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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!

From Leads to Clients: How Aligning Sales and Marketing Fuels Sustainable Growth

There’s a common sentiment among sales teams this time of year: a sense of urgency. The calendar flips, Q4 starts, and suddenly it feels like you’re already behind. Sound familiar? That mid-Q4 pressure is real. But before you sprint into outreach and activity, step back and assess what’s actually fueling your pipeline? More importantly, is it aligned with long-term growth?

Sales leaders and CEOs often default to lead generation as the focal point. It’s understandable. More leads, more conversations, more deals, right? But that mindset skips a critical first step. You can’t scale what isn’t aligned. If your marketing message doesn’t match your sales conversations, you’re wasting time and budget. If your sales team is chasing poorly qualified leads, you’re burning cycles. And if your customers can’t articulate why they bought from you, you’ve got a positioning problem.

The foundation starts with clarity. What value do you truly deliver? Why do customers choose you over alternatives? If you can’t answer that in a clear, 50-word statement, your team is likely improvising in the field, and that’s costing you revenue. This is where sales and marketing alignment becomes more than just a buzzword. It’s operationally necessary.

Sales enablement isn’t only about tools and training. It’s about empowering sales with the right message at the right time. That starts with defining three core customer states:

  1. leads,
  2. prospects,
  3. clients.

Each phase requires different messaging, timing, and expectations. Most organizations blur those lines. That’s where inefficiency creeps in.

Leads sit at the top of the funnel. They are either unaware or only lightly aware of your offering. At this stage, marketing owns the responsibility. However, marketing without sales feedback is akin to shooting in the dark. Sales needs to inform marketing what makes a lead qualified.

  • What signals intent?
  • What common objections surface early?

Without that feedback loop, marketing tends to optimize for volume rather than quality.

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Two Tall Guys Talking Sales – The Hidden Driver of Every Sale: Mike Dowhan Explains How Compelling Events Shape Business Acumen and Sales Strategies – Episode 160

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome Mike Dowhan, founder of Bedrock Sales. Together, they explore one of the most overlooked yet transformative aspects of sales management: the compelling event. Mike brings over two decades of experience helping organizations refine their sales processes, understand buyer motivation, and drive consistent revenue generation. Whether you’re a frontline seller or a sales leader guiding a team, this episode unpacks how identifying and leveraging compelling events can be the difference between chasing deals and closing them confidently.

Key Topics Discussed

  • The Power of the Compelling Event (01:12) – What defines a compelling event and why it’s the “why” behind every great sale.
  • Asking Better Discovery Questions (03:00) – How to uncover the root cause that motivates buyers to act now rather than later.
  • Getting Permission to Go Deep (07:17) – Why earning trust allows salespeople to ask the tough, business-critical questions.
  • Compelling Events vs. Compelling Needs (09:53) – The distinction between recognizing a real deadline versus a vague desire for change.
  • Surfacing the Cost of Inaction (10:38) – How to use timing, impact, and risk to create urgency without manufacturing pressure.

Key Quotes

  • Mike Dowhan (03:49): “What caused you to pick up the phone or take my call today? What’s different today than yesterday? That’s where you find the real reason a buyer is ready to move.”
  • Sean O’Shaughnessey (02:29): “If there’s no compelling event, it becomes very difficult. You’re pushing the boulder uphill, fighting the same battle over and over.”
  • Kevin Lawson (12:00): “Finding permission and tracking back to that event is where we create real value, and avoid the trap of commoditization.”

Additional Resources

A Significant Actionable Item from this Podcast

Start every discovery conversation with one simple question:

“What changed today that made you want to talk to me?”

This question reveals your buyer’s compelling event, the emotional and operational trigger that drives their need to act. Understanding that moment transforms your sales strategy from reactive to consultative. Use it to align your messaging, reinforce your value-selling approach, and accelerate revenue growth.

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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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Stop Researching, Start Connecting: An AI-Powered System for Warm Introductions

Most sales teams begin the week by opening a dozen browser tabs and grinding through scattered research, LinkedIn, Google News, company websites, and databases. Hours later, they emerge with a few generic talking points and a cold list that still feels cold. The deeper issue isn’t inefficiency; it’s invisibility. Warm introductions already exist across your company’s network, in email histories, calendars, and executives’ LinkedIn connections, but you can’t see them on Monday morning.

The Relationship-First approach changes that default. Before a single cold call or email, you perform a deliberate “Warm Path Check.” You ask, “Who do we know who knows them?” This question transforms prospecting from random outreach into a repeatable, data-driven process that prioritizes relationships. When you start as a referred conversation rather than an interruption, skepticism drops, credibility rises, and the sales cycle compresses dramatically.

The Hidden Network You’re Not Using

Every organization has an untapped network, a web of past colleagues, vendors, and clients who could open doors to your dream accounts. The problem is that this network is hidden in plain sight. It lives in the collective memory of your company’s communication patterns, but there’s no easy way to access it manually. That’s where KnowledgeNet comes in.

KnowledgeNet serves as your organization’s “relationship intelligence” layer. It analyzes communication data (emails, meetings, messages) to reveal who knows whom, and how strong those connections really are. Instead of guessing, you can instantly see that a colleague in engineering once worked closely with the CFO of a target account. That’s a warm path waiting to be used.

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Beyond Spell Check: How Grammarly’s AI Can Transform Sales Communication

Clear, professional communication is the foundation of sales success. Yet, in 2025, much of our selling occurs not face-to-face, but through written words, emails, proposals, CRM notes, and social media messages. This shift means your writing is no longer just a form of communication; it’s your personal brand, your first impression, and often the deciding factor in whether a conversation continues or comes to a halt.

Grammarly has evolved far beyond its original purpose as a grammar checker. Today, it’s an artificial intelligence–powered platform that helps sales teams increase efficiency, refine their messaging, and accelerate revenue growth. It works directly within the tools you already use, such as Gmail, LinkedIn, Salesforce, and HubSpot, helping sales professionals write with greater confidence and clarity.

Sales organizations using Grammarly have seen measurable improvements: Databricks saved $1.4 million annually; Smartsheet cut thousands of hours from proposal creation; and Zoom reported higher customer satisfaction thanks to improved written communication. These results aren’t luck; they’re the product of refined sales processes, consistent messaging, and clear communication supported by AI.

For individual salespeople, Grammarly helps improve value selling by ensuring that every message is professional, engaging, and on-brand. Its AI engine not only corrects errors but also suggests stronger phrasing, predicts reader reactions, and even aligns your tone with your business acumen and brand voice. For sales leaders, it standardizes team communication and reinforces a culture of professionalism across departments.

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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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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 – Future-Proofing Your Sales Career with AI, Strategy, and Smarter Workflows – Episode 144

Is artificial intelligence coming for your sales job? Not if you understand the power of business acumen, value selling, and strategic adoption of tools that amplify, not replace, human expertise. In this high-impact episode of Two Tall Guys Talking Sales, Kevin and Sean tackle the loud claims of AI-induced layoffs with a grounded, practical message for salespeople and sales managers: evolve or fall behind. This is not a doomsday episode; it’s a wake-up call, a… Two Tall Guys Talking Sales – Future-Proofing Your Sales Career with AI, Strategy, and Smarter Workflows – Episode 144

Two Tall Guys Talking Sales – Building a Sales Powerhouse—The 3 Most Underrated Skills with Jeff Parris – Episode 143

Sales isn’t about persuasion but service, resilience, and growth. In this episode of Two Tall Guys Talking Sales, co-hosts Kevin Lawson and Sean O’Shaughnessey welcome sales leader and former professional athlete Jeff Parris to explore the fundamental skills that separate elite salespeople from the rest. Drawing on decades of experience, Jeff shares three often-overlooked yet foundational competencies that drive sales success, and they’re not what you’d expect. Whether you’re a VP of Sales building a… Two Tall Guys Talking Sales – Building a Sales Powerhouse—The 3 Most Underrated Skills with Jeff Parris – Episode 143

Two Tall Guys Talking Sales – Chris Spanier Explains Marketing Professional Services: Sales Strategies That Actually Work – Episode 142

When marketing professional services, the playbook isn’t the same as product sales, and today’s episode dives into exactly why. Sean O’Shaughnessey and Kevin Lawson are joined by returning guest Chris Spanier, CEO of Carpe Diem Consulting Group and host of the Practical Actionable Marketing podcast. This conversation tackles the nuances of sales strategies for service-based businesses, blending value selling with measurable marketing and aligning both functions for stronger revenue generation. If you’re a business owner,… Two Tall Guys Talking Sales – Chris Spanier Explains Marketing Professional Services: Sales Strategies That Actually Work – Episode 142