, expand influence inside target accounts, and improve Sales success in longer, more competitive sales cycles. Key Topics Discussed Customer Interaction Hours as a better measure of meeting quality — 00:53 Sean introduces CIH, a metric built around the value of longer meetings with more customer stakeholders. Rather than treating every sales call as equal, CIH forces sellers and sales managers to ask a harder question: Did this meeting create enough interaction to advance the deal? Why bigger meetings create better sales intelligence — 02:09 Sean explains why larger, longer meetings often reveal more useful information than short, single-threaded conversations. More people in the room usually means more questions, more objections, more hidden politics, and more clues about the real buying process. How CIH helps sellers stay alive in competitive deals — 05:49 Sean frames one of the episode's central ideas: if the customer is still talking to you, you are still in the deal. CIH gives salespeople a way to measure whether they are creating enough meaningful interaction to remain relevant, especially in enterprise-level opportunities. Using customer conversations to diagnose business pain — 08:22 Kevin connects CIH to Value selling, Business acumen, and better discovery. When sellers involve more people across the customer's organization, they uncover operational issues, technical constraints, conflicting expectations, and financial priorities that would never surface in a narrow conversation. Reducing the risk of ghosted deals through multi-threading — 10:19 Sean explains why deals often disappear when sellers know only two or three people within the account. Customer Interaction Hours push sellers to build more relationships, improving deal visibility and making it harder for an opportunity to die quietly. Applying CIH in small and mid-sized business sales — 11:45 Kevin and Sean make clear that this is not only an enterprise sales strategy. Whether selling to a company of 10 or 10,000, sellers need to understand who influences the buying decision, who uses the product, who owns the risk, and who can block Revenue generation. Key Quotes Sean O'Shaughnessey — 01:45 "If you have a relatively long, complicated sales cycle, CIH or Customer Interaction Hours is a great way to think about it." Sean O'Shaughnessey — 05:49 "If we are still talking, then we are still in the deal." Kevin Lawson — 08:22 "We have to get in front of the right people at the right time with the right message, and getting them talking about their problems is key." Kevin Lawson — 09:14 "Don't sell the product you have. Sell the problem you solve." Sean O'Shaughnessey — 11:31 "You do not get ghosted if you know a dozen people at the company. It takes a big conspiracy to have 12 people not return your phone call." Sean O'Shaughnessey — 14:22 "Do it yourself because it's a way to keep the salesperson going the right direction and thinking about, 'How do I make my deals bigger, my meetings bigger?'" Additional Resources Sean invites listeners to continue the conversation inside B2B Sales Lab, where salespeople and sales leaders can ask questions about Customer Interaction Hours, sales metrics, Sales strategies, Sales processes, Messaging, Revenue management, and practical ways to improve complex B2B selling. A Significant Actionable Item from this Podcast Review the last five meaningful sales meetings on your calendar and calculate your Customer Interaction Hours. Look at how long each meeting lasted and how many customer participants were involved, then ask whether your most important opportunities have enough interaction to justify confidence. If your largest deals are built around short meetings with one or two contacts, that is not a pipeline strategy. That is hope wearing a CRM costume. The next step is direct: choose one active opportunity and identify three additional stakeholders who should care about the business problem you solve. Then create a reason to engage them. Not a generic "checking in" message. A real business reason tied to risk, implementation, financial impact, user adoption, or strategic value. Summary This episode gives salespeople and sales managers a sharper way to think about deal momentum. Customer Interaction Hours are not just another metric to stuff into a CRM dashboard; they are a practical lens for understanding whether a seller is creating enough customer engagement to win. Kevin and Sean make the case that bigger meetings, broader stakeholder coverage, and deeper conversations are not administrative extras. They are core to Value selling, better qualification, stronger Business acumen, and more predictable Revenue generation. Listen to this episode if you manage complex opportunities, sell into competitive accounts, or want a better way to know whether your sales pipeline is real or just politely optimistic. 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/

    18 min

  7. May 18

    Sales Metrics That Matter: How to Protect Your Pipeline, Quota, and Commission Check

    Metrics are not just a sales management dashboard issue. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey make the case that salespeople need their own working metrics, the numbers that help them protect commission income, smooth the revenue rollercoaster, improve forecast accuracy, and make better decisions about where to spend time. This is a practical conversation about pipeline coverage, deal velocity, prospecting discipline, relationship touches, product mix, and the sales processes that turn activity into Sales success. Key Topics Discussed Salesperson Metrics vs. Management Metrics — 00:00 Kevin opens by separating metrics that matter to salespeople from the broader numbers that matter to marketers or sales managers. The real issue is not reporting. It is knowing whether you are doing enough of the right work to make quota. Pipeline Coverage and Forecasting for Yourself — 01:26 The conversation moves into pipeline coverage, deal movement, and the danger of being able to hit quota without knowing when you will hit it. That gap creates weak forecasting, poor Revenue management, and avoidable stress. Avoiding the Sales Commission Rollercoaster — 03:41 Sean explains why inconsistent revenue hurts individual salespeople more than sales managers. A manager can average performance across a team, but a salesperson lives with the direct financial impact of pipeline gaps, delayed deals, and uneven prospecting. Matching Sales Activity to Sales Cycle Length — 05:28 Sean makes the point that a 60-day sales cycle and a six-month sales cycle require different behavior. The salesperson must understand how much time belongs in prospecting, discovery, qualification, scoping, closing, and relationship development. Measuring Deal Creation and Customer Touches — 07:07 Kevin discusses why the number of new deals created matters, especially when viewed by time period and business model. He also shifts into relationship metrics, including how often salespeople intentionally reconnect with customers, former customers, and referral sources. Planning to 110% with A, B, and C Deals — 12:12 Sean closes with a practical quota-planning model: build the year around 110%, then break the number into A, B, and C deal sizes. This forces better Sales strategies, sharper prioritization, and more realistic Revenue generation planning. Key Quotes Kevin Lawson — 00:00 "I want to talk about metrics that matter to salespeople, not marketers, not sales managers… but the people out there carrying the bag." Sean O'Shaughnessey — 03:41 "I want to talk about the ability to not ride the rollercoaster." Sean O'Shaughnessey — 05:50 "If you have a six-month sales cycle, same problem, but you have more time to budget it out. You can go a week without prospecting, but you can't go a month without prospecting." Kevin Lawson — 07:40 "I really like for all sales teams to know how many deals need to come into their pipeline per time period." Kevin Lawson — 10:24 "Being intentional with the relationship is as important." Sean O'Shaughnessey — 12:34 "Start the year assuming you're going to go to 110%. Build your plan to go to 110%." Additional Resources B2B Sales Lab Sean and Kevin referenced the B2B Sales Lab, a community where B2B salespeople can ask questions, get feedback, and talk through real-world Sales strategies, sales processes, Value selling, Messaging, Business acumen, and Revenue generation challenges. Learn more at b2b-sales-lab.com. Traction by Gino Wickman https://a.co/d/0c9rXQMz Kevin referenced the idea of "traction" while discussing relationship discipline and consistent outreach. The point was not about theory. It was about keeping sales relationships active before the pipeline forces you to care. A Significant Actionable Item from this Podcast Build a simple personal pipeline math model this week. Start with your annual quota, then plan to 110%. Break that number into A, B, and C deal sizes. Estimate how many of each deal type you need, then work backward into how many opportunities must be created each month based on your close rate and sales cycle length. From there, decide whether your current prospecting, customer outreach, referral activity, and deal advancement work can actually support the number. If the math does not work, the problem is not motivation. It is the plan. Summary This episode is worth listening to because Kevin and Sean take a topic many salespeople avoid, metrics, and make it directly relevant to the person carrying the number. The conversation is not about building a prettier CRM report or giving sales management more inspection points. It is about using metrics to protect your income, reduce uncertainty, improve your forecast, and make better daily decisions. If you have ever had a great month followed by a weak one, or a full pipeline that somehow failed to convert when you needed it, this episode will sound uncomfortably familiar. More importantly, it gives you a practical way to regain control before the rollercoaster starts again.

    18 min

  8. May 12

    Stop Celebrating B2B Sales Wins Without Learning Why You Won

    In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey break down a sales management practice that too many teams underuse: reviewing won deals with the same discipline they apply to lost deals. The conversation moves past celebration alone and into the real operating question: did the team win because the sales process worked, or because someone hit a lucky buzzer-beater? For leaders serious about Sales success, Revenue generation, and building repeatable Sales processes, this episode is a reminder that the best wins are not always the dramatic ones. Often, they are the boring, well-managed, properly documented deals that never should have been in doubt. Key Topics Discussed Why Won Deal Reviews Matter as Much as Lost Deal Reviews — 00:20 Kevin opens the episode by comparing won deal reviews to a SportsCenter highlight reel. Lost deal reviews help teams understand what went wrong, but won deal reviews reveal whether success came from strong Sales strategies, disciplined execution, or simple luck. Celebrate the Whole Team, Not Just the Closer — 01:40 Sean emphasizes that a true win often involves more than the salesperson. Proposal writers, credit teams, delivery teams, operations, and others may have played a role. Strong sales management means recognizing the system behind the win, not creating a hero culture around one person. Buzzer-Beater Wins vs. Controlled Wins — 03:00 Sean challenges leaders to determine whether the deal was won late through a heroic save or whether the team was in control from the beginning. The better business model is not dramatic last-second selling. It is predictable Revenue management through process discipline. Doing "Winner Stuff" in the Sales Process — 04:06 Kevin lays out the behaviors that separate consistent winners from lucky sellers: good notes, timely follow-up, clear problem statements, expectation management, proper sequencing, and bringing the right people into the deal at the right time. That is where Business acumen meets execution. Review Wins by Sales Stage, Not Storytelling — 06:41 Sean argues that leaders should avoid letting won deal reviews become casual storytelling sessions. Instead, they should walk the team through each stage in the CRM: discovery, scoping, economic buyer engagement, validation, proposal, and close. That structure turns a win into training, reinforcement, and better future Messaging. How New Sellers Learn from Won Deal Reviews — 09:27 Kevin explains why won deal reviews are especially valuable for newer reps. They may not yet have their own deep sales stories, but they can learn the questions, positioning, Value selling behaviors, and customer impact examples that successful sellers used. Key Quotes Kevin Lawson — 01:09 "You never know until you start doing the analysis, which is the same thing as not doing the analysis on your lost deals." Sean O'Shaughnessey — 03:40 "Sure, it makes you, puts you on SportsCenter, but let's be honest. Let's be boring. Let's just bring in the revenue." Kevin Lawson — 05:29 "The simple stuff done well at scale becomes quota-busting kind of behaviors and quota-busting kind of performance." Sean O'Shaughnessey — 07:53 "Step by step, walk through the story as stages of the sales process." Kevin Lawson — 11:17 "How could I instead go value, impact, value, impact, value? Because that's what drives customer expectation, which drives reputation, which drives stickiness." Sean O'Shaughnessey — 13:40 "When you're doing a win deal, celebrate the win. Really give the right team all of the credit." Additional Resources B2B Sales Lab Sean refers listeners to B2B Sales Lab, a community where sales professionals and sales leaders can discuss real sales challenges, share wins, and sharpen their Sales processes. Visit b2b-sales-lab.com to learn more. Moneyball / Billy Beane Reference Kevin references the Moneyball idea of winning through disciplined, repeatable base hits instead of relying on grand slams. The sales parallel is clear: sustainable Revenue generation comes from consistent execution, not occasional heroics. A Significant Actionable Item from this Podcast Pick one recently won deal and run a formal won deal review by CRM stage. Do not ask the salesperson to "tell the story." Walk through discovery, qualification, scoping, economic buyer access, validation, proposal, negotiation, and close. At each stage, identify what was done well, what was skipped, who contributed, what customer insight was captured, and what should be repeated. The decision you are making is simple: was this win evidence of a repeatable sales process, or was it a lucky outcome dressed up as Sales success? Summary This episode is a sharp reminder that winning is not enough. Sales leaders have to understand why the team won, whether the win can be repeated, and whether the process created value for the customer before the proposal ever arrived. Kevin and Sean make the case that won deal reviews are not administrative exercises. They are sales management tools that improve business acumen, strengthen messaging, reinforce value selling, and help create a team that wins more often without relying on last-minute heroics. Listen to this episode if your team celebrates wins but has not yet extracted the operating lessons from them. 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/

    18 min
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Ratings & Reviews

5
out of 5
7 Ratings

About

"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.

Information

  • Creator
    Kevin Lawson and Sean O'Shaughnessey
  • Years Active
    2023 - 2026
  • Episodes
    194
  • Rating
    Clean
  • Copyright
    © 2024
  • Show Website
    Two Tall Guys Talking Sales

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