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Assessment

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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The AI Sales Process Map: The Ten-Stage Sales Process Framework

Sales leaders today often fall into the trap of using artificial intelligence tools randomly rather than systematically. This sporadic usage is like owning a Swiss Army knife but only using the bottle opener; you miss out on ninety percent of the available value. AI’s real power comes not from isolated tools but from integrating capabilities across every stage of your sales processes. When mapped correctly, AI accelerates every interaction, shortens sales cycles, and makes revenue generation more predictable.

Random AI adoption leads to inconsistent results. Some reps use it effectively, while others revert to manual methods under pressure, resulting in uneven performance. Systematic AI integration, however, compounds improvements across the entire sales cycle. Data captured at one stage strengthens the next, creating a virtuous cycle of sales success that is scalable, measurable, and sustainable. The outcome is not just faster deals, but stronger business acumen and more consistent revenue management.

The ten-stage AI sales process framework provides a structured way to apply AI:

  1. Prospecting,
  2. Outreach,
  3. Qualification,
  4. Scoping,
  5. Presentation,
  6. Economic Buyer meetings,
  7. Validation Events,
  8. Proposals,
  9. Closing,
  10. Onboarding/expansion.
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Hiring for Growth: How to Build a Sales Team That Drives Long-Term Success

Building a successful sales team requires more than just filling open seats with available candidates. Company leadership must strategically align its hiring process with business objectives, market needs, and long-term goals. 

Whether you’re a solopreneur transitioning to a team-based approach or a CEO managing a growing sales force, the principles of intentional recruitment and onboarding remain the same. Hiring the right people is an investment in the future of your business.

One of the most common pitfalls in sales hiring is a lack of intentionality. Too often, small businesses hire out of convenience, choosing candidates from their immediate network or taking the first person who seems interested. While this approach may solve an immediate need, it rarely leads to long-term success. 

Hiring a salesperson means selecting someone who can actively drive growth and represent your brand with competence and integrity. The stakes are even higher when you’re working with a lean team; every hire matters, and mediocrity is not an option.

To avoid these missteps, it’s essential to approach hiring with the same rigor you apply to your sales process. Think of recruiting as a parallel to securing a high-value client. Just as you wouldn’t sell your product without qualifying leads or understanding their needs, you shouldn’t hire without a structured process to evaluate candidates. 

Begin by defining what success looks like for the role. What skills and attributes are non-negotiable? What specific outcomes do you expect this person to achieve within their first 90 days? A clear job description and measurable KPIs set the foundation for finding the right fit.

Cultural alignment is another critical factor. Your salespeople are the face of your business to prospects and customers. Their ability to embody your company’s values and mission can make or break the customer experience. A candidate might have a stellar track record, but if their approach clashes with your team’s culture, the partnership is unlikely to succeed. At the same time, skills and experience must align with the specific demands of the role. For instance, if your goal is aggressive market penetration, you need a hunter mentality, someone skilled in building relationships from scratch and closing deals in uncharted territory.

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Two Tall Guys Talking Sales – Mastering Sales Hiring with John Lee – Sales Management Insights for Growth-Focused Teams – Episode 138

In this week’s episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey are joined by the “Elder Statesman” of fractional sales management: John Lee. With nearly four decades of experience and a deep track record of helping companies hire top-performing sales professionals, John shares a masterclass in sales hiring strategy. Whether you’re scaling from a two-person team to ten or trying to avoid costly hiring mistakes, this episode delivers practical, field-tested advice… Two Tall Guys Talking Sales – Mastering Sales Hiring with John Lee – Sales Management Insights for Growth-Focused Teams – Episode 138

Two Tall Guys Talking Sales – The Four Buckets of Sales Growth with Steve Wittal

In this dynamic episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome Canadian SalesXceleration expert Steve Wittal for an in-depth look into the foundations of effective sales strategies. Steve brings decades of experience in startup advisory, sales management, and business growth, sharing a robust framework that simplifies complex growth challenges into four digestible buckets: desirability, clarity, predictability, and deliverability. If you’re a business leader looking to strengthen your sales processes,… Two Tall Guys Talking Sales – The Four Buckets of Sales Growth with Steve Wittal

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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Two Tall Guys Talking Sales – Tom Gottlieb of Berkshire Hathaway Explains How Buyers Want Growth- How Sales Leaders Can Increase Company Worth – E131

In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome business intermediary Tom Gottlieb of Berkshire Hathaway. Tom brings decades of experience in buying, selling, and valuing businesses across the Midwest. The conversation dives deep into what truly drives the value of a company—and how sales leaders and business owners alike can prepare their organizations for a future transition. Whether you’re a business owner considering a sale or… Two Tall Guys Talking Sales – Tom Gottlieb of Berkshire Hathaway Explains How Buyers Want Growth- How Sales Leaders Can Increase Company Worth – E131

Two Tall Guys Talking Sales – Prepping for Q2 – Getting Ahead, Catching Up, and Staying on Track – E129

As the first quarter comes to a close, sales leaders and professionals must assess their performance and gear up for the challenges and opportunities ahead in Q2. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey break down the essential strategies for those ahead of the plan and those struggling to catch up. From refining your sales process to maximizing customer relationships, this discussion has insights to help you dominate… Two Tall Guys Talking Sales – Prepping for Q2 – Getting Ahead, Catching Up, and Staying on Track – E129

Two Tall Guys Talking Sales – Sales Prospecting: Are You Chasing Leads or Cultivating Success? – E127

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive into the art of sales prospecting using an unusual but powerful analogy—chasing butterflies versus building a garden. Are you tirelessly running after leads or cultivating an environment where ideal prospects naturally come to you? Learn how to create a long-term strategy for consistent revenue growth by positioning your business as the go-to solution for your ideal customers. Key Topics Discussed:… Two Tall Guys Talking Sales – Sales Prospecting: Are You Chasing Leads or Cultivating Success? – E127