sales leaders – Page 5

Two Tall Guys Talking Sales – AI for Sales Success: Tools, Tactics, and Why You Can’t Ignore It – E124

By Sean O'Shaughnessey

Artificial intelligence (AI) is transforming the sales industry, but does that mean salespeople are becoming obsolete? Absolutely not! In this high-energy episode, Kevin and Sean debunk the myth that AI will replace sales professionals. Instead, they reveal how AI can be a game-changing tool for sales success.

From using AI to refine communication to automating time-consuming tasks, this episode is packed with insights on how AI can help sales leaders and reps work smarter, sell better, and stay ahead of the competition. Tune in to discover practical ways to leverage AI, improve efficiency, and dominate your market.

Key Topics Discussed

🔹 Will AI Replace Salespeople? – The truth about AI’s role in sales and why your job isn’t at risk—but your quota might be. (00:00:45)

🔹 The Evolution of Sales Tools – A nostalgic (and hilarious) look at how tools have always changed work processes—remember manual garage doors and TV dials? (00:02:21)

🔹 AI for Writing & Communication – How tools like Grammarly can make your emails, proposals, and presentations sharper, clearer, and more professional. (00:04:00)

🔹 Boosting Productivity with AI – From auto-generating customized sales presentations to intelligent scheduling, AI can free up time for what matters most: selling. (00:06:01)

🔹 The AI-Powered CRM – If your CRM doesn’t have AI integration or a plan for it, it’s time to rethink your strategy. A modern CRM is essential for competitive sales teams. (00:12:00)

Key Quotes

🗣️ Sean O’Shaughnessey: “You are not going to be replaced by AI. You’re going to be replaced by a salesperson using AI.” (00:01:00)

🗣️ Kevin Lawson: “AI isn’t here to take your job—it’s here to make you a better salesperson. Weaponize your tools and sharpen your axe.” (00:07:33)

🗣️ Sean O’Shaughnessey: “Being afraid of AI is like being afraid of Microsoft Word instead of a typewriter.” (00:10:18)

Additional Resources

🔗 Grammarly – AI-powered writing assistant for better emails, proposals, and reports.

🔗 Canva – AI-enhanced design tool for creating presentations and marketing materials in seconds.

A Significant Actionable Item from this Podcast

🚀 Start Using AI Today! Don’t wait—integrate AI into your daily sales routine now. Whether it’s improving your writing with Grammarly, using AI for scheduling, or leveraging AI-powered CRM features, pick one AI tool and start experimenting. The sooner you adopt AI, the further ahead you’ll be.

Final Thoughts

AI isn’t a threat—it’s an opportunity. The best salespeople will be the ones who embrace AI to work smarter, sell more efficiently, and build stronger customer relationships. Want to future-proof your sales career? It starts here.

👉 Hit play now and learn how AI can be your competitive advantage in sales!

Two Tall Guys Talking Sales – Mastering Time Management: Essential Strategies for Sales Managers – E123

By Sean O'Shaughnessey

Time is the most valuable resource for any professional, but for sales managers, it is the linchpin of success. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive into the critical strategies for effective time management as a sales leader. Whether you’re a new sales manager, an aspiring leader, or a business owner overseeing a sales team, this discussion is packed with insights to help you optimize your calendar, empower your team, and drive performance without falling into the trap of micromanagement.

Key Topics Discussed

The Shift from Salesperson to Sales Manager (00:03:00)
Understanding the common pitfalls new sales managers face when transitioning from an individual contributor to a leadership role.
The Role of a Sales Manager: Player vs. Coach (00:04:00)
Why sales managers must avoid the “player-coach” mindset and instead focus on leading, mentoring, and enabling their team’s success.
Structuring Your Calendar for Maximum Impact (00:05:45)
How to design your weekly schedule to balance coaching, strategy, internal meetings, and team availability while avoiding distractions.
The Power of Shared Calendars and CRMs (00:07:00)
Best practices for leveraging shared calendars and CRM tools to improve communication, transparency, and sales efficiency.
Why Sales Managers Should Be Like Basketball Coaches (00:13:30)
The importance of stepping back and allowing sales reps to take the lead in deals—coaching them rather than closing for them.

Key Quotes

🗣 Sean O’Shaughnessey (00:02:55):
“When you are a sales manager, your job is to make others better. You shouldn’t be stealing deals from your sales reps—you should be empowering them to succeed.”

🗣 Kevin Lawson (00:04:00):
“A player is different from being a coach. Players take direction, coaches give direction. If you’re leading a team, you need to be coaching, not competing.”

🗣 Sean O’Shaughnessey (00:14:00):
“Watch a basketball game and look at the coach. How many times do they step onto the court to take a free throw for their players? Never. That’s how sales management should work too.”

Additional Resources

📘 The One Minute Manager by Ken Blanchard & Spencer Johnson – A classic guide to leadership and effective management.
📅 Book Time with Sean – Need help refining your sales management strategy? Schedule a consultation.

A Significant Actionable Item from this Podcast

Audit Your Calendar and Block Time for Success
Sales managers must structure their schedules intentionally. Take 30 minutes to review your calendar for the upcoming week:
✅ Block out time for coaching your team.
✅ Set aside dedicated slots for strategy and internal meetings.
✅ Ensure your calendar is updated and visible for your team.
✅ Reserve time for proactive sales engagement, like voice-of-the-customer calls.

Making these adjustments will free you from constant firefighting and allow you to lead effectively.

Why You Should Listen to This Episode

If you’re a sales manager—or aspiring to be one—this episode is a must-listen. Kevin and Sean deliver practical, real-world strategies to help you break free from micromanagement, structure your time effectively, and lead your team to success. Stop getting caught up in the weeds and start managing like a pro. Listen now and take control of your sales leadership journey!

🎧 Hit play and start optimizing your sales management strategy today! 🚀

Building Winning Sales Teams for the Future: Insights for CEOs and Sales Leaders

By Sean O'Shaughnessey

What are the key moves that CEOs and sales leaders must make to prepare their teams for success in 2025? That’s exactly what we explored in a recent episode of the Art and Science of Complex Sales podcast hosted by Paul Fuller of Membrain. I had the pleasure of joining Kevin Lawson, President of Lighthouse Sales Advisors, for a deep dive into the strategies defining high-performing sales organizations in the year ahead.

You may recognize Kevin’s name. He is my co-host on the Two Tall Guys Talking Sales podcast. Paul titled our interview with him “Building Winning Sales Teams for the Future with Two Tall Guys.”

In the episode, we uncover the real-world tactics and leadership insights that can help CEOs transform their sales organizations—from defining who to sell to building processes that deliver consistent results. If you’re serious about leading a sales team that thrives amid complexity, I highly encourage you to listen to the full conversation. The link is below—don’t miss it.

Driving Growth Through Data-Driven Leadership

One of the central themes we cover is the role of data in guiding strategic decisions. Successful sales leadership today hinges on the ability to read the right signals—metrics like call volumes, deal velocity, customer life cycles, and attrition rates. We discuss how to turn that data into insights that refine your ideal customer profile (ICP) and strengthen your sales and marketing efforts.

We also discuss how a CEO’s dashboard isn’t static. It must evolve based on the business environment, market pressures, and geopolitical events. Paul Fuller helps steer the conversation into practical territory, where we explore how CEOs can stay ahead by making data-informed decisions and leading their teams with clarity and focus.

This podcast episode will be particularly valuable if you’re a CEO or revenue leader aiming to refine your strategic lens. Be sure to check it out through the link below.

Coaching for Consistent Performance Improvement

Data might show you where to focus, but coaching is what gets you results. Kevin and I discuss the importance of coaching for incremental gains—not just pushing reps to hit more numbers but helping them level up in ability and mindset.

We show how leaders can move salespeople from C-level to B-level performers and beyond through relatable sports analogies and real-world examples. These small, steady improvements compound over time and create a team of confident, capable sellers who know how to win.

We also touch on the need for structured coaching frameworks and repeatable systems, which we provide through website resources. If you lead a team that could benefit from a morale, performance, or accountability boost, this is a conversation you won’t want to miss.

Building a Repeatable, Scalable Sales Process

We close the episode with a focused discussion on sales process discipline. By taking a structured approach to evaluating leads—based on product fit, probability, and alignment with your ICP—leaders can drive better forecasting and higher win rates.

Even modest improvements in key areas like win rate, deal size, and sales cycle length can produce exponential results. We explore how a 7% uptick in core metrics could double your revenue. The message is clear: Clarity, consistency, and customer focus are non-negotiable in 2025.

If you’re looking to future-proof your sales organization, this podcast episode is packed with strategies and examples that can serve as a roadmap. Listen to the full episode and learn how to apply these concepts to your company.

Listen to the Full Episode

This is a powerful episode for CEOs, sales leaders, and anyone responsible for building and leading high-performance sales teams. If you’re ready to equip your team for 2025 and beyond, don’t miss this conversation on the Art and Science of Complex Sales podcast.

🎧 Episode: Building Winning Sales Teams for the Future with Two Tall Guys
🎙 Host: Paul Fuller of Membrain
🔗 https://podcasts.apple.com/us/podcast/building-winning-sales-teams-for-the-future-with-two/id1723340327?i=1000684372709

Click the link to listen now—you’ll walk away with actionable ideas to implement immediately.

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?

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

By Sean O'Shaughnessey

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

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

Your best salespeople are leaving. Team morale is plummeting.

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

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

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Roadblocks, Detours, and Destinations: The Intricate Art of Sales Strategy

By Sean O'Shaughnessey

There’s an ongoing conversation about the importance of strategy, process, and anticipating potential challenges in B2B sales. There’s an analogy that encapsulates this perfectly – imagine you’re on a road trip. You have a destination in mind but are unfamiliar with the route. This is where tools like Waze, Google Maps, or Apple Maps come into play. They direct you to your destination and alert you about potential roadblocks, construction, traffic, or other unexpected events that might delay your journey.

This is precisely how a sales strategy should work. It’s not just about getting from point A to point B but also about understanding the complexities of the journey and preparing for potential roadblocks. For salespeople, managers, and CEOs, understanding the strategy is critical to increasing revenue and improving productivity.

Understanding that a strategy involves more than just the turns along the way is vital. It also involves how to navigate through different areas, understand the speed limit, and anticipate any warnings that might come up. Many salespeople don’t fully grasp these challenges and tend to take them as they come rather than anticipating them and planning accordingly.

Like Waze uses real-time data to adapt to changes on the road, a sales strategy should adjust to new information and circumstances. For example, if there’s construction up ahead or a detour is required, Waze will adapt and provide a new route. Similarly, salespeople should be able to adjust their strategies based on new information or unexpected challenges.

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The Right Person in the Right Seat: Unleashing Company Growth through Strategic Sales Leadership

By Sean O'Shaughnessey

A recurring issue for small companies has emerged; the company’s owner or CEO often leads the sales department. This might be because they believe no one else can sell their product or service better than they can. However, this mindset might be hampering the company’s growth potential.

If you’re a company owner or CEO who leads sales, it’s crucial to consider the risk of this approach. When the person leading the company also heads sales, the business is constrained by the amount of time that leader has. If your salespeople consistently wait for your input or response, you might face a growth opportunity and a challenge simultaneously.

The solution lies in de-risking your organization’s growth potential by getting a sales leader in the sales leadership seat separate from you. This concept resonates with the theory of constraints, a principle often applied in the manufacturing industry but equally applicable in sales. The theory of constraints focuses on identifying the factors that limit your success.

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Unlocking Growth: How TriState Fabricators Transformed Their Sales Approach

By Sean O'Shaughnessey

Have you ever wondered how a well-established manufacturing company can revolutionize its sales strategy? The journey of TriState Fabricators, a premier metal fabrication shop in the Midwest, offers compelling insights into this process. In a recent interview, I sat down with Joe Vogt, President and Owner, and Jonathon Padial, VP of Sales, to discuss their transformative experience.

With his 20-year tenure at TriState, Joe Vogt recognized the need for change to scale the business. The company’s sales approach was primarily reactive, relying on RFPs and inside sales personnel. But how do you shift from this traditional model to a proactive, growth-oriented strategy?

Enter the game-changers: a fractional VP of Sales, a robust CRM system, and comprehensive sales leadership training. These tools provided the structure and visibility that TriState had been lacking. Joe Vogt hired Sean O’Shaughnessey, CEO of New Sales Expert, to come in and revamp the sales organization and install best-in-class practices. Sean entered as the VP of Sales and quickly assessed the need to understand the deals better, so he installed Pipedrive as their CRM system. He also started to train the salespeople in the needed sales skills during L10-style meetings patterned after EOS L10 management meetings. To get closer to the biggest customers, the company started to have quarterly business reviews with the biggest and most profitable customers.

Vogt praises O’Shaughnessey several times in the full interview but at one place said, “So I look at Vistage as my board of directors essentially. You were an internal board member for me. I never met anybody with more sales knowledge in my life.”

After several months, Vogt and O’Shaughnessey agreed it was time for TSF to run autonomously and without Sean’s help. After an intense interview process, they hired Jonathon Padial to be Sean’s heir apparent in sales leadership. Coming from a software background, Jonathon continued the emphasis on Pipedrive and a structured sales process. “It’s allowed us to really capture more and for my team to see what’s coming in,” Padial noted. But is technology alone enough to drive change?

The fundamental transformation came from empowering the sales team. Vogt and Padial underwent Certified Sales Leadership (CSL) training, which Padial described as his “bible” for navigating leadership challenges. This training, coupled with their involvement in Vistage and implementing the Entrepreneurial Operating System (EOS), created a powerful trifecta for growth.

But how do you manage such significant changes in an established company culture? Vogt stressed the importance of communication and structure. “If you give structure with the change, it really helps. And you get the people to understand why you’re changing and what the benefits are going to be,” he explained. This approach has led to a more engaged and cohesive sales team than ever before.

Looking to the future, TriState Fabricators is poised for controlled, strategic growth. With plans to incorporate AI and new manufacturing technologies, they’re positioning themselves at the forefront of the industry. But as Padial reminded us, success in manufacturing isn’t just about technology – it’s about relationships and exceptional customer service.

Are you curious to hear more about TriState Fabricators’ journey and gain insights that could transform your business? The full video interview delves into their experiences, challenges, and strategies. It’s a must-watch for any business leader looking to drive growth and embrace organizational change. Don’t miss out on these valuable insights – check out the full interview today!

Unstick Your Sales: The Importance of Understanding the Buyer’s Journey

By Sean O'Shaughnessey

It’s no secret that the dynamics between the buyer and the salesperson play a pivotal role in sealing the deal. The conversation often revolves around real sales issues, selling situations, and sales leadership.

Let’s delve into a scenario. You’re selling to a beer industry manufacturer, and their first question is about your price. This immediate focus on cost might make you think this may not be a good prospect. However, it’s crucial to remember that you can’t be disrespectful or dismissive. As salespeople, it’s our job to work with what we have.

In this situation, the salesperson has to conduct a discovery call and engage a subject matter expert to understand the prospect’s business process, adaptation, and conversion. Unfortunately, the interaction turned into a commodity exchange, with the buyer solely interested in the number of users and the price per user.

This scenario illustrates a common challenge in sales: the sales and buying processes often need to align. How your Customer Relationship Management (CRM) system is set up may not necessarily mirror how the buyer decides. Therefore, figuring out how to sell more effectively based on the buyer’s journey is crucial. Understanding the buyer is discussed in great detail in my book Eliminate Your Competition, which is available wherever you buy books.

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