Two Tall Guys Talking Sales

In a world where artificial intelligence can generate thousands of prospecting emails in minutes, what actually makes a B2B salesperson stand out? Trust, authenticity, and a personal brand that buyers genuinely respect. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey challenge conventional sales management thinking, particularly the obsession with activit...

Tired of competing on features, price, and product specifications while your prospects struggle to understand why they should buy? In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey challenge one of the most persistent mistakes in B2B sales: selling what your product does instead of what your customer wants to accomplish. From breaking through revenue growth...

In competitive B2B sales, knowing your product is only half the battle. Do you really know who you're losing deals to, why they're winning, and what makes your company meaningfully different? In this episode of Two Tall Guys Talking Sales , hosts Kevin Lawson and Sean O'Shaughnessey unpack the discipline of competitive analysis, revealing how salespeople, sales managers, and business owners can id...

Discovery calls can determine whether a B2B sales opportunity advances or stalls, but too many salespeople rely on generic questions that reveal little about the prospect's business. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey explore how to build a discovery question bank that uncovers business challenges, identifies decision-makers, and positions sa...

Artificial intelligence is changing B2B sales, but using AI to send more automated emails or accelerate ineffective sales processes misses the real opportunity. What if AI could help you understand your customers more deeply, identify hidden opportunities in your pipeline, and deliver the kind of personalized attention that once defined great customer relationships? In this episode of Two Tall Guy...

What happens when your best salesperson hits quota in October? A poorly designed compensation plan may quietly tell them to slow down. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey examine why sales compensation accelerators can be one of the most profitable tools available to a sales leader. They break down the economics behind above-quota sales, explain why...

Most sales organizations are surrounded by useful customer data, but too often, they only examine it after something goes wrong. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey explore a more proactive approach to B2B sales management: using white-space analysis, customer segmentation, executive relationships, and disciplined account reviews to uncover un...

Sales organizations often assume that revenue growth starts with finding more leads. Kevin Lawson and Sean O'Shaughnessey challenge that assumption in this episode of Two Tall Guys Talking Sales. For manufacturers, distributors, and other B2B companies that generate a high volume of quotes, substantial revenue may already sit in the existing pipeline—buried under unanswered proposals, unclosed opp...

Filling every box in MEDDPICC does not mean you actually understand the deal. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey dig into one of the most dangerous problems in B2B sales: confidently believing you have identified the economic buyer, decision process, decision criteria, and business impact—only to discover late in the cycle that your assumptions wer...

What if the biggest obstacle to hitting your sales quota isn't your territory, your product, or even your competition, but the way you manage yourself? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey challenge sales professionals to stop thinking only like employees and start managing their territories like businesses. They break down the numbers every seller s...

Most salespeople do not lose because they cannot make the spectacular play. They lose because they miss the layups. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey challenge the conventional wisdom that sales success requires ever-larger pipelines and more activity. Instead, they make the case for disciplined sales processes, tighter qualification, faster follo...

There is a hidden cost in every sales pipeline: the deals that consume time, attention, and internal resources without a compelling reason to remain there. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey challenge B2B salespeople to stop treating every opportunity as something that deserves to be won. They examine how strong sales management starts with decidin...

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 salesp...

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 se...

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...

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...

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 scri...

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...

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.

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...

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 leade...

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, mindse...

Two Tall Guys Talking Sales takes a practical look at one of the most common sales management mistakes: assuming all salespeople are built for the same job. Sean O'Shaughnessey and Kevin Lawson use a basketball analogy to unpack the difference between hunters, farmers, lone wolves, challengers, relationship sellers, transactional sellers, and trappers. This episode challenges owners, sales leaders...

Opening a prospecting conversation with "we have 180 million contacts" may sound impressive inside the seller's company, but it often misses the buyer's reality. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey challenge salespeople and sales leaders to stop confusing features with value. They unpack why strong Messaging starts with the buyer's problem, how Valu...