Two Tall Guys Talking Sales

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

Two Tall Guys Talking Sales is a business podcast hosted by Kevin Lawson and Sean O'Shaughnessey, with 200 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Kevin Lawson and Sean O'Shaughnessey hosts Two Tall Guys Talking Sales, a business show with 200 episodes published.

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  Episode #202

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

  Aug 18, 202617 minS1

  A one-on-one sales meeting should not be a passive status report where the salesperson waits for the manager to ask questions. Done correctly, it becomes one of the most valuable tools for improving sales performance, removing obstacles, strengthening skills, and accelerating revenue generation. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey explain how salespeople can take greater ownership of these conversations—even when their sales manager has not created an effective structure. From forecasting the deals you expect to close to asking for resources, coaching, and candid feedback, Sean and Kevin lay out a practical framework for turning recurring one-on-ones into working sessions that support better sales processes, stronger sales management, and ultimately greater sales success. Key Topics Discussed Take Ownership of Your One-on-One Sales Meeting — 01:18 The salesperson should arrive prepared rather than treating the meeting as something the manager owns. Know the details of your opportunities, understand where you need help, and be ready to direct attention toward the issues that could materially affect your results. Kevin describes the meeting as an enablement resource: your job is to own the deal, while your sales leader can help mobilize marketing, technical, consulting, or other internal resources needed to win it. Start With the Scoreboard: Dollars, Deals, and Obstacles — 03:23 Sean recommends beginning with a clear statement of what you expect to close during the relevant sales period—whether that is the week, month, quarter, or another cadence appropriate to the business. Then identify the concerns surrounding those opportunities. Where is the deal blocked? What support is missing? What could prevent the projected revenue from becoming real revenue? This moves the discussion beyond vague pipeline updates and toward concrete decisions that can improve Pipeline Velocity and deal execution. Use the Meeting to Close the Loop on Commitments — 06:32 Kevin breaks the meeting into a scoreboard followed by the outstanding to-do items from prior conversations. That accountability runs in both directions. Salespeople should report on what they committed to doing, but they should also appropriately "lead up" by asking managers about resources, introductions, or assistance that was previously promised. Doing this prevents half-completed initiatives from accumulating and ensures the AE or salesperson receives the Sales Enablement support needed to move Complex Deals forward. Your Pipeline Is Not the Entire Meeting — 08:28 Pipeline matters, but Kevin warns against allowing pipeline inspection to consume the entire conversation. A productive one-on-one should also address problems, resources, execution, and development. A sales management system that does nothing more than repeatedly ask, "When is this deal closing?" leaves enormous value on the table. The meeting should help the salesperson improve the business, not merely describe it. Run Your Territory Like a Business—and Ask to Be Coached — 09:11 Sean suggests thinking of yourself as the CEO of your territory, with your sales leader serving as the chair of your board. You are responsible for the performance of that business, but you should also expect the leadership team to provide resources and guidance. That includes skills development. Ask your manager to review recorded calls, presentations, and customer conversations and provide specific coaching about what could have been done better. Demand Useful Feedback, Not Empty Praise — 11:01 Sean tells the story of challenging a newly promoted VP of Sales who accompanied him on customer calls but initially offered nothing beyond praise. Sean had already identified five things he could have done better and pushed his manager to provide equally substantive feedback. The lesson is not to imitate Sean's rather dramatic airport maneuver; rather, experienced salespeople still need coaching, and leaders have an obligation to help them improve. Key Quotes Sean O'Shaughnessey — 01:18 "You should have the philosophy of this is your meeting." Salespeople who take responsibility for the preparation, agenda, and desired outcomes of their one-on-one put themselves in a far stronger position to get the resources and coaching they need. Kevin Lawson — 02:47 "Your name's on the deal, and so it's up to you to figure out how you're going to win the deal and reach your quota." The manager can provide resources, coaching, and organizational support, but ownership of the opportunity remains with the salesperson. Kevin Lawson — 08:52 "Pipeline is not the only content for a pipeline meeting." Forecasting matters, but simply reviewing opportunity stages and expected close dates does little to develop the salesperson or remove the problems preventing deals from advancing. Sean O'Shaughnessey — 13:09 "You need your leadership to help you get better, and you need to demand it if they're not doing it." Strong salespeople do not outgrow coaching. They become more intentional about seeking useful feedback rather than accepting generic reassurance. Additional Resources B2B Sales Lab — Sean and Kevin invite listeners who want to go deeper into structuring effective one-on-one sales meetings to join the B2B Sales Lab and bring their specific challenges to office hours. The discussion can be tailored to the organization's particular sales process, sales cycle, and management environment. b2b-sales-lab.com A Significant Actionable Item from this Podcast Before your next one-on-one, create a simple, standardized agenda that begins with three things: the deals and revenue you expect to close, the specific risks or obstacles that threaten those deals, and the help you need from your sales leader. Then add outstanding commitments from the previous meeting and at least one skill you want your manager to help you improve. Do not wait for your VP of Sales, manager, or company to design the perfect process for you. Take ownership of the meeting yourself. Over the course of 50 or more meetings each year, improving the quality of these conversations can lead to meaningful gains in sales productivity, better resource allocation, stronger sales strategies, and more predictable revenue. Summary Most salespeople spend far too little of their week actually speaking with customers, which makes poorly structured internal meetings particularly expensive. In this episode, Kevin and Sean challenge both salespeople and sales leaders to stop treating the one-on-one as just another routine pipeline inspection and to start using it as a serious business management session. You will learn how to arrive with a clear scoreboard, surface the barriers threatening important opportunities, hold both sides accountable for commitments, secure the resources necessary to move deals forward, and make coaching an expected part of the conversation. If you want better sales management, sharper execution, stronger business acumen, and one-on-one meetings that actually contribute to B2B sales success, this episode gives you a framework you can put to work before your next meeting. B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/ You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/ You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/

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  Episode #200

  200 Episodes of B2B Sales Advice - The Lessons That Still Drive Sales Success

  Aug 11, 20261h 18mS1

  For the 200th episode of Two Tall Guys Talking Sales, Sean O'Shaughnessey and Kevin Lawson do something they have never done before: record together, in person, with a live studio audience asking the questions. What follows is less a celebration than a wide-ranging examination of what actually drives B2B sales success. Sean and Kevin tackle the resurgence of human relationships in an AI-enabled selling environment, the discipline required to define an ideal client profile, how artificial intelligence and Workflow Automation should eliminate non-selling activities, why great salespeople do not necessarily need industry experience, and what sales management must do differently to coach rather than rescue. They also dig into compensation, value selling, sales productivity gains, and the danger of single-threading Complex Deals. It is 200 episodes of experience compressed into one candid conversation about building sales processes that work when the sales leader is not in the room. Key Topics Discussed 04:04 – What 200 Episodes Have Revealed About Sales Fundamentals Sean and Kevin reflect on the recurring problems they continue to see across sales organizations: unclear ideal client profiles, weak Messaging, inconsistent prospecting, and critical sales knowledge that exists in someone's head instead of in a documented process. Kevin makes the case that documentation turns tribal knowledge into an operating system that can connect sales, marketing, customer service, and delivery. A repeatable sales process must actually be written down before it can be taught, measured, or improved. 14:27 – The Return of Real Relationships in an AI-Enabled Sales World Asked what has changed most over the life of the podcast—other than AI—Kevin points to the renewed importance of authentic, in-person relationships and value realization. Sean pushes the idea further: when prospects are overwhelmed by email, social outreach, and text messages, effective Sales strategies may sometimes look surprisingly old-fashioned. Knock on the door. Attend the event. Send a thoughtful physical note. The technology may be new, but trust still separates signal from noise. 17:45 – Using AI to Create More Selling Time James Sayer asks how salespeople should think about artificial intelligence right now, and Sean immediately frames AI as a productivity tool rather than a novelty. Research, CRM administration, account preparation, and other non-selling activities consume enormous amounts of a salesperson's day. The objective is not to use Generative AI because it is fashionable; it is to use AI, automation, and better tools to create additional opportunities for actual selling. Kevin recommends identifying the most time-intensive task inside prospecting, selling, or customer retention and finding a way to automate it. That is where meaningful sales productivity gains begin. 23:30 – Curiosity, Business Acumen, and Solving Problems Instead of Selling Products When the audience asks what young sales professionals should learn, Kevin argues that sellers need to stop concentrating on what they want to sell and start understanding the problem the customer needs solved. Sean adds curiosity as a foundational skill: understand the customer's business, how it makes money, and—critically—how it loses money. That becomes especially important when selling to a CFO or defending ROI. Later, Sean connects the same curiosity to relationship building: ask open-ended questions, stop talking about yourself, and give the prospect room to reveal what is actually driving the opportunity. 33:43 – Hiring Salespeople, Defining the ICP, and Building a System They Can Enter The discussion turns to one of the most expensive mistakes a business owner can make: hiring a salesperson for an industry Rolodex instead of hiring someone who knows how to sell. Kevin argues that salespeople should be hired into a documented system with clear expectations, onboarding, knowledge checks, and a defined sales process. Sean makes the complementary case that industry knowledge can often be taught far faster than genuine selling skill. The conversation then moves into ICP development: study your friendliest or favorite customers, identify what they have in common, understand their buying signals and psychographics, and use those insights to improve prospecting, Messaging, hiring, and pipeline quality. 49:53 – Sales Leadership, Compensation, Trust, and Multi-Threading Complex Deals Mary Tutton asks what capability matters most for a sales manager, prompting Kevin to identify consistency and analytical thinking. At the same time, Sean draws a sharp distinction between coaching and taking over the salesperson's job. The discussion expands into compensation design—simple enough that the seller should be able to estimate the payout mentally—and then into the realities of Enterprise Sales. In a significant B2B opportunity, one relationship is rarely enough. Sean warns against being single-threaded, while Kevin introduces a relationship-mapping exercise to expose gaps across the Buying Committee. In Complex Deals, sales success requires trust across the organization, not dependence on one friendly contact. Key Quotes Kevin Lawson — 25:29 "Don't sell the product you have. Sell the problem you solve." Sean O'Shaughnessey — 26:37 "Have you actually asked them, 'How do they lose money at their company?'" Audience Guest Al Lindemann — 39:58 "It is so much easier when you find the right person that has a need for what you want to sell." Kevin Lawson — 50:24 "The biggest impact a sales leader can have on a team is consistency." Sean O'Shaughnessey — 69:19 "Sales is about maybe not making friends, but definitely developing trust." Additional Resources The Challenger Sale — recommended by Kevin for developing a stronger perspective on customer-focused selling. Traction — Kevin recommends it for its broader business-management perspective. Atomic Habits — another recommendation for early-career professionals developing stronger personal disciplines. How to Win Friends and Influence People by Dale Carnegie — Sean recommends this classic for interpersonal skills and later connects its lessons directly to developing trust in B2B sales. Strategic Selling by Miller Heiman — Sean recommends finding the original edition and considers it foundational reading for professional salespeople. Grammarly — Sean strongly recommends it as a practical tool for improving written sales communication. B2B Sales Lab — Sean and Kevin discuss the community they created to give salespeople and sales leaders a place to ask questions, compare approaches, and learn from other practitioners. b2b-sales-lab.com If you want to watch the video version of this podcast, go to https://youtu.be/cEUfjs0rsnI A Significant Actionable Item from this Podcast Build—or rebuild—your ideal client profile from evidence instead of aspiration. Identify approximately ten of your friendliest or favorite customers, not simply the ten with the most revenue. Look for the customers who understood your value quickly, successfully adopted what you sold, became good references, and were enjoyable and profitable to serve. Then ask what they have in common: industry characteristics, business conditions, goals, buying signals, organizational traits, and even psychographic similarities. Do the reverse exercise with your hardest customers to identify characteristics that should disqualify an account. Finally, reduce the result to a clear ICP that can be explained in a few sentences and certainly in fewer than 100 words. Then use it against the opportunities already in your pipeline. Which deals genuinely fit—and which ones are consuming Pipeline Velocity because your team is trying to force-fit a prospect that was never a good customer in the first place? An ICP is not merely a prospecting definition. Done correctly, it becomes a decision tool for Revenue generation, hiring, qualification, Messaging, pipeline management, and sales strategy. Summary Episode 200 of Two Tall Guys Talking Sales is different from the typical milestone episode. Sean O'Shaughnessey and Kevin Lawson do not spend 75 minutes reminiscing; their live audience keeps pulling them back into the problems salespeople, sales leaders, and company owners are wrestling with right now. How should AI actually improve salesperson productivity? What makes an ICP useful instead of theoretical? Should you hire industry experience or sales talent? How should a VP of Sales coach the team? What makes a compensation plan motivational instead of confusing? And how many relationships do you really need inside an important B2B opportunity before you have earned the right to forecast it confidently? The answers repeatedly return to the same principle: better sales results come from disciplined systems combined with better human judgment. Technology can accelerate research. AI can reduce administrative work. Sales Enablement can make information easier to access. But curiosity, trust, Business acumen, coaching, clear sales processes, and genuine relationships still determine whether those tools translate into revenue. For anyone responsible for selling, managing sellers, or building a scalable revenue organization, this 200th episode offers something better than a retrospective: a practical examination of what still works, what has changed, and what deserves attention next. B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/ You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/ You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/

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  Episode #201

  Stop Losing Deals: Map the Buying Committee Before You Sell

  Aug 4, 202617 minS1

  Salespeople rarely lose complex deals because they forgot to follow up. They lose because they never developed a clear hypothesis about how the decision would be made, who would influence it, and what each stakeholder needed to believe. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey explain how a practical deal plan helps an AE move beyond the purchasing contact, understand the full buying committee, anticipate competitive threats, and coordinate the internal resources required to win. Using examples from sports, construction, manufacturing, and distribution, they show how disciplined planning improves sales execution, pipeline velocity, and long-term account growth. Key Topics Discussed Why Every Important Opportunity Needs a Deal Plan — 00:00 Kevin compares deal planning to the preparation elite athletes complete before taking the field. Great players do not simply understand their own position; they study their competition, anticipate likely reactions, and enter the game with a strategy. The same principle applies to B2B sales. A written deal plan increases the likelihood of closing the opportunity faster, executing more effectively, and avoiding preventable losses. Turning Assumptions into a Written Sales Hypothesis — 01:23 Sean explains that salespeople function as the quarterback of the opportunity. They must determine what they will do, how their teammates will contribute, and how the overall sales process should unfold. A sales hypothesis makes those assumptions visible: who will buy, what problem they are trying to solve, who benefits, and what conditions must exist for the deal to advance. If the hypothesis is not written down, it cannot be tested, improved, or consistently executed. Looking Beyond the Transactional Buyer — 02:32 A purchasing contact may control the transaction without receiving the greatest value from the product. Sean uses an HVAC compressor example to illustrate the broader stakeholder network: procurement, contractors, electricians, installers, building owners, maintenance teams, and eventual occupants may all influence the decision. Effective value selling requires messaging that addresses each stakeholder's priorities—not merely the requirements of the person issuing the purchase order. Understanding Decision Criteria and Stakeholder Influence — 05:05 Kevin expands the discussion through construction and engineered-specification sales. Manufacturers may need to influence architects, engineers, distributors, contractors, materials managers, and procurement teams long before an order is placed. Product specifications, installation requirements, availability, regional codes, service levels, and delivery capabilities can all become decision criteria. Strong business acumen allows a seller to connect those operational details to the buyer's desired outcome and measurable ROI. Mapping the Buying Committee and Informal Relationships — 08:32 Studying competitors is not enough. Salespeople must understand everyone "on the field," including the individuals who benefit from the solution, those who may resist it, and those who influence one another behind the scenes. Sean recommends creating a simple visual stakeholder map: write down the names, circle them, and connect the people who communicate, have worked together, attended school together, or maintain trusted relationships. Mapping the buying committee helps expose the informal decision network that a CRM contact list alone may not reveal. How Deal Plans Evolve into Account Plans — 10:45 A single stakeholder map supports one opportunity. Repeated deal plans reveal patterns across the account. Over time, the seller develops a record of who influenced previous decisions, why stakeholders supported or resisted the solution, and how internal relationships affected the outcome. That knowledge becomes the foundation of an account plan, giving sales management and Revenue management teams a stronger platform for expansion, retention, and more predictable revenue generation. Key Quotes Kevin Lawson — 00:57 "If you're not doing deal plans for your next deal, you're probably missing an opportunity to either close faster or more effectively, or you might even be increasing the chances that you're going to lose." Sean O'Shaughnessey — 01:44 "You are the quarterback of the team. Your job is to figure out what all of your teammates are going to help you do, but also what you're going to do." Kevin Lawson — 05:41 "It's just your opinion about who's going to buy, who it's going to benefit—which may be a different person—and then what are the other related people that could have influence over the deal?" Sean O'Shaughnessey — 09:15 "You need to understand everybody on the court, everybody on the pitch, everybody on the field." Sean O'Shaughnessey — 12:02 "Before long, your deal plans are becoming account plans." Additional Resources B2B Sales Lab The B2B Sales Lab is a place where sales professionals and sales leaders can continue developing practical tools for deal planning, account planning, and navigating complex deals. www.b2b-sales-lab.com A Significant Actionable Item from this Podcast Choose one of your five most important active opportunities and create a one-page stakeholder map before your next sales meeting. Write down every person who may buy, use, approve, implement, support, oppose, or benefit from your solution. Circle each name and draw lines showing formal reporting structures and informal relationships. Beside each stakeholder, record four things: What outcome does this person want? How will this person evaluate the decision? Whom does this person influence? What evidence or messaging does this person need from you? Then identify the most important relationship you have not yet developed. Define one action that will help you reach that person directly or through an existing contact. This simple exercise turns an opportunity record into an executable deal plan and gives your VP of Sales or sales leader something concrete to coach. Summary Winning an Enterprise Sales opportunity requires more than activity, product knowledge, or a strong relationship with procurement. The salesperson must understand the full buying committee, recognize the informal lines of influence, align the value proposition with multiple decision criteria, and create a written hypothesis for how the deal will be won. In this episode, Kevin and Sean provide a practical framework for navigating multi-stakeholder deals without adding unnecessary complexity to the sales process. Listen to the episode to learn how a blank sheet of paper, a few circles, and the right questions can sharpen your sales strategy, improve B2B sales pipeline predictability, and turn individual deal knowledge into a scalable account-growth system. B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/ You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/ You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/

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  Episode #199

  Sindre Haaland Coaches on Managing the Game, Not the Scoreboard: Building Predictable Sales Performance

  Jul 28, 202617 minS1

  Sales teams rarely fail because the quota was unclear. They fail because the daily behaviors required to reach it were never defined, measured, or reinforced. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey speak with Sindre Haaland, founder and CEO of SalesScreen, about why effective sales management requires leaders to manage the game, not merely watch the scoreboard. The conversation explores sales gamification, revenue architecture, CRM adoption, qualification discipline, and how AI can support more predictable B2B revenue generation without removing the human motivation that drives consistent execution. Key Topics Discussed Why sales leaders must manage the game, not the scoreboard — 01:19 Revenue targets tell salespeople where they are expected to finish, but they do not explain how to get there. Sindre argues that sales success begins by translating the quota into controllable, revenue-generating activities: calls, meetings, qualified opportunities, pipeline creation, and consistent execution throughout the quarter. Using gamification to change behavior—not merely celebrate outcomes — 02:19 Most sales contests reward closed business, but a salesperson cannot always control when a complex deal closes. Effective gamification focuses instead on meaningful behaviors that sellers can execute every day. Applied correctly, it can improve motivation, consistency, pipeline velocity, and performance among the middle of the sales team, not just recognize the top performers. Connecting activity metrics to conversion quality — 04:07 More activity is not automatically better activity. Measuring calls without examining results can produce meaningless behavior and distorted data. Sean, Kevin, and Sindre discuss the importance of combining activity targets with conversion rates, opportunity progression, and clear definitions of what good execution looks like. Building energy, recognition, and teamwork across the sales organization — 05:25 Sindre describes the moment SalesScreen demonstrated how software could create excitement throughout a sales floor when a deal closed. The larger lesson goes beyond celebration: real-time recognition helps managers reinforce productive behavior, improve engagement, and ensure individual accomplishments are not overlooked inside large sales organizations. Reverse-engineering the quota through revenue architecture — 08:15 Many sales teams know their targets but have never calculated how many calls, meetings, opportunities, and conversions are required to reach them. Without that basic revenue management discipline, prospecting becomes inconsistent, and the pipeline follows a predictable boom-and-bust cycle. Strong sales processes create continuity before pipeline weakness becomes a forecasting crisis. Gamifying qualification and opportunity progression in complex B2B sales — 09:25 In enterprise sales, closed deals may occur too infrequently to serve as useful daily performance signals. Teams can instead quantify progress through qualification frameworks such as MEDDPICC and SPICED, including CRM completeness, opportunity advancement, metric validation, and buying committee coverage. This creates better sales coaching data while reinforcing the behaviors that move complex deals forward. Key Quotes Sindre Haaland — 01:25 "Managers get one thing wrong: they're managing the scoreboard versus managing the game." Sindre Haaland — 04:07 "If you want to change behavior, you need to be in control of those behaviors." Sean O'Shaughnessey — 03:13 "The things you do at the beginning are going to affect the things that you do two, three, four, six, or ten months from now." Sindre Haaland — 08:27 "You need to understand how to get to goal and what real activity you need to put in, day in and day out, to get there." Kevin Lawson — 13:44 "Managing the game, not the scoreboard, is a key behavior." Additional Resources Sindre Haaland CEO and Founder at SalesScreen can be contacted on LinkedIn at linkedin.com/in/shaaland/ SalesScreen A sales performance management and gamification platform designed to quantify sales processes, reinforce productive activity, increase CRM engagement, and create more predictable sales performance. MEDDPICCC A qualification framework commonly used in enterprise sales and complex deals to evaluate metrics, the economic buyer, decision criteria, decision process, paperwork process, goal identification, coaches, champions, and competition. SPICED A sales qualification and discovery framework that helps sellers understand a buyer's situation, pain, impact, critical event, and decision process. A Significant Actionable Item from this Podcast Choose one sales role and reverse-engineer its quarterly quota into a weekly activity model. Start with the revenue target, then calculate the required number of closed deals, qualified opportunities, first meetings, and prospecting activities based on actual conversion rates. Do not stop at activity volume. Add at least one quality measure at each stage, such as meeting-to-opportunity conversion, MEDDPICC completion, stakeholder engagement, or opportunity progression. Once the model is built, ask a harder question: Are managers coaching these controllable behaviors every week, or are they simply reviewing the forecast after the damage has already been done? That distinction determines whether the organization is practicing sales management or merely reporting revenue history. Summary This episode challenges one of the most persistent weaknesses in B2B sales leadership: setting an ambitious target without building the operating system required to achieve it. Sindre Haaland explains how thoughtful gamification, disciplined sales processes, CRM data, and AI-supported performance insights can help leaders reinforce the right behaviors before the quarter slips away. For VPs of Sales, RevOps leaders, AEs, SDR managers, and business owners seeking better pipeline predictability, stronger CRM adoption, and measurable gains in sales productivity, this conversation provides a practical framework for turning quotas into consistent execution. Listen to the episode to learn why predictable revenue does not begin with the forecast; it begins with the behaviors your team repeats every day. B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/ You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/ You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/

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  Episode #198

  Stop Asking Bad Discovery Questions: How Top B2B Sellers Earn Buyer Trust

  Jul 21, 202616 minS1

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

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