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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!

Two Tall Guys Talking Sales – Why Consistent Sales Strategies Win: Forecasting, Messaging, and Revenue Management – Episode 151

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey delve into the crucial role of deal qualification in driving sales success. From simple frameworks like BANT to advanced methodologies such as MEDDIC and MEDDPICCC, Kevin and Sean explain how consistent sales processes, value selling, and business acumen can sharpen forecasting, strengthen messaging, and ultimately accelerate revenue generation. Whether you’re managing a sales team or selling solo, this discussion will… Two Tall Guys Talking Sales – Why Consistent Sales Strategies Win: Forecasting, Messaging, and Revenue Management – Episode 151

From Reporting to Coaching: Elevate Your One-on-One Sales Meetings to Drive Performance and Trust

A one-on-one sales meeting is not a reporting meeting. It’s not about reviewing what already happened. And it’s definitely not about the manager doing most of the talking. The purpose of a one-on-one pipeline review is to develop the salesperson, surface challenges, and accelerate opportunities. If your one-on-ones are anything less, you’re leaving performance on the table.

Sales leaders often default to micromanagement. 

Especially when the rep is new or struggling. But that approach backfires. It creates dependency and stifles problem-solving. The goal is to coach your reps into leading the meeting. That shift changes everything. When reps own the agenda and bring forward deal-level insights, they’re forced to think critically. That’s where growth happens.

If you’re leading a sales team or are a CEO playing the role of sales manager, you need to establish a clear structure. But the rep does the prep. You define the meeting cadence and format. Weekly or bi-weekly, depending on your velocity. You outline the sections: committed deals, stalled deals, and at-risk deals. 

But the rep fills in the content. They come to the meeting ready to walk you through each opportunity, with specific updates and clear asks.

Preparation is non-negotiable. For both sides. 

The salesperson should have updated their CRM before the meeting. The manager should have reviewed that data in advance. If either party shows up unprepared, the meeting becomes reactive. 

A waste of time. And it erodes trust quickly. 

Reps notice when you haven’t read the notes. They know when you’re winging it. And if they feel their effort isn’t valued, they’ll stop putting in the effort.

You want to create a culture where preparation is expected and rewarded. 

The fastest way to management failure is to ask questions that could have been answered by reading the CRM. Instead, use that time: 

  • To probe deeper. 
  • Ask about the deal strategy. 
  • Challenge assumptions. 
  • Help salespeople spot gaps they missed. 

That’s where your experience has real value.

It’s tempting to jump in and solve the problem. Especially when you see the red flags before the rep does. But resist the urge. Let them talk it through. Coach them toward the insight. Your job isn’t to close the deal; it’s to build someone who can. That means teaching them how to identify weak spots, how to pressure test a deal, and how to re-engage a stalled buyer. The real value of one-on-ones is in that development.

Think about how you coach. 

Are you diagnosing for them? Or are you helping them diagnose for themselves? When a rep says “this deal is solid, no issues,” that’s a red flag. Every deal has risk. Your job is to help them uncover it. Ask: “What’s the biggest thing that could derail this?” Or “What’s the last thing the buyer said that gave you pause?” These questions surface the truth. And they teach reps to self-assess more effectively.

There’s a fine line between coaching and grading. You want reps to be honest about their pipeline without fear of judgment. 

If a deal is weak, that’s not a character flaw. It’s a coaching moment. 

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APIs Explained for Sales Leaders: Drive Growth Without Extra Headcount

A sales manager recently told me, “I have to copy the same prospect data into five different tools. There has to be a better way.” That frustration is more common than most sales leaders realize, and fortunately, there is a better way. The reality is that sales teams are hemorrhaging productivity due to disconnected systems. Top performers spend hours manually entering data, bouncing between platforms, and correcting inevitable errors. This administrative overhead steals time from… APIs Explained for Sales Leaders: Drive Growth Without Extra Headcount

Cut Through the AI Hype: Practical Definitions for Sales Professionals

Artificial intelligence is transforming sales, but too many leaders are investing in tools they don’t fully understand. The result? Costly mistakes, poor adoption, and missed opportunities. This episode of AI Tools for Sales Pros breaks down the three core technologies behind AI: and explains them in plain language that every sales professional can use. The episode compares the current AI confusion to the database revolution of the 1990s. Just as sales leaders once needed to… Cut Through the AI Hype: Practical Definitions for Sales Professionals

Two Tall Guys Talking Sales – No Leads, No Problem: Sales Strategies to Reignite Momentum – Episode 148

When your sales pipeline hits a wall—or worse, goes completely flat—it can feel like you’re spinning your wheels. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into what to do when your sales team is facing a revenue generation stall. This is a fast-paced, actionable conversation focused entirely on what sales leaders can do to recharge a stalled pipeline—without relying on marketing. Whether you’re in B2B… Two Tall Guys Talking Sales – No Leads, No Problem: Sales Strategies to Reignite Momentum – Episode 148

AI in B2B Sales Isn’t Optional Anymore

Several months ago, I was serving as a fractional VP of Sales for a $50 million manufacturing company. Their top salesperson was a 15-year veteran who knew the industry inside and out. Yet he was consistently being outsold by a competitor’s much newer hire. At first, it didn’t make sense until we discovered the reason. The competitor’s rep wasn’t just more energetic or aggressive. They were AI-enabled. While my client’s rep was manually scrolling LinkedIn… AI in B2B Sales Isn’t Optional Anymore

B2B Sales in the Age of AI: Why Top Salespeople Will Thrive While the Repetitive Roles Disappear

The buzz surrounding artificial intelligence has left many professionals wondering about the future of their careers. For B2B sales professionals, the rise of AI presents a fundamental question: Will AI replace salespeople?

The short answer is no, but it will replace some of their work. More accurately, AI will redefine the B2B sales landscape by eliminating lower-value activities, consolidating support roles, and enhancing the capabilities of top performers. In doing so, it will widen the gap between average and great salespeople.

Several years ago, I wrote a similar explanation about the fear that “the internet” would replace salespeople. That didn’t happen. You can find that article on the blog that supports my first sales book. Are salespeople necessary in the Internet age?

This blog post explores how B2B sales is positioned relative to AI disruption, referencing key insights from Benjamin Todd’s article, “How Not to Lose Your Job to AI” (80,000 Hours, 2025). Todd’s framework on skill types that increase in value in the age of AI helps us understand how high-functioning sales teams should evolve and how sales professionals can future-proof their careers.

Understanding AI’s True Impact: Augmentation, Not Replacement

A common misconception about AI is that it simply replaces humans. This isn’t true. AI devalues tasks it can perform while increasing the importance of the skills it cannot. Todd explains this dynamic through examples like the ATM: while the ATM reduced the need for transactional teller tasks, it actually increased demand for bank branch workers by allowing banks to open more branches. AI follows a similar pattern.

In B2B sales, AI will handle the most automatable tasks, such as data entry, follow-ups, list-building, and basic prospecting emails. However, this doesn’t eliminate the sales role; it sharpens its focus.

Instead of dialing hundreds of prospects daily, sales professionals will focus more on strategic engagement, account planning, and using AI-generated insights to elevate conversations. The result? Sales has become a more thoughtful, human, and strategic discipline for those who can keep up.

Four Categories of Skills That AI Will Make More Valuable

In Todd’s excellent article, he identifies four skill types that increase in value in an AI-enhanced workplace:

  1. Hard-to-automate skills
  2. Deployment-related skills
  3. Scarce, high-utility skills
  4. Skills hard for others to learn or replicate

Each of these aligns tightly with the demands of modern B2B sales.

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The Key to Profitable Sales Organizations: Understanding and Adhering to the Sales Process

Many salespeople, sales managers, and CEOs face a unique problem. This issue concerns the sales process, particularly when specific steps are skipped. The challenge is common among sales teams across various industries, and there are different perspectives on its causes and solutions.

This issue is concerning since, according to Harvard Business Review, 28% of companies that master at least three stages of their sales process will see an increase in revenue growth. (https://hbr.org/2015/01/companies-with-a-formal-sales-process-generate-more-revenue). That same study states that companies that had trained their sales managers to manage their pipelines saw their revenue grow 9% faster than those that didn’t. But not just any training will do. Sales managers need targeted training to address specific pipeline management challenges.

Sometimes, the sales process might seem tedious, and salespeople may skip steps out of impatience or eagerness to close a deal. However, skipping these steps can lead to further complications down the line. When a sales team is not following the process that has been identified, it can disrupt the team’s rhythm and efficiency. Some might argue that this is a sign that the process needs to change or that more training is required.

This issue extends beyond the sales team. When a company hires a fractional VP of sales, it brings an outside perspective to evaluate its sales process. The fractional VP will often encounter resistance from the existing team, who may feel their industry is unique. While every business has its distinctive elements, the fundamentals of a sales process are universal.

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Validation Events: The Unsung Hero of Sales Process Discipline

In the complex world of B2B selling, trust is built in stages. The challenge in all sales campaigns is ensuring the prospect trusts they are making the best decision for their business.

  1. Do they trust that the salesperson is giving them all of the information?
  2. Do they trust that the company will support them after the sale?
  3. Do they trust that the product will perform as they expect it to perform?

As I have explained in my book, Eliminate Your Competition, as well as the blog for that book and in this blog, the prospect needs to trust all three elements the salesperson is selling:

  1. They need to trust the product.
  2. They need to trust the company behind the product.
  3. They need to trust the salesperson.

Prospects listen to your sales message, review your materials, and hear your claims, but none of that guarantees belief or trust. Trust is validated when your claims are validated. That’s why validation events are crucial to any rigorous sales process.

In The Qualified Sales Leader, John McMahon stresses the importance of customer-driven validation. He cautions sales leaders against relying on internal optimism or anecdotal “good signals” from prospects. Instead, McMahon emphasizes observable proof—real buyer behavior that confirms alignment, commitment, and value. Validation events are when the customer takes action to validate that what you’ve promised is accurate and valuable.

An excellent sample sale process flow looks like this:

  1. Discover
  2. Scoping
  3. Economic Buyer Meeting
  4. Validation Event
  5. Business Case and Final Proposal
  6. Negotiate and Close

As you can see, the Validation Event is the last step before creating the final business case, which will be bundled with your final proposal.

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