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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 Dual Blueprint Requirement: Why Growth Demands Two Plans, Not One

Launching a company or steering one through a merger, turnaround, or major transition requires clarity about how value will be created and, just as importantly, how revenue will actually be generated.

Many leadership teams recognize the need for a Business Plan, but overlook that sustainable growth requires a second, complementary plan. The main breakdown is not the strategy itself, but the assumption that strategy automatically creates revenue. Bridging strategy and revenue requires a distinct plan for that conversion, targeting a different audience.

The Business Plan sets direction from the top down. The Sales Plan is validated by demonstrating how that direction can become actual revenue from the bottom up.

Both are essential. Neither works in isolation.

The Business Plan: Charting the Course (Top-Down)

The Business Plan exists to answer specific questions for a particular audience. Its primary readers are CEOs, CFOs, bankers, private equity partners, and venture investors. These stakeholders are evaluating risk, scale, and return. They want to know where the company is going and why the destination is worth the journey.

At its core, the Business Plan articulates strategic intent. It defines the mission, the long-term objectives, and the differentiated value proposition that the company believes the market will reward. It frames the opportunity in language that aligns leadership, capital, and governance.

Market analysis in this context is necessarily high-level. It focuses on the total addressable market, industry dynamics, competitive positioning, and macro trends. The goal is not to explain how every deal will be won, but to establish that a meaningful opportunity exists and that the company has a credible right to pursue it.

Financial projections follow the same logic. They are built on broad assumptions: projected market share, average selling price, renewal and retention rates, inflation, and multi-year revenue targets. These numbers are directional. They signal ambition and scale rather than operational certainty.

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Stop Betting on Superstars: How Operating Standards Turn Sellers into Predictable Producers

Many teams grow, but few truly scale revenue beyond individual hero efforts. That difference changes everything for leaders today and in the future. Growth relies on hustle; scaling depends on repeatability across segments and individuals. Your strategy must reflect that hard truth in practice.

Are you relying on one standout to win deals month after month? That looks strong until risk turns visible and costly. One resignation can cripple momentum and expose brittle systems that you had previously ignored.

Scalable sales replaces heroics with defined, teachable operating rhythms that everyone follows. It turns chaos into predictable pipeline progress and results. It clarifies markets, messages, motions, and measurable expectations for every seller on a weekly basis. It builds leverage into onboarding and coaching for consistency. It protects margins while systematically accelerating win rates and velocity across territories.

The foundation begins with a clear picture of your ideal customer, including any disqualifying factors. Having an accurate Ideal Client Profile (ICP) helps minimize waste and reduce uncertainty in your efforts. Take time to define firmographics, pain points, triggers, and buying behaviors using consistent language based on shared evidence. Understand who cares about these issues and why it matters to them now. Also, identify negative personas to sharpen your focus and qualification processes in marketing and sales. A well-defined ICP can significantly boost your conversion rates and shorten the sales cycle.

Next, turn your ICP into straightforward messaging and discovery frameworks tailored for each stage. Consider what unique problems you solve for your customers. What outcomes are most important to them, and who are the key stakeholders by role and priority?

Build talk tracks that lead buyers, not chase buyers with purpose always. Anchor questions to the business metrics and risks they feel. Teach a qualification that tests mutual commitment and outlines next steps with attached dates. Avoid fluffy demos; design relevant proofs using their data. Process specificity turns B players into consistent producers without copying another personality.

I suggest you establish a practical, stage-based operating rhythm that everyone can easily understand and follow. By sharing clear definitions and expectations, managing the pipeline becomes a consistent and smooth process each week. Define each stage with specific exit criteria—avoiding vague intentions or subjective feelings. For example, discovery is considered complete when stakeholders confirm the consequences and impact, and solution fit is achieved when success criteria and ownership are clearly aligned. The commit stage should be backed by a shared plan with clear dates and assigned owners. During weekly reviews, focus on assessing quality rather than just quantity or activity counts. Ask yourself:

  • Does evidence from buyers’ backstage moves have a direct impact on their purchasing decisions?
  • Are the next steps specific, mutually agreed upon, and already scheduled on both calendars?
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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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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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Transforming Quota-Setting: Strategies for Sales Leaders to Optimize Performance and Revenue

Quota-setting is one of the most misunderstood elements of sales leadership. Too often, it’s treated as a spreadsheet exercise or a top-down directive, rather than a strategic lever that drives behavior, performance, and growth.

Whether you’re leading a team of 20 or you’re the founder managing three reps, how you define quotas has a direct impact on your revenue trajectory and your team’s motivation.

So, where do you start?

With timing. If you’re not delivering quotas to your team until February or March, you’re already behind. Salespeople need clarity by December. That gives them runway to plan, prioritize, and hit the ground running in January. Delayed quotas create confusion and stall momentum. To achieve a strong Q1, you need to equip your team early.

Quota-setting varies depending on the size of your company. Larger teams offer more flexibility. With 10 or more reps, you can spread risk, balance performance, and model averages. You’ll have top performers who consistently overdeliver, alongside newer reps who are still ramping up. The law of averages works in your favor. You can afford some variance. Smaller teams don’t have that luxury.

When you’re running a small team, maybe two or three reps or founder-led sales, every individual matters. One person missing quota can tank your number.

You can’t rely on averages. You need precision.

That means tying quotas to actual relationships, known opportunities, and real probability. It’s not about slicing up a target evenly. It’s about assigning numbers based on what’s realistically achievable in each territory or account list.

Territory design plays a big role here. Whether it’s geographic, vertical, or named accounts, quota must reflect the market potential. You can’t expect equal performance from unequal opportunity. If Rep A has 500 viable accounts and Rep B has 50, their quotas shouldn’t look the same unless you have data that says Rep B’s accounts are closer to your Ideal Client Profile. Use available market data to inform the number. Don’t assign quotas in a vacuum. 

In larger organizations, quotas often originate from the top down, typically from finance. The CEO and CFO commit a growth number to the board, investors, or in public filings to the SEC. They have no choice but to pass it down. It’s not uncommon for the sales team to receive the number without context. That’s a problem. If you’re in a leadership role, you need to pressure test that number. Can your team realistically hit it? If not, what additional resources are required?

  • More headcount?
  • Better enablement?
  • Marketing support?

In large organizations where the quota is driven by investor expectations, the VP of Sales must establish an organization well before the new year that achieves this year’s goal, while also meeting the expectation of growth for the next year. Planning ahead, sometimes years in advance, is part of the job.

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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?

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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Two Tall Guys Talking Sales – Elevate Your Sales Game with B2B Sales Lab: A New Resource for Revenue Growth – Episode 141

When sales professionals hit a roadblock, where do they turn? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey unveil an exciting new initiative: B2B Sales Lab, a private peer networking community designed to support salespeople, sales managers, and business owners in their journey toward revenue generation excellence. This isn’t just a conversation; rather, we are offering an invitation to join something powerful. If you’ve ever felt alone in a… Two Tall Guys Talking Sales – Elevate Your Sales Game with B2B Sales Lab: A New Resource for Revenue Growth – Episode 141

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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