analysis

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

Previous episodes featuring CMO Amy: Deep dives into top-of-funnel strategies, lead quality, and the marketing–sales handoff.
https://sites.libsyn.com/458454/site/measuring-marketing-success-with-amy-connor-of-cmo-onloan
https://sites.libsyn.com/458454/site/amy-connor-discusses-salespeople-vs-lead-generation-are-you-using-your-team-wisely
“Chasing Butterflies vs. Building a Garden” episode: A useful metaphorical framework for thinking about inbound sales strategies.
https://sites.libsyn.com/458454/site/sales-prospecting-are-you-chasing-leads-or-cultivating-success

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 – 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/

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…

Driving Sales Performance with Strategic Competitive Analysis

By Sean O'Shaughnessey

Ever wonder why some sales teams consistently outperform their competitors while others struggle to close deals? The answer often lies in how well they understand and leverage competitive analysis in their sales process.

Let’s talk about competitive analysis in sales. It’s not just about knowing your competition – it’s about understanding how to use that knowledge to drive results. You need to grasp why prospects choose specific solutions over others and, more importantly, why they sometimes choose to do nothing at all.

Have you considered how many deals you’ve lost not to competitors but to indecision? These “no decision” outcomes often stem from a fundamental gap in prospect qualification. Intelligent sales professionals dig deeper, asking targeted questions about organizational priorities, resource allocation, and strategic initiatives. They understand that timing can be just as crucial as the solution itself.

The modern sales landscape demands a sophisticated approach to competitive analysis. Your success hinges on aligning your organization’s strengths with your prospect’s needs. But here’s the real question: Do you truly understand what your ideal client values most?

Many sales professionals miss the mark by focusing solely on feature comparisons. While product capabilities matter, they’re just one piece of the puzzle. The real power lies in understanding how your solution addresses your prospect’s challenges. This requires a comprehensive view of your competitive landscape, including direct and indirect competitors.

Think about your last few lost deals. What patterns emerge when you analyze the feedback? Every objection and hesitation after presenting pricing are valuable data points that should shape your competitive strategy. Your sales conversations must reflect a deep understanding of your prospect’s value metrics.

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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.

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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?

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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.

Two Tall Guys Talking Sales Podcast – The Art of Targeting: How Small Sales Teams Can Win Big in Expansive Territories – E111

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the challenges and strategies of managing large sales territories, especially for teams with fewer than five sellers. Reflecting on their extensive sales careers, they explore the intricacies of balancing time, travel, and targeting the right clients when facing expansive regions. Kevin and Sean share actionable insights on refining the ideal client profile (ICP) and discuss how small business owners and sales leaders can make intentional, high-impact decisions in their outreach efforts. Tune in to discover effective approaches to optimizing sales territories and maximizing limited resources to achieve sustainable growth in the new year.

Key Topics Discussed

The Impact of Large Sales Territories on Small Teams (00:01:38): Kevin and Sean discuss the demands of covering extensive sales regions, whether a few states or half the country and why focus and territory management are crucial for smaller sales teams.
The Importance of Ideal Client Profiles (00:04:57): Sean explains how understanding and refining your ICP can simplify prospecting, ensure each lead mirrors your most valuable clients, and avoid wasted effort on non-ideal targets.
Leveraging Top Clients for Networking and Referrals (00:09:03): Sean and Kevin emphasize the value of networking over cold prospecting, suggesting that current clients can provide introductions and case studies that open doors to similar high-potential accounts.
Using Personas to Deepen Client Relationships (00:11:00): Kevin discusses how personas complement the ICP by focusing on individual motivators, ensuring sellers speak directly to what matters most to each prospect.
Strategic Territory Planning for the Coming Year (00:12:59): The hosts explain how to plan for realistic, growth-oriented targets and advise on which regions and clients to prioritize based on resources and client potential.

Key Quotes

Kevin Lawson (00:05:34): “When you have less than five sellers on your team, your ideal client profile becomes really, really important… Look at your prospect list and ask yourself: do they fit my ICP? It’s something you can do today, quickly.”
Sean O’Shaughnessey (00:10:48): “If you have the world as your territory…your quota needs to be based on how many people you can actually see and deal with—not on everyone who could theoretically buy your product.”
Kevin Lawson (00:11:18): “Ask yourself this: how does your ideal client persona earn a bonus? If your product doesn’t align with what matters to them, you’re likely speaking to the wrong person.”

A Significant Actionable Item from this Podcast

Refine Your Ideal Client Profile and Persona Today: Identify your top 10 favorite customers and analyze their shared traits. Compare these traits to your current prospect list, removing prospects that don’t align with your top client characteristics. This simple but powerful action helps ensure you’re spending time on prospects more likely to become valuable clients.

Closing Summary:

As you prepare for the upcoming year, Kevin and Sean’s conversation provides invaluable advice for small sales teams navigating large territories. Whether you’re a business owner, a solo seller, or a sales leader with a lean team, this episode reveals practical tactics for honing in on your ideal client profile, leveraging client relationships, and maximizing the impact of each sales call. Dive in to learn how to set your sales strategy up for success, and walk away with actionable tips you can implement immediately. Listen now and take your sales approach to new heights with Two Tall Guys Talking Sales!

Two Tall Guys Talking Sales Podcast – From First Sales Hire to Revenue Powerhouse: Essential Strategies for Business Owners – E110

By Sean O'Shaughnessey

In this episode of “Two Tall Guys Talking Sales,” hosts Kevin Lawson and Sean O’Shaughnessey dive into the unique challenges and opportunities of hiring your second salesperson. Many small business owners face a pivotal moment when they bring on a sales team member who may know the company but not the ins and outs of professional selling. Join Kevin and Sean as they explore how to make the first and second salespeople truly effective, how to ramp up revenue, and how to know when it’s time to expand your sales team. Packed with actionable insights, this episode is a roadmap for business leaders looking to maximize their early sales hires and foster sustainable growth.

Key Topics Discussed:

The First Sales Hire: Opportunity or Risk? – Sean and Kevin discuss the challenges owners face when hiring a single salesperson who may lack deep sales expertise (00:00:17).
How to Make Your Second Sales Hire Successful – Kevin emphasizes the importance of a structured onboarding process focused on accountability, consistent communication, and setting measurable outcomes for new hires (00:02:24).
The Power of Accountability and Communication – Kevin and Sean lay out practical steps for holding a first salesperson accountable and how to provide actionable, regular feedback for improved performance (00:04:00).
Setting Success Metrics and Revenue Goals – Sean covers the critical role of defining success metrics and how to know when it’s time to hire a second salesperson or replace your current one (00:06:31).
Shortening the Sales Ramp-Up Time – Kevin challenges the assumption that onboarding takes years, urging owners to implement processes that cut onboarding from years to months (00:10:00).
Revenue Abundance Mindset – Sean closes with a motivational segment about the abundance of revenue potential in every industry, stressing the importance of targeting the ideal client profile (00:12:23).

Key Quotes:

Kevin: “The ‘how’ question is so important. How do we get someone into our organization in a way where they feel valued, are producing value, and we can all measure and feel the growth of that value throughout the organization?” (00:02:39)
Sean: “If you’re concerned that the salesperson is successful, but you’re not quite there, start by pushing two numbers—closing deals faster or bringing in more revenue per deal.” (00:07:55)
Kevin: “We need you as an owner to set a goal for yourself that this year, this next 12 months, you’re going to reduce the ramp time to one year. And in three years, we’re going from a two-year ramp to a 90-day ramp.” (00:10:24)
Sean: “There’s an abundance of people out there who want to buy your product and who have problems you can solve. Go after your ideal client profile, help them achieve their goals, and you will find more revenue than you ever imagined.” (00:14:23)

Additional Resources:

Sean’s Book – Eliminate Your Competition – Referenced as a comprehensive guide for building sales plans. Available for purchase on major book retailers’ websites. https://amzn.to/2K37ugx

A Significant Actionable Item from this Podcast:

Set Regular Checkpoints for New Sales Hires – Create a structured, regular feedback and accountability process for any new salesperson. Schedule weekly check-ins to evaluate progress on specific metrics such as speed of closing deals and revenue per deal. Adjust goals as needed to encourage growth and provide timely support.

Summary:

Whether you’re just starting to build your sales team or looking to improve your existing process, this episode of “Two Tall Guys Talking Sales” with Kevin Lawson and Sean O’Shaughnessey offers practical advice to drive real change. They dive deep into how to turn your first and second salesperson into a powerhouse by fostering accountability, clear communication, and a strategic growth mindset. Subscribe now and get ready to learn from the experts how to structure, support, and scale your sales efforts—taking your business to new heights.

Two Tall Guys Talking Sales – Empowering Non-Sales Employees to Boost Customer Value – E109

By Sean O'Shaughnessey

In this episode, hosts Kevin Lawson and Sean O’Shaughnessey, take listeners on a journey to understand the power of non-sales roles in supporting a sales-centric culture. Expanding on prior discussions about sales planning and execution, they explore how professionals outside the sales department—think programmers, customer service reps, delivery drivers, and even truckers—can play a pivotal role in enhancing client satisfaction and identifying new opportunities. Kevin and Sean dive into practical steps sales leaders can take to foster a collaborative environment where everyone contributes to sales success, making this an unmissable episode for business leaders, sales professionals, and anyone looking to understand the value of cross-functional synergy in achieving enterprise growth.

Key Topics Discussed

The Sales Quadrant Framework [00:01:00]: Kevin and Sean introduce a framework for effective sales planning, dividing it into four quadrants: Strategy, Process, People, and KPIs. This framework guides leaders on fostering a holistic sales ecosystem.
Sales for Non-Salespeople: Defining the Role [00:01:40]: The hosts discuss how non-sales team members, from programmers to quality agents, can pass along valuable customer insights without selling directly. It’s about listening and relaying information to sales, not cold calls or quotas.
Leveraging Customer Interactions for Insight [00:03:14]: Sean shares a vivid example from his software background, where consultants gathering customer feedback created substantial upsell opportunities. He emphasizes the value of customer-facing team members in providing sales with a view from the trenches.
Building Relationships Across Teams [00:07:00]: Kevin discusses strategies to align cross-functional team goals with sales objectives, creating a supportive network that encourages the entire team to spot potential sales opportunities.
The Importance of Gratitude and Recognition [00:12:07]: Sean underscores the value of acknowledging and thanking team members who help sales, reinforcing their role in supporting company-wide goals and deepening relationships across departments.

Key Quotes

Kevin Lawson: “We’re not asking non-salespeople to sell, but we are asking them to raise their hand when they see something we might need to know about to help our customers better.” [00:01:59]
Sean O’Shaughnessey: “In every company, people need help achieving their goals. And often, the folks who see where we can help the most aren’t in the sales department—they’re on the front lines, interacting with customers daily.” [00:04:11]
Kevin Lawson: “Be a better person in business. Support your teammates, your vendors, and your community, and that support will circle back, lifting everyone’s success.” [00:14:04]
Sean O’Shaughnessey: “A simple ‘thank you’ can be the most valuable recognition, and it builds bridges with your team. Make it a habit.” [00:12:46]

A Significant Actionable Item from this Podcast

Empower Non-Sales Team Members to Listen for Opportunities
Sales leaders should hold short training sessions or casual discussions with non-sales staff, educating them on key signals that may indicate an opportunity. Encourage these team members to feel comfortable sharing insights with sales and clarify that they won’t be pressured to sell—just to observe and communicate.

Summary: This Two Tall Guys Talking Sales episode delivers essential insights for any sales-driven organization. Kevin and Sean emphasize the untapped potential within non-sales teams, showing how they can indirectly yet powerfully support sales efforts by sharing customer feedback and needs. With practical strategies for fostering collaboration and recognizing the contributions of non-sales staff, this episode is a must-listen for sales leaders looking to unlock every possible avenue of client satisfaction and revenue growth. Tune in and discover how even a small tweak in team communication can significantly impact your bottom line.