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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 – Building a Mission-Led Sales Culture: Insights from Richard Cogswell – E106

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey sit down with Richard Cogswell, a 20-year sales veteran and author who leads the APAC region in the FinTech space. Richard shares his journey from commission-only sales in the insurance industry to becoming a B2B sales leader in the complex world of payments. Together, they discuss the critical importance of developing a mission-led culture, the pitfalls of sales leadership without… Two Tall Guys Talking Sales – Building a Mission-Led Sales Culture: Insights from Richard Cogswell – E106

Two Tall Guys Talking Sales Podcast – Strategic Sales Planning: Finish Strong and Prepare for FY25 – E105

As the year winds down and football season takes over, Sean O’Shaughnessey and Kevin Lawson remind us that it’s time for sales leaders to focus on the coming year. In this episode of Two Tall Guys Talking Sales, Sean and Kevin dive into actionable strategies for building a strong foundation in FY25, including compensation plan design, strategic projects, and investing in your sales team. Whether you’re a sales leader, business owner, or manager, this episode… Two Tall Guys Talking Sales Podcast – Strategic Sales Planning: Finish Strong and Prepare for FY25 – E105

Two Tall Guys Talking Sales Podcast – Sales Success and Growing Pains: How to Build Systems That Scale – E104

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey explore the complexities of rapid sales growth. While many companies aspire to grow, not all are ready for the operational strain accompanying success. The hosts share insights on scaling systems, optimizing sales operations, and ensuring growth doesn’t break your business. This episode offers actionable strategies for businesses facing fast-paced expansion, from onboarding salespeople to expanding infrastructure. Key Topics Discussed: Key Quotes: A… Two Tall Guys Talking Sales Podcast – Sales Success and Growing Pains: How to Build Systems That Scale – E104

Two Tall Guys Talking Sales Podcast – Daily Habits for Deepening Sales Relationships: A Guide for Busy Sales Professionals – E103

In this insightful episode, Kevin Lawson and Sean O’Shaughnessey delve into practical strategies for deepening relationships and boosting sales without extensive outreach efforts. Whether you’re a seasoned sales professional or just starting out, this episode is packed with actionable tips to enhance your sales approach by focusing on the people you already know. Key Topics Discussed: Key Quotes: Additional Resources: A Significant Actionable Item from this Podcast: Daily Personalized Outreach: Dedicate a few minutes daily… Two Tall Guys Talking Sales Podcast – Daily Habits for Deepening Sales Relationships: A Guide for Busy Sales Professionals – E103

Two Tall Guys Talking Sales Podcast – Sales Strategy Deep Dive: How to Align Offers with Client Expectations – E102

Join hosts Kevin Lawson and Sean O’Shaughnessey in a dynamic episode of “Two Tall Guys Talking Sales,” where they dive deep into the essential elements of crafting an effective sales strategy. Whether you’re a sales newbie or a seasoned pro, this episode promises insights into refining your approach to acquiring new clients and boosting your sales performance. Key Topics Discussed: Key Quotes: Additional Resources: A Significant Actionable Item from this Podcast: Reflect on Your Client… Two Tall Guys Talking Sales Podcast – Sales Strategy Deep Dive: How to Align Offers with Client Expectations – E102

Designing Sales Compensation Plans That Drive Performance

The success of any sales-driven organization in the business-to-business (B2B) space hinges on the sales team’s compensation plan. Over my four decades in B2B sales, I’ve observed that nothing influences the performance of sales personnel more directly than the design and implementation of their compensation plans. Compensation is not merely about rewarding sales achievements but crafting a strategy aligning individual salespeople’s goals with the company’s broader objectives.

A well-structured compensation plan acts as both a motivator and a guide. It compels sales teams not only to meet but exceed their targets, fostering an environment where continuous improvement is not just encouraged but becomes a natural byproduct of the system. For small business CEOs, understanding this dynamic is critical for sustaining and driving growth. Sales compensation is more than just a cost; it’s an investment in the company’s future.

In any sales environment, whether the market is brimming with potential or tightly contested, the compensation plan must be a living document that evolves in response to market conditions, company goals, and team performance. With this adaptability, companies can avoid stagnation or regression in their market positions. As businesses strive to scale and adapt, constructing a compensation plan that genuinely drives the right behaviors becomes all the more pertinent.

To delve deeper into this vital subject, CEOs should consider the immediate impacts of their compensation strategies and their long-term implications on sales culture and employee retention. For those ready to explore the intricacies of effective sales compensation and ensure their strategies are well-suited to their specific business contexts, I am here to lend my expertise. With extensive experience tailoring compensation plans to enhance sales productivity and company profitability, I invite you to reach out for further guidance on crafting a plan that meets and exceeds your strategic goals. You can set a time to talk to me using my link above Book Appointment With Sean.

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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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From Education to Improvement: The Essential Elements of Effective Sales Meetings

The importance of effective internal sales meetings with your sales team cannot be overstated. These meetings are not just about discussing individual deals or pipelines but serve a much larger purpose. They are opportunities for education, alignment, and improvement. They are a platform where the entire sales ecosystem comes together to discuss what’s happening in the industry, target market, or the company and how to move in the same direction.

A key reason for having larger quarterly meetings is education. As a sales leader or a CEO, the goal should be to make the sales team more effective and knowledgeable about ongoing developments. This can be achieved by inviting guest speakers, working on sales messaging, or understanding what’s happening in a particular vertical. However, these meetings should not be held just because the quarter came up. They should have a purpose and should add value to the team. If the same information can be shared through a well-written email or a quick update on Zoom, then there is no need for a meeting.

One effective practice for these meetings is role plays. This is a great way to practice and improve skills. However, it’s important to conduct these role plays correctly. There should be three roles: a customer, a seller, and an observer. The customer should be competent, the seller should sell something, and the observer should observe. After each role-play, feedback should be provided on what was done well and what could be improved.

However, while conducting these meetings, it is important to avoid a few pitfalls. One such pitfall is not having enough variation in the meeting for different learning types. If the meeting only consists of slides or videos, it might not cater to everyone’s learning style. Therefore, mixing up the media and providing breaks is important to keep the team engaged.

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Enhancing Sales Performance Through Effective One-on-One Coaching Meetings

The effectiveness of sales management is paramount, particularly in how sales managers support their team members to enhance performance. The nuanced relationship between a salesperson and their manager can significantly influence their success, a topic that is gaining traction among CEOs and sales leaders seeking to maximize their team’s capabilities. One-on-one meetings between sales managers and salespeople are not just routine check-ins but pivotal moments that can define a sales team’s success trajectory. These interactions… Enhancing Sales Performance Through Effective One-on-One Coaching Meetings

From Crisis to Control: Managing Expectations in Sales Leadership

The concept of “managing up” emphasizes the importance of aligning a sales team’s objectives with the expectations of upper management. This approach is particularly crucial during periods of sales turnaround, where the usual metrics might falter and innovative, agile responses are required. “Managing up” involves treating higher management as an internal customer whose needs must be understood and met with the same diligence as those of external clients. For sales leaders, this means crafting a… From Crisis to Control: Managing Expectations in Sales Leadership