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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!


Transform Your Sales Team: Strategic Compensation Adjustments for Year-End Momentum

Autumn is the time of year for sales leaders, managers, and CEOs to begin laying the groundwork for next year’s success. Have you considered how your current sales compensation plans impact your team’s motivation and productivity? Now is the ideal moment to evaluate, adjust, and deliver these plans, preferably by December 1st. Doing so can significantly influence your team’s drive to close deals in December and build momentum heading into the next fiscal year.

Sales compensation should be motivating and rewarding for employees. It directly shapes your sales team’s behaviors and priorities. An effective plan incentivizes the right actions and deters the wrong ones.

Consider a common pitfall: salespeople holding back deals to inflate their numbers for the following year. Does your current compensation structure inadvertently reward this practice? If so, you’re unintentionally harming your year-end results.

To counter this, strategically incorporate compensation escalators and cliffs into your plan. Escalators progressively reward increased sales performance throughout the year. Higher performance equals higher commission rates, driving your sales team to push forward continually. 

Commission cliffs reset commission rates at the beginning of each year, creating a sense of urgency to close deals before the end of December. Communicating these compensation details clearly by early December ensures your team understands what’s at stake.

Don’t hold your team back!

Another critical compensation consideration is eliminating commission caps. While some organizations cap commissions to control expenses, this practice can backfire dramatically. Caps tell your top-performing salespeople that their exceptional efforts are neither valued nor rewarded appropriately. This demotivates your top talent and encourages them to seek opportunities elsewhere that offer uncapped rewards. 

Removing commission caps signals that the organization fully supports and rewards outstanding performance. Have you considered how much growth your company might achieve if artificial constraints didn’t limit your sales team?

When evaluating compensation, look beyond simple cost containment. Consider the true profitability of incentivizing increased sales volume. Once salespeople reach their targets and enter accelerators, each additional dollar earned typically comes at a lower incremental cost to your organization. 

Sales transactions earlier in the year have already covered the salesperson’s base salary once they have met their annual quota. In fact, at 100% of quota, the salesperson should have covered all their costs and their share of the overall company’s revenue needs. Thus, every extra sale at escalated commission rates still contributes positively to your overall profitability. 

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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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Stop Guessing, Start Growing: How Strategic Sales Assessments Drive Real Revenue

You’ll eventually hit a wall if you’re running a sales organization—or wearing multiple hats as founder, CEO, and sales manager. That wall is often invisible until growth stalls, key deals slip through the cracks, or your top salesperson burns out. So, what’s the next move? It’s not more hustle. It’s assessment.

A sales assessment isn’t about checking boxes. It’s about understanding where you are, how you operate, and what’s holding you back. Too many small business leaders assume they’re doing fine because revenue is growing or the team is hitting their quotas. But are you growing at the rate your market allows? Are your sales activities aligned with your long-term goals? Are you building a repeatable system, or are you just getting lucky?

Let’s get tactical. A sales plan isn’t just a revenue target. It’s your go-to-market strategy. It defines your audience, your message, and your motion. It answers why you’re talking to those prospects and what value you’re bringing to them. Without a plan, you’re reacting instead of executing. You’re chasing leads instead of building a pipeline.

If you’re a small company—perhaps under $30 million in revenue—and selling into a national market, chances are your market potential is hundreds of millions, maybe billions. That means your market share is a rounding error, which means there’s room to grow. The question is: Are you operating in a way that allows you to capture that growth?

Even if you’re running lean, you should benchmark your performance against top-tier organizations. Not because you’re competing with them directly, but because they set the standard. What are they doing that you’re not? Where are they more efficient? How do they structure their teams? You’re leaving money on the table if you’re not asking those questions.

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Turning Competition into Opportunity: A Guide for Success in Sales

Competition in B2B sales isn’t your enemy. It’s your greatest catalyst for growth and innovation in today’s dynamic market landscape. Have you considered how viewing competitors as opportunities rather than threats could transform your sales approach? Let me show you why this mindset shift matters for your bottom line.

Think beyond the obvious when identifying your competition. Your real rivals aren’t just companies selling similar products or services. They’re anyone competing for your prospect’s budget allocation. This includes businesses offering solutions with capabilities or price points different from yours and other priorities within the prospect. The competitive landscape extends far beyond your direct market segment.

The most formidable opponent often lurks in the shadows of customer inertia. This “no-decision” competitor manifests as your prospect’s resistance to change. It’s the comfort zone that whispers, “Maybe later,” or “What we have works fine.” Understanding this psychological barrier is crucial for your sales strategy.

You need a systematic approach to analyzing and outmaneuvering your competition. Start with an honest assessment of your position in the market. What unique value do you bring to your customers? Where do you consistently outperform others? This self-awareness forms the foundation of your competitive strategy.

Know your competition inside and out. Study their strengths, weaknesses, market positioning, and customer relationships. Your competitive analysis must go deeper than surface-level observations. Map out how their strengths align with your weaknesses. This intelligence helps you craft more compelling value propositions and sales approaches.

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Strategizing Success: A Small Business Guide to Sales Mastery

Understanding the intricacies of sales plans, processes, and methodologies is beneficial and crucial for sustained growth and success in B2B sales. This deep dive offers invaluable insights for salespeople, sales managers, and CEOs of small companies looking to refine their sales strategies and enhance management capabilities. A sales plan is more than just setting targets; it’s about crafting a roadmap to market success, focusing on who you’re engaging with and the value you bring to… Strategizing Success: A Small Business Guide to Sales Mastery

Jack of Spades: Setting Up Performance Improvement Plans: Offer structured guidance for those not meeting benchmarks.

In the tightly woven tapestry of a sales organization, each thread—each salesperson—must hold its own for the entire structure to maintain its integrity. Imagine a well-practiced orchestra where each musician is critical to the harmonious output. If even one violinist is off-key, it disrupts not just the symphony but also influences the collective perception of the audience. Similarly, when one salesperson consistently misses the mark, the dissonance affects not just their numbers but the collective… Jack of Spades: Setting Up Performance Improvement Plans: Offer structured guidance for those not meeting benchmarks.

Nine of Spades: Addressing Salesperson Underperformance: Setting Performance Benchmarks: Define standards for success to measure against.

Understanding the Nature of Sales Benchmarks Let’s start by grounding ourselves in the foundational premise: Sales benchmarks are not merely numerical goals but the defining coordinates of success. If you will, consider them as your organization’s North Star, guiding your sales team through the complexities of quotas, customer relationships, and revenue targets. Benchmarks transcend the limitations of raw numbers and extend into the realm of qualitative assessment—whether it’s the ability to understand customer needs or… Nine of Spades: Addressing Salesperson Underperformance: Setting Performance Benchmarks: Define standards for success to measure against.

Eight of Spades: Defining your corporate sales strategy: Crafting a Sales Process Flowchart: Visualize the stages in your sales process for consistency

The Quintessential Blueprint for Sales Mastery In architecture, the blueprint guides turn an imagined design into a tangible, functional building. Similarly, a Sales Process Flowchart is the foundational structure upon which sales organizations can build scalable, consistent, and successful strategies. The importance of this tool lies in its ability to crystallize the sales process into a series of actionable steps, thereby providing a roadmap to success. The goal is to achieve consistency, predictability, and scalability,… Eight of Spades: Defining your corporate sales strategy: Crafting a Sales Process Flowchart: Visualize the stages in your sales process for consistency

The Art of Motivation: Designing Sales Compensation Plans That Drive Results

Designing an effective sales compensation plan is critical to any successful sales organization. A well-crafted plan motivates your sales team, drives revenue growth, and aligns the interests of both the company and the sales representatives. 

It’s essential to understand the impact of compensation on salespeople. Sales reps are highly motivated by money, and their income is directly tied to their performance. Incentives such as bonuses, commissions, and accelerators can all play a key role in driving sales performance. However, these incentives can have unintended consequences if not implemented correctly.

This blog post will explore various aspects of creating a successful sales compensation plan, including setting quotas, selecting base and variable pay, using accelerators, and employing rewards and contests. We’ll also discuss strategies for designing effective compensation plans for different types of sales roles and tips for continuously improving your compensation plan.

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Two Tall Guys Talking Sales Podcast: Why Should a Company Assess Its Practices in Sales?

In this podcast, Kevin and Sean discuss why it is important for companies to assess their sales plans and processes. They explain that having a sales plan is about more than just setting quotas and involves figuring out how to bring value to the customer. It is also important for smaller businesses that are transitioning from founder-led sales organizations to have an assessment to build the right infrastructure. The conversation also touches on how CEOs should still be involved in customer conversations regardless of company size and that competition, complacency, and consistency should all be considered when assessing one’s own organization. Lastly, they invite listeners to reach out with any questions they may have about creating a great sales organization.

You can subscribe to our podcast by searching in your favorite podcast player for “Two Tall Guys Talking Sales,” or you can listen to the embedded version here.

The following is a transcript of the podcast above. It has been sparsely edited to increase its readability, but many of the idioms and poor spoken grammar have been left in place. Fireflies.ai automatically generated the transcription, and, as capable as that product is, there are times when words are missed or the sentence structure is incorrectly interpreted. We have tried to catch all of these software misses, but we are confident that some still remain. The below text is provided for those that would rather read than listen to a podcast.

 00:00

Kevin Lawson

Hello, and welcome to Two Guys Talking Sales. I’m Kevin. 

 00:06

Sean O’Shaughnessey

And I’m Sean. 

 00:08

Kevin Lawson

We’re glad you’re here. In this podcast, we’ll tackle real sales issues big and small for salespeople selling situations and sales leadership. We’ve collectively built successful careers around the problems and solutions used in B2B selling, from software to services, manufacturing, and distribution. We have sold to and for many of the world’s most recognized brands as well as some you’ve never heard of. For roughly the next 15 minutes, we invite you into our world of experience, where we’ll take one issue and dig into it so you might have a solution for when you encounter a similar situation in your career. Let’s dive in. Sean, what are we talking about tonight? 

 00:48

Sean O’Shaughnessey

Kevin, we should discuss why a company should assess its sales plan, process, and methodologies. How about that? 

 00:57

Kevin Lawson

Sounds Good. Maybe we should start by asking, “What are a sales plan, system, and methodology.”

 01:03

Sean O’Shaughnessey

That makes sense to me. Do you want to start? Go Ahead.

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