Two Tall Guys Talking Sales

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...

In complex B2B sales, the best opportunities rarely move forward because of a single perfect conversation with a single perfect buyer. They move because the seller creates enough meaningful customer interaction to uncover problems, build internal consensus, reduce the risk of being ghosted, and increase the odds of winning larger deals. In this episode of Two Tall Guys Talking Sales, Kevin Lawson...

Metrics are not just a sales management dashboard issue. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey make the case that salespeople need their own working metrics, the numbers that help them protect commission income, smooth the revenue rollercoaster, improve forecast accuracy, and make better decisions about where to spend time. This is a practical convers...

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey break down a sales management practice that too many teams underuse: reviewing won deals with the same discipline they apply to lost deals. The conversation moves past celebration alone and into the real operating question: did the team win because the sales process worked, or because someone hit a lucky buz...

Lost deals are not just missed revenue. They are evidence. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey challenge the easy excuses salespeople often use after a loss, especially "we lost on price" and "the customer made no decision." The real issue is usually deeper: weak value selling, poor discovery, unclear messaging, bad fit, or a failure to create enoug...

For many sales teams, the leads problem is not really a leads problem. It is an ideal client profile problem, a value proposition problem, and a focus problem disguised as pipeline activity. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey dig into the practical discipline of building a lead list that salespeople can actually use, one grounded in clear ICP defin...

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 reven...

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 pract...

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 per...

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 se...

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...

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...

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, im...

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, a...

This episode of Two Tall Guys Talking Sales is a rapid-fire masterclass in what actually happens in the field—when sales calls go sideways, when leaders show up unannounced, and when a "small" mistake exposes a bigger gap in sales management. Kevin Lawson and Sean O'Shaughnessey are joined by fractional VP of Sales Steve Landrum to swap real stories with real lessons: territory planning that's mor...

If you've ever tried to "coach the team" by telling everyone to sell like the top rep, this episode is your reality check. Sean O'Shaughnessey and Kevin Lawson use March Madness, dynasties, and training-room discipline to unpack a serious sales management issue: what kind of coach are you, and are your sales processes actually buildable, or just a personality contest? The conversation lands in a p...

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey sit down with Keith LaHonta to unpack a truth many teams overlook: sales success is rarely a solo act. It is built through mentor-mentee relationships that sharpen judgment, accelerate business acumen, and improve real-world execution. This conversation goes beyond career nostalgia and gets practical about how men...

In this episode, Sean and Kevin get brutally practical about a problem most sellers underestimate: you don't just market your company and your product—you have to market you. If prospects can't trust you, they won't trust your solution, your messaging, or your ability to deliver outcomes. The conversation turns "personal brand" into real sales processes you can run weekly to improve revenue genera...

Sales leaders don't lose deals on product. They lose them on trust signals—especially the ones buyers pick up before the second conversation even happens. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey break down how your team's digital presence either reinforces credibility or quietly undermines it. The throughline is simple: your sellers' profiles and posts...

If you're serious about sales success in 2026, this episode is a gut-check and a blueprint. Sean and Kevin break down what a real territory plan looks like (not a fluffy "be more productive" wish list), how to map first-half revenue to specific accounts, and how to build a second-half pipeline before it's an emergency. The throughline is sales management discipline: define the goal, allocate time...