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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!

Automating Sales Workflows: When to Use Automation Over Chat

In sales management, there’s often some confusion about when to use artificial intelligence chat interfaces versus automation workflows. Chat interfaces are ideal for creative problem-solving, learning, and strategic research, while automation excels in repetitive, high-volume, data-driven sales tasks. The trick is to recognize when consistency and scalability are more important than customization.

Automation delivers consistent execution, eliminates human error, and operates 24/7. Sales leaders can rely on it for triggered communications, data synchronization across systems, CRM updates, and compliance tasks that require accuracy and complete audit trails. By moving these routine tasks into automated workflows, sales teams free up valuable time for relationship building, revenue generation, and refining sales strategies.

Real-world examples highlight the impact: a team once spent three hours daily crafting manual follow-up emails. Shifting to automated sequences not only saved time but also improved messaging consistency and pipeline response rates. Similarly, another team utilized automation to synchronize sales data across six systems, thereby eliminating bottlenecks and enabling sellers to focus fully on sales.

Hybrid approaches really take things to the next level! By merging human creativity in chat interactions with the quick and precise power of automation, businesses can craft workflows that beautifully balance personalized service with the ability to grow. This type of teamwork enhances value-driven selling, sharpens business skills, and accelerates revenue management throughout the sales journey.

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From 10 to 100 Customers: Scaling Your Sales Process for Growth

For founders of companies, the journey of a business is a narrative of evolution, growth, and constant adaptation. As salespeople, sales managers, and CEOs, we are all too familiar with the challenges and triumphs that punctuate this journey. In the world of sales, one of the most critical turning points is the transition from acquiring your first ten customers to expanding your customer base to 50 or even 100. This pivotal moment sets the trajectory of a business and is a key focus of our discussion.

When you’re starting, the founding team is focused on acquiring those first ten customers. They’re trying to find their footing in the market, identify their target audience, and refine their product or service offering. You might be customizing your product or service for each customer to ensure it fits their specific needs. However, as you aim for the next level of growth, it’s crucial to start thinking about systemizing your sales process. This will ensure efficiency and prepare you for the next level of growth. 

To scale effectively, company leaders need to standardize their product or service offering. While customization can be beneficial in the early stages, it becomes impractical and inefficient as your customer base grows. The key here is to create a product or service that can be sold repeatedly with minimal adjustments. This streamlines the sales process, making it easier for others to sell the product or service.

In the early stages of a business, the founders might be the ones doing all the selling. But as the company grows, this becomes less feasible. To reach a larger number of customers, you need to bring others on board to sell for you. This is where standardization comes into play. By standardizing your product or service, you make it easier for others to understand and sell it. 

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Energize and Motivate: Essential Tips for an Effective Sales Kickoff Meeting

Before the year comes to a close, it’s time for sales teams and their leaders to prepare for the annual kickoff meeting. Don’t wait until December to start this process. If you have 50 or more people to invite, you may have to plan 6-9 months in advance. If your group is smaller (under 50), you should start planning by late September or early October.

This crucial event sets the stage for the upcoming year, establishing goals, strategies, and the motivation necessary to hit the ground running. Whether you are a salesperson, a sales manager, or the CEO of a small company, organizing an effective kickoff meeting is imperative to ensure a successful year ahead.

The first step in planning your annual sales meeting is to choose an appropriate venue. While it may be tempting to hold the meeting in your usual office space, it’s beneficial to opt for a location outside of your daily work environment. This helps to minimize distractions and fosters a creative atmosphere. 

A nearby hotel or a conference center can serve as an excellent venue. The key is to find a place where your team can focus entirely on the meeting without the usual interruptions from their day-to-day responsibilities.

Once the venue is secured, it’s time to think about who should be in attendance. While the primary focus will be on your sales team, consider including key personnel from other departments such as marketing, IT, and customer service. These individuals play a crucial role in supporting the sales process and can provide valuable insights and updates that will help your sales team achieve success. Additionally, involving them in the kickoff meeting promotes a sense of unity and collaboration across the company.

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Two Tall Guys Talking Sales – How Sales and Marketing Partnerships Drive Lead Generation and Sales Success – Episode 155

As the year draws to a close, sales leaders and professionals are already looking ahead to the next year. In this episode of Two Tall Guys Talking Sales, hosts Sean O’Shaughnessey and Kevin Lawson dig into the perennial challenge of lead generation, the importance of collaborating with marketing, and why proactive planning is essential for sales success. From refining your messaging to building thought leadership, this conversation is packed with strategies to help you drive revenue generation and sharpen your sales processes.

Key Topics Discussed

  • Why Salespeople Always Say “I Need More Leads” (01:00)
  • The Importance of Partnering with Marketing for Effective Sales Strategies (03:40)
  • Going Beyond Marketing—Referrals, Networking, and Thought Leadership (05:07)
  • Leveraging LinkedIn and Personal Branding to Generate Leads (06:25)
  • The Three Things Every Salesperson Really Sells (09:00)
  • Planning with Intention: Mapping the Next 12 Months for Sales Success (12:57)

Key Quotes

  • Sean O’Shaughnessey (01:48): “You as a salesperson… it’s your job to sit with the marketing people you have and map out the next 12 months of how to get better leads and cover your territory more effectively.”
  • Kevin Lawson (03:40): “Go down the hallway, knock on the door and say, here’s what I’m working on, what are you working on, and how can I help? Be a resource, be a partner to marketing.”
  • Sean O’Shaughnessey (09:24): “There are three things you sell: your product, your company, and—most importantly—you.”
  • Kevin Lawson (13:16): “If you’re only giving 50% effort to your professional practice, you can’t expect championship-level results.”

Additional Resources

  • B2B Sales Lab Community – A peer group for sales professionals to exchange best practices and strengthen their sales management and revenue generation capabilities. Go to https://b2b-sales-lab.com/

A Significant Actionable Item from this Podcast

Schedule a working session with your marketing team this week. Map out the next 12 months of sales and marketing activities, focusing on how you’ll generate leads, build messaging, and increase visibility in your target accounts. Even if it starts with a simple spreadsheet, writing down the plan creates accountability and aligns sales strategies with marketing efforts.

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Sales Management with AI: Chat Interfaces vs. Automation Workflows

Sales organizations today face a critical decision: should they rely on interactive chat interfaces like ChatGPT, Claude, or Gemini, or should they focus on automation workflows? The answer isn’t either/or. Each approach has unique strengths, and choosing the right one directly impacts sales processes, productivity, and revenue generation.

The problem many sales teams encounter is “random implementation.” They hear about a new AI tool, adopt it quickly, and use it for the wrong purpose. The result? Chat interfaces get bogged down with repetitive work, and automation gets tasked with jobs that require creativity and nuance. Misuse not only reduces efficiency but also frustrates teams and erodes trust in artificial intelligence altogether.

So how do you know when chat is the right fit? The decision comes down to task complexity and uniqueness. Chat excels in situations that require creativity, flexibility, and human judgment. Four categories consistently stand out:

  • Creative and strategic tasks: proposals, executive messaging, strategic planning, and competitive positioning.
  • Complex problem-solving: sales opportunity strategy sessions, unique customer needs, and crisis management.
  • Learning and development: role-playing objection handling, skill coaching, and competitive intelligence training.
  • Research and analysis: prospect research, market analysis, and strategic planning.
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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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Two Tall Guys Talking Sales – How to Define Sales Territories for Maximum Revenue Generation – Episode 154

Sales leaders and sales professionals: are your territories setting you up for sales success or holding your team back? 

In this episode, hosts Kevin Lawson and Sean O’Shaughnessey tackle the critical role of defining territories, commission plans, and account strategies. From building fair but effective territories to creating actionable plans that drive revenue generation, this conversation blends sales management insight with practical sales strategies to help you win more consistently and grow with intention.

Key Topics Discussed

  • Defining Territories with Purpose (00:23) – Why intentional design matters more than “spray and pray” selling.
  • Fairness vs. Evenness in Territories (01:27) – Sean explains why territories don’t need to be identical, but they must be logical and fair to prevent turnover.
  • How Salespeople Should Approach New Territories (04:53) – Kevin outlines the mindset and business acumen required to succeed under a new commission plan.
  • Planning Ahead for Sales Success (08:21) – Sean breaks down how early planning impacts Q1 results, revenue management, and long-term sales processes.
  • The Power of Written Territory and Account Plans (12:23) – Kevin explains how documenting your strategies in a CRM enhances value selling and accountability.

Key Quotes

  • Sean O’Shaughnessey (01:10): “When you’re driving down the road, you’re not driving with the mirrors—you’re driving with the windshield. Defining your territory is incredibly important to know where you’re going.”
  • Kevin Lawson (06:00): “A new commission plan is not an indictment of past performance; it’s your executives telling you how and where they want the company to grow.”
  • Kevin Lawson (12:42): “When a plan is written, it’s real. You win more often when your goals and account strategies are captured, documented, and revisited.”

A Significant Actionable Item from this Podcast

Write down your territory and account growth plan before the new year begins. Identify 20 accounts to expand, document the cast of characters (champions, blockers, decision-makers), and map a path to increase revenue generation. Then, enter this plan into your CRM to hold yourself accountable and align with your company’s sales strategies.

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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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Choosing the Right AI Stack for Your Sales Organization

A VP of Sales recently confided in me: “We have six different AI tools, but our reps are still doing manual work. What went wrong?”

This is the AI tool proliferation problem. Sales leaders often collect tools without a strategy, mistaking a pile of features for a cohesive system. It’s like buying a hammer, screwdriver, saw, and drill without realizing you’re actually trying to build a house. An effective AI stack means integration. When tools work together, they amplify each other’s value. When they don’t, they add complexity, confusion, and wasted money.

Why Strategy Beats Random Adoption

Random tool adoption is rampant across sales organizations. Teams chase shiny new software, often ending up with overlapping features, siloed data, and productivity lost to tool-switching. Instead of solving problems, the stack itself becomes the problem.

But when built strategically, the benefits are profound. Integrated systems reduce manual data entry, accelerate response times, and deliver actionable insights for reps. Three well-chosen, well-connected tools can outperform six isolated ones. Integrated stacks also improve adoption rates by providing consistent interfaces and reducing training overhead.

The Five-Layer AI Stack Framework

To avoid the chaos of random adoption, I use a five-layer framework for structuring sales AI tools:

  1. Data Foundation – Your CRM and data management system, enriched and maintained for accuracy.
  2. Intelligence & Analytics – AI-driven insights, lead scoring, forecasting, and market intelligence.
  3. Automation & Workflow – Sequences, task automation, and cross-platform orchestration.
  4. Content & Communication – AI writing, proposal generation, and customer-facing tools.
  5. Optimization & Learning – Conversation analysis, performance tracking, and continuous improvement.
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