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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!

Beyond Spell Check: How Grammarly’s AI Can Transform Sales Communication

Clear, professional communication is the foundation of sales success. Yet, in 2025, much of our selling occurs not face-to-face, but through written words, emails, proposals, CRM notes, and social media messages. This shift means your writing is no longer just a form of communication; it’s your personal brand, your first impression, and often the deciding factor in whether a conversation continues or comes to a halt.

Grammarly has evolved far beyond its original purpose as a grammar checker. Today, it’s an artificial intelligence–powered platform that helps sales teams increase efficiency, refine their messaging, and accelerate revenue growth. It works directly within the tools you already use, such as Gmail, LinkedIn, Salesforce, and HubSpot, helping sales professionals write with greater confidence and clarity.

Sales organizations using Grammarly have seen measurable improvements: Databricks saved $1.4 million annually; Smartsheet cut thousands of hours from proposal creation; and Zoom reported higher customer satisfaction thanks to improved written communication. These results aren’t luck; they’re the product of refined sales processes, consistent messaging, and clear communication supported by AI.

For individual salespeople, Grammarly helps improve value selling by ensuring that every message is professional, engaging, and on-brand. Its AI engine not only corrects errors but also suggests stronger phrasing, predicts reader reactions, and even aligns your tone with your business acumen and brand voice. For sales leaders, it standardizes team communication and reinforces a culture of professionalism across departments.

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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.

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The Power of Personal Branding in Enhancing Sales Productivity

Navigating the world of sales can sometimes feel like traversing a labyrinth. Salespeople, sales managers, and CEOs alike grapple with the challenge of increasing revenue and enhancing productivity in their sales processes. To be successful, you need more than knowledge of products and services; you need to develop trust and a strong personal brand.

Business-to-business (B2B) sales involves transferring trust from ourselves to our prospects. We trust in our products and company, but convincing prospects to share that trust is the real challenge. This trust should encompass the product, the company, and perhaps most crucially, the salesperson. Remember, B2B sales could be defined as helping prospects decide in our favor within the desired timeframe.

The key to B2B sales is developing a personal brand that inspires trust in salespeople. The salesperson’s ability to convey reliability, expertise, and credibility can significantly influence how fast a prospect invests in a product or service.

Developing a strong personal brand begins with creating a presence that signals control and understanding of the business. This can be achieved by showcasing the benefits of your product or service to your customer’s business. A straightforward way to build your brand is by seeking references from your network, former employers, and customers, and showcasing these on professional platforms like LinkedIn.

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Driving Sales Success through Collaborative Learning and Knowledge Sharing

Aiming to increase revenue and boost productivity in sales processes, sales managers and company CEOs are constantly searching for effective strategies to streamline their operations and ensure optimal results. One such strategy involves conducting sales meetings for educational purposes. These meetings focus on enhancing knowledge and skills, and this is where the real game begins. 

Imagine a sales meeting where, instead of a mundane round-up of weekly activities, there’s an engaging discussion about a new book that can potentially revolutionize the sales process. Picture a team of four or five salespeople, including you, each reading two chapters of a book overnight. The next day, everyone shares the high-level takeaways from their assigned chapters. This practice allows the team to consume an entire book’s content in a day and empowers each member to become an authority on the subject matter because they’re teaching others. The exercise is educational, promotes team collaboration, and enhances communication skills. 

This approach can be extended beyond books to other areas, such as market research. For instance, if a company is looking to enter a new vertical, different aspects of the industry, like market influencers, challenges, and political, economic, and legal factors, can be assigned to team members for research. Each member returns their findings to the team, comprehensively understanding the new market. This practice is not merely busy work; it’s sales-driving work that benefits the entire team and accelerates learning about the new market.

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Ten of Spades: Addressing Salesperson Underperformance: Identifying Training Needs: Recognize areas for skill development to boost performance

Elevating Sales Performance: Why Targeted Training is Non-Negotiable Visualize your sales team as a high-performance sports car: every part is intricately designed to maximize output and speed. When one part fails or underperforms, the entire machine is impacted. An underperforming salesperson isn’t just a localized problem; their performance deficit has a cascading effect on the entire team and, by extension, the organization. It’s critical to realize that top-performing salespeople—let’s call them the eagles of the… Ten of Spades: Addressing Salesperson Underperformance: Identifying Training Needs: Recognize areas for skill development to boost performance

Two Tall Guys Talking Sales Podcast – Mastering Mid-Year Reviews: The Sales Perspective – Episode 35

In this enlightening episode of “Two Tall Guys Talking Sales,” Sean O’Shaughnessey and Kevin Lawson delve into the fundamental aspect of setting clear expectations in sales, mirroring the way parents do with their children. With mid-year reviews around the corner, it’s time to reflect, analyze, and readjust your sales strategies. Kevin starts with a compelling anecdote about his childhood bedtime routine to explain the critical importance of clear communication and setting expectations. The duo emphasizes… Two Tall Guys Talking Sales Podcast – Mastering Mid-Year Reviews: The Sales Perspective – Episode 35

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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Sales Coaching: A Key Tool for Achieving Business Growth in B2B Sales

Sales coaching has become integral to the modern business environment, particularly in business-to-business (B2B) sales. The sales coaching process enhances salespeople’s skills, knowledge, and capabilities to achieve their goals, deliver value to customers, and improve organizational performance. In this article, we will examine the importance of sales coaching in B2B sales organizations, explore the best practices for effective coaching, and discuss the key benefits that result from a well-executed sales coaching program. Sales coaching has… Sales Coaching: A Key Tool for Achieving Business Growth in B2B Sales