The Three Pillars of Sales Success: Ideal Client Profiles, Effective Messaging, and Aspirational Offers

The Three Pillars of Sales Success: Ideal Client Profiles, Effective Messaging, and Aspirational Offers

By Sean O'Shaughnessey

Let’s start this article with a rhetorical question to the sales professionals, sales managers, or CEOs: Have you ever found yourself guilty of sending messages to prospects without fully considering their specific needs or how your offer aligns with them?

If so, you’re not alone—this is a common pitfall in sales. The good news is, it’s entirely fixable by developing a straightforward, strategic approach.

An effective sales strategy hinges on three core components: defining your ideal client profile (ICP), crafting a resonant message, and presenting a compelling offer. These elements are interconnected. Mastering their alignment will significantly enhance your sales effectiveness.

Ideal Client Profile

Let’s start with the ideal client profile. How well do you know the companies you’re targeting? Identifying your ideal customer is foundational to your entire sales approach. It’s not enough to say that your market is “small businesses” or “tech companies.” Instead, think about your best clients—the ones you genuinely enjoy working with, who value your product, and who generate profitable, sustainable business. Think about companies that rarely devalue your product or service by asking for a discount. What do these clients have in common?

Now that you have your favorite customers from above, reflect on your top five or ten accounts. Are they in the same industry? Do they share similar challenges or company structures? Perhaps they all have common goals that your product consistently solves. Pinpoint these commonalities. This process will help you create a precise and actionable ideal client profile.

But don’t stop at company-level characteristics. Remember, even in B2B sales, you’re ultimately selling to individuals. Identify the specific roles or buyers within these organizations that are responsible for making buying decisions. Who are these decision-makers? What motivates them personally and professionally? Do they all have the same kind of college education? Do they all have similar career paths? Understanding the people behind the logo makes your outreach more personal, targeted, and effective.

What is your message?

Once you’ve developed a clear picture of your ideal client and the people within those companies, the next step is crafting a message that reflects your value-selling message. This message is how you communicate your value proposition—it’s the bridge between your product and your prospect’s needs. Too often, sales messaging falls flat because it focuses heavily on the seller rather than the buyer. Statements that emphasize “we,” “I,” or “our product” rarely resonate deeply. Instead, effective messaging highlights the customer’s perspective, clearly communicating the benefits they will experience.

Consider your value selling proposition (your message) carefully. If you’re consistently receiving inquiries that don’t match your offering, such as prospects reaching out for unrelated services, this signals a misalignment. Your messaging should explicitly and directly address your ideal client’s goals and aspirations. Ask yourself, “If I were my ideal client, would this message resonate with me?”

A practical exercise to refine your messaging is the three-column method. On a blank page, create three columns. Column one lists your target prospects. Column two identifies the specific goals your product or service helps the prospect achieve. The third column—the most important one—defines how your prospects measure value. This last column isn’t about your features; it’s about the outcomes your customers genuinely care about, expressed in their language.

Over time, you’ll notice patterns in this third column. These patterns can become the cornerstone of your marketing and messaging strategies. By clearly articulating value in your client’s terms, your outreach becomes significantly more compelling.

Your offer to help the prospect achieve their goals

Now, let’s discuss the third critical component of your sales strategy: your offer. Many sales professionals misunderstand what constitutes an offer. It’s not your pricing structure, discounts, or terms. Instead, your offer encapsulates the transformative value your product or service delivers. Your offer is how your solution makes your customer’s business better, easier, more profitable, or more competitive.

Think about it this way: your prospects have a current state and a desired future state. Your offer is the vehicle that bridges this gap, enabling them to reach or even surpass their aspirations. To illustrate, consider a car manufacturer’s advertisement. Instead of emphasizing the car’s features—four wheels, doors, and mirrors—they highlight the vehicle’s safety, showing a family surviving a severe collision. The offer, in this case, isn’t just a car; it’s peace of mind, safety, and protection for loved ones.

Applying this concept to your own sales strategy, ask yourself: What ultimate benefit does my client achieve by investing in my product or service? If you’re selling sales coaching or consulting, you’re not merely offering advice or strategies. Instead, you’re providing outcomes like predictable revenue growth, scalable processes, and enhanced team performance. You’re offering your client the capability to achieve their business goals consistently, hire confidently into proven systems, and forecast revenue reliably.

To effectively communicate your offer, focus on aspirations rather than baseline improvements. If a prospect’s stated goal is to increase efficiency by twenty percent, demonstrate how your solution can help them achieve thirty or even forty percent improvement. Positioning your offer aspirationally differentiates you from competitors and provides clients with a compelling reason to choose your solution.

Refine all three until they are symbiotic

All three components—ideal client profile, message, and offer—are closely intertwined. You can’t develop a resonant message without first understanding your ideal client. You can’t articulate a meaningful offer without clearly knowing what your client values. Therefore, it’s essential to approach these elements as interconnected pieces of your strategy. You may start by defining your client profile, then craft your message and offer, but you’ll likely revisit and refine each component multiple times. This iterative process ensures alignment and effectiveness across your entire sales approach.

Implementing this strategic framework brings clarity and consistency to sales managers and CEOs who oversee sales teams. It provides your salespeople with clear guidelines on whom to target, how to communicate, and what compelling value to emphasize. This alignment also facilitates better forecasting, pipeline management, and revenue predictability—critical outcomes for any business leader seeking growth and stability.

Remember, as a salesperson or sales manager, your role extends beyond closing deals. You are responsible for generating revenue that sustains your entire organization. From manufacturing and finance to distribution and administration, your colleagues depend on your effectiveness. Approaching your sales strategy with this mindset underscores the importance of clarity, intentionality, and strategic alignment.

Consider the opportunities you lost when your ideal client profile, message, and offer are not aligned. Prospects may misunderstand your value, ignore your outreach, or mistakenly categorize your solution. Alternatively, a clearly articulated strategy positions your product or service as an essential investment, reducing friction in the sales process and accelerating deal velocity.

Finally, remember that refining your sales strategy is an ongoing process. Market conditions evolve, client priorities shift, and competitive landscapes change regularly. Periodically revisiting your ideal client profile, messaging, and offers ensures that your sales approach remains current and effective.

As you move forward, set aside dedicated time to assess and refine these strategic components. Engage your sales team in collaborative discussions around client needs, messaging effectiveness, and offer positioning. Encourage open feedback loops to improve and adapt your strategy continually. Building this discipline into your sales culture fosters agility, responsiveness, and sustained growth.

In your following outreach, pause before hitting send. Reflect carefully:

  • Does your prospect perfectly match your ideal client profile?
  • Does your message clearly articulate the benefits they’ll receive, framed in their language?
  • Is your offer aspirational, compelling, and clearly differentiated from competitors?

By answering these questions affirmatively, you significantly increase your chances of resonating deeply, engaging meaningfully, and ultimately converting prospects into long-term, satisfied clients.

Your sales strategy is critical to your company’s success. By clearly defining your ideal clients, crafting messages that resonate deeply, and presenting compelling, aspirational offers, you build a robust foundation for growth. Invest in refining these elements today, and watch your sales effectiveness soar.

Here Are Four Actionable Steps Sales Leaders Can Implement Today:

  1. Clearly Define Your Ideal Client Profile
    Take time today to analyze your top five to ten customer accounts. Identify common characteristics, such as industry, company size, pain points, and roles of decision-makers. Document these findings into a precise, detailed ideal client profile to guide immediate targeting and messaging.
  2. Conduct a Messaging Audit Using the Three-Column Method
    Grab a sheet of paper and create three columns: one listing your target prospects, the second identifying the specific problems your solution addresses, and the third outlining how your prospects measure value (using their own language). Complete this exercise today to ensure your messaging genuinely resonates with your ideal clients.
  3. Reframe Your Offer Around Client Aspirations
    Review your current sales materials and outreach communication. Shift your messaging from focusing on product features or incremental improvements to emphasizing transformational outcomes, such as dramatically improved efficiency, increased profitability, or greater competitive advantage. Clearly articulate the aspirational benefits your clients truly desire.
  4. Schedule Regular Strategy Reviews
    Take immediate action by scheduling recurring meetings (weekly or monthly) with your sales team to revisit and refine your ideal client profile, messaging, and offer. Create a structured agenda to ensure ongoing alignment, responsiveness to market changes, and continuous improvement of your sales strategy.
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 – Know Your Numbers: A Sales Leader’s Guide to Growth Metrics – E132

Two Tall Guys Talking Sales – Know Your Numbers: A Sales Leader’s Guide to Growth Metrics – E132

By Sean O'Shaughnessey

As Q2 kicks into full gear, it’s time to pause and reflect—are you ahead, on pace, or falling behind on your sales targets? In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey unpack one of a sales leader’s most crucial yet often overlooked responsibilities: knowing your numbers. With equal parts practical advice and strategic vision, this conversation walks you through the foundational metrics every sales leader should track—customer acquisition cost, average transaction size, support staffing ratios, and more. Whether you’re forecasting growth, scaling headcount, or simply trying to stay ahead of the competition, this episode is your playbook for building a metrics-driven sales organization that thrives.

Key Topics Discussed

  • Why “Keeping Score” Matters in Sales Leadership (00:00)
    Kevin kicks off the episode with a strong analogy to competitive sports, emphasizing that tracking performance metrics is non-negotiable for sales leaders aiming to grow.
  • Building a Forward-Looking Sales Metrics Matrix (00:01)
    Kevin walks through how to build a simple but powerful matrix using transaction volume, average deal size, and headcount to visualize both current performance and future goals.
  • Calculating Average Transaction Size and Quota Coverage (00:02)
    Learn how to reverse-engineer quota achievement by dividing sales goals by average transaction size to determine activity targets for your team.
  • Understanding Customer Acquisition Cost (CAC) (00:05)
    Sean breaks down the components of CAC and explains why every sales leader must know this figure to scale sustainably and profitably.
  • Debunking the “Geopolitics Are Killing Sales” Excuse (00:09)
    Sean challenges the notion that global events are valid reasons for missed quotas, reinforcing that internal execution and strategic clarity are what really matter.
  • Aligning Sales Activity with Strategic Growth Goals (00:12)
    Kevin closes the episode with a systems-thinking approach to leadership, showing how small adjustments in metrics, team development, and compensation can drive exponential growth.

Key Quotes

Kevin Lawson: “Keeping score is important. Really important. I’m talking like March Madness. Final game. Important.” (00:00)

Sean O’Shaughnessey: “If it takes you more than 20 minutes to figure out this information, then you need a better bookkeeping system.” (00:06)

Sean O’Shaughnessey: “You need to know what your average deal size is. You need to know how long it takes you to get a customer. Your CRM should be solving that.” (00:07)

Kevin Lawson: “We want to gently steer our company towards our goals. So the thinking about this process is all about knowing your numbers.” (00:12)

A Significant Actionable Item from this Podcast

Build Your Sales Metrics Matrix This Week
Start with your annual revenue goal. Break it down by the number of salespeople, average transaction value, and number of transactions needed per rep per month. Then layer in your customer acquisition cost, support staffing ratios, and expected margin. This matrix becomes your roadmap for scaling intelligently—whether you’re doubling headcount, expanding territory, or just trying to hit a consistent quota.

Episode Summary

In a world of uncertainty, Two Tall Guys Talking Sales reminds us that clarity comes from data. Kevin and Sean deliver a compelling, no-nonsense discussion about how to take control of your revenue engine by genuinely understanding the math behind your sales motion. Whether you’re a CEO, VP of Sales, or just starting to lead a team, this episode offers an essential primer on aligning your operations to your goals. Don’t miss this one—it might be the wake-up call your spreadsheet has been waiting for.

👉 Hit play now to future-proof your sales strategy by learning how to know your numbers like a pro.

Level Up Your Sales Prospecting with Advanced Research Techniques

Level Up Your Sales Prospecting with Advanced Research Techniques

By Sean O'Shaughnessey

A shoutout to Chris Spanier and Episode #85 of the Practical, Actionable Marketing Podcast

Sales prospecting has always been a grind. What if you could cut your research time in half and dramatically improve your outreach results?

In Episode #85 of the Practical, Actionable Marketing podcast, host Chris Spanier delivers a masterclass on how to do just that. Titled “Advanced Prospecting Research Tools,” the episode is packed with time-saving techniques and tools that help sales professionals build sharper prospect profiles faster.

As someone with over four decades in sales and sales management, I believe this kind of tactical insight makes a difference. If you haven’t already, listen to the episode. Then, come back here for a quick breakdown of what Chris covered—plus a few of my thoughts.

Why Prospect Research Matters More Than Ever

In a market saturated with sales messages, relevance is your only competitive advantage. The days of blasting generic emails to massive lists are over. Today, the winners are the ones who personalize their outreach with precision—and that begins with better research.

Unfortunately, most salespeople waste hours digging through irrelevant or incomplete data. They either under-research and go in blind or over-research and burn time on unqualified leads. The trick is finding a balance—doing more innovative research, not just more research.

That’s precisely what Chris addresses in this episode.

Build a Tiered Research Stack Based on Prospect Value

One of the most practical ideas Chris shares is a three-tiered research strategy—matching your level of research effort to the potential value of the opportunity.

  • High-value prospects deserve premium research. Tools like Nimbler, Apollo, and Snovio provide the relatively accurate contact data, firmographics, and context for tailored outreach. If you’re tight on budget, these tools often offer free plans with limited monthly records.
  • Mid-funnel prospects are well-suited for tools like LinkedIn Sales Navigator or KnowledgeNet. But here’s the twist: don’t just skim the surface of their profiles. Instead, dig into their activity feed—what they post, like, and comment on. This gives you insight into their priorities, pain points, and current initiatives.
  • Top-of-funnel prospecting at scale can be handled with data platforms like Data Axle. While the data may not always be fresh, the breadth of filters available can help you uncover new accounts that match your ideal customer profile.

This tiered approach lets you allocate your time and tools effectively, ensuring you invest the most effort where it will yield the greatest return.

Go Beyond Firmographics: Create a 360° Prospect Profile

Many sales professionals stop at company size, revenue, and industry. But those are just the basics. Chris recommends creating a “360-degree view” of each prospect.

Here’s what that looks like in practice:

  • Technographics – What software or platforms are they already using? Are they a fit for your stack?
  • Intent Data – Are they actively researching topics related to your solution?
  • Engagement History – Have they interacted with your content or team before?
  • Social Signals – What are their professional interests, and who do they engage with in their network?

When you combine these elements, you get a richer picture of the prospect and their current stage in their buying journey.

Master Boolean Search to Uncover the Hidden Gems

Advanced search operators—especially Boolean logic—can help you cut through the noise and zero in on the right leads. Chris drops a great example:

"marketing director" AND (automation OR personalization) NOT agency

This logic narrows your scope, helping you find prospects that fit your ICP more precisely. You can apply these operators on LinkedIn, Google, and many sales tools that support custom queries. It’s a slight shift that delivers big impact.

Use Trigger Events to Time Your Outreach

Timing matters in sales. A well-timed email—sent when a company has just secured funding or hired a new executive—can dramatically increase your odds of getting a response.

Chris suggests setting up Google Alerts for trigger events such as:

  • New product launches
  • C-suite leadership changes
  • Job postings that suggest a strategic shift
  • Funding rounds or acquisitions

These events signal a company’s openness to change, making it the perfect moment to introduce your solution.

Try This: Audit and Optimize Your Current Workflow

Chris closes the episode with a challenge worth taking seriously. Time how long it takes you to research ten prospects using your current method. Then, apply just one new tool or technique from this episode and time it again.

I’ve done this with sales teams; the results are consistently striking. You save time, uncover better-fit prospects, and send messages that resonate.

Final Thoughts: Practical, Actionable, and Results-Driven

Chris Spanier’s Practical, Actionable Marketing podcast consistently lives up to its name—and Episode #85 stands out. It’s a treasure trove of real-world advice bridging the marketing and sales gap.

If you’re tired of spinning your wheels on prospecting, this episode gives you the tools and tactics to move faster, smarter, and more confidently.

🟦 Listen to Episode #85 now → Practical, Actionable Marketing with Chris Spanier

📌 Take action: Choose one tactic, implement it this week, and measure the difference. The results may surprise you.

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/

Why Cold Calling is Dead: The Shift to Relationship-Based Selling

Why Cold Calling is Dead: The Shift to Relationship-Based Selling

By Sean O'Shaughnessey

Building an effective sales pipeline requires a shift in strategy. Traditional cold calling has become increasingly ineffective, with decision-makers ignoring unsolicited calls and emails.

In the spring of 2021, Bank of America Corp.’s Merrill Lynch Wealth Management unit banned trainee brokers from making cold calls. According to the Wall Street Journal, it is hard to succeed with cold phone calls in an era when no one picks up. Merrill executives said personal referrals lead to a response around 40% of the time, but less than 2% of people who are cold-called even answer the phone.

Sales teams must adopt a more strategic approach, focusing on relationships rather than volume-based outreach. The key is leveraging existing networks to create warm introductions, significantly improving engagement rates and overall success.

Cold outreach has become expensive and inefficient, and the time spent dialing numbers, leaving voicemails, and sending emails that never get opened results in diminishing returns. Many executives no longer answer unknown calls, and email filters automatically sort cold outreach into spam. Even when messages get through, recipients are skeptical, assuming they are generated by automation rather than a genuine human connection. In reality, sales professionals must find a better way to reach their target audience.

Relationship-based selling offers a more effective alternative. Salespeople should focus on leveraging their connections instead of reaching out to strangers. This approach involves identifying key contacts who can provide warm introductions to potential prospects. These “super connectors” are individuals with strong networks and the ability to facilitate meaningful introductions. By tapping into these relationships, sales teams can bypass the skepticism associated with cold outreach and start conversations with credibility.

Read the rest of the article…
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.

Becoming a Trusted Advisor: Solve Problems, Not Just Sell Products

Becoming a Trusted Advisor: Solve Problems, Not Just Sell Products

By Sean O'Shaughnessey

In B2B sales and sales leadership, problem-solving is an art that goes beyond selling a product or service. The secret to becoming a trusted advisor is addressing business problems, not just selling a product. This concept resonates with salespeople, sales managers, and small business CEOs who sell themselves or manage a team of salespeople. 

Sales is not just about pushing a product or closing a deal; it’s about forging relationships, understanding businesses and their unique challenges, and offering solutions to these problems. The role of a trusted advisor is not to sell a product and become a trusted advisor, but rather to become a trusted advisor who can sell a product. 

The reward for earning trusted advisor status is immeasurable. It is fantastic to receive a call from a client asking for advice on solving problems they have never discussed with you. Imagine having relationships that stand the test of time and outlast competition and challenges. 

So, how does one become a trusted advisor and solve problems for clients rather than just selling them a great product? It starts with building a relationship from scratch. When starting with a prospect list or an ideal client profile, the goal is not to find anyone who will respond but to seek opportunities to build meaningful relationships. 

The cornerstone of these relationships is reliability. 

  • Are you always punctual? 
  • Do you cancel at the last minute? 
  • Do you forget to return phone calls? 

These behaviors erode trust. On the other hand, showing up when needed, providing solutions even when they are not directly related to your product or service, and connecting clients to others who can help them are behaviors that build trust. 

Becoming a trusted advisor also involves understanding and curiosity about the client’s business. Do you ask questions about how the prospective company makes and loses money, how it dealt with past challenges like the pandemic, and how it deals with current challenges like rising inflation or supply chain disruption? The aim is to understand the client’s business, challenges, and competitors and offer insights and parallels to other companies. 

Read the rest of the article…
Two Tall Guys Talking Sales – From Regular Season to Postseason: Coaching Your Sales Team to Win – E128

Two Tall Guys Talking Sales – From Regular Season to Postseason: Coaching Your Sales Team to Win – E128

By Sean O'Shaughnessey

As a sales leader, are you coaching your team for the long haul, or are you scrambling in the final weeks of the quarter? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey break down the difference between regular season and postseason play—whether in sports or sales. They explore why last-minute Hail Mary strategies can be damaging, how to manage time, and the importance of effective and consistent coaching. With March Madness and The Masters as the backdrop, this conversation is packed with insights to help you refine your sales approach and ensure your team is always in winning form.

Key Topics Discussed

  • The Sales Tournament Mentality (00:02:00) – What sales teams can learn from March Madness and The Masters, and why only one team wins while the rest lose.
  • Building a Winning Sales Team (00:03:30) – How business owners can prepare their sales teams to perform under pressure by ensuring the right people are in the right seats.
  • The Role of Sales Coaching (00:05:00) – Why sales leaders must incorporate skills development into every sales meeting instead of just reviewing the pipeline.
  • The Pitfalls of End-of-Quarter Desperation (00:07:50) – How last-minute discounting and rushed deals create long-term problems and train customers to buy at a discount.
  • Mastering Time Management in Sales (00:10:00) – How prioritization and disciplined execution throughout the quarter prevent last-minute chaos and boost consistent performance.

Key Quotes

  • Kevin Lawson (00:07:53): “If you’re behind in sales right now, don’t throw Hail Marys. Don’t discount. You’re teaching your prospects to wait until the end of the quarter for a better deal—and that’s a losing game.”
  • Sean O’Shaughnessey (00:13:00): “You have one thing in sales you can never get back: time. If you wasted today, it’s gone forever. You can’t go back and fix it.”
  • Kevin Lawson (00:09:00): “Salespeople with commission breath stink. If your only focus is closing the deal before Friday, your prospects will smell it a mile away—and that’s not how you build relationships.”

A Significant Actionable Item from this Podcast

Develop a Five-Week Sales Training Plan – Sales leaders should map out the next five sales meetings, dedicating at least five minutes to skills development in each session. Focus on topics such as pipeline progression, prospect qualification, and closing techniques. Training should not be an afterthought—it should be a fundamental part of your sales strategy.

Why You Should Listen to This Episode

Whether you’re a sales leader or a frontline salesperson, this episode is your playbook for maintaining momentum all year long. Avoid the common traps of end-of-quarter desperation, build a disciplined approach to sales training, and master the art of time management. Just like in sports, sales success isn’t about last-minute heroics—it’s about consistent execution.

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