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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!


Stop Betting on Superstars: How Operating Standards Turn Sellers into Predictable Producers

Many teams grow, but few truly scale revenue beyond individual hero efforts. That difference changes everything for leaders today and in the future. Growth relies on hustle; scaling depends on repeatability across segments and individuals. Your strategy must reflect that hard truth in practice.

Are you relying on one standout to win deals month after month? That looks strong until risk turns visible and costly. One resignation can cripple momentum and expose brittle systems that you had previously ignored.

Scalable sales replaces heroics with defined, teachable operating rhythms that everyone follows. It turns chaos into predictable pipeline progress and results. It clarifies markets, messages, motions, and measurable expectations for every seller on a weekly basis. It builds leverage into onboarding and coaching for consistency. It protects margins while systematically accelerating win rates and velocity across territories.

The foundation begins with a clear picture of your ideal customer, including any disqualifying factors. Having an accurate Ideal Client Profile (ICP) helps minimize waste and reduce uncertainty in your efforts. Take time to define firmographics, pain points, triggers, and buying behaviors using consistent language based on shared evidence. Understand who cares about these issues and why it matters to them now. Also, identify negative personas to sharpen your focus and qualification processes in marketing and sales. A well-defined ICP can significantly boost your conversion rates and shorten the sales cycle.

Next, turn your ICP into straightforward messaging and discovery frameworks tailored for each stage. Consider what unique problems you solve for your customers. What outcomes are most important to them, and who are the key stakeholders by role and priority?

Build talk tracks that lead buyers, not chase buyers with purpose always. Anchor questions to the business metrics and risks they feel. Teach a qualification that tests mutual commitment and outlines next steps with attached dates. Avoid fluffy demos; design relevant proofs using their data. Process specificity turns B players into consistent producers without copying another personality.

I suggest you establish a practical, stage-based operating rhythm that everyone can easily understand and follow. By sharing clear definitions and expectations, managing the pipeline becomes a consistent and smooth process each week. Define each stage with specific exit criteria—avoiding vague intentions or subjective feelings. For example, discovery is considered complete when stakeholders confirm the consequences and impact, and solution fit is achieved when success criteria and ownership are clearly aligned. The commit stage should be backed by a shared plan with clear dates and assigned owners. During weekly reviews, focus on assessing quality rather than just quantity or activity counts. Ask yourself:

  • Does evidence from buyers’ backstage moves have a direct impact on their purchasing decisions?
  • Are the next steps specific, mutually agreed upon, and already scheduled on both calendars?
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Two Tall Guys Talking Sales – The Hidden Driver of Every Sale: Mike Dowhan Explains How Compelling Events Shape Business Acumen and Sales Strategies – Episode 160

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome Mike Dowhan, founder of Bedrock Sales. Together, they explore one of the most overlooked yet transformative aspects of sales management: the compelling event. Mike brings over two decades of experience helping organizations refine their sales processes, understand buyer motivation, and drive consistent revenue generation. Whether you’re a frontline seller or a sales leader guiding a team, this episode unpacks how identifying and leveraging compelling events can be the difference between chasing deals and closing them confidently.

Key Topics Discussed

  • The Power of the Compelling Event (01:12) – What defines a compelling event and why it’s the “why” behind every great sale.
  • Asking Better Discovery Questions (03:00) – How to uncover the root cause that motivates buyers to act now rather than later.
  • Getting Permission to Go Deep (07:17) – Why earning trust allows salespeople to ask the tough, business-critical questions.
  • Compelling Events vs. Compelling Needs (09:53) – The distinction between recognizing a real deadline versus a vague desire for change.
  • Surfacing the Cost of Inaction (10:38) – How to use timing, impact, and risk to create urgency without manufacturing pressure.

Key Quotes

  • Mike Dowhan (03:49): “What caused you to pick up the phone or take my call today? What’s different today than yesterday? That’s where you find the real reason a buyer is ready to move.”
  • Sean O’Shaughnessey (02:29): “If there’s no compelling event, it becomes very difficult. You’re pushing the boulder uphill, fighting the same battle over and over.”
  • Kevin Lawson (12:00): “Finding permission and tracking back to that event is where we create real value, and avoid the trap of commoditization.”

Additional Resources

A Significant Actionable Item from this Podcast

Start every discovery conversation with one simple question:

“What changed today that made you want to talk to me?”

This question reveals your buyer’s compelling event, the emotional and operational trigger that drives their need to act. Understanding that moment transforms your sales strategy from reactive to consultative. Use it to align your messaging, reinforce your value-selling approach, and accelerate revenue growth.

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Two Tall Guys Talking Sales Podcast – Destination Success: Mapping Your Sales Strategy with Precision – E97

Join hosts Kevin Lawson and Sean O’Shaughnessey as they dive into the intricacies of sales strategy, drawing parallels to planning a family vacation. As we edge closer to our 100th episode, this session unpacks why having a well-documented and aligned business plan is crucial—akin to knowing your vacation destination to ensure everything goes smoothly. Whether you’re a business owner or a sales professional, this episode provides vital insights into simplifying and aligning your sales strategy… Two Tall Guys Talking Sales Podcast – Destination Success: Mapping Your Sales Strategy with Precision – E97

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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Two Tall Guys Talking Sales Podcast – Selling the Hole, Not the Drill: Understanding the Real Value Behind Your Sales – E91

Welcome to another insightful episode of “Two Tall Guys Talking Sales,” where our hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the complexities and strategies of sales. In this episode, they explore the nuanced dynamics of selling through distribution and understanding the real needs of your customers. Whether you’re a seasoned sales veteran or just starting in your career, this episode offers a wealth of knowledge on refining your sales approach to maximize effectiveness and customer satisfaction.

Key Topics Discussed:

  1. Selling Through Distribution: Sean shares his early career mistakes and the pivotal lessons of focusing beyond just the product features.
  2. Understanding Your Customer’s Needs: Strategies to grasp what the end-user truly requires from a product, rather than just its specifications.
  3. The Importance of Simplicity in Sales: Kevin emphasizes how simplifying your sales message can vastly improve understanding and efficiency in sales processes.
  4. Sales Training and Knowledge Transfer: Both hosts discuss how proper training and knowledge sharing with channel partners and sales teams can lead to better sales outcomes.
  5. The Role of Value in Sales: How to communicate the unique value of a product or service to stand out in a competitive market.
  6. Referral Partnerships and Networks: Sean elaborates on the significance of nurturing relationships with referral partners to enhance lead generation for smaller businesses.
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Maximizing Productivity in Sales Meetings: Key Principles and Best Practices

Sales meetings are the lifeblood of any sales-driven organization, providing an essential forum for communication, collaboration, and strategy development. Yet, despite their significance, many salespeople, managers, and CEOs struggle to conduct productive and efficient meetings. This issue often stems from a lack of understanding of key meeting principles and best practices, particularly in the areas of time management, content planning, and participant engagement.

The adage “time is money” holds especially true in sales. Every minute counts, and wasted time equates to lost opportunities. This is why punctuality is of the utmost importance. A meeting that starts late or runs over time is disrespectful to participants and detrimental to the team’s overall productivity. 

To avoid this pitfall, sales leaders should ensure they always arrive early to meetings and start them on time, without exception. This requires careful planning and preparation, as well as a commitment to respecting the time and schedules of others. The same principle applies to the end of the meeting. Sales leaders should always strive to conclude meetings on time, which requires careful meeting agenda management and a willingness to keep discussions focused and on track.

Content planning is another crucial aspect of effective meeting management. Just as a ship needs a compass to navigate the seas, a meeting needs an agenda to guide its proceedings. A well-crafted agenda provides a clear structure for the meeting and helps to keep discussions focused and productive. It also sets clear expectations for participants and helps to ensure that all relevant topics are covered.

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Two Tall Guys Talking Sales Podcast – The Gap Analysis Advantage: Bridging Client Needs with Optimal Solutions with Chris Cocca – E86

Welcome to this week’s episode of Two Tall Guys Talking Sales, where hosts Kevin Lawson and Sean O’Shaughnessey are joined by Chris Cocca, a sales expert, to discuss the vital aspects of discovery meetings and qualifying prospects for a robust sales pipeline. Tune in as they delve into the methodologies that distinguish successful sales strategies, particularly focusing on the RAIN training concept and the essential practice of understanding client aspirations and afflictions. Key Topics Discussed:… Two Tall Guys Talking Sales Podcast – The Gap Analysis Advantage: Bridging Client Needs with Optimal Solutions with Chris Cocca – E86