Two Tall Guys Talking Sales – Details, episodes & analysis

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Two Tall Guys Talking Sales

Kevin Lawson and Sean O'Shaughnessey

Business

Frequency: 1 episode/7d. Total Eps: 143

"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.

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Apple Podcasts

🇨🇦 Canada - management
12/07/2025
#98
🇨🇦 Canada - management
11/07/2025
#57

Spotify

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https://www.linkedin.com/in/soshaughnessey/
235 shares
https://www.linkedin.com/in/kwlawson/
229 shares
https://www.linkedin.com/in/scaton/
5 shares

https://amzn.to/2K37ugx
7 shares
https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951
3 shares
https://www.amazon.com/Traction-Get-Grip-Your-Business/dp/1936661837
3 shares

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RSS feed quality

Good

Score global : 73%

Publication history

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Future-Proofing Your Sales Career with AI, Strategy, and Smarter Workflows

Season 1 · Episode 144

Tuesday, July 8, 2025 • Duration 19:30

Is artificial intelligence coming for your sales job? Not if you understand the power of business acumen, value selling, and strategic adoption of tools that amplify, not replace, human expertise. In this high-impact episode of Two Tall Guys Talking Sales, Kevin and Sean tackle the loud claims of AI-induced layoffs with a grounded, practical message for salespeople and sales managers: evolve or fall behind. This is not a doomsday episode; it's a wake-up call, a roadmap, and a motivational boost for anyone in the world of revenue generation, sales processes, and messaging strategy.

Whether you're a frontline salesperson or a VP of sales leading a team, this conversation will inspire you to rethink how you work, what skills future-proof your career, and how AI can become your competitive advantage instead of your competitor.

Key Topics Discussed

The 4 Irreplaceable Skills That Safeguard Sales Careers (01:00)
Sean breaks down a framework for evaluating whether your job is AI-proof, hint: if you’re in B2B sales and good at it, you're likely already building a durable edge.
How AI Mirrors the Arrival of the Internet in Sales Evolution (04:10)
Kevin draws a compelling parallel between today's AI landscape and the early days of the internet, showing why this shift is just as transformative.
Sales Management and Strategic Value in an AI World (02:46 & 07:31)
From leadership and team building to messaging and workflow design, the episode highlights why sales managers need to think beyond quotas and towards long-term enablement.
A Personal Story of Old-School Sales and the Power of Adapting Tools (08:00)
Sean shares a nostalgic (and relevant) story about his father’s sales career before personal computers, offering perspective on how sales adapts across generations.
Weaponizing Your Time: Using AI to Amplify Human Strengths (13:00)
Kevin delivers a call to action on how to audit your own sales day and offload low-value tasks through automation, freeing up more time for high-impact strategy and consultation.

Key Quotes

“You won’t lose your job to AI, you’ll lose your job to a better salesperson who uses AI.”
– Sean O’Shaughnessey (01:02)

“If you’re not using AI, or any sales technology, you’re not doing your job. You’re underperforming.”
– Kevin Lawson (06:11)

“Sales worked before computers, and it will work after AI. What changes is how well you adapt the tools available.”
– Sean O’Shaughnessey (10:04)

“Your time is your greatest asset, and your biggest liability, when you’re not using it to its highest utility.”
– Kevin Lawson (14:00)

Additional Resources

Sean’s original blog post on this topic (available in the B2B Sales Lab and LinkedIn) https://newsales.expert/2025/06/b2b-sales-in-the-age-of-ai-why-top-salespeople-will-thrive-while-the-repetitive-roles-disappear/
B2B Sales Lab community discussion on sales evolution and AI https://b2b-sales-lab.com/
Tools mentioned: ChatGPT, Perplexity, Gemini (as starting points for AI integration)

A Significant Actionable Item from this Podcast

Audit your sales day for repeatable, low-value tasks that can be automated.
Pick one of them, like researching prospects, summarizing meeting notes, or drafting follow-ups, and replace it with an AI tool like ChatGPT or Perplexity. You’ll recover time, increase productivity, and move closer to building a modern, AI-augmented sales practice.

Final Summary

This episode of Two Tall Guys Talking Sales isn’t about fear, it’s about focus. Sales success today requires a sharp blend of strategic thinking, tool adoption, and human skills that are nearly impossible to replicate. Kevin and Sean lay out a blueprint that every sales leader, rep, and business owner should follow to thrive in this new era. If you’re serious about sales management, value selling, messaging clarity, and staying ahead of disruption, this episode will give you the mindset and tactical clarity to act now. Don’t just listen, level up.

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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Building a Sales Powerhouse—The 3 Most Underrated Skills with Jeff Parris

Season 1 · Episode 143

Tuesday, June 24, 2025 • Duration 17:30

Sales isn’t about persuasion but service, resilience, and growth. In this episode of Two Tall Guys Talking Sales, co-hosts Kevin Lawson and Sean O’Shaughnessey welcome sales leader and former professional athlete Jeff Parris to explore the fundamental skills that separate elite salespeople from the rest. Drawing on decades of experience, Jeff shares three often-overlooked yet foundational competencies that drive sales success, and they’re not what you’d expect. Whether you're a VP of Sales building a high-performance team or a seller looking to level up, this episode delivers sharp insights on value selling, business acumen, and sales management excellence.

Key Topics Discussed

Why great salespeople see themselves as servants first (approx. 04:00)
Jeff outlines why a “motivation to serve” mindset creates stronger client relationships and more consistent revenue generation.
Ego Drive vs. Ego Trip: Understanding the will to win without arrogance (approx. 07:30)
Learn how ego drive, a hunger to persuade for the buyer’s benefit, builds durable sales performance.
Curiosity as the gateway to sales mastery (approx. 10:15)
Jeff and Sean dig into why curiosity fuels continuous improvement and business acumen across every sales process.
How to coach the “accidental salesperson” into a top performer (approx. 11:45)
Kevin asks how people without formal sales backgrounds can thrive by developing the right mindset.
Sales leaders as talent architects: Building high-performance teams (approx. 02:00)
Jeff draws on his athletic past to share what makes a sales team championship-worthy.

Key Quotes

“Sales isn’t something we do to people, it’s something we do for people.”
— Jeff Parris (04:00)

“The real goal of a great salesperson is: ‘Mr. Prospect, let me help you solve that problem.” — Sean O’Shaughnessey (05:55)

Additional Resources A Significant Actionable Item from this Podcast Why You Should Listen to This Episode

The Four Buckets of Sales Growth with Steve Wittal

Season 1 · Episode 134

Tuesday, April 22, 2025 • Duration 17:34

In this dynamic episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey welcome Canadian SalesXceleration expert Steve Wittal for an in-depth look into the foundations of effective sales strategies. Steve brings decades of experience in startup advisory, sales management, and business growth, sharing a robust framework that simplifies complex growth challenges into four digestible buckets: desirability, clarity, predictability, and deliverability. If you’re a business leader looking to strengthen your sales processes, sharpen your messaging, or improve revenue generation, this conversation is a goldmine.

Key Topics Discussed

The Power of Leadership in Change Management (~01:02)
Steve opens by explaining why leadership is the starting point for any growth initiative, especially when change is involved.
The Four Buckets Framework for Growth (~03:00)
Steve outlines his method for diagnosing and resolving growth issues by focusing on four pillars: desirability, clarity, predictability, and deliverability.
Desirability and Understanding the Customer’s Pain (~04:00)
Why identifying whether your product is a “must-have” or “nice-to-have” is critical to sales success.
The Importance of Clarity and Quantifying the Cost of Inaction (~06:39)
Sean and Steve unpack how clarity in messaging and value proposition can move buyers from indecision to action.
Predictability, Scalability, and Sales Playbooks (~09:20)
How aligning your sales process with the customer’s buying journey enables scale and drives predictable revenue.
Deliverability and the Voice of the Customer (~10:50)
Steve emphasizes the importance of retention, early wins, and referrals as indicators that your solution truly delivers.

Key Quotes

Sales Leadership Mastery: How to Coach, Not Micromanage, Your Team

Season 1 · Episode 44

Tuesday, August 8, 2023 • Duration 15:03

Welcome to another riveting episode of Two Tall Guys Talking Sales with your dynamic hosts, Sean O'Shaughnessey and Kevin Lawson. In this episode, our duo takes on a subject that stirs strong emotions in the sales world: micromanagement. With a combined experience of several decades in sales, Sean and Kevin delve into their philosophies, personal experiences, and provide actionable insights on transitioning from micromanagement to effective leadership. Whether you're a salesperson, a manager, or a business leader, you're going to find value in their candid conversation.

Key Topics Discussed:

Micromanagement in Sales: Sean's personal aversion to micromanagement, his challenges, and how he navigated them during his 38-year career.
Transitioning from Micromanaging to Leadership: Kevin’s insights into the delicate balance between engaging the team and inadvertently falling into micromanagement.
Differentiating Between Green and Seasoned Salespeople: How to manage new salespeople who need structure versus seasoned reps who require trust.
The Importance of Trust in a Sales Team: Bad examples of trust violations and the cultivation of a culture of trust within the sales organization.
Becoming a Leader: Strategies and practical advice for transitioning from a micromanager to a leader, and the value it brings to the sales culture.

Key Quotes:

Sean: "I despised anybody who was going to drive me day to day, ask me every single thing, question every single deal just didn't fit well with my personality."
Kevin: "How can I help? That's how the shift comes in my mind from a micromanager to an effective leader. Instead of asking detail, detail, detail, they're asking about resource, resource, strategy, that's the big shift for me."

In this engaging episode of Two Tall Guys Talking Sales, Sean and Kevin don't just identify the problems associated with micromanagement but provide actionable insights and solutions for how to evolve into an effective leader. Whether you're just beginning in sales or leading a team, their candid conversation will offer you strategies to avoid micromanagement, build trust within your team, and create a culture of success. Don't miss this chance to learn from two seasoned sales veterans - tune in to this episode and take your sales leadership skills to the next level!

Revamping Your Outbound Sales Approach: Value Proposition, Touch Points, and Tactics

Season 1 · Episode 43

Tuesday, August 1, 2023 • Duration 15:40

Welcome to another exciting episode of Two Tall Guys Talking Sales with hosts Kevin Lawson and Sean O'Shaughnessey. On this episode, we delve into the vital world of outbound sales in a post-COVID landscape. We discuss strategies for creating an effective outbound pipeline, reflecting on our experiences with trade shows, and how to nail your unique value proposition. Discover how to master omnichannel outreach and understand why persistence is key in today's competitive market.

Key Topics Discussed:

The Trade Show Experience: Kevin and Sean open up about the highs and lows of trade shows and how the pandemic has shifted the industry’s focus from this traditional method of sales and marketing.
Creating an Effective Outbound Pipeline: Our hosts emphasize the importance of having a clear, unique value proposition and understanding how it can resonate with your potential customers.
Omni Channel Outreach: Kevin and Sean highlight the significance of reaching out to prospects across various channels - emails, phone calls, social media, and even traditional mail. They discuss the need for persistence in reaching out and making numerous touches to get a prospect's attention.
Prospecting and Value Proposition: Sean shares insights on how a value proposition can differ based on the industry and target audience. They talk about understanding and tailoring your value proposition to your audience for better customer engagement.
Leveraging Tools for Sales Outreach: The hosts discuss a range of tools that can assist in streamlining and tracking your outreach efforts, from LinkedIn prospecting tools to CRMs and even task management tools.

Key Quotes:

Kevin: "Trade shows in a pre COVID environment were the lifeblood of many sales organizations... But here we are in a post-COVID world, and what we saw in the midst of COVID was pipeline evacuation."

Three-Legged Stool of Sales Success: Networking, Direct Prospecting, and Customer Referrals

Season 1 · Episode 42

Tuesday, July 25, 2023 • Duration 16:27

In this episode of Two Tall Guys Talking Sales, hosts Sean O'Shaughnessey and Kevin Lawson get tactical on sales prospecting. They dive deep into sales strategies and tactics, discussing how to build momentum for the latter half of the year and beyond. Whether your sales pipeline is currently thriving or needs a refill, this episode offers valuable insights that apply to all sales situations.

Key Topics Discussed

The Art of Prospecting: Uncover practical ways to refill your sales pipeline effectively, leveraging both direct and networking-based prospecting.
Direct vs Networking-based Prospecting: Understand the differences, subtleties, and strategies in both approaches and learn how to optimize them based on your business context and audience.
Balancing Prospecting Behaviors: Discover the importance of inbound marketing, outbound sales force, and customer success models in driving a well-rounded prospecting strategy.
Sales Funnel Structure: Explore the analogy of a three-legged stool representing a solid sales structure consisting of networking, direct prospecting, and customer referrals.
Building Trust within Your Network: Learn the value of trust-building within your network for long-term sales success and how to ensure your network is well-informed about your product/service offerings.

Key Quotes

"Prospecting your network requires a different focus and a different type of how you present yourself because you're not asking someone for business. You're asking to have someone else introduce you to the right prospect for you." - Kevin Lawson

"Don't depend on any one thing to always work within your organization. In fact, you will be more successful if all three of those legs are just as strong and just as good because if you only have two legs working well, you don't have that third leg, you've got a weak stool, you're going to fall over." - Sean O'Shaughnessey

Creating True Value in Sales: Redefining Problems and Delivering Unique Solutions

Season 1 · Episode 41

Tuesday, July 18, 2023 • Duration 15:06

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey delve deep into the salesperson's value in the modern sales process. Our hosts discuss how the role of the salesperson has evolved with the advent of the internet and the importance of building trust with potential buyers. They also talk about redefining buyer needs and how to differentiate your product or service in the market.

Key Topics Discussed

The Salesperson as a Value Carrier: With a wealth of information available online, the salesperson's role is to add value to a buyer's perceived problem.
The Importance of Trust: Building and transferring trust from the seller to the buyer is the essence of a successful sale.
Unique Selling Propositions: Every salesperson has a unique aspect of their product, their company, and themselves.
Redefining Buyer Problems: It's important for the salesperson to understand the root cause of the buyer's problem to provide a tailored solution.
Ask Better Questions: To create value separation and reframe buyer problems, salespeople need to ask insightful questions.

Key Quotes

From Sean: “Sales is nothing more than the transfer of trust from me because I trust my product... Transferring that trust to the buyer and having the buyer then have that trust that I can actually solve the problem that's at hand is what sales is all about."

From Kevin: “The salesperson and sales leader, their whole job is to become the differentiators. The salesperson has to become that value. And it's not just a value of, 'Hey, I'm different. Hey, I'm cheaper.' We're not competing on price here; we're competing on actual customer-facing value."

In the age of readily available online information, a salesperson's job is no longer just about conveying product details. It's about building trust, understanding the root of the customer's problem, and providing them with unique solutions. Join Kevin and Sean in this enlightening episode as they redefine the role of the modern salesperson and provide actionable insights to excel in the evolving sales landscape. If you're ready to take your sales skills to the next level, this episode is a must-listen. Remember, sales success is not just about selling a product but also about being the value a buyer seeks.

Breaking Growth Barriers: When Should CEOs Stop Leading Sales?

Season 1 · Episode 40

Tuesday, July 11, 2023 • Duration 15:37

In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey deep-dive into the crucial topic of assigning the right person to the sales leadership role within a company, and the risks and opportunities that come with it. Leveraging their experiences in sales consultancy and drawing from the wisdom of thought leaders and successful entrepreneurs, they explore how CEOs can de-risk their company's growth potential by stepping back from direct sales and fostering a culture of accountability, infrastructure, and high performance in their sales teams.

Key Topics Discussed:

The Risk of CEO-led Sales: The episode starts with a discussion on the potential risks of having a CEO or owner-operator as the sales leader, emphasizing how this could constrain business growth.
The Theory of Constraints: The hosts explain the theory of constraints using a compelling example from a book called The Goal, drawing parallels to how constraints can hinder sales and growth within a company.
Building a Sales Organization: They delve into the necessity of professional salespeople and a dedicated sales manager to bring in new revenue, enabling the CEO to focus on larger issues within the organization.
EOS and Right Person, Right Seat: Sean mentions EOS (Entrepreneurial Operating System) and the importance of having the right person in the right seat to drive growth, particularly once a company reaches a certain size.
Building a High-Performance Culture: The hosts discuss how to build a high-performance sales culture that is systematic and repeatable, using examples from sports dynasties and successful companies.

Key Quotes:

"What is the risk of the owner-operator being the only salesperson or the sales leader when the person is leading the company and leading sales? What you end up with is a business that is constrained by the amount of time that leader has." -

Happy Independence Day!

Season 1 · Episode 39

Tuesday, July 4, 2023 • Duration 00:41

The hosts of Two Tall Guys Talking Sales wish you a Happy Independence Day!

You can reach out to Sean at New Sales Expert, LLC & Sales Xceleration - 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/

Two Tall Guys Talking Sales – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

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Two Tall Guys Talking Sales – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

LinkedIn48

Other76

Amazon10

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities

LinkedIn48

Other76

Amazon10