Two Tall Guys Talking Sales – Fixing the Funnel – Building a Sales Pipeline That Actually Works – E130

Two Tall Guys Talking Sales – Fixing the Funnel – Building a Sales Pipeline That Actually Works – E130

By Sean O'Shaughnessey

Welcome back to Two Tall Guys Talking Sales with hosts Kevin Lawson and Sean O’Shaughnessey. In this episode, the tall guys dive deep into one of the most critical yet commonly broken elements in any sales organization: the sales funnel. Whether you’re stuck with a clunky three-stage process that tells you nothing or overwhelmed with 35 micro-stages that only confuse your reps, Sean and Kevin offer a practical guide to rethinking and rebuilding your pipeline strategy. Packed with metaphors (yes, even superhero ones) and sharp analysis, this episode will leave you inspired to take a hard look at your funnel—and finally fix it.


Key Topics Discussed

  • Why Most Sales Funnels Are Broken (00:00:45)
    Sean unpacks the common pitfalls in how companies define and manage their sales stages, including oversimplified or overly complex CRM setups.
  • Defining Sales Stages Based on the Buyer Journey (00:04:30)
    Kevin emphasizes the need to align your sales stages with how buyers actually buy—not how your company wants to sell.
  • How Many Sales Stages Are Too Many? (00:05:00)
    The guys explore the delicate balance between not enough insight and too much complexity in stage design.
  • The Case for Multiple Pipelines (00:08:00)
    When does it make sense to separate budgetary planning pipelines from active sales discussions? Kevin and Sean explain.
  • What a Healthy Funnel Actually Looks Like (00:10:45)
    Sean introduces a visual and mathematical approach to evaluating whether your funnel is properly shaped—and what to do if it’s not.


Key Quotes

“The Avengers became a team, not just Iron Man. You need to have a team. Even superhero salespeople like to have support.”
— Sean O’Shaughnessey (00:02:50)

“Fixing the funnel starts visually. Does it fit well on one sheet of paper? If not, you’ve already lost the battle for clarity.”
— Kevin Lawson (00:04:45)

“Stages should be built to qualify someone into the next step—not just to log an activity. Every transition should represent progress, not busyness.”
— Kevin Lawson (00:06:15)

“If your pipeline doesn’t look like a funnel, then you’re either wasting time or losing deals. Probably both.”
— Sean O’Shaughnessey (00:12:20)

Additional Resources Referenced

A Significant Actionable Item from this Podcast

Audit Your Sales Funnel for Shape and Stage Effectiveness
Pull a report from your CRM and visualize your current pipeline by number of deals and total revenue per stage. Does it actually look like a funnel? If it doesn’t, dig deeper. Are your stages aligned with your buyer’s journey? Are reps stuck in certain stages too long? This snapshot identifies gaps and opportunities for stage redefinition or activity refinement.

Summary

Whether managing a sales team or closing deals yourself, this episode of Two Tall Guys Talking Sales gives you the blueprint to diagnose and repair a misaligned funnel. Sean and Kevin combine humor, hard truths, and highly actionable insights to help you bring structure and sanity back to your sales process. If you’re ready to create a pipeline that reflects how buyers buy—and helps your team win more deals—this episode is a must-listen.

🎧 Listen now and take the first step in fixing your funnel for good.

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/

Two Tall Guys Talking Sales – Amy Connor discusses Salespeople vs. Lead Generation: Are You Using Your Team Wisely? – E125

Two Tall Guys Talking Sales – Amy Connor discusses Salespeople vs. Lead Generation: Are You Using Your Team Wisely? – E125

By Sean O'Shaughnessey

How do you measure the success of your sales and marketing efforts? If you’ve ever wondered whether your marketing dollars are driving revenue or if your sales team is making the most of their leads, this episode is for you. 

Kevin Lawson and Sean O’Shaughnessey sit down with Amy Connor, founder of CMO on Loan, to discuss how marketing and sales should work together for growth. Amy brings her extensive experience from Procter & Gamble, Luxottica, and other top brands to help mid-market companies build marketing confidence, align with sales, and drive measurable results.

Key Topics Discussed

  • The Basketball Analogy: Why Tracking Performance Matters (~00:01:00)
    • Just like basketball teams analyze stats post-game, businesses need to measure marketing and sales effectiveness.
  • How to Decide Between Investing in Sales or Marketing (~00:04:30)
    • Business owners often wonder whether they should put more resources into sales teams or marketing initiatives—Amy breaks it down.
  • Aligning Marketing and Sales for Lead Generation (~00:07:30)
    • Should salespeople generate their own leads, or is there a more efficient way to bring prospects to the table?
  • The Role of a Fractional CMO: How Businesses Can Engage Marketing Leadership (~00:11:20)
    • Amy explains how a fractional CMO helps companies make smarter marketing decisions without the full-time executive cost.
  • A Sneak Peek into Next Week: Measuring Marketing Effectiveness (~00:13:52)
    • Tune in next week as Amy shares the tools and strategies that help businesses track what’s working and what’s not.

Key Quotes

  • Sean O’Shaughnessey (~00:06:41):
    “So many of my clients assume that salespeople will find their own leads, but is that really the best use of their time?”
  • Amy Connor (~00:07:51):
    “Your sales team is often being asked to do too much. Something will suffer if they have to hunt for leads and nurture accounts at the same time.”
  • Kevin Lawson (~00:11:00):
    “When companies say, ‘I need more sales,’ what they often mean is, ‘I need more leads.’ But are they solving the right problem?”

Additional Resources

A Significant Actionable Item from this Podcast

Evaluate your marketing and sales alignment. Take a step back and ask:

  • Do I have a clear process for tracking where leads come from and how they convert?
  • Is my sales team spending too much time prospecting instead of closing deals?
  • Would marketing support help my business generate higher-quality leads?

If you’re not sure, it may be time to review your funnel and define a strategy that ensures sales and marketing work together—not in silos.

Why You Should Listen to This Episode

This episode is a must-listen for business owners, sales leaders, and marketing professionals looking to make smarter investments in growth. Amy Connor shares real-world insights on how marketing can drive measurable business results and how sales and marketing can function as a united force. Plus, next week’s episode will dive even deeper into how to measure marketing effectiveness, so don’t miss it!

🎧 Download now and take the first step toward a more effective marketing and sales strategy!

Two Tall Guys Talking Sales – Sales Slumps & Hot Streaks: How to Build a Predictable Pipeline – E122

Two Tall Guys Talking Sales – Sales Slumps & Hot Streaks: How to Build a Predictable Pipeline – E122

By Sean O'Shaughnessey

Sales is a game of ups and downs, but what separates top performers from the rest is their ability to keep the funnel full—even when they’re closing deals. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive into the art and science of building a consistent pipeline. They discuss strategic approaches to prospecting, leveraging data tools, and the importance of curiosity in sales conversations. Whether you’re starting fresh in Q1 or looking to level up your approach, this episode is packed with actionable insights to keep your sales engine running smoothly.

Key Topics Discussed

🔹 The Sales Roller Coaster – Why salespeople experience cycles of high revenue followed by dry spells and how to smooth out the dips. (00:01:15)

🔹 The First Step: Re-engage Past Clients – Why checking in with existing customers is the easiest way to generate immediate opportunities. (00:02:23)

🔹 Using Free Data Resources to Prospect – How Data Axle and Apollo.io can help salespeople generate lists of high-potential prospects at no cost. (00:03:00)

🔹 Turning Leads Into Prospects – The difference between having a database of names and actually engaging with real sales opportunities. (00:05:31)

🔹 The Power of Networking and Curiosity – How to leverage your network to gain insights about a company before reaching out to decision-makers. (00:10:39)

🔹 Climbing the Ladder to the Decision-Maker – Why you shouldn’t start at the top and how building relationships within an organization can earn you a trusted introduction. (00:14:37)

Key Quotes

💬 Sean O’Shaughnessey on avoiding the sales roller coaster:
“If I go back to my drain-the-swamp analogy, you gotta put water back in the swamp, you gotta let it rain, gotta make it rain.” (00:02:02)

💬 Kevin Lawson on the importance of planning:
“Too often, salespeople stop after the second or third introduction. Timing is everything—keep going, keep networking, and keep qualifying your ideal client profile.” (00:12:39)

💬 Sean O’Shaughnessey on reaching executives:
“You cannot send an email to the CEO and expect it to be read. You are just a salesperson. If you want to sell to the top, you need a referral—and probably from someone lower in the organization.” (00:14:37)

Additional Resources

📌 Data Axle – A powerful business database often available through public libraries. Check with your local library for free access.

📌 Apollo.io – A free tool offering up to 10,000 business contacts per month to help with prospecting.

📌 Lighthouse Sales Advisors Coaching – Kevin Lawson offers 1:1 coaching to help sales professionals refine their strategies. Learn more here.

A Significant Actionable Item from this Podcast

Take 30 minutes this week to evaluate your sales pipeline using the “circle exercise.”

  1. Draw a circle and estimate what percentage of your revenue will come from existing clients vs. new clients.
  2. Identify how many new deals you need to hit your quota.
  3. Rank your existing leads based on fit and potential.
  4. Develop a networking plan to move from a name on a list to an engaged prospect.

Doing this exercise will give you clarity on where to focus your efforts and how to strategically fill your pipeline.

Why You Should Listen to This Episode

Struggling with an empty pipeline after closing strong last year? You’re not alone. In this fast-paced, insight-packed episode, Kevin and Sean break down the fundamental strategies that separate high-performing salespeople from those stuck on the revenue roller coaster. Whether you’re looking for free prospecting tools, better ways to approach networking, or a foolproof plan to keep your sales funnel full, this episode delivers practical tactics you can apply immediately.

🎧 Tune in now and take control of your sales pipeline!

Two Tall Guys Talking Sales – The Death of Cold Calling and the Rise of Relationship Selling – E119

Two Tall Guys Talking Sales – The Death of Cold Calling and the Rise of Relationship Selling – E119

By Sean O'Shaughnessey

Cold calling is dead—or so claims our guest, Ben Victorica, in this thought-provoking Two Tall Guys Talking Sales episode. Hosts Kevin Lawson and Sean O’Shaughnessey dive deep with Ben into the challenges of modern sales pipelines and explore why traditional outreach methods are no longer effective. Together, they uncover how relationship selling, fueled by emotional intelligence and strategic connections, is reshaping the future of sales. Whether you’re a seasoned sales professional or just starting out, this episode is packed with actionable insights you can’t afford to miss.

Key Topics Discussed

  • Why Cold Calling is Ineffective Today
    Ben discusses the inefficiency of cold outreach in the modern era, citing Bank of America’s 2021 decision to ban cold calling as a pivotal moment in sales strategy. (Approx. 00:01:00)
  • The Economics of Cold Outreach vs. Relationship Selling
    Sean explains the hidden costs of cold calling, emphasizing the expensive hourly rate of quota-bearing sales reps and its low ROI. (Approx. 00:02:20)
  • Leveraging LinkedIn for Strategic Connections
    Ben provides a practical, step-by-step guide to mining LinkedIn connections for warm referrals, using your network intelligently without costly tools. (Approx. 00:05:35)
  • The Role of Emotional Intelligence in Modern Sales
    Kevin and Ben discuss how sales professionals can use emotional intelligence and relationship intelligence tools to identify and nurture stronger business relationships. (Approx. 00:10:45)
  • Maximizing Relationship Capital with Technology
    Ben introduces KnowledgeNet, a tool that helps sales teams unlock and scale their relationship capital to drive business growth. (Approx. 00:12:00)

Key Quotes

  • Kevin Lawson:
    “Top of funnel cold outreach with no relationship is nearly impossible—it’s a cost line on any P&L.” (Approx. 00:04:48)
  • Sean O’Shaughnessey:
    “If you hand someone a list of 100 people you’d like an introduction to, you’ll get zero. But ask for five or ten, and you’ll get meaningful connections.” (Approx. 00:07:45)
  • Ben Victorica:
    “Cold calling is dead. Relationship selling instead.” (Approx. 00:01:49)

Additional Resources Mentioned

  • KnowledgeNet.ai: A powerful tool to uncover and leverage relationship capital within your organization. Visit KnowledgeNet
  • Wall Street Journal 2021 Article: Referenced by Ben regarding Bank of America’s decision to ban cold calling – https://www.wsj.com/articles/bank-of-americas-merrill-lynch-to-ban-trainee-brokers-from-making-cold-calls-11621850400.

A Significant Actionable Item from this Podcast

Use LinkedIn as a referral engine.
List key LinkedIn connections that align with your ideal customer profile. Then, approach your strongest network contacts—your “super connectors”—with a curated list of five to ten potential introductions. Respect their time and include a pre-written email template to make the referral process seamless.

Why You Should Listen to This Episode

The sales landscape has shifted, and the old playbook of cold calling no longer delivers results. This episode offers a fresh perspective on building pipelines using strategic relationships and modern tools like KnowledgeNet. Packed with real-world advice from Kevin, Sean, and Ben, this conversation will inspire you to rethink your sales approach. Ready to ditch outdated tactics and embrace the future of selling? Tune in now to gain the edge you need.

Understanding Your Customers: The Role of Buyer Personas and Quarterly Business Reviews

Understanding Your Customers: The Role of Buyer Personas and Quarterly Business Reviews

By Sean O'Shaughnessey

Want to know the real secret behind successful sales? It’s not just about knowing what your customers need. The true power lies in understanding who they are at their core.

Have you ever wondered why some sales professionals consistently outperform their peers? The answer often comes down to their mastery of buyer personas and detailed profiles that capture the essence of your ideal customers.

Think of buyer personas as your secret weapon in the sales battlefield. These aren’t just random customer profiles thrown together in a rushed afternoon meeting. They represent carefully crafted composites of your most valuable clients, built from real-world data and insights. Your company might need several of these personas, each targeting different market segments with laser precision.

Creating effective buyer personas demands more than just surface-level observation. Start with a thorough analysis of your business landscape. Examine your strengths and weaknesses. Map out the opportunities that excite you and the threats that keep you up at night. This foundation helps you understand exactly where you fit in your customers’ world.

What makes your top customers tick? The answer lies in meaningful conversations with your best clients. These discussions should dig deep into both quantitative and qualitative factors. Demographics tell part of the story – age, position, education, family status. But the real gold comes from understanding their motivations. Why did they choose you? What problems do you solve that keep them coming back?

Read the rest of the article…
Unlocking Sales Success: The Power of KPIs in Sales Processes

Unlocking Sales Success: The Power of KPIs in Sales Processes

By Sean O'Shaughnessey

Are your sales KPIs helping your team succeed? Many sales leaders focus solely on closed deals. This narrow view misses crucial elements of sustainable sales growth.

The journey matters more than the destination. Sales excellence follows a similar path. Your team’s daily actions and behaviors create the foundation for lasting success.

Effective sales measurement requires a comprehensive view of your team’s activities. Top performers consistently execute vital behaviors that drive results. They prospect strategically, nurture relationships, and expand their presence within existing accounts. These leading indicators paint a clearer picture of future performance than lagging metrics alone.

Your KPI framework must evolve beyond historical analysis. Forward-looking metrics help you spot opportunities and challenges before they impact revenue. What’s happening in your pipeline right now? How are your teams finding new prospects? Which accounts show growth potential?

Experience levels significantly impact appropriate performance measures. New salespeople face different challenges than seasoned veterans. A rookie might need help with fundamental sales behaviors while learning your company’s approach. They need clear operational guidance and structured metrics that reinforce proper execution.

Veteran salespeople bring established skills and proven track records. Their KPIs should emphasize continuous improvement and cultural alignment. How are they advancing their capabilities? What value do they add to the broader sales organization?

Read the rest of the article…
Adapting to the New Sales Landscape: The Importance of Omni-Channel Outreach

Adapting to the New Sales Landscape: The Importance of Omni-Channel Outreach

By Sean O'Shaughnessey

Are you still relying on trade shows as your primary sales driver? The sales landscape has undergone a seismic shift. Those packed convention halls and endless rows of booths no longer serve as the bedrock of business development they once were.

Let’s talk about what works in today’s sales environment. Building an effective outbound pipeline isn’t just an option anymore – it’s your survival toolkit. But here’s the challenge: how do you stand out in a market where everyone’s fighting for attention?

Your unique value proposition makes all the difference. Yet many sales professionals miss a crucial point: your value proposition isn’t static. What resonates with a manufacturing client might fall flat with a distribution company. Have you tailored your message to address each industry’s pain points?

Think about your last prospecting campaign. Did you give up after four or five attempts? Research shows it takes 12 to 16 touches before prospects typically respond. This gap between persistence and practice often determines success or failure in modern sales.

The game has changed. Your prospects live in an omnichannel world. They check email between Zoom calls, scroll LinkedIn during lunch, and scan their phones throughout the day. How are you showing up in their digital world?

Consider this: every unanswered email or phone call might be a messaging problem. Are you talking about your features when you should be solving your prospects’ problems? Your prospects don’t care about your product specifications. They care about their challenges, their goals, and their bottom line.

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Balancing Act: Networking, Direct Prospecting, and Customer Referrals for Revenue Growth

Balancing Act: Networking, Direct Prospecting, and Customer Referrals for Revenue Growth

By Sean O'Shaughnessey

Is your sales pipeline running dry? We’ve all been there.

Let me share a personal story that might resonate with you. After spending months securing a major deal, I found myself staring at an empty pipeline. The celebration of landing that giant whale quickly became a stark reality check. This experience taught me an invaluable lesson about sustainable sales growth.

Revenue generation isn’t just about closing deals—it’s about maintaining a consistent flow of opportunities. Your success depends on mastering the art of prospecting, yet many salespeople struggle with this fundamental skill. Are you dedicating enough time to building your pipeline, or are you caught in the feast-and-famine cycle?

The most effective sales professionals understand that prospecting isn’t a one-dimensional activity. Think of your prospecting strategy as a carefully orchestrated symphony, where different elements work together to create a harmonious result. Direct outreach and network-based approaches each play their unique roles in this composition.

Visualize a three-legged stool symbolizing the three-pronged approach to sales: networking and referrals, direct prospecting, and existing customers. Each of these legs supports growing your business and consistently achieving your revenue goals.

Consider how a software company might approach this dual strategy. While tracking metrics for direct outreach is straightforward, measuring networking success requires a different lens. How many new relationships have you cultivated? Which dormant connections have you rekindled? These indicators matter just as much as your cold call statistics.

I recently spoke with a consulting professional who shared an interesting perspective on networking metrics. Rather than counting sales pitches, he measures success by the number of times he naturally introduces his services in conversations. This subtle shift transforms aggressive selling into educational opportunities. Have you considered how this approach might work in your context?

Your prospecting strategy must align with your target audience’s expectations and behaviors. Waiting for inbound leads isn’t a strategy—it’s a recipe for inconsistent results. When you prospect through your network, the goal isn’t to ask for immediate business. Instead, you’re planting seeds for future opportunities through strategic introductions.

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Two Tall Guys Talking Sales – Sales Intelligence 101: Using AI and Networking to Target Ideal Customers – E112

Two Tall Guys Talking Sales – Sales Intelligence 101: Using AI and Networking to Target Ideal Customers – E112

By Sean O'Shaughnessey

Welcome to another compelling episode of Two Tall Guys Talking Sales with hosts Kevin Lawson and Sean O’Shaughnessey! Kevin and Sean dive deep into a central challenge for sales teams: identifying ideal customers and building a robust prospect list. In this episode, they uncover practical strategies, share indispensable tools, and illustrate how a strong grasp of your customer can turn prospects into loyal clients. Whether you’re part of a lean sales team or managing large territories, this episode is loaded with insights to help you grow.

Key Topics Discussed

  • Building Your Prospect List (approx. 2:00): Kevin introduces the concept of creating an ideal prospect list and breaks down the importance of strategic targeting beyond mere proximity or broad industry fit.
  • Activating and Leveraging Networks (approx. 3:00): Both hosts discuss the value of networking to uncover warm referrals, emphasizing the need to build a customized, one-to-one outreach strategy.
  • Effective Tools for Targeting Customers (approx. 4:45): Sean and Kevin highlight essential tools like LinkedIn Sales Navigator, KnowledgeNet, and AI-powered tools like Perplexity to streamline the process of finding and qualifying leads.
  • Understanding the Customer’s Goals and Structure (approx. 7:20): Sean shares a story about understanding internal company dynamics and how knowing a prospect’s structure and goals helps in creating value-oriented solutions.
  • Actionable Research Insights (approx. 10:15): The duo dives into practical research techniques to understand client organizations and stakeholders, stressing that informed sellers are empowered sellers.

Key Quotes

  • Kevin: “To build a good prospect list, it doesn’t have to mean endless hours on Google or hundreds of cold calls. With the right tools, you can have a list ready before lunch.” (approx. 5:55)
  • Sean: “Your job isn’t just to sell a product; it’s to solve a problem. When you start with that goal, the sale becomes almost inevitable.” (approx. 14:40)
  • Kevin: “Whether you’re a team of one or a team of five, using the tools at hand to maximize your reach and impact makes you competitive.” (approx. 13:00)

Additional Resources

A Significant Actionable Item from this Podcast

Leverage AI-powered tools to gain deeper insights into target companies and individuals before engaging in outreach. By using resources like Perplexity to understand a client’s structure, goals, and decision-making processes, salespeople can craft highly personalized solutions that add immediate value.

In the episode, Sean challenged people to use Perplexity to research his fellow co-host, Kevin Lawson. Here is that Perplexity search: https://www.perplexity.ai/search/can-you-help-me-with-informati-Hdjvd9OgQTWFXrODrlhHnQ


In this episode, Kevin and Sean clarify that sales is about more than products—it’s about partnerships. Discover how to empower yourself with the right tools, refine your approach to prospecting, and bring authentic value to each client. Tune in to Two Tall Guys Talking Sales for actionable strategies to transform how you engage, connect, and close.