Stop Guessing. Start Assessing: The First Step Toward Sales Growth

Stop Guessing. Start Assessing: The First Step Toward Sales Growth

By Sean O'Shaughnessey

Are you feeling stuck in your sales organization? You’re not alone. Many founders, CEOs, and sales leaders eventually hit an invisible wall—a growth plateau. Key deals slip away. Your top salesperson, who carries far too much weight, starts to burn out.

In these moments, the instinct is often to push harder. But what’s needed isn’t more hustle. It’s clarity. And clarity starts with a strategic sales assessment.

What a Sales Assessment Means

Too often, leaders see assessments as formalities—checklists that confirm what they already believe. That’s a mistake. An accurate sales assessment is diagnostic. It reveals what’s working, what’s broken, and what’s missing.

Revenue growth doesn’t always mean you’re on the right path. Many companies are growing despite misalignment, not because of strategic execution. Are your sales activities aligned with your market opportunity? Are you pursuing the right prospects with the right message? Or are you just getting lucky?

Read the rest of the article…
Stop Guessing, Start Growing: How Strategic Sales Assessments Drive Real Revenue

Stop Guessing, Start Growing: How Strategic Sales Assessments Drive Real Revenue

By Sean O'Shaughnessey

You’ll eventually hit a wall if you’re running a sales organization—or wearing multiple hats as founder, CEO, and sales manager. That wall is often invisible until growth stalls, key deals slip through the cracks, or your top salesperson burns out. So, what’s the next move? It’s not more hustle. It’s assessment.

A sales assessment isn’t about checking boxes. It’s about understanding where you are, how you operate, and what’s holding you back. Too many small business leaders assume they’re doing fine because revenue is growing or the team is hitting their quotas. But are you growing at the rate your market allows? Are your sales activities aligned with your long-term goals? Are you building a repeatable system, or are you just getting lucky?

Let’s get tactical. A sales plan isn’t just a revenue target. It’s your go-to-market strategy. It defines your audience, your message, and your motion. It answers why you’re talking to those prospects and what value you’re bringing to them. Without a plan, you’re reacting instead of executing. You’re chasing leads instead of building a pipeline.

If you’re a small company—perhaps under $30 million in revenue—and selling into a national market, chances are your market potential is hundreds of millions, maybe billions. That means your market share is a rounding error, which means there’s room to grow. The question is: Are you operating in a way that allows you to capture that growth?

Even if you’re running lean, you should benchmark your performance against top-tier organizations. Not because you’re competing with them directly, but because they set the standard. What are they doing that you’re not? Where are they more efficient? How do they structure their teams? You’re leaving money on the table if you’re not asking those questions.

Read the rest of the article…
Two Tall Guys Talking Sales – Tom Gottlieb of Berkshire Hathaway Explains How Buyers Want Growth- How Sales Leaders Can Increase Company Worth – E131

Two Tall Guys Talking Sales – Tom Gottlieb of Berkshire Hathaway Explains How Buyers Want Growth- How Sales Leaders Can Increase Company Worth – E131

By Sean O'Shaughnessey

In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome business intermediary Tom Gottlieb of Berkshire Hathaway. Tom brings decades of experience in buying, selling, and valuing businesses across the Midwest. The conversation dives deep into what truly drives the value of a company—and how sales leaders and business owners alike can prepare their organizations for a future transition. Whether you’re a business owner considering a sale or a sales executive interested in how sales performance impacts company valuation, this episode delivers invaluable guidance. It’s part education, part strategy session, and all high-value insight.

Key Topics Discussed

  • The Three Core Approaches to Business Valuation – Asset, income, and comparative market methods explained simply and practically. (04:22)
  • Preparing a Business for Sale: Lessons from Real Estate – Why “curb appeal” matters for companies and how to improve it over time. (07:36)
  • What Buyers Want: Sales Growth, Consistency, and Processes – How prospective buyers assess the health of a business beyond profit margins. (09:00)
  • The Hidden Red Flag: When the Owner Is the Only Salesperson – Risks for buyers and strategies for mitigating dependency on the founder. (13:31)
  • Leveraging AI to Gain Competitive Market Intelligence – How technology is transforming buyer and seller knowledge in M&A. (11:32)

Key Quotes

Tom Gottlieb: “Every buyer wants the same thing: a business that works without the owner. That means strong processes, steady sales growth, and predictable profitability.” (09:01)
Sean O’Shaughnessey: “So if you don’t want to stick around after the sale, then train your sales team now—and watch the value of your company go up.” (14:16)
Kevin Lawson: “Tom, every time we talk, I walk away with something new. This episode is no exception.” (11:31)
Tom Gottlieb: “Buyers rarely show up with a bag of cash. There’s a timeline. A deal doesn’t close in a weekend—it’s often a year-long journey.” (07:00)

Additional Resources

A Significant Actionable Item from this Podcast

Start documenting your sales process today.
If you are a business owner—or advise one—and the majority of revenue hinges on a single salesperson (often the owner themselves), that’s a red flag for any future buyer. Begin formalizing your sales process, distribute responsibilities among team members, and track sales metrics consistently. This improves operational resilience and significantly enhances company value in a potential sale.

Why You Should Listen to This Episode

Selling a business isn’t just about profit, perception, process, and preparedness. In this episode, Kevin and Sean extract wisdom from Tom Gottlieb that applies to any B2B organization considering an exit in the next 3 to 10 years. It’s packed with strategic takeaways, sales insights, and behind-the-scenes truths about what makes a business attractive to buyers. Whether you’re a founder, an investor, or a sales leader, this episode will reshape how you think about long-term value creation. Tune in and learn how to make your business sell-ready—starting now.

To understand if your company is doing a great job in sales, take this quick and easy assessment: https://newsales.expert/b2b-sales-capability-assessment/

Two Tall Guys Talking Sales – Prepping for Q2 – Getting Ahead, Catching Up, and Staying on Track – E129

Two Tall Guys Talking Sales – Prepping for Q2 – Getting Ahead, Catching Up, and Staying on Track – E129

By Sean O'Shaughnessey

As the first quarter comes to a close, sales leaders and professionals must assess their performance and gear up for the challenges and opportunities ahead in Q2. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey break down the essential strategies for those ahead of the plan and those struggling to catch up. From refining your sales process to maximizing customer relationships, this discussion has insights to help you dominate your numbers in the coming months.

Key Topics Discussed:

  • The Reality of Q1 Performance and the Need for Urgency (00:00:31)
    • Why waiting until Q2 to fix Q1 is too late, and how to position yourself for success early in the year.
  • Strategies for Those Ahead of Plan (00:01:00)
    • How to maintain momentum, close key deals, and ensure a strong Q4 while staying ahead of quota.
  • Critical Steps for Those Behind on Quota (00:04:01)
    • Conducting a win-loss analysis, diagnosing deal flow issues, and fine-tuning lead generation strategies.
  • The Importance of CRM Usage and Sales Efficiency (00:06:35)
    • How sales leaders and reps can maximize their CRM to drive efficiency and uncover missed opportunities.
  • Pricing Strategies and Customer Engagement (00:09:13)
    • Why now is the time to strengthen relationships with your top customers and confidently raise prices to improve margins?

Key Quotes:

  • Sean O’Shaughnessey (00:01:32): “You have a chance at greatness if you are even or ahead at the end of Q1. Now’s the time to double down and make sure you close deals that will set you up for an incredible year.”
  • Kevin Lawson (00:05:00): “Everyone has a leads problem. Either you don’t have enough, they’re not the right fit, or you’re not communicating your value effectively. That’s where the real focus should be.”
  • Sean O’Shaughnessey (00:11:00): “Your best customers likely don’t know you as well as you think. Strengthening those relationships can open up new revenue streams and prevent you from falling behind.”

A Significant Actionable Item from this Podcast:

Perform a rapid win-loss analysis on your Q1 deals. If you’re ahead, identify the behaviors and strategies that got you there and double down. If you’re behind, determine whether the issue is a lack of quality leads, poor messaging, or weak follow-through. Adjust your sales approach immediately so you can enter Q2 with a clear plan to recover lost ground.

Summary:

Whether you’re ahead of plan, right on track, or scrambling to catch up, the strategies discussed in this episode will help you refine your sales process and make Q2 a success. Sean and Kevin share actionable insights on deal flow, CRM optimization, pricing strategies, and customer engagement that will set you up for a strong year. Don’t let another quarter slip away—tune in now to get ahead, stay ahead, and finish the year on top!

To understand if your company is doing a great job in sales, take this quick and easy assessment: https://newsales.expert/b2b-sales-capability-assessment/

Two Tall Guys Talking Sales – Sales Prospecting: Are You Chasing Leads or Cultivating Success? – E127

Two Tall Guys Talking Sales – Sales Prospecting: Are You Chasing Leads or Cultivating Success? – E127

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive into the art of sales prospecting using an unusual but powerful analogy—chasing butterflies versus building a garden. Are you tirelessly running after leads or cultivating an environment where ideal prospects naturally come to you? Learn how to create a long-term strategy for consistent revenue growth by positioning your business as the go-to solution for your ideal customers.

Key Topics Discussed:

  • The Butterfly Effect in Sales (00:01:00) – The difference between chasing every lead and strategically attracting the right ones.
  • Building a Sales Garden (00:02:49) – Developing a long-term strategy that consistently nurtures and attracts the best-fit prospects.
  • Marketing & Content Strategy Alignment (00:04:22) – Collaborating with marketing to ensure the right messaging.
  • The Value of Inbound Leads (00:06:11) – Why leads that come through your marketing efforts are often easier to close and more profitable.
  • Tactical Steps for Sales Leaders (00:08:00) – Actionable insights for sales managers to help their teams attract, engage, and convert better.
  • Crafting a Strong Value Proposition (00:10:18) – The foundation of effective lead generation and how to align it with your ideal customer profile.

Key Quotes:

  • Sean O’Shaughnessey (00:01:52): “If you’re hungry for revenue, you’re probably running around chasing butterflies. But if you want sustainable growth, you need to create an environment where prospects naturally come to you.”
  • Kevin Lawson (00:03:55): “Sales leaders, think about your team—have you equipped them with butterfly nets, or have you taught them how to build a garden?”
  • Sean O’Shaughnessey (00:06:44): “The best prospects aren’t the ones you chase—they’re the ones who find their way to your garden because you’ve built something valuable for them.”

Additional Resources:

A Significant Actionable Item from this Podcast:

If you rely solely on outbound prospecting, evaluate your value proposition and content strategy today. Align your marketing and sales teams to ensure your messaging is clear, consistent, and tailored to your ideal buyer. Identify gaps in your digital presence and take the first step toward creating a sales garden that nurtures and attracts the right leads.

Final Thoughts:

Sales is more than just chasing down deals—it’s creating an ecosystem where prospects feel drawn to your expertise, insights, and solutions. In this episode, Sean and Kevin explain shifting from frantic outbound prospecting to a methodical approach that fosters sustainable revenue growth. Whether you’re a sales leader or an individual contributor, you’ll walk away with practical steps to build your high-converting sales garden.

Tune in now and take your sales strategy to the next level!

To understand if your company is doing a great job in sales, take this quick and easy assessment: https://newsales.expert/b2b-sales-capability-assessment/

Turning Competition into Opportunity: A Guide for Success in Sales

Turning Competition into Opportunity: A Guide for Success in Sales

By Sean O'Shaughnessey

Competition in B2B sales isn’t your enemy. It’s your greatest catalyst for growth and innovation in today’s dynamic market landscape. Have you considered how viewing competitors as opportunities rather than threats could transform your sales approach? Let me show you why this mindset shift matters for your bottom line.

Think beyond the obvious when identifying your competition. Your real rivals aren’t just companies selling similar products or services. They’re anyone competing for your prospect’s budget allocation. This includes businesses offering solutions with capabilities or price points different from yours and other priorities within the prospect. The competitive landscape extends far beyond your direct market segment.

The most formidable opponent often lurks in the shadows of customer inertia. This “no-decision” competitor manifests as your prospect’s resistance to change. It’s the comfort zone that whispers, “Maybe later,” or “What we have works fine.” Understanding this psychological barrier is crucial for your sales strategy.

You need a systematic approach to analyzing and outmaneuvering your competition. Start with an honest assessment of your position in the market. What unique value do you bring to your customers? Where do you consistently outperform others? This self-awareness forms the foundation of your competitive strategy.

Know your competition inside and out. Study their strengths, weaknesses, market positioning, and customer relationships. Your competitive analysis must go deeper than surface-level observations. Map out how their strengths align with your weaknesses. This intelligence helps you craft more compelling value propositions and sales approaches.

Read the rest of the article…
From Micro-Manager to Leader: Fostering Growth in Your Sales Team

From Micro-Manager to Leader: Fostering Growth in Your Sales Team

By Sean O'Shaughnessey

Are you unknowingly sabotaging your sales team’s success? The answer might surprise you. The actual cost of micromanagement extends far beyond immediate productivity concerns.

Trust forms the bedrock of every high-performing sales organization. Yet many sales leaders unconsciously undermine this foundation through micromanagement. You’ve seen the signs – constant check-ins, questioning every decision, and hovering over your team’s shoulders. The culture you’ve worked so hard to build is slowly eroding.

Your best salespeople are leaving. Team morale is plummeting.

Let’s be clear about what constitutes micromanagement in sales. It’s not about being involved or interested in your team’s work. The real issue emerges when you start dictating every move and creating an atmosphere of constant surveillance.

Consider the cost of replacing top sales talent in today’s market. Beyond the substantial financial investment, you’re losing institutional knowledge and client relationships. Your organization can’t afford this drain on resources, and the impact reverberates throughout your entire sales ecosystem.

Read the rest of the article…
Two Tall Guys Talking Sales Podcast – From Microphones to Mountains – Reflecting on 100 Episodes of Sales Wisdom – E100

Two Tall Guys Talking Sales Podcast – From Microphones to Mountains – Reflecting on 100 Episodes of Sales Wisdom – E100

By Sean O'Shaughnessey

Join hosts Kevin Lawson and Sean O’Shaughnessey in this milestone 100th episode of “Two Tall Guys Talking Sales.” They take a nostalgic trip down memory lane, revisiting the evolution of their podcast from simple LinkedIn live events to a thriving sales discussion platform on Spotify and Apple Podcasts. They delve into their personal growth, the transformative insights gained, and the invaluable lessons they’ve shared across 100 episodes.

Key Topics Discussed:

  • Evolution of the Podcast [00:00:21]: Kevin and Sean reflect on the technological and methodological shifts they’ve embraced to enhance their podcast experience.
  • Insights on Sales Excellence [00:01:35]: Sean shares his journey of continuous learning in sales, emphasizing the wisdom imparted by Kevin and its impact on his professional development.
  • Role of Content Creation [00:03:11]: Kevin discusses the significance of creating and repurposing valuable content, drawing parallels with daily writing practices to improve skill.
  • Interviews with Industry Experts [00:04:14]: The hosts highlight the diverse insights gained from interviews with visionaries across various sectors, from SaaS founders to business coaches.
  • Future of the Podcast [00:08:31]: Looking ahead, Kevin outlines their aspirations to scale the podcast’s impact and deepen listener engagement.

Key Quotes:

  • Kevin [00:00:00]: “It’s basically a stack of wires and plastic…a lost and found of sorts for electronics equipment.”
  • Sean [00:01:35]: “Listening to Kevin explain sales is insightful…I have learned an immense amount in the last 100 episodes.”

Additional Resources:

Previous episodes on building a comprehensive sales process.

  1. https://sites.libsyn.com/458454/site/e1-inaugural-episode-why-should-a-company-assess-its-practices-in-sales
  2. https://sites.libsyn.com/458454/site/e2-how-do-you-determine-your-companys-sales-objectives-each-year
  3. https://sites.libsyn.com/458454/site/e3-are-your-sales-representatives-consistently-hitting-their-assigned-quotas
  4. https://sites.libsyn.com/458454/site/e4-how-do-you-compensate-your-salespeople
  5. https://sites.libsyn.com/458454/site/e5-do-you-have-a-documented-sales-process-that-is-followed-all-the-time
  6. https://sites.libsyn.com/458454/site/e6-how-do-salespeople-retain-client-information-and-document-sales-opportunities
  7. https://sites.libsyn.com/458454/site/e8-can-your-salespeople-clearly-communicate-your-unique-selling-proposition-what-makes-you-different-than-your-competition
  8. https://sites.libsyn.com/458454/site/e9-do-you-have-a-dashboard-view-into-the-major-determinants-of-sales-success
  9. https://sites.libsyn.com/458454/site/e10-do-you-feel-you-have-the-right-salespeople-to-get-you-where-you-want-to-go
  10. https://sites.libsyn.com/458454/site/e11-does-your-organization-hold-salespeople-accountable-for-lack-of-performance

Summary:

This 100th episode is a celebration and a testament to continuous improvement and shared growth in the sales world. Kevin and Sean unpack the layers of learning they’ve experienced and the wealth of knowledge they’ve gathered from various experts. Whether you’re a seasoned sales professional or a newcomer to the field, this episode offers a wealth of practical advice, humor, and insights that can transform your approach to sales and leadership.

A Significant Actionable Item from this Podcast:

Adopt the practice of discussing and refining your craft regularly. As highlighted by Kevin, talking about your sales strategies and processes, much like writers improve by writing daily, can significantly enhance your expertise and execution in sales.

To understand if your company is doing a great job in sales, take this quick and easy 10-question assessment: https://salesxceleration.com/sales-agility-assessment/?locationid=26671639

Two Tall Guys Talking Sales Podcast – From Process to Performance: Elevating Your Sales Game – E99

Two Tall Guys Talking Sales Podcast – From Process to Performance: Elevating Your Sales Game – E99

By Sean O'Shaughnessey

Join hosts Kevin Lawson and Sean O’Shaughnessey as they edge closer to their milestone 100th episode, diving deep into the critical components of a successful sales organization. 

Episode 99 zooms in on the third pillar: “Process.” Kevin revisits his iconic saying, exploring the significance of a repeatable sales process and the consequences of lacking one, framed by rich personal anecdotes and professional insights. 

Don’t miss this episode packed with practical advice on refining your sales techniques and strategies.

Key Topics Discussed:

  • The Importance of a Repeatable Sales Process: Discussing the necessity of having a structured approach to sales. [00:00:44]
  • Emotional Intelligence and Its Impact on Sales: Exploring how emotional intelligence influences sales interactions and outcomes. [00:01:19]
  • The Role of Discovery in Sales Success: Emphasizing discovery as a critical phase in understanding customer needs. [00:04:23]
  • Integrating Marketing and Sales for Better Customer Acquisition: How aligning marketing and sales efforts can enhance customer acquisition strategies. [00:06:59]
  • The Essential Nature of Trust in Sales: Identifying trust as the cornerstone of successful sales relationships. [00:05:24]
  • Sales Process Alignment with Buyer’s Journey: Highlighting the importance of aligning the sales process with the buyer’s procedures and expectations. [00:11:17]

Key Quotes:

  • Kevin: “If you don’t have a repeatable sales process, you don’t have a repeatable sales process.” [00:00:44]
  • Sean: “Sales is nothing more than the transferring of trust.” [00:05:24]

Additional Resources:

  • Harvard Business Review Study on Sales Process Effectiveness – Mentioned by Kevin as a source confirming the impact of a documented process on sales performance. [00:13:48] – https://hbr.org/2015/01/companies-with-a-formal-sales-process-generate-more-revenue

Summary:

In this episode, Kevin and Sean unpack the essence of a repeatable sales process and its undeniable role in achieving consistent success. Whether you’re a seasoned sales professional or new to the field, this discussion offers invaluable insights into making your sales efforts more effective and efficient. From the foundational role of trust to integrating marketing and sales, this episode is a must-listen for anyone looking to enhance their sales strategies. 

As we approach the 100th episode, stay tuned for more wisdom from “Two Tall Guys Talking Sales.” Ready to elevate your sales game? Listen to this episode now on your favorite podcast platform!

To understand if your company is doing a great job in sales, take this quick and easy 10-question assessment: https://salesxceleration.com/sales-agility-assessment/?locationid=26671639

Two Tall Guys Talking Sales Podcast – The Art of the Hire: Crafting a Winning Sales Team – E98

Two Tall Guys Talking Sales Podcast – The Art of the Hire: Crafting a Winning Sales Team – E98

By Sean O'Shaughnessey

Join hosts Kevin Lawson and Sean O’Shaughnessey on this revealing episode of “Two Tall Guys Talking Sales” where they dive deep into the intricacies of hiring and motivating sales teams. Whether you’re a solopreneur or heading a growing business, this episode delivers crucial insights into creating a robust sales force to propel your business forward.

Key Topics Discussed

  • Hiring Challenges and Solutions [00:00:00]: Kevin opens the discussion by highlighting the universal challenge of hiring effective sales personnel, emphasizing their critical role in delivering solutions to the market.
  • Diversity in Sales Recruitment [00:01:19]: Sean expands on the need for a varied recruitment strategy that aligns with business geography and market scope, from local to global scales.
  • Strategic Hiring Practices [00:02:00]: The conversation shifts towards strategic hiring, avoiding common pitfalls, and setting up a structured hiring process.
  • Aligning Sales and Hiring Processes [00:03:42]: Kevin parallels the sales process with hiring, stressing the importance of a methodical approach to selecting the right candidates.
  • Cultural Fit and Skills Assessment [00:04:52]: This section discusses the importance of cultural fit and rigorous skills assessment in the hiring process, which ensures candidates align with company values and capabilities.
  • Long-term Sales Success [00:06:48]: Sean discusses the broader implications of hiring decisions for long-term sales success and the essential qualities of a top-notch salesperson.

Key Quotes

  • Kevin Lawson [00:00:00]: “When it comes down to delivering your solution to the market, that solution is often sold and carried forward by a salesperson.”
  • Sean O’Shaughnessey [00:02:17]: “You can’t have the strategy to grow at 3X this year if you don’t have enough people or a big enough factory.”

Additional Resources

Summary

In this episode, Kevin and Sean tackle the often-overlooked but vital elements of building a successful sales team. From the necessity of a diverse hiring strategy to aligning the recruitment process with your business’s sales methodology, they cover a spectrum of topics that promise to enhance your hiring practices. Insightful, practical, and filled with expert advice, this episode is a must-listen for anyone looking to scale their sales efforts effectively. Tune in to “Two Tall Guys Talking Sales” to transform your approach to hiring and watch your business grow!

To understand if your company is doing a great job in sales, take this quick and easy 10-question assessment: https://salesxceleration.com/sales-agility-assessment/?locationid=26671639