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. 1D AGO

    With Great Pipeline Power Comes Great Responsibility: Fix Your Sales Forecast

    Two Tall Guys Talking Sales hosts Kevin Lawson and Sean O'Shaughnessey tackle one of the most overlooked drivers of sales success: forecast accuracy. This episode goes beyond the usual conversation about CRM hygiene and quota pressure to get to the real issue: salespeople and sales managers carry critical information that the rest of the company depends on for hiring, staffing, planning, and revenue generation. Sean and Kevin argue that forecasting is not administrative overhead. It is a direct reflection of discovery quality, business acumen, value selling, and the discipline of running strong sales processes. If you want sharper sales management, more credible messaging, and a more reliable path to revenue management, this conversation is worth your time. Key Topics Discussed Why forecasting is a leadership responsibility, not just a sales task (00:00) Sean opens with a memorable analogy: with great power comes great responsibility. Salespeople hold information no one else in the company has—what is likely to close, when it will close, what the buyer needs, and what revenue is actually coming. That knowledge creates an obligation to communicate with accuracy. How poor forecast data affects hiring, staffing, and company decisions (02:00) Kevin makes the stakes clear. Forecast data is not trapped inside the sales department. Executive teams use it to make staffing decisions, resource plans, and growth bets. When the data is weak, the business makes bad decisions. Why discovery is the foundation of accurate forecasting (05:00) Sean ties forecasting directly to discovery. If you do not ask tough questions early, you will eventually pay for it later in the sales cycle. Strong discovery clarifies the customer's business drivers, strengthens messaging, improves value selling, and makes forecast confidence more credible. Why sales strategies fail when pipeline discipline is weak (08:07) Kevin connects forecasting to pipeline reality. Leaders cannot force a number into existence simply because they want growth. If the top of the funnel, qualification discipline, and relationship development are not in place, the revenue generation target is a fantasy, not a strategy. Why customers buy outcomes, not features (09:21) Both hosts reinforce a central truth of value selling: buyers care much more about business impact than about technical specifications. The real issue is not the drill, but the hole—and even more than that, what the hole allows them to accomplish. How inaccurate forecasting damages real people and real businesses (13:13) Sean closes with a story from early in his career that shows the human cost of bad forecasting. A low forecast contributed to layoffs that, in hindsight, were unnecessary. It is a sharp reminder that revenue management is not theoretical. Accuracy matters. Key Quotes Sean O'Shaughnessey (00:00) "One of the wisest men in all of sales is a gentleman by the name of Stan Lee." Kevin Lawson (02:02) "The entire company is basing its hiring and staffing decisions on your data." Kevin Lawson (03:25) "You have to ask tough questions early." Sean O'Shaughnessey (07:46) "You document all that, and you tell your boss the truth. It's as simple as that." Kevin Lawson (11:20) "Put the date that the customer should buy based on the insight you've gleaned, not the date that you want them to buy." Sean O'Shaughnessey (12:00) "You don't sell the drill, you sell the hole, and more importantly than that, you sell what goes through the hole." Additional Resources B2B Sales Lab Sean references the B2B Sales Lab community as a place for sales professionals and sales managers to ask questions, refine their thinking, and improve their skills in areas such as forecasting, sales processes, and revenue generation. Chris Cocca on the importance of Discover Sean mentions episode 85 featuring Chris Cocca, particularly his point that discovery is the most important part of the sales process. https://sites.libsyn.com/458454/transforming-opportunities-chris-coccas-insights-on-perfecting-the-discovery-meeting A Significant Actionable Item from this Podcast Audit your current pipeline and rewrite the expected close date for every meaningful deal based on buyer evidence, not seller hope. That means looking at each opportunity and asking: What business issue is driving this purchase? Who has validated the urgency? What internal steps does the customer still need to complete? What evidence supports the date in CRM? This one habit sharpens sales management, improves forecast reliability, strengthens messaging, and forces better value selling. Most missed forecasts are not caused by bad luck. They are caused by untested assumptions that stayed in the pipeline too long. Summary This episode is a concise but serious discussion about forecasting, discovery, and the responsibility that comes with carrying the company's most important field intelligence. Sean and Kevin do not treat forecasting like a spreadsheet exercise. They treat it as a reflection of business acumen, selling discipline, and the quality of a seller's thinking. If you want better sales strategies, more reliable sales processes, and a stronger grasp of how forecasting affects the entire business, this is an episode worth downloading. It will challenge how you look at your pipeline—and probably how you communicate it. 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

  2. APR 14

    The Sales Meeting Prep Advantage: How Top Sellers Win Before the Call Starts

    This episode of Two Tall Guys Talking Sales gets after a basic truth that too many salespeople ignore: meeting prep is not administrative overhead, it is a competitive weapon. Kevin Lawson and Sean O'Shaughnessey break down why organized sellers create better first impressions, ask sharper questions, and build trust faster than competitors who show up improvising. The conversation moves from practical prospect research to the sales management discipline, then to how modern AI tools can reduce prep time without lowering quality. If you care about Sales success, stronger Messaging, and more consistent Revenue generation, this episode gives you a simple edge you can apply immediately. Key Topics Discussed Why meeting prep still separates serious sellers from average ones (00:00) Kevin opens with a frustration most professionals recognize instantly: the seller who accepted the meeting but clearly did not do the homework. The discussion makes the case that doing the simple things well is still one of the most reliable Sales strategies in B2B selling. How preparation signals respect, credibility, and Business acumen (01:00) Sean shares an early-career story about using a Wall Street Journal mention to walk into a customer meeting knowing more about the company's current situation than the contact did. The point is not cleverness. It is that informed preparation communicates seriousness and creates trust. What sellers should actually know before a prospect or customer meeting (03:10) Kevin lays out the practical standard: know the business model, know how the company creates value, understand the people involved, and have a working sales hypothesis. He also ties preparation back to documented ICPs, personas, value propositions, and the broader Sales processes that support effective prospecting. Using frameworks like PESTEL to improve Value selling conversations (06:19) The conversation moves beyond surface-level research into structured analysis. Kevin explains how frameworks such as PESTEL help a seller understand the customer's operating environment and bring relevant insight into the meeting, which is where real Value selling starts. How Google Alerts and AI can compress research time without lowering quality (07:25) Sean introduces Google Alerts as a low-friction way to stay current on target accounts and local developments. He then connects that to AI, showing how sellers can save prompts, generate company or industry briefings, and use tools like PESTEL analysis on demand before calls and meetings. Why current research matters more than favorite tools (12:00) Kevin closes by warning against relying on stale assumptions or outdated tooling. Platforms change. Commercial products evolve. What matters is staying current and using the available tools to support better Revenue management, stronger Messaging, and more informed customer conversations. Key Quotes Kevin Lawson (00:40): "Being ready for a meeting is so simple. It's often overlooked, and it's a huge opportunity to outshine your competition as a seller." Sean O'Shaughnessey (02:08): "He was so impressed that we knew his business and we knew what was going on about his company that until the last day that I knew him, he always mentioned it." Kevin Lawson (03:28): "Your ducks in a row means you know the business you're calling on, what they do, how they create value, how you can have your sales hypothesis, how you can create value for them." Sean O'Shaughnessey (11:19): "There is no excuse that you don't know today's announcement about your prospect when you walk in the door or pick up the phone to contact that prospect." Kevin Lawson (14:06): "Be current with your research. Be current with the commercially available products so that you can serve your prospects and customers well." Additional Resources Google Alerts Sean recommends Google Alerts as a simple, proven way to monitor prospect companies, industries, and geographic territories to stay relevant in conversations. PESTEL Framework Kevin references PESTEL as a useful framework for understanding the political, economic, social, technological, environmental, and legal factors affecting a customer's business. B2B Sales Lab B2B Sales Lab is a place where sales professionals and sales leaders can work through practical selling and sales management challenges in more depth. A Significant Actionable Item from this Podcast Open your calendar and identify all upcoming prospect meetings and prospecting blocks. Then make the first 15 minutes of each one non-negotiable research time. Use that window to review company news, confirm the contact's role and influence, revisit your ICP and persona fit, and build a working hypothesis about where you can create value. This is a small discipline, but it sharpens Messaging, improves call quality, and separates a seller who is merely active from one who is actually driving Sales success. Summary This episode is a sharp reminder that strong selling does not begin when the meeting starts. It begins before the meeting exists in the customer's mind. Kevin and Sean show how disciplined preparation improves trust, differentiation, and execution across prospecting, account management, and broader sales management efforts. They also make the modern case clearly: AI should not replace thinking; it should accelerate the research that improves thinking. If you want tighter Sales processes, better value-selling conversations, and more reliable revenue generation, this episode is worth your time. 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

  3. APR 7

    Pipeline Hygiene, Forecast Accuracy, and Sales Success in Q2

    In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey turn an informal B2B Sales Lab office-hours conversation into a sharp discussion on pipeline hygiene, forecast accuracy, and the habits that separate serious sellers from hopeful ones. What starts as a conversation about cleaning up Q2 quickly becomes a broader lesson in sales management, business acumen, and personal accountability. They dig into why sloppy CRM data creates bad decisions, why aspirational close dates damage credibility, and why real sales success still comes back to disciplined sales processes and direct customer contact. For sales professionals, sales leaders, and anyone responsible for revenue generation, this episode is a practical reset. Key Topics Discussed Why pipeline hygiene matters right now (02:11) Kevin opens with a blunt point: whether you are ahead, behind, or exactly on plan, now is the time to clean up your pipeline. Dead leads need to be removed, stalled opportunities need clear next steps, and unrealistic deals need to be moved to a timeline that reflects reality. This is more than administration. It is the foundation of reliable sales management and cleaner revenue management. The danger of aspirational forecasting (08:08) Sean and Kevin take aim at one of the oldest problems in selling: the fantasy close date. They explain why putting deals into the quarter just to make the pipeline look healthier undermines trust, makes leadership harder, and creates unnecessary scrutiny. Good forecasting is not about optimism. It is about judgment, honest messaging, and the discipline to call a deal what it is. How to handle slipped deals before they slip again (06:00) Sean breaks down what a slipped deal really means. If an opportunity slips once, it may be explainable. If it slips twice, the seller needs to challenge the underlying need, timing, and pain more aggressively. That turns the conversation from passive deal chasing into value selling, where the seller must re-establish why the problem matters now. What accurate CRM ownership really signals (10:38) Sean makes the standard clear: if your name is on the deal, the record should reflect your best understanding of reality. That includes dates, scope, amount, risks, and notes. He also draws an important distinction between uncertainty and carelessness. Missing information can be understandable. Failing to document what you do know is not. This is where disciplined sales processes and professional credibility meet. How strong sellers earn trust and promotion opportunities (14:27) The conversation shifts from data quality to career trajectory. Sean argues that sellers who forecast accurately, exceed quota, and help others improve naturally build the reputation that leads to advancement. Kevin reinforces that when a manager asks you to teach the rest of the team how you work, that is one of the clearest signals that your approach is working. The KPIs that actually move performance (17:55) As they wrap up, Kevin and Sean focus on useful performance indicators. Not vanity metrics. Not activity for activity's sake. They emphasize developing new relationships, preparing for meetings, asking for next steps, requesting the order, requesting referrals, and increasing one-to-one customer conversations. The point is simple: better sales strategies come from better behaviors, repeated consistently. Key Quotes Kevin Lawson (08:26) "Aspirational close date is absolute garbage." Sean O'Shaughnessey (10:38) "Your name is on the deal… I expect it to be an accurate representation as you understand it." Sean O'Shaughnessey (19:13) "The metric that always works, always, always works is if you're talking to a customer, you're probably doing good things." Kevin Lawson (17:04) "He really cares about how many people he helped get to President's Club." Additional Resources B2B Sales Lab Sean and Kevin refer throughout the episode to the B2B Sales Lab community, a peer environment for salespeople, sales leaders, and sales professionals who want to sharpen execution, exchange insight, and improve sales success through practical discussion. Previous episode featuring Joe English (16:53) Kevin references the March 31 episode with Joe English, particularly around leadership, development, and the idea that strong leaders measure success by how many people they help reach top performance. A Significant Actionable Item from this Podcast Run a hard review of every open deal and lead in your CRM this week. Remove dead opportunities, reset unrealistic close dates, document the real blockers, and assign a next step with a deadline. Then identify every deal that has slipped more than once and ask a tougher question: what is the real business pain of not solving this now? That one exercise improves messaging, strengthens forecast credibility, and gives you a cleaner base for revenue generation in the quarter ahead. Summary This episode is a useful listen for anyone who wants a more credible pipeline, stronger forecasting, and better execution going into the next quarter. Kevin and Sean do not romanticize selling. They treat it as a discipline built on accuracy, ownership, customer contact, and sound judgment. If you care about sales management, sales strategies, value selling, and building the kind of habits that support long-term sales success, this conversation will give you something immediately usable. It is practical, direct, and worth downloading before your next pipeline review. 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/

    22 min

  4. MAR 31

    Joe English Helps the Two Tall Guys Understand How to Build Profitable Growth with Better Sales Management and Sales Processes

    This episode of Two Tall Guys Talking Sales digs into a question that sits underneath almost every stalled growth story: why do good companies with solid offerings still fail to scale profitably? Kevin Lawson and Sean O'Shaughnessey sit down with Joe English of 360 Consulting to unpack what separates random sales activity from a real growth system. The conversation moves past personality-driven selling and into the mechanics of sales management, sales processes, messaging, and execution. Joe makes the case that revenue generation becomes fragile when a business depends on heroics, and durable when leaders build repeatable systems around the right customers, the right value, and the right internal structure. For leaders focused on sales success, business acumen, and profitable scale, this episode is a sharp discussion of how to turn growth into an engineered outcome instead of a hopeful one. Key Topics Discussed 00:43 – Profitable growth versus growth for its own sake Sean frames the central issue: many companies have decent products and some good processes, yet still are not growing at the rate their model demands. Joe responds by arguing that growth matters only if it produces EBITDA and bankable outcomes, not just top-line growth. 01:42 – The four pillars of a repeatable growth system Joe outlines the foundation he uses with clients: go-to-market, people, process, and execution. His point is straightforward—sales success is not driven by charisma alone. Sustainable revenue generation comes from combining the art of selling with disciplined system design. 04:15 – Why ICP, value selling, and sales processes come first When Kevin asks what Joe looks for first, Joe explains that his advisory process starts by clarifying the ideal customer profile, then refining the company's value propositions, and then documenting the actual sales process. That sequence matters because weak positioning and vague targeting often lead to poor execution downstream. 06:23 – The danger of selling the wrong value Sean raises a common market mistake: companies often describe their offering one way while customers actually buy it for a different reason. That disconnect creates weak messaging, confused sales conversations, and slower growth. Joe agrees and argues that many firms try to be all things to all buyers instead of owning a specific problem they solve exceptionally well. 08:07 – Change management and getting people to adopt better selling habits The conversation shifts into change management, where Joe says the hardest part of any transformation is people. His approach is to help individuals understand how structure, tools, and clearer expectations make them better and more efficient rather than simply creating management overhead. 10:39 – Why sales is often not the strongest function in a growing company Sean asks whether owners truly think their job is to make salespeople great. Joe's answer is nuanced: most owners do want success for their people, but they often only know how to systematize the function they personally came from. In many firms, that means operations is stronger than sales, and sales management becomes an afterthought until growth stalls. Key Quotes Kevin Lawson (00:00) "Success is determined by the eyes of the beholder." Joe English (01:42) "Growth is super important for any business, right? You're growing or you're shrinking." Joe English (03:29) "It has to be profitable growth. It can't just be growth for growth's sake." Joe English (05:38) "How do we have conversations and tell stories to clients that are relevant to them, not us pitching?" Sean O'Shaughnessey (06:23) "You're not actually talking about what the value is that the customer gets from your product." Joe English (09:55) "We're here to make you better because if you are successful in your role, that just makes everybody else more successful." Additional Resources Joe English, 360 Consulting DFW - Joe@360consultingdfw.com Jim Collins' Good to Great - https://a.co/d/05TQ0K3d A Significant Actionable Item from this Podcast Audit whether your company's messaging matches the value your best customers actually receive. That sounds simple, but it is usually where revenue management starts to break. If your team describes the product one way while customers buy it for another outcome, your sales strategies, value selling, and sales processes are all built on a false premise. Start with three questions: Who is our best customer? What problem do they uniquely hire us to solve? What does our sales team say that proves we understand the problem better than our competitors? That exercise forces sharper messaging, stronger sales management, and more reliable revenue generation. Summary If you care about sales success beyond motivational noise, this episode is worth your time. Kevin, Sean, and Joe English get into the real mechanics of profitable growth: ideal customer profile discipline, stronger messaging, better sales processes, practical change management, and the difference between a founder-dependent business and one built for scale. It is a compact yet useful conversation for leaders trying to improve their business acumen, tighten their sales strategies, and build a company that grows with intention rather than strain.

    18 min

  5. MAR 24

    How to Use AI and 10-K Reports to Uncover Sales Insights That Win More Deals

    This episode of Two Tall Guys Talking Sales tackles a problem most B2B sellers know they should solve but rarely do: how to turn a customer's annual report into practical sales insight. Sean O'Shaughnessey and Kevin Lawson argue that modern selling requires more than relationship instinct and product knowledge. It requires stronger business acumen, sharper messaging, and a willingness to use AI as a real thinking partner. In a compact but highly practical discussion, they show how sales professionals can use a company's 10-K, executive commentary, and AI prompts to uncover priorities, hiring plans, risks, and revenue direction. The result is a smarter approach to discovery, stronger value selling, and more relevant conversations, all of which improve revenue generation and long-term sales success. Key Topics Discussed Why sales in 2030 will not look like sales in 1990, 2000, 2010, or even 2020 (00:00) Sean opens with a direct challenge to outdated sales practices, arguing that the pace of change is forcing sales leaders and front-line sellers to rethink how they prepare, learn, and compete. AI versus automation and why both matter to modern sales management (02:00) Kevin draws an important distinction between workflow automation and artificial intelligence, explaining that while this episode focuses on AI, many companies can improve sales processes immediately by exploring both. How to use a customer's 10-K annual report as a sales intelligence asset (03:22) Sean lays out a practical method for finding and downloading annual reports, then reframes them as a powerful source of insight for discovery calls, QBRs, and strategic account conversations. How to prompt AI to extract selling insight without making assumptions (07:38) Kevin shares a simple but effective prompting structure that positions AI as a senior analyst tasked with identifying the company's top priorities, using only exact language from the report and transcript. How to tailor prompts to your offer, industry, and customer problems (10:29) Sean expands the technique by showing why sellers should add their own elevator pitch, industry context, and solution focus so the AI can return insights that are actually useful for sales strategies and revenue management. Which business questions matter most when mining annual reports (12:00) The conversation moves from theory to execution as Sean suggests high-value questions around projected revenue, hiring plans, geopolitical pressures, tariffs, fuel costs, and lawsuits that could affect a company's direction. Key Quotes Sean O'Shaughnessey (00:00) "How you sold in 1990 and 2000 and 2010 in 2020 is not how you're going to sell in 2030." Kevin Lawson (02:20) "I want AI to be a thinking partner alongside of me." Kevin Lawson (09:00) "It's so important to understand why it's not just because we don't have the time. It's because the company we're calling on, the prospect is telling us in no uncertain terms what they're about to do." Sean O'Shaughnessey (12:00) "You can get an immense amount of data about your client, about your prospect by just having AI, your AI assistant, your AI intern to figure all that stuff out." Additional Resources B2B Sales Lab Sean and Kevin reference the B2B Sales Lab as a community for salespeople, sales leaders, and business owners who want to exchange ideas, strengthen sales management capability, and improve how they grow revenue. Company Investor Relations Pages Sean recommends starting with the customer's own website to locate investor relations materials and annual reports. SEC Filings / 10-K Reports Kevin specifically notes that sellers should focus on the 10-K annual report rather than confusing it with an 8-K or 10-Q. A Significant Actionable Item from this Podcast Take one target account this week and download its most recent 10-K annual report, plus the executive transcript, if available. Then upload those materials into your preferred AI platform and ask it to identify the company's top five strategic initiatives, expected risks, hiring priorities, and revenue direction using only what is explicitly stated in the source material. This is a meaningful discipline because it strengthens business acumen, improves messaging, and gives you a more credible point of view before your next call. Done consistently, it can elevate both individual sales success and the overall quality of your sales processes. Summary This episode is a strong listen for any seller, sales leader, or business owner who wants to stop showing up underprepared to important customer conversations. Sean and Kevin take a dense, intimidating source of corporate information and turn it into a usable framework for better discovery, better value selling, and smarter account planning. If you want sharper sales strategies, stronger revenue generation, and a more practical way to use AI in the real world of B2B selling, this episode gives you a concrete place to start.   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. MAR 17

    Sales Success Starts Here: Find Customer Pain, Align Goals, Win Bigger Deals

    This episode of Two Tall Guys Talking Sales gets to the heart of a mistake too many sellers make: they confuse product talk with real value. Kevin Lawson and Sean O'Shaughnessey unpack the difference between pain and goals, then push the conversation further into what actually matters in sales success, understanding how buyers measure outcomes, how decisions get made, and how to connect your offer to revenue generation, business acumen, and meaningful results. This is not a discussion about clever wording. It is a discussion about how better sales strategies, sharper messaging, and stronger value selling lead to better sales management and more credible revenue management conversations. If you sell into complex environments, this episode will sharpen the way you think about sales processes and how customers justify change. Key Topics Discussed Pain vs. goals in the buying decision (01:00) Sean breaks down the practical difference between a problem someone can tolerate and a goal important enough to fund. That distinction matters because many stalled deals are not really lost deals; they were never priority deals in the first place. Why value selling must be framed in the customer's terms (05:00) Kevin argues that buyers do not care about features, benefits, or polished collateral unless those things connect to outcomes they actually measure. This is a strong lesson in messaging, sales processes, and how sales success depends on tying effort to business value. How to quantify what matters to the buyer (08:00) The conversation shifts into measurement. Kevin explains that whether you start with pain or start with goals, the real work is quantifying the impact. That means understanding the individual persona, how they are evaluated, what drives their bonus, and what creates personal and professional value for them. Small deals are often pain deals. Big deals are usually goal deals. (10:00) Sean makes an important distinction for sellers working on larger opportunities. Small purchases often solve immediate operational pain. Larger purchases require alignment with broader corporate priorities, capital allocation, and the economics of long-term return. How value selling connects cost, payoff, and timing (11:00) Sean brings the discussion back to core business acumen: what does it cost to live with the problem, what does it cost to solve it, and what is the payback? That is where revenue management, value selling, and serious sales strategies stop being theory and start becoming executive-level conversations. Key Quotes Kevin Lawson (00:01) "Don't get wrapped around the axle on words, but get wrapped around the axle on how you're gonna create value for your next deal." Kevin Lawson (07:03) "Our job as salespeople is to create insights around what value we bring." Kevin Lawson (09:16) "People don't buy the project, they buy the outcome." Sean O'Shaughnessey (09:45) "Drills are about putting holes in something else. Buying a drill is worthless." Sean O'Shaughnessey (11:37) "How much does it cost to put up with it, and how much does it cost to solve it?" Additional Resources B2B Sales Lab A private community for sales professionals who want help solving real sales problems in a non-public setting. b2b-sales-lab.com A Significant Actionable Item from this Podcast Take one active opportunity in your pipeline and force yourself to answer three questions in writing: Is this deal driven by pain or by a goal? How is that pain or goal quantified in business terms? Who inside the account actually has the authority to fund the solution? That exercise sounds simple, but it exposes weak sales thinking fast. It improves messaging, strengthens value selling, and helps you determine whether you are dealing with a tolerated inconvenience or a real business priority. In practical terms, it will make your sales processes more disciplined and improve your ability to pursue revenue-generating opportunities that can actually close. Summary This episode is worth your time because it strips away a lot of the lazy thinking that weakens modern selling. Kevin and Sean do not merely debate pain versus goals as abstract concepts. They show why that distinction shapes sales management, sales success, value selling, and the quality of your revenue management conversations. If you want to sharpen your business acumen, improve your sales strategies, and learn how better messaging can move opportunities forward, this episode will give you a more useful way to think about how deals really get done. 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

  7. MAR 10

    Are You Coachable? The Sales Skill That Quietly Drives Quota Attainment

    Kevin Lawson and Sean O'Shaughnessey take on a question that exposes more than technique: Are you actually coachable? This episode of Two Tall Guys Talking Sales digs into the connection between coachability, trust, quota attainment, and long-term sales success. Along the way, they move beyond generic advice and into the real mechanics of growth in selling—how coaching sharpens business acumen, improves sales management, strengthens sales processes, and ultimately drives stronger revenue generation. If you care about becoming more effective in high-pressure sales moments, this episode is worth downloading. Key Topics Discussed Why coachability matters in sales and sales leadership (00:00) Kevin opens by tying coachability to performance, preparation, and intentional execution. Sean expands the lens, arguing that coachability is not just a seller issue. Sales leaders need it too, especially when they are accountable to a CEO, president, CFO, or board and must adapt in real time to what the field is actually seeing. The difference between getting coaching and applying coaching (03:13) Sean makes a critical distinction: being coachable is not nodding politely at advice. It is trying the idea, evaluating the outcome, and returning with thoughtful feedback about what worked, what missed, and how to adapt the tactic to your own style, messaging, and customer context. The basketball free-throw analogy for pressure-selling moments (04:29) One of the strongest sections in the episode compares a live sales moment to stepping to the free-throw line with the game on the line. The coach cannot take the shot for you. In the same way, no manager can rescue you when the CEO unexpectedly joins the meeting and says, "Let's make a deal right now." That is where preparation, coaching, and value-selling discipline show up. Coaching comes from more places than your manager (06:33) Kevin broadens the definition of coach to include peers, internal champions, prospect-side advocates, customers, and even deals you lost. That is an important shift for anyone serious about sales strategies and revenue management. The lesson is simple: if you accept input from only one source, you limit your own development. Why coachability increases quota attainment (08:24) Kevin makes the case that coachability is not a soft trait. It has hard commercial consequences. Sellers who stay open to wise counsel, surround themselves with strong peers, and learn from feedback tend to improve execution and increase quota attainment. This is where personal growth meets real sales success. Trust as the real product being sold (09:47) Sean closes with the episode's most durable idea: sellers do not merely sell products or services. They sell trust. Trust in themselves, in the offering, in the company behind it, and in the process that follows the sale. That framing has major implications for messaging, value selling, and every part of the sales process. Key Quotes Kevin Lawson (07:51) "If you are not willing in an interview scenario to take coaching and feedback, you're probably not going to make it as a seller." Kevin Lawson (08:24) "Being coachable has the magic outcome of quota attainment increases." Sean O'Shaughnessey (03:34) "You need to try the ideas. Now, the key to being coachable though, is to try it, think about what happened, and then respond back to your coach and say, 'I tried to do that and it didn't quite work. What did I miss?'" Sean O'Shaughnessey (09:47) "You sell trust." Sean O'Shaughnessey (10:22) "If you always think that I am selling trust... that I am not a liar... that what I tell you, Mr. Prospect, is the truth... we'll do validation events or whatever, but you've got to trust that the product's going to work." A Significant Actionable Item from this Podcast Audit one recent coaching moment and ask yourself a harder question than "Did I hear the advice?" Ask, "Did I actually apply it, reflect on the result, and return with a better question?" That is the real test of coachability. Pick one deal, one lost opportunity, or one upcoming customer conversation and intentionally apply a piece of coaching before your next call. Consistently done, this improves business acumen, tightens sales processes, and makes revenue generation more predictable. Summary This episode of Two Tall Guys Talking Sales is not really about whether you like feedback. It is about whether you can convert feedback into better execution under pressure. Kevin Lawson and Sean O'Shaughnessey connect coachability to trust, sales management, messaging, value selling, and the daily behaviors that separate average performers from professionals who consistently create sales success. If you want sharper sales strategies and a more mature approach to revenue management, this conversation offers more than just inspiration. It gives you a standard. 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/

    14 min

  8. MAR 3

    Sales Success Playbook: Ethical Gifting, Better Messaging, and Higher Win Rates with Sendoso's Kris Rudeegraap

    Kevin Lawson and Sean O'Shaughnessey sit down with Kris Rudeegraap, Co-CEO of Sendoso, to get brutally practical about one thing most reps underestimate: how to cut through noise without sounding gimmicky or "bribey." This episode breaks down gifting as a repeatable, ethical sales strategy that supports sales management and revenue generation, whether you're trying to break into target accounts, accelerate a stalled deal, or reinforce relationships with customers who already trust you. Key Topics Discussed Breaking through the gatekeeper and digital noise with modern sales strategies (00:05) Kevin frames the real question sellers are asking: what actually drives sales success when inboxes are flooded, and attention is scarce? The "right vs. wrong" of gifting: tactic beats timing (02:13) Kris outlines the difference between thoughtful outreach and a clumsy "gift-for-meeting" move that damages credibility. Building a gifting sequence inside your sales processes (ABM + long-cycle deals) (03:55) How to use gifting as a deliberate step in your outreach and pipeline motion, not a one-off stunt. Value selling through gratitude: gifts as relationship reinforcement (04:45) Sean connects gifting to thanking customers for orders and references—small moves that strengthen champions and improve revenue management. AI-driven gifting: recommendations, timing, messaging, and address intelligence (10:24) Kris explains how AI improves targeting and relevance, reducing research time and enhancing personalization and response rates. Metrics that matter: win rates, meeting rates, and attribution (11:45) Sean pushes for numbers; Kris shares performance lifts and points listeners to deeper case studies. Key Quotes Kevin Lawson (00:05): "How am I actually going to make my number? What is actually going to get through the gatekeeper… and help me meet my number?" Sean O'Shaughnessey (01:20): "How can we use tools like gifts appropriately so that we're not bribing the customer… but we are making it like, 'wow, these guys are pretty cool. I wanna talk to them.'" Kris Rudeegraap (02:25): "I don't think the problem is when to send. It's like the tactic of how you're sending is what could be wrong." Kris Rudeegraap (12:18): "We've seen [win rates] increased up to nine x by using gifting in the sales cycle… and… up to four x increase the likelihood of booking a meeting." Additional Resources Sendoso website (case studies and data studies): Sendoso.com  Kris Rudeegraap: kris@sendoso.com https://www.linkedin.com/in/rudeegraap/ Sendoso on LinkedIn https://www.linkedin.com/company/sendoso/ A Significant Actionable Item from this Podcast Pick 10 target accounts and design a two-touch gifting step that fits your current sales processes. One touch is for prospecting (to earn attention), one touch is for late-stage momentum (to reduce friction). The requirement: pair each gift with a message that tightens messaging around either (a) your value proposition in the customer's world or (b) a real personal detail you've validated. If you can't explain why that specific item fits that specific recipient, don't send it. This is business acumen applied to outreach, not arts-and-crafts. Summary If your outreach feels interchangeable—and your deals slow down the moment you ask for something—this episode gives you a cleaner play. Kris lays out how gifting can support sales management, sharpen value selling, and improve revenue generation when it's integrated into real sales strategies and measured like any other lever in revenue management. You'll leave with clear guardrails for what not to do, vivid examples of what works, and a practical view of how AI can raise relevance and response rates without adding more busywork. 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
    184
  • Rating
    Clean
  • Copyright
    © 2024
  • Show Website
    Two Tall Guys Talking Sales

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