Weak Sales Discovery Creates a Weak Pipeline

Weak Sales Discovery Creates a Weak Pipeline

Discovery is not a preliminary conversation before the "real" selling begins. It is where complex B2B deals are either built on credible business value—or quietly undermined by weak assumptions, missing stakeholders, artificial urgency, and an unreliable forecast. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey examine why strong discovery is essential to value selling, accurate revenue management, and sales success. They also explain how experienced sellers use business acumen to uncover operational constraints, quantify ROI, navigate the buying committee, and guide customers through decisions they may not yet understand how to make. Key Topics Discussed Why weak discovery creates a weak pipeline — 00:28 Poor discovery does not merely cause an awkward sales meeting. It produces shallow opportunities, fake urgency, premature proposals, discount pressure, inaccurate forecasts, and stalled decisions. Sean and Kevin establish discovery as the foundation of effective sales processes and B2B sales pipeline predictability. Understanding the business reason behind the purchase — 01:27 Knowing what the buyer wants is not enough. Sellers must uncover why the organization needs it, what business problem is driving the investment, who holds influence and authority, and what happens if the problem remains unresolved. This is where business acumen and value selling begin—and where the seller gathers the evidence needed to defend price and demonstrate ROI later in the deal. Why quoting without discovery makes the salesperson expendable — 02:43 Kevin challenges sellers who rush to educate the prospect, demonstrate features, and produce a quote. If the seller's contribution is limited to product information and pricing, the buyer can often replace that salesperson with a website, product sheet, or artificial intelligence tool. Discovery is what separates professional selling from order processing. Finding the hidden requirements that can derail complex deals — 04:28 A new CNC machine may require more than equipment and installation. Floor space, structural changes, utilities, drainage, environmental requirements, permits, contractors, and operational disruption may all affect the buying decision. In enterprise sales, the apparent purchase is often only one component of a much larger initiative. Effective discovery exposes those dependencies before they destroy pipeline velocity. Using expertise to guide the customer's buying process — 07:53 The seller has typically sold the solution more often than the customer has purchased it. That experience creates an obligation—and an advantage. By identifying questions the buyer has not considered, mapping the buying committee, and navigating multi-stakeholder deals, the salesperson becomes a trusted guide rather than another vendor competing on features and price. How discovery improves forecasting, marketing, and revenue generation — 08:49 Robust discovery strengthens more than the individual opportunity. It improves forecast integrity, exposes the true urgency of the problem, creates better feedback loops with marketing and RevOps, and helps the organization attract more qualified prospects. Weaknesses introduced during discovery inevitably reappear during proposals, negotiations, implementation planning, and closing. Key Quotes "Discovery is not just the stage of the sales process. Discovery is the foundation of the very deal." — Sean O'Shaughnessey, 00:44 "If you're just doing a volume of quoting with no discovery, your job is in jeopardy. Discovery is what separates us from a product sheet." — Kevin Lawson, 03:56 "You have sold your product more than your customer has bought your product. You know more about selling your product than they know about buying your product." — Sean O'Shaughnessey, 08:08 "Anything you do poorly in discovery is going to show up in the proposal, timeline, close, and negotiation stages." — Kevin Lawson, 10:09 Additional Resources Sean also discusses the B2B Sales Lab, a community where salespeople, sales leaders, founders, AEs, SDRs, and VPs of Sales can discuss active selling challenges, improve their sales strategies, and participate in live office-hours conversations with Kevin and Sean. Visit: b2b-sales-lab.com A Significant Actionable Item from this Podcast Before advancing to your next meaningful opportunity, conduct a discovery-gap review. Write down the business problem, the measurable financial or operational impact, the cost of inaction, the decision-making process, the economic buyer, the key influencers, the implementation requirements, and any external dependencies that could delay approval or execution. Do not rely on impressions. Identify what you know, what you have merely assumed, and what remains unanswered. Then use the next customer conversation to close the highest-risk gaps before preparing a detailed proposal or committing the opportunity to the forecast. This single discipline can improve value messaging, reduce unnecessary discounting, expose weak opportunities, and prevent late-stage surprises. Summary Strong discovery gives a seller more than information. It provides the business case, stakeholder map, implementation reality, urgency, and financial logic required to move a complex deal forward. In this episode, Kevin and Sean show why discovery is central to sales management, value selling, forecast accuracy, and sustainable revenue generation—and why skipping it creates problems that no proposal, discount, AI-powered sales coaching platform, or sales enablement strategy can repair later. Listen to the episode before your next discovery meeting, and reconsider whether you are genuinely helping the customer make a sound decision or simply gathering enough information to produce a quote. 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 [Sean@NewSales.Expert] - https://www.linkedin.com/in/soshaughnessey/ [https://www.linkedin.com/in/soshaughnessey/] You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com [kevin@lighthousesalesadvisors.com] - https://www.linkedin.com/in/kwlawson/ [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 [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/

Happy 250th Birthday, America

No big topics in this episode. Just a quick acknowledgment that the United States of America is now 250 years old. Go back to your family and enjoy your time with them. Check us out next week when we will be sharing great sales advice again.

Should Sales Leaders Reset Quotas at Midyear

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

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

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey sit down with Paul Anthony Claxton of Digirati Investments for a sharp conversation on venture capital, founder readiness, sales architecture, and why early-stage companies cannot hide behind product obsession or incomplete data. Paul brings a rare blend of Marine Corps reconnaissance discipline, sales leadership, investment judgment, and AI perspective to the table. The result is a fast-moving discussion about Business acumen, customer conversations, market intelligence, Sales processes, and the practical realities of Revenue generation when founders are trying to build something the market may not yet know it needs. Key Topics Discussed Founder adaptability and the path from Marine to venture capitalist — 00:20 Paul explains how adaptability, opportunity recognition, and power networking shaped his move from the Marines into venture capital. His point lands hard for anyone in sales management: the best salespeople and founders do not simply follow the plan. They adjust when the market, the customer, or life changes direction. Why investors look beyond the product — 02:19 Paul discusses what he looks for when evaluating founders and companies. Product matters, but it is not enough. Founders need to understand macroeconomics, microeconomics, contracts, deal structure, customer impact, and the broader commercial environment. That is where Business acumen becomes a serious differentiator. Inventing necessity and creating surrounding market demand — 03:24 Paul introduces Digirati Investments' phrase "inventing necessity" and explains why strong products do more than solve one isolated problem. They create adjacent needs, new sub-industries, and additional opportunities for Revenue generation. This is a useful framing for founders, sales leaders, and anyone building Sales strategies around emerging markets. The danger of product-centric founders — 04:43 Sean pushes into a critical founder question: how often do companies believe they have a market-changing product before they have validated the market? Paul's answer is direct. Too many founders are product-centric instead of people-centric. Real Sales success starts with human conversations long before the product is fully built. Data, AI, and consultative selling in modern sales ecosystems — 05:33 Paul argues that strong data flow is essential, but data alone cannot replace human interaction. He connects AI, CRM automation, customer engagement, and consultative selling to a broader point: modern Sales processes need both high-quality data and high-quality conversations. Reconnaissance, competitor intelligence, and explainable AI — 09:15 Drawing from his Marine background, Paul explains why companies must gather intelligence from both customers and competitors. AI can support that work, but leaders must understand where the data came from and whether it reflects the actual market. Bad assumptions create bad Messaging, weak qualification, and flawed Revenue management decisions. Key Quotes Paul Anthony Claxton — 00:35 "The best salespeople are the most adaptable people." Paul Anthony Claxton — 05:33 "A lot of times I'll run across founders that are product-centric instead of being people-centric." Sean O'Shaughnessey — 08:41 "How do you know that what you're doing is going to work if you don't have salespeople out pre-talking and pre-building up what that problem is?" Paul Anthony Claxton — 09:15 "If you don't have people gathering reconnaissance, it's not just talking to who you think your prospective customers are, but it's also understanding how your competitors qualify." Kevin Lawson — 11:49 "Not only do we have to know as sellers who our total addressable market is, but our service obtainable market is, but it's important to keep that data current." Additional Resources Paul Anthony Claxton — Venture capitalist, U.S. Marine, sales architecture thinker, and guest on this episode. https://www.linkedin.com/in/businessmanathletemarine/ Digirati Investments — Paul's investment firm, discussed in the episode through the lens of "inventing necessity." Explainable AI — Paul's podcast, referenced during the conversation about understanding the origin, quality, and accuracy of AI-driven data. PaulClaxton.io — Paul's personal website, where you can learn more about his work, investments, and related ventures. A Significant Actionable Item from this Podcast Before investing more time, money, or sales effort into a product, schedule direct market conversations with prospective customers and competitive intelligence reviews. Do not rely only on internal conviction, CRM data, AI summaries, or founder enthusiasm. Validate the problem, study how competitors qualify and sell, and pressure-test whether your Value selling story connects to a real business need. This one discipline improves Sales strategies, sharpens Messaging, and prevents companies from building sales motions around assumptions the market has not confirmed. Summary This episode is a compact but high-value conversation for founders, investors, sales leaders, and anyone responsible for Revenue generation in an uncertain market. Paul Anthony Claxton brings a different lens to sales and investment evaluation: part Marine reconnaissance, part venture capitalist, part sales architect. Kevin and Sean guide the discussion into the practical questions that matter most: Does the founder understand the market? Is the product creating real necessity? Is the data explainable? Are customer conversations happening early enough to shape the business before money and time are wasted? Listen to this episode of Two Tall Guys Talking Sales if you want a sharper view of founder readiness, modern sales management, AI-informed selling, and the kind of Business acumen required for durable Sales success. B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert [Sean@NewSales.Expert] - https://www.linkedin.com/in/soshaughnessey/ [https://www.linkedin.com/in/soshaughnessey/] You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com [kevin@lighthousesalesadvisors.com] - https://www.linkedin.com/in/kwlawson/ [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 [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/

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

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