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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!

AI Isn’t Replacing Salespeople, It’s Giving Them a Competitive Edge

AI isn’t replacing salespeople, it’s making them more effective. The real risk isn’t losing your job to AI; it’s losing to a competitor who uses AI better than you do. Sales professionals who integrate AI into their workflow will outperform those who don’t. 

It’s not about technology taking over but about using technology to gain an edge. The market is becoming increasingly competitive, and the most efficient salespeople will emerge victorious.

Time is a salesperson’s most valuable asset. 

Every minute spent on administrative tasks is a minute not spent selling. AI helps reclaim those lost hours. Tools that automate writing, scheduling, and research allow salespeople to focus on what matters: building relationships and closing deals. If you’re not leveraging AI to increase productivity, you’re leaving opportunities on the table.

Sales emails need to be clear and professional. AI-powered writing assistants ensure your messages are polished and effective. A poorly written email can cost you a deal. AI tools catch grammatical mistakes, improve clarity, and even suggest more effective phrasing. This isn’t just about looking professional; it’s about being understood. 

If your message isn’t clear, it won’t convert.

Presentations are another time-consuming task. AI can generate professional decks in minutes. Instead of spending hours designing slides, salespeople can focus on developing effective strategies. AI-powered tools create branded, structured presentations based on simple inputs. This ensures consistency while saving time. Sales professionals who utilize AI for presentations can focus on delivering insights rather than formatting slides.

CRM systems are the backbone of sales operations. AI enhances CRM by automating data entry, tracking customer interactions, and suggesting next steps. Salespeople often struggle with keeping CRM data updated. AI reduces this friction by automatically capturing and organizing information. A well-maintained CRM leads to better forecasting and stronger customer relationships. 

If your CRM doesn’t have AI capabilities, it’s time to upgrade.

AI-driven insights enable sales managers to make more informed decisions, rather than relying on instinct. Managers can use AI to analyze performance trends, identify coaching opportunities, and predict revenue outcomes. AI doesn’t replace leadership; it enhances it. 

Sales managers who adopt AI can build stronger teams and achieve better results. Ignoring AI in sales management is a strategic mistake.

Lead generation is another area where AI adds value. AI-powered tools can analyze vast amounts of data to identify high-potential prospects. Instead of spending hours researching leads, salespeople can receive AI-generated recommendations. This allows for more targeted outreach and higher conversion rates. AI doesn’t just find leads, it finds the right leads.

Sales follow-up is often inconsistent. AI ensures follow-ups happen at the right time with the right message. Automated reminders and AI-generated responses keep deals moving forward. 

A well-timed follow-up can be the difference between closing a deal and losing it. AI helps salespeople stay on top of their pipeline without relying on memory.

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Two Tall Guys Talking Sales – How Sales Leaders Use CRMs to Align Sales Processes, Value Selling, and Revenue Management – Episode 152

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey build on last week’s discussion of qualification methodologies and take the conversation further—into how these frameworks should live inside your CRM. From aligning sales processes with the buyer’s journey to enforcing accountability at each stage, this conversation offers practical strategies that every sales leader and salesperson can implement. Expect a deep dive into sales management, revenue generation, sales processes, and… Two Tall Guys Talking Sales – How Sales Leaders Use CRMs to Align Sales Processes, Value Selling, and Revenue Management – Episode 152

From Manual to Automated: A Sales Pro’s Guide to Zapier, Make.com, n8n, and Pipedream

A sales manager recently told me something that stuck: “We went from twenty hours per week of manual work to two hours. Our lead response time dropped from four hours to four minutes.” That dramatic transformation wasn’t magic—it was automation. The reality is that sales teams today have more automation tools available than ever before. But with options like Zapier, Make.com, n8n, and Pipedream, the real challenge isn’t whether you should automate—it’s choosing the right… From Manual to Automated: A Sales Pro’s Guide to Zapier, Make.com, n8n, and Pipedream

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

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?

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

Two Tall Guys Talking Sales – Breaking the Silos: Aligning Sales and Marketing for Real Revenue Growth – Episode 147

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive deep into one of the most misunderstood dynamics in business: the relationship between sales and marketing. Pulled directly from a thought-provoking question inside the B2B Sales Lab community, this conversation explores how sales teams can contribute meaningfully to marketing efforts and why that collaboration drives better revenue generation. Whether you lead a sales team, run marketing campaigns, or wear both… Two Tall Guys Talking Sales – Breaking the Silos: Aligning Sales and Marketing for Real Revenue Growth – Episode 147

Two Tall Guys Talking Sales – Managing the Maverick: How to Lead Top Sales Performers Without Breaking Team Culture – Episode 146

When a top-performing salesperson refuses to follow the rules, tensions flare, and your culture might suffer. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey tackle a question straight from their B2B Sales Lab community: What do you do with a sales rockstar who drives the rest of the team nuts? If you’ve ever struggled with managing high-output, low-alignment team members, this conversation is packed with valuable insights, practical… Two Tall Guys Talking Sales – Managing the Maverick: How to Lead Top Sales Performers Without Breaking Team Culture – Episode 146