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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 – 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… 

B2B Sales in the Age of AI: Why Top Salespeople Will Thrive While the Repetitive Roles Disappear

The buzz surrounding artificial intelligence has left many professionals wondering about the future of their careers. For B2B sales professionals, the rise of AI presents a fundamental question: Will AI replace salespeople?

The short answer is no, but it will replace some of their work. More accurately, AI will redefine the B2B sales landscape by eliminating lower-value activities, consolidating support roles, and enhancing the capabilities of top performers. In doing so, it will widen the gap between average and great salespeople.

Several years ago, I wrote a similar explanation about the fear that “the internet” would replace salespeople. That didn’t happen. You can find that article on the blog that supports my first sales book. Are salespeople necessary in the Internet age?

This blog post explores how B2B sales is positioned relative to AI disruption, referencing key insights from Benjamin Todd’s article, “How Not to Lose Your Job to AI” (80,000 Hours, 2025). Todd’s framework on skill types that increase in value in the age of AI helps us understand how high-functioning sales teams should evolve and how sales professionals can future-proof their careers.

Understanding AI’s True Impact: Augmentation, Not Replacement

A common misconception about AI is that it simply replaces humans. This isn’t true. AI devalues tasks it can perform while increasing the importance of the skills it cannot. Todd explains this dynamic through examples like the ATM: while the ATM reduced the need for transactional teller tasks, it actually increased demand for bank branch workers by allowing banks to open more branches. AI follows a similar pattern.

In B2B sales, AI will handle the most automatable tasks, such as data entry, follow-ups, list-building, and basic prospecting emails. However, this doesn’t eliminate the sales role; it sharpens its focus.

Instead of dialing hundreds of prospects daily, sales professionals will focus more on strategic engagement, account planning, and using AI-generated insights to elevate conversations. The result? Sales has become a more thoughtful, human, and strategic discipline for those who can keep up.

Four Categories of Skills That AI Will Make More Valuable

In Todd’s excellent article, he identifies four skill types that increase in value in an AI-enhanced workplace:

  1. Hard-to-automate skills
  2. Deployment-related skills
  3. Scarce, high-utility skills
  4. Skills hard for others to learn or replicate

Each of these aligns tightly with the demands of modern B2B sales.

Read the rest of the article…

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

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… 

Two Tall Guys Talking Sales – Sales Intelligence 101: Using AI and Networking to Target Ideal Customers – E112

Welcome to another compelling episode of Two Tall Guys Talking Sales with hosts Kevin Lawson and Sean O’Shaughnessey! Kevin and Sean dive deep into a central challenge for sales teams: identifying ideal customers and building a robust prospect list. In this episode, they uncover practical strategies, share indispensable tools, and illustrate how a strong grasp of your customer can turn prospects into loyal clients. Whether you’re part of a lean sales team or managing large territories, this… 

Two Tall Guys Talking Sales Podcast – From SWOT to Success: Navigating the Competitive Sales Landscape – Episode 46

In this invigorating episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the realm of competition in sales. From understanding the various forms competition can take to harnessing the power of artificial intelligence in competitive analysis, this episode is packed with insights and actionable advice for sales professionals at all levels. Key Topics Discussed: Key Quotes: Additional Resources: Don’t be a part of the 57% that remains oblivious… 

August Newsletter

I hope you enjoy my August Newsletter Posts Subscribe I hope you enjoy my August Newsletter Published: Tue, 08/15/23 I hope that you enjoy my latest newsletter View the online version of this email. Football is starting at your local school and in the NFL. That used to mean that we were in Autumn, but now it means that we are simply in the dog days of summer. I hope the summer has been great… 

Fractional Executives Are Better Than Consultants For Driving Valuable Changes in Small Businesses

Change is inevitable, and small business owners must constantly adapt to stay ahead of their competition. While traditional consultants may offer valuable insights and recommendations, they often lack the hands-on commitment to implement these changes effectively. A consultant will write a report and presentation to advise management of required changes and then count on management to deploy the advice effectively. More than a report or playbook is usually needed to drive tangible results.

Enter the concept of a fractional executive. This innovative solution provides small businesses the strategic guidance and support they need to grow and evolve. In this blog post, we’ll explore the role of a fractional executive, discuss their benefits, and share tips for finding the right fit for your business.

A fractional executive is a seasoned professional who offers expertise and leadership on a part-time or project basis. These individuals often have extensive experience in their respective fields and can fill critical gaps in a company’s leadership team. From acting as a temporary CEO to guiding sales or financial strategies, fractional executives provide services tailored to your business’s unique needs.

The critical difference between a fractional executive and a traditional consultant lies in their level of commitment. While consultants often deliver a one-time report or set of recommendations, fractional executives are actively involved in the day-to-day operations of your business. They work closely with your team to implement changes, monitor progress, and adjust strategies as needed, ensuring that your business thrives in the long term.

Consultants can create beautiful reports using modern tools like Chat GPT. While a report generated by Chat GPT can provide valuable insights and recommendations for a business, it is crucial to recognize that such a report alone is insufficient to drive meaningful changes. To successfully implement and manage the recommended changes, businesses require a more hands-on and personalized approach that addresses their unique challenges and opportunities. A report can serve as an excellent starting point, but companies must invest in dedicated human expertise to ensure that the proposed changes are effectively integrated into their operations.

A Chat GPT report may be insufficient for driving change because it cannot fully account for the intricacies and nuances of each business. While AI-generated reports can be well-researched and informative, they may need a more profound understanding of company culture, team dynamics, and specific market conditions necessary to develop tailored strategies. On the other hand, a human expert can work closely with stakeholders, employees, and customers to gain a comprehensive understanding of the business’s unique needs and challenges, allowing them to develop and implement more effective change initiatives.

Additionally, change management requires ongoing support and guidance, which a Chat GPT report or an absentee consultant cannot provide. Implementing changes often involves overcoming obstacles, refining strategies, and addressing unforeseen issues that arise during the process. A human expert, such as a fractional executive, can provide the necessary support and adaptability to navigate these challenges and ensure the success of the change initiatives. By working closely with the business daily, they can monitor progress, identify areas for improvement, and make real-time adjustments to keep the change process on track.

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Fractional Sales Leadership Increases the Value of My Client by 167%

A common question that I receive is about the value of adding fractional sales leadership to their company. I typically answer their concern with a story about one of my clients who had a fantastic experience and increased the company’s value by 167% in about 12 months. The true benefit of the efforts of fractional sales leadership is that revenue and pipeline will increase your company’s value. Several years ago, I was hired by a… 

Tip #6 of 12 – How To Start The New Year STRONG! – Embrace new technology

New technologies are dramatically changing how businesses operate across all industries, from analytics to artificial intelligence and from automation to social media. As our world becomes more technologically advanced, so does the competitive landscape for salespeople looking to grow their organizations. To stay ahead of this curve, salespeople must learn to embrace these growing technological trends and leverage them for competitive advantage to remain successful in today’s marketplace. In this video, we’ll explore how these…