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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!

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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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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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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The Evolution of Sales: Scaling from 10 to 100 Customers

The journey of a business unfolds as a story of growth, change, and ongoing adaptation. As salespeople, sales managers, and CEOs, we all share the ups and downs that come with this path. One of the most exciting moments in sales is the shift from landing your first ten customers to growing your family of clients to 50 or even 100. This milestone is truly a game-changer, shaping the future direction of your business.

When you’re starting, your focus is on acquiring those first ten customers. You’re trying to find your footing in the market, identify your target audience, and refine your 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, you need to start thinking about systemizing your sales process. 

To grow successfully, it’s helpful to have a standardized product or service. While customizing can be useful when you’re just starting out, it can become hard to manage and slow you down as your customer base expands. 

Focus on creating a product or service that you can sell over and over again with just small tweaks. This approach simplifies your sales process and makes it easier for others to sell your offerings, too.

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Two Tall Guys Talking Sales – What Got You Here Won’t Get You There: How Sales Leaders Master the Pivot for Revenue Growth – Episode 158

In this episode, hosts Kevin Lawson and Sean O’Shaughnessey tackle one of the most fundamental truths in business and sales leadership: change is inevitable. Whether you’re managing a sales team, scaling from $5M to $50M, or repositioning your company for new markets, your success depends on your ability to pivot,  intelligently, decisively, and confidently. Sean and Kevin unpack the concept of organizational pivots through real-world examples, from manufacturing supply challenges to Domino’s Pizza’s legendary turnaround, and offer practical advice for how sales leaders can prepare their teams to thrive through transformation.

Key Topics Discussed

  • The Only Constant Is Change (00:16) — Why modern business demands leaders who can adapt and guide teams through shifting markets.
  • The Power of the Pivot (02:52) — Kevin explains what a pivot really means and how small, consistent course corrections can transform outcomes.
  • Real-World Example: Domino’s Pizza Reinvention (06:10) — A masterclass in transparency and messaging that rebuilt a brand from the ground up.
  • Training as the Foundation of Change (09:21) — Sean breaks down how strategic training helps sales teams pivot effectively into new markets or industries.
  • Peer Learning and the Role of Community (12:33) — The importance of collaboration, conversation, and communities like the B2B Sales Lab for accelerating sales success.

Key Quotes

  • “As CEOs and sales leaders, we have to lead through change. What got us here is not going to get us there.”
    — Sean O’Shaughnessey (01:34)
  • “Sometimes people don’t need a 180-degree pivot. They just need to be repointed — one degree of change over time can take you somewhere entirely new.”
    — Kevin Lawson (04:42)
  • “The first part of making a pivot is planting your foot — and that’s training. You can’t change direction until your team knows how.”
    — Sean O’Shaughnessey (11:22)

Additional Resources

  • Book Mentioned: Who Moved My Cheese? by Spencer Johnson — A timeless read on navigating change in business and life. https://a.co/d/cCEXuwA
  • Community Resource: B2B Sales Lab — A peer-driven community for B2B sales professionals and leaders to exchange ideas, test messaging, and sharpen their skills. www.b2b-sales-lab.com

A Significant Actionable Item from this Podcast

Before the day ends, write down five things you could do to change the trajectory of your sales growth or turnaround.
Then, rank them:

  • Which are big strategic plays?
  • Which are medium-term moves?
  • Which are quick wins you could execute immediately? Assign probability, effort, and impact to each, then commit to one action this week. Leadership begins with deliberate motion, not massive overhauls.
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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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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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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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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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