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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!

Reclaiming Hours of Selling Time with AI – Lessons from MAICON 2025

You just checked your team’s dashboard. Activity looks fine. But deep down, you know that the numbers don’t tell the whole story.

Every salesperson loses time to the same unseen burden: administrative drag. After each successful discovery call, there’s a 20-minute grind with CRM updates, email summaries, and internal handoffs. This “sales tax” cuts into selling time, hurts momentum, and costs your company thousands weekly in lost productivity.

I just returned from MAICON 2025, and I was so inspired that I wanted to share some of the biggest lessons. At the MAICON 2025 conference in Cleveland, the message was clear: artificial intelligence is changing sales management, not by replacing people, but by empowering them. The winning teams are using AI to eliminate “digital grunt work” through orchestration, not standardization.

Orchestration, Not Standardization

MAICON’s main message was that sales leaders should stop searching for the “one magical platform.” Instead, the most successful organizations coordinate several top-tier tools. Their AI ecosystems are modular, flexible, and collaborative.

It starts with three pieces:

  1. a transcription tool like Fireflies,
  2. an automation hub like Make.com or Zapier,
  3. your existing CRM and communication systems.
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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 – Engage, Listen, Succeed: Unlocking Client Conversations That Close Deals – E121

Active listening isn’t just a soft skill; it’s a sales superpower. In this episode of Two Tall Guys Talking Sales, Kevin and Sean unravel the nuances of listening to clients, capturing their pain points, and building trust through meaningful interactions. With tips ranging from non-verbal cues to the tactical use of note-taking, this conversation equips you with tools to elevate your sales game. Whether you’re preparing for a discovery call, a QBR, or a cold call, this episode is a must-listen for actionable insights. Tune in and transform the way you engage with your clients.

Two Tall Guys Talking Sales – The Art of the Discovery Call: Build Respect and Close More Deals – E120

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey tackle one of the most critical yet underestimated aspects of sales: the discovery call. Are you guilty of “winging it” during these pivotal conversations? Tune in as Kevin and Sean break down the importance of crafting a tailored question bank, share actionable tips to elevate your discovery process, and reveal how asking the right questions can transform your sales game. If… Two Tall Guys Talking Sales – The Art of the Discovery Call: Build Respect and Close More Deals – E120

Unstick Your Sales: The Importance of Understanding the Buyer’s Journey

It’s no secret that the dynamics between the buyer and the salesperson play a pivotal role in sealing the deal. The conversation often revolves around real sales issues, selling situations, and sales leadership. 

Let’s delve into a scenario. You’re selling to a beer industry manufacturer, and their first question is about your price. This immediate focus on cost might make you think this may not be a good prospect. However, it’s crucial to remember that you can’t be disrespectful or dismissive. As salespeople, it’s our job to work with what we have. 

In this situation, the salesperson has to conduct a discovery call and engage a subject matter expert to understand the prospect’s business process, adaptation, and conversion. Unfortunately, the interaction turned into a commodity exchange, with the buyer solely interested in the number of users and the price per user. 

This scenario illustrates a common challenge in sales: the sales and buying processes often need to align. How your Customer Relationship Management (CRM) system is set up may not necessarily mirror how the buyer decides. Therefore, figuring out how to sell more effectively based on the buyer’s journey is crucial. Understanding the buyer is discussed in great detail in my book Eliminate Your Competition, which is available wherever you buy books.

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