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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!

The Future of Prospecting: Using Artificial Intelligence to Read Buyer Intent

The modern salesperson faces two extremes: total blindness or total overload. Some still cold call a list of fifty prospects hoping one will answer, while others drown in dashboards flashing with “intent data.” Both approaches fail because neither interprets what the data truly means.

The future of sales management lies in balance — using artificial intelligence to translate buyer behavior into clear, prioritized action. AI can read digital body language, scoring every click, visit, and download to reveal genuine purchase intent. This isn’t about replacing salespeople. It’s about enabling them with sharper business acumen and faster, more precise decision-making.

When sales leaders align technology with disciplined sales processes, they move from guesswork to guidance. Value selling becomes tangible because messaging is timed to the buyer’s journey, not to the rep’s quota. The best teams build standardized playbooks for each stage — from early curiosity to re-engagement — and rely on revenue management data to decide when to act.

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Differentiating Through Value: Mastering the Art of Consumable Sales

Navigating the competitive landscape of consumable sales calls for a thoughtful and kind-hearted approach. Salespeople, sales managers, and CEOs of small companies should remember that their role is about more than just making transactions. In a market where products often seem very alike in quality and price, what truly sets you apart is your ability to consistently show value. So, how can you create lasting relationships with your customers, even when many options are available?

Consider the analogy of fast-food giants like Burger King and McDonald’s. Both offer similar products, yet they each have a dedicated customer base. The key lies in creating a unique selling proposition that resonates with your target audience. 

As a salesperson, your goal is to become indispensable to your customers. This means transforming from a mere vendor to a trusted advisor who is deeply integrated into the customer’s business operations.

Become Part of Their Team

A critical part of this integration is understanding what a “gatherer” is. A gatherer is more than just an account manager. They build a close, almost inseparable bond with the customer. They become a trusted part of the customer’s team, often turning to them for advice and solving problems together. Building this kind of trust requires a genuine understanding of the customer’s business, enabling you to offer insights and solutions that extend beyond the products you provide.

In the realm of consumable sales, where products are used and replaced regularly, the salesperson’s value lies in their ability to maintain and continually grow the relationship. This involves not just selling a product but also selling yourself and your company. Your expertise, reliability, and ability to anticipate and solve problems become the key differentiators. When customers face challenges, they should instinctively think of you as the go-to person for solutions, regardless of minor price differences or delivery times.

To attain this trusted advisor status, you must focus on three core elements: 

  1. the product, 
  2. the company, 
  3. yourself. 

While the product and the company are essential, the most significant value often comes from you as the salesperson. Your ability to understand the prospect’s needs, guide their purchasing decisions, and challenge them to think differently about their business can set you apart from the competition.

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Two Tall Guys Talking Sales – Sales Management Masterclass: Paul Rafferty’s Proven Framework for Smarter Deal Reviews and Revenue Generation – Episode 159

Welcome back to Two Tall Guys Talking Sales with hosts Kevin Lawson and Sean O’Shaughnessey. In this dynamic episode, the Tall Guys welcome Paul Rafferty from Sales Xceleration to explore the art and science of sales coaching, deal qualification, and the importance of building sales acumen. Paul brings decades of experience in sales management, value selling, and revenue generation, offering a practical framework for sales leaders who want to coach their teams more effectively and for reps who want to stop chasing the wrong deals.

Discover how to transform your team’s approach to sales processes—from opportunity scoring to understanding a buyer’s “pain chain.” This conversation is packed with actionable insights that blend sales strategy, business acumen, and real-world stories you can immediately apply to your own selling environment.

Key Topics Discussed

  • 03:00 — Building a Deal Coaching Framework:
    Paul introduces his 100-point scorecard system that evaluates the Ideal Prospect Profile, the Pain Chain, and Commitment to Decision. This framework transforms deal reviews into powerful coaching sessions rather than mere forecast updates.
  • 05:10 — The “Pain Chain” and Sales Philosophy:
    Sean and Paul discuss how understanding buyer pain isn’t optional—it’s foundational to value selling. Without real pain, there’s no compelling reason for your buyer to act.
  • 06:45 — From Friendly to Effective Salesperson:
    Paul and Sean discuss how friendliness can open doors, but it’s teaching and insight that ultimately win deals. Sales success comes from challenging your prospects and helping them think differently.
  • 08:00 — Why Deals Get Stuck:
    Kevin and Paul explore how most stalled deals trace back to weak discovery. Coaching your team to go deeper early in the sales process prevents gridlock later.
  • 10:30 — The Currency of Knowledge:
    Paul explains that in modern selling, gifts and lunches no longer move the needle—information does. Great salespeople earn influence by being teachers, not vendors.

Key Quotes

  • Paul Rafferty (03:50):
    “It’s not what you do—it’s what they do. The scorecard helps you coach reps to spend time where there’s real buying intent, not just big logos.”
  • Sean O’Shaughnessey (05:43):
    “Salespeople need to understand the theory of sales. Without knowing the frameworks—like the pain chain or solution selling—you’re just saying, ‘I’m a nice guy, buy from me.’”
  • Kevin Lawson (08:38):
    “Most deals go to die in the discovery phase. Coaching means rewinding the tape and helping reps fix what wasn’t done early enough.”
  • Paul Rafferty (12:51):
    “Your currency is information—help your buyer look smart, get promoted, and win internally. That’s real value selling.”

Additional Resources

  • Paul Rafferty
    • prafferty@salesxceleration.com 
    • https://www.linkedin.com/in/pauljrafferty/
  • Books referenced:
    • Solution Selling by Michael Bosworth – https://a.co/d/hHtYSiX
    • The Challenger Sale by Matthew Dixon & Brent Adamson – https://a.co/d/2kJsbDU
    • Strategic Selling by Robert Miller & Stephen Heiman – https://a.co/d/icPcC6H

A Significant Actionable Item from this Podcast

Implement a Deal Coaching Scorecard.
Instead of subjective forecasting (“This deal is 70% likely to close”), create an objective scoring model based on:

  1. Ideal Prospect Fit (25 pts) – Does this prospect align with your best customer profile?
  2. Pain Chain (25 pts) – Have they admitted to a real, solvable pain?
  3. Commitment to Decision (50 pts) – Have they engaged decision-makers and committed to next steps?

Use this tool in your next pipeline review. It will sharpen your sales management coaching, improve revenue forecasting, and elevate your team’s overall sales success. If you want more information about this scorecard, reach out to Paul Rafferty at his address above.

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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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Two Tall Guys Talking Sales – The First 90 Days as a Sales Leader: Proven Strategies for Sales Management Success – Episode 157

When a company hires or promotes its first sales manager, expectations run high, but clarity can be low. In this episode of Two Tall Guys Talking Sales, hosts Sean O’Shaughnessey and Kevin Lawson unpack what the first 90 days should look like for a new sales leader. Whether you’re a CEO onboarding a new manager or that manager stepping into the role themselves, this discussion provides practical guidance on setting realistic expectations, building trust, and establishing the foundation for long-term sales success and revenue growth.

Key Topics Discussed

  • Setting Realistic Expectations as an Owner (02:00)
    Kevin explores how CEOs should frame success during the first 90 days, emphasizing the importance of patience, trust-building, and understanding that sales management transformation takes time.
  • Avoiding the “Fix This First” Trap (06:30)
    Sean cautions business owners against dumping old personnel problems on new leaders, explaining why cleaning up someone else’s mess undermines early business acumen and trust.
  • Building Relationships and Learning the Business (08:30)
    Sean shares tactical advice for new sales managers: conduct one-on-ones, ride along with reps, and build rapport across departments, marketing, operations, and finance, to master internal sales processes and interdepartmental alignment.
  • Understanding Internal and External Tools (11:12)
    Kevin discusses discovering hidden tools and levers, people, systems, vendor programs, or product configurations that can immediately improve team performance and value-selling opportunities.
  • Repackaging and Aligning Offers to the Market (12:30)
    The hosts outline how sales leaders can rethink product structures and messaging to better serve customer needs, thereby improving revenue management and profitability.

Key Quotes

  • “Trust is a currency. It has to be earned by customers, by salespeople, by peers, and you can’t buy it in the first 30 days.”,  Kevin Lawson (03:00)
  • “Don’t make your new sales leader the bad guy. If there’s a tough personnel decision, handle it before they start.”,  Sean O’Shaughnessey (07:00)
  • “Learn your company inside and out. If you don’t know who runs manufacturing or how the supply chain works, you can’t lead your salespeople effectively.”,  Sean O’Shaughnessey (10:00)
  • “You might have 20 products, but 100 possible solutions. The smart leader finds ways to repackage and sell in ways the customer actually values.”,  Kevin Lawson (13:00)

Additional Resources

  • Episodes on sales onboarding, marketing alignment, and ideal customer profiling (ICP) were referenced throughout the conversation.
  • Explore more insights and tools for sales leaders at b2b-sales-lab.com.

A Significant Actionable Item from this Podcast

Create a 90-Day Integration Plan.
If you’re a new sales manager, spend your first month listening and learning. Conduct one-on-ones with every salesperson, schedule cross-department meetings, and document what each function needs from sales. In the second month, identify process gaps and start designing improvements. By the third month, implement one or two visible wins, such as improving forecasting accuracy or clarifying sales messaging, to demonstrate value and build momentum.

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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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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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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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