Sean O’Shaughnessey

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.”

Draw a circle and estimate what percentage of your revenue will come from existing clients vs. new clients.
Identify how many new deals you need to hit your quota.
Rank your existing leads based on fit and potential.
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 – Engage, Listen, Succeed: Unlocking Client Conversations That Close Deals – E121

By Sean O'Shaughnessey

In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the art of active listening and its transformative potential in sales. Building on the discussion from last week’s episode about discovery questions, Kevin and Sean provide actionable strategies to improve your listening skills, enhance your client interactions, and ultimately close more deals. Whether you’re a seasoned sales professional or new to the field, this episode is packed with valuable lessons you can apply immediately.

Key Topics Discussed

The Role of Active Listening in Sales Success
Kevin and Sean discuss how active listening differentiates successful salespeople from the rest and why it’s critical for uncovering client pain points.
The Power of Note-Taking
Kevin shares his transition from paper to digital note-taking and how capturing accurate information leads to better follow-ups and stronger client relationships.
Body Language and Visual Cues in Client Meetings
Sean emphasizes the importance of leaning forward, maintaining eye contact, and using other non-verbal cues to demonstrate engagement during conversations.
Learning from Reporters: Listening Like a Pro
Sean compares salespeople to seasoned reporters and outlines how active listening and asking thoughtful follow-up questions can set the stage for impactful discussions.
Upskilling Through Active Listening
Kevin highlights how organizations can improve their pipeline and closing rates by investing in training that focuses on active listening and effective questioning techniques.

Key Quotes

Sean O’Shaughnessey:
“Don’t ever book a meeting without educating the client or making them a better business. That’s the only reason you’re allowed in their office.” (Approx. 8:00)
Kevin Lawson:
“Active listening is your skeleton key to unlock doors that were previously closed. It’s the gateway to uncovering real pain points and creating meaningful solutions.” (Approx. 13:15)
Sean O’Shaughnessey:
“Leaning forward in your chair isn’t just about posture; it’s a powerful signal to your client that you’re fully engaged and ready to understand their needs.” (Approx. 10:00)

Additional Resources

Sean and Kevin refer to the previous episode on discovery questions as a foundation for this discussion. If you haven’t listened to it, consider downloading it for additional context.

A Significant Actionable Item from this Podcast

Apply Active Listening in Your Next Sales Call
In your next client interaction, focus on active listening by using these three steps:

Lean forward and maintain engaged body language.
Paraphrase the client’s statements to ensure understanding.
Take detailed notes and review them to tailor your follow-up responses.

These small adjustments can significantly affect the quality of your client conversations and help you close more deals.

Summary

Active listening isn’t just a soft skill; it’s a sales superpower. In this episode of Two Tall Guys Talking Sales, Kevin and Sean unravel the nuances of listening to clients, capturing their pain points, and building trust through meaningful interactions. With tips ranging from non-verbal cues to the tactical use of note-taking, this conversation equips you with tools to elevate your sales game. Whether you’re preparing for a discovery call, a QBR, or a cold call, this episode is a must-listen for actionable insights. Tune in and transform the way you engage with your clients.

Happy listening—and selling!

Two Tall Guys Talking Sales – The Art of the Discovery Call: Build Respect and Close More Deals – E120

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey tackle one of the most critical yet underestimated aspects of sales: the discovery call. Are you guilty of “winging it” during these pivotal conversations? Tune in as Kevin and Sean break down the importance of crafting a tailored question bank, share actionable tips to elevate your discovery process, and reveal how asking the right questions can transform your sales game. If you’re looking to close more deals and gain the respect of your prospects, this is the episode for you.

Key Topics Discussed

The Danger of Winging It in Discovery Calls (Approx. 00:00:00)
Kevin and Sean explain why improvising during discovery calls can lead to missed opportunities and how a question bank can save the day.
Building an Effective Question Bank (Approx. 00:01:00)
Learn how to create a dynamic set of questions tailored to different industries and titles, ensuring every prospect feels understood.
The Power of Open-Ended Questions (Approx. 00:05:00)
Discover why “what” and “how” questions are more effective than “why” questions in fostering productive, trust-building conversations.
The ROI of Better Discovery Questions (Approx. 00:07:00)
Explore how better discovery leads to more accurate forecasts, stronger relationships, and increased respect from prospects.
Refining Your Question Bank Over Time (Approx. 00:12:00)
Kevin and Sean emphasize the importance of regularly reviewing and updating your questions to stay relevant and effective.

Key Quotes

Kevin Lawson: “You should never ask a question on a discovery call that you could find the answer to with public information. That’s a waste of your prospect’s time and shows you haven’t earned their business.” (Approx. 00:10:27)
Sean O’Shaughnessey: “Why questions feel like interrogation. Great discovery questions start with what and how—they build trust and uncover real insights.” (Approx. 00:06:25)
Kevin Lawson: “Writing down your questions allows you to tweak, hone, and refine them. It’s the preparation that separates good sellers from great ones.” (Approx. 00:09:05)

A Significant Actionable Item from this Podcast

Start Your Own Question Bank Today
Set aside 30 minutes to brainstorm 10-15 open-ended questions for your next discovery call. Categorize them by industry and prospect title. Use these questions in your next call, then evaluate their effectiveness. Adjust and refine over time to create a winning formula.

Summary

Mastering the discovery call is essential for any successful salesperson, and in this episode, Kevin and Sean provide the ultimate guide to getting it right. From crafting a versatile question bank to leveraging open-ended questions that build trust and uncover insights, this episode is packed with actionable advice to transform your sales process. Don’t miss this opportunity to elevate your skills and close more deals—listen now and discover the art of the perfect discovery call!

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

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…

Unlock Revenue Growth with a Fractional VP of Sales

By Sean O'Shaughnessey

Are you feeling stuck trying to grow your company’s revenue? Do you find yourself juggling too many responsibilities, struggling with outdated sales methods, or unsure how to take your sales team to the next level? You’re not alone.

Many business owners face these challenges, and at New Sales Expert, we’re here to help.

I’m Sean O’Shaughnessey, founder of New Sales Expert, and we specialize in helping B2B companies accelerate revenue production by implementing proven sales strategies, developing top talent, and creating scalable processes.

In our latest video, I outline how we address some of the most common sales problems business owners encounter, such as:

No formal sales process,
Inaccurate revenue forecasting,
Losing a big customer and not knowing how to recover,
Struggling to hire and retain the right salespeople.

As a Fractional Vice President of Sales, we work alongside business owners to provide expert leadership and guidance. Here’s how we do it:

Assessing your current sales team and processes.
Defining winning strategies with clear metrics for success.
Building accurate forecasting tools for long-term planning.
Hiring and developing top-performing sales talent.

We operate on a fractional basis, allowing us to bring discipline, accountability, and focus to your sales organization without the full-time cost. Our detailed Scope of Work outlines clear schedules and timelines, ensuring sustained execution and measurable results.

Ready to accelerate your revenue growth? Watch the full video to learn more about how we can help your business thrive.

📌 Contact us today for a free consultation at www.NewSales.Expert.

Let’s build a culture of sales success and drive the growth your business deserves.

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.

Read the rest of the article…

Turning Competition into Opportunity: A Guide for Success in Sales

By Sean O'Shaughnessey

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

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

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

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

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

Read the rest of the article…

Two Tall Guys Talking Sales – The Motivation Formula: Achieving Big Wins in Sales – E116

By Sean O'Shaughnessey

In this compelling episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the heart of sales motivation and goal setting. They share relatable stories, actionable insights, and practical strategies for salespeople and sales leaders. Using a vivid sports analogy, Sean sets the tone for an episode packed with strategies to stay driven—even when the path isn’t clear. Whether you’re grappling with setting goals or maximizing your commission potential, this episode is a goldmine for actionable advice and personal growth.

Key Topics Discussed

The Athlete Analogy: Personal Motivation Meets Team Success (0:00)
Sean parallels a high school sprinter’s rigorous training and the dedication needed to succeed in sales.
The Importance of Personal “Why” in Sales Motivation (6:00)
Kevin and Sean explore how individual motivations—whether financial goals, family obligations, or personal growth—shape sales performance.
Breaking Down Your Sales Math to Achieve Success (10:00)
Kevin explains how to reverse-engineer your earnings goal, calculate deal requirements, and align your activities with desired outcomes.
Creating Personal Rewards for Milestone Achievements (9:00)
Sean shares a story about a salesperson’s unique approach to celebrating significant deals and how small rewards can drive consistent motivation.
The Art of Setting Goals When None Are Provided (3:30)
Kevin and Sean discuss practical steps for creating your own sales targets when your organization hasn’t assigned any.

Key Quotes

Sean O’Shaughnessey (2:00):
“What motivates you as a salesperson to do incredibly well? What are you doing to achieve your goals, and because you achieve your goals, maybe you’re inspiring someone else on your team to do the same.”
Kevin Lawson (4:29):
“If you’re not given a goal, do the math that gets you to success. It starts with understanding your economic driver and building a plan from there.”
Sean O’Shaughnessey (9:20):
“Choose something unique to reward yourself when something good happens. It’s a motivator for the day and can become the beginning of your career motivation.”

A Significant Actionable Item from this Podcast
Reverse-engineer your sales goals for 2024. Start by defining your desired income, break it down into weekly targets, and calculate how many deals you need to close. Then, analyze your closing rates to determine how many leads and opportunities you need to generate. Finally, track your progress weekly and adjust your strategy to stay on course.

Summary Paragraph
This episode of Two Tall Guys Talking Sales delivers powerful insights into staying motivated and setting actionable sales goals. Sean and Kevin expertly weave relatable analogies with proven strategies to help you master the art of self-motivation and goal achievement. Whether you’re working towards a personal milestone or aiming to inspire your team, this episode provides the tools to elevate your performance. Tune in and take control of your sales journey today!

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…