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strategic sales

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!

ChatGPT vs. Claude vs. Gemini vs. Copilot: Which AI Wins in Sales?

A few days ago, a sales manager asked me which AI platform to use for writing cold emails. I told him it depends on what kind of emails he’s writing, and he looked confused. That confusion is common and costly. ChatGPT, Claude, Gemini, and Copilot all look similar at first glance, but in reality, they serve very different purposes depending on your sales workflow. Choosing the right platform matters because the wrong choice drains time,… ChatGPT vs. Claude vs. Gemini vs. Copilot: Which AI Wins in Sales?

Two Tall Guys Talking Sales – John McLeod Explains How to Avoid the AI Trap: Using New Tools Without Losing Your Sales Message – Episode 140

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey are joined by veteran fractional VP of Sales, John McLeod. Together, they dive into a critical topic for today’s sales leaders: embracing artificial intelligence tools without compromising your value proposition, messaging, or sales processes. John brings deep expertise in sales management, business acumen, and revenue generation strategies, offering a measured approach to evaluating sales tech, especially AI solutions, through a… Two Tall Guys Talking Sales – John McLeod Explains How to Avoid the AI Trap: Using New Tools Without Losing Your Sales Message – Episode 140

Two Tall Guys Talking Sales – Steve Caton Shares When to Sell, When to Coach, and When to Hire: Strategic Sales Management That Drives Growth – Episode 137

In this powerful episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey are joined once again by Steve Caton, CEO of Altezza Solutions, for a thought-provoking conversation that zeroes in on one of the toughest decisions in sales leadership: when to sell, when to coach, and when to hire. Whether you’re a business owner, VP of Sales, or a player-coach juggling a quota and a team, this episode brings clarity to the… Two Tall Guys Talking Sales – Steve Caton Shares When to Sell, When to Coach, and When to Hire: Strategic Sales Management That Drives Growth – Episode 137

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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Roadblocks, Detours, and Destinations: The Intricate Art of Sales Strategy

There’s an ongoing conversation about the importance of strategy, process, and anticipating potential challenges in B2B sales. There’s an analogy that encapsulates this perfectly – imagine you’re on a road trip. You have a destination in mind but are unfamiliar with the route. This is where tools like Waze, Google Maps, or Apple Maps come into play. They direct you to your destination and alert you about potential roadblocks, construction, traffic, or other unexpected events that might delay your journey. 

This is precisely how a sales strategy should work. It’s not just about getting from point A to point B but also about understanding the complexities of the journey and preparing for potential roadblocks. For salespeople, managers, and CEOs, understanding the strategy is critical to increasing revenue and improving productivity.

Understanding that a strategy involves more than just the turns along the way is vital. It also involves how to navigate through different areas, understand the speed limit, and anticipate any warnings that might come up. Many salespeople don’t fully grasp these challenges and tend to take them as they come rather than anticipating them and planning accordingly. 

Like Waze uses real-time data to adapt to changes on the road, a sales strategy should adjust to new information and circumstances. For example, if there’s construction up ahead or a detour is required, Waze will adapt and provide a new route. Similarly, salespeople should be able to adjust their strategies based on new information or unexpected challenges. 

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The Right Person in the Right Seat: Unleashing Company Growth through Strategic Sales Leadership

A recurring issue for small companies has emerged; the company’s owner or CEO often leads the sales department. This might be because they believe no one else can sell their product or service better than they can. However, this mindset might be hampering the company’s growth potential.

If you’re a company owner or CEO who leads sales, it’s crucial to consider the risk of this approach. When the person leading the company also heads sales, the business is constrained by the amount of time that leader has. If your salespeople consistently wait for your input or response, you might face a growth opportunity and a challenge simultaneously.

The solution lies in de-risking your organization’s growth potential by getting a sales leader in the sales leadership seat separate from you. This concept resonates with the theory of constraints, a principle often applied in the manufacturing industry but equally applicable in sales. The theory of constraints focuses on identifying the factors that limit your success. 

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