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What An MBA Didn’t Teach You About Sales

The sales profession is challenging. You need to work hard at it to succeed. You need to learn from the best. You need to improve your skills continuously. If you think you can sell since you are a hit at parties and have a lot of friends, you may soon find that you are a failure as a salesperson. Blunt truth:

because the sales profession is so hard, you have to focus on doing everything in sales very well, or you will be considered a failure.

I call this blog, Skinned Knees because I try to relate all of the learning that I have done over the past 4+ decades (while skinning my knees in the learning process).

I hope that you learn from my mistakes so that your business will grow!

Two Tall Guys Talking Sales – From Comp Plans to Territory Alignment: Sales Strategies Every Leader Needs for Revenue Generation – Episode 153

As the year draws to a close, sales leaders and business owners face a critical challenge: preparing for growth in the year ahead. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into sales management strategies that set the stage for long-term sales success. From refining compensation plans and aligning territories to planning product lifecycles and avoiding the dreaded “hockey stick” growth trap, this conversation is packed with insights on business acumen, value selling, and revenue generation strategies that every sales leader should master.

Key Topics Discussed

  • 01:00 – Planning Beyond This Year: Why sales leaders need to start preparing now for next year’s revenue generation and sales processes.
  • 02:11 – Building Smarter Compensation Plans: Evaluating and refining comp structures to drive sales success and attract top talent.
  • 03:13 – Product Lifecycle & AI Readiness: How shifts in markets and technology demand updates to your offerings and messaging.
  • 05:00 – Departmental Alignment for Growth: Understanding how revenue management and sales growth affect every department in your business.
  • 07:12 – Right People, Right Roles: Assessing whether your sales team is positioned for success in the next stage of your growth plan.
  • 11:20 – Avoiding the “Hockey Stick” Trap: Why spreading growth evenly across years is a better long-term sales strategy.

Key Quotes

  • Sean O’Shaughnessey (01:07): “If I asked you to write out your three-year plan, next year already knocks off the first year. Are you one-third of the way there, or do you need to rethink your path?”
  • Kevin Lawson (02:33): “Be planning ahead. Compensation plans aren’t a set-and-forget item—you need to revisit them every year to make sure they’re delivering the right results.”
  • Sean O’Shaughnessey (07:59): “Do I have the right people in the right place in my sales organization for next year? Not every salesperson has to leave, but maybe their role needs to evolve.”
  • Kevin Lawson (11:38): “You don’t want that third year of your plan to be a hockey stick. Don’t put yourself in a position where you suddenly need 40% growth in one year to hit your goals.”

Additional Resources

  • B2B Sales Lab: A peer community for sales leaders and professionals to sharpen strategies, exchange best practices, and get actionable feedback.
  • EOS Framework: For leaders who want to align messaging, sales strategies, and revenue management with long-term goals.

A Significant Actionable Item from this Podcast

Review and finalize your sales compensation plans by December 1st. This gives your team enough time to digest changes, ask questions, and align their sales strategies before the new year begins. Waiting until January leaves your salespeople unprepared, which can delay revenue generation and momentum.

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AI Isn’t Replacing Salespeople, It’s Giving Them a Competitive Edge

AI isn’t replacing salespeople, it’s making them more effective. The real risk isn’t losing your job to AI; it’s losing to a competitor who uses AI better than you do. Sales professionals who integrate AI into their workflow will outperform those who don’t. 

It’s not about technology taking over but about using technology to gain an edge. The market is becoming increasingly competitive, and the most efficient salespeople will emerge victorious.

Time is a salesperson’s most valuable asset. 

Every minute spent on administrative tasks is a minute not spent selling. AI helps reclaim those lost hours. Tools that automate writing, scheduling, and research allow salespeople to focus on what matters: building relationships and closing deals. If you’re not leveraging AI to increase productivity, you’re leaving opportunities on the table.

Sales emails need to be clear and professional. AI-powered writing assistants ensure your messages are polished and effective. A poorly written email can cost you a deal. AI tools catch grammatical mistakes, improve clarity, and even suggest more effective phrasing. This isn’t just about looking professional; it’s about being understood. 

If your message isn’t clear, it won’t convert.

Presentations are another time-consuming task. AI can generate professional decks in minutes. Instead of spending hours designing slides, salespeople can focus on developing effective strategies. AI-powered tools create branded, structured presentations based on simple inputs. This ensures consistency while saving time. Sales professionals who utilize AI for presentations can focus on delivering insights rather than formatting slides.

CRM systems are the backbone of sales operations. AI enhances CRM by automating data entry, tracking customer interactions, and suggesting next steps. Salespeople often struggle with keeping CRM data updated. AI reduces this friction by automatically capturing and organizing information. A well-maintained CRM leads to better forecasting and stronger customer relationships. 

If your CRM doesn’t have AI capabilities, it’s time to upgrade.

AI-driven insights enable sales managers to make more informed decisions, rather than relying on instinct. Managers can use AI to analyze performance trends, identify coaching opportunities, and predict revenue outcomes. AI doesn’t replace leadership; it enhances it. 

Sales managers who adopt AI can build stronger teams and achieve better results. Ignoring AI in sales management is a strategic mistake.

Lead generation is another area where AI adds value. AI-powered tools can analyze vast amounts of data to identify high-potential prospects. Instead of spending hours researching leads, salespeople can receive AI-generated recommendations. This allows for more targeted outreach and higher conversion rates. AI doesn’t just find leads, it finds the right leads.

Sales follow-up is often inconsistent. AI ensures follow-ups happen at the right time with the right message. Automated reminders and AI-generated responses keep deals moving forward. 

A well-timed follow-up can be the difference between closing a deal and losing it. AI helps salespeople stay on top of their pipeline without relying on memory.

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Two Tall Guys Talking Sales – Workflows, Automation, and AI: Building a Smarter Sales Organization – Episode 145

In this compelling episode, co-hosts Kevin Lawson and Sean O’Shaughnessey delve into the crucial distinctions between workflows, automations, and artificial intelligence (AI), and why understanding these differences isn’t just technical trivia, but foundational to improving sales processes, enhancing sales management, and accelerating revenue generation. If you’re a sales leader, business owner, or B2B rep striving to improve how you use technology to boost sales success, this episode is a must-listen. Packed with real-world examples and… Two Tall Guys Talking Sales – Workflows, Automation, and AI: Building a Smarter Sales Organization – Episode 145

Two Tall Guys Talking Sales – Future-Proofing Your Sales Career with AI, Strategy, and Smarter Workflows – Episode 144

Is artificial intelligence coming for your sales job? Not if you understand the power of business acumen, value selling, and strategic adoption of tools that amplify, not replace, human expertise. In this high-impact episode of Two Tall Guys Talking Sales, Kevin and Sean tackle the loud claims of AI-induced layoffs with a grounded, practical message for salespeople and sales managers: evolve or fall behind. This is not a doomsday episode; it’s a wake-up call, a… Two Tall Guys Talking Sales – Future-Proofing Your Sales Career with AI, Strategy, and Smarter Workflows – Episode 144

Two Tall Guys Talking Sales – John McLeod Explains How to Avoid the AI Trap: Using New Tools Without Losing Your Sales Message – Episode 140

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey are joined by veteran fractional VP of Sales, John McLeod. Together, they dive into a critical topic for today’s sales leaders: embracing artificial intelligence tools without compromising your value proposition, messaging, or sales processes. John brings deep expertise in sales management, business acumen, and revenue generation strategies, offering a measured approach to evaluating sales tech, especially AI solutions, through a… Two Tall Guys Talking Sales – John McLeod Explains How to Avoid the AI Trap: Using New Tools Without Losing Your Sales Message – Episode 140

Two Tall Guys Talking Sales – Mastering Sales Hiring with John Lee – Sales Management Insights for Growth-Focused Teams – Episode 138

In this week’s episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey are joined by the “Elder Statesman” of fractional sales management: John Lee. With nearly four decades of experience and a deep track record of helping companies hire top-performing sales professionals, John shares a masterclass in sales hiring strategy. Whether you’re scaling from a two-person team to ten or trying to avoid costly hiring mistakes, this episode delivers practical, field-tested advice… Two Tall Guys Talking Sales – Mastering Sales Hiring with John Lee – Sales Management Insights for Growth-Focused Teams – Episode 138

Two Tall Guys Talking Sales – Steve Caton Shares When to Sell, When to Coach, and When to Hire: Strategic Sales Management That Drives Growth – Episode 137

In this powerful episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey are joined once again by Steve Caton, CEO of Altezza Solutions, for a thought-provoking conversation that zeroes in on one of the toughest decisions in sales leadership: when to sell, when to coach, and when to hire. Whether you’re a business owner, VP of Sales, or a player-coach juggling a quota and a team, this episode brings clarity to the… Two Tall Guys Talking Sales – Steve Caton Shares When to Sell, When to Coach, and When to Hire: Strategic Sales Management That Drives Growth – Episode 137

Two Tall Guys Talking Sales – Scaling Smarter: Building Sales Teams with Steve Caton – Episode 136

What does it take to scale a sales organization in today’s unpredictable business environment? In this dynamic episode of Two Tall Guys Talking Sales, hosts Sean O’Shaughnessey and Kevin Lawson welcome back Steve Caton, CEO of Altezza Solutions, to unpack the nuances of scaling sales teams, especially through the power of fractional sales professionals. Together, they explore the critical role that sales processes, sales management, and business acumen play in enabling organizations to grow without… Two Tall Guys Talking Sales – Scaling Smarter: Building Sales Teams with Steve Caton – Episode 136

Stop Guessing. Start Assessing: The First Step Toward Sales Growth

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?

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