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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!

How to Build a Sales Organization That Survives a Founder Exit

Navigating the complexities of business transitions can be quite a journey, especially for those in sales and leadership roles. When a founder chooses to pass the baton, whether through selling to someone outside the company, passing it within the family, or setting up an employee stock ownership plan, each option comes with its own unique challenges and chances for growth. For salespeople, sales managers, and CEOs of small companies, understanding these dynamics is really important.

When a business owner considers selling to an external buyer, they often experience a surprising realization: the valuation shock. It’s common for owners to overestimate their company’s worth, only to encounter a reality check during the valuation process. This moment is so important because it influences all future negotiations and strategies. Buyers don’t just look at the numbers; they also carefully examine the business’s sales processes and the owner’s involvement. Here, the owner’s role as the main salesperson can be both a strength and a challenge. If the owner accounts for a large share of sales, such as 30%, it can worry potential buyers. 

The key is to build a business that can thrive even when the owner isn’t around, supported by a solid sales system and a talented team eager to keep everything running smoothly.

For the owner contemplating a sale, preparation is key. 

The question to ponder is: what if you were suddenly unavailable? 

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Build a Repeatable Sales Process Using Buyer Personas

In the world of sales, consistency is a cornerstone for success. Salespeople, sales managers, and CEOs alike strive to find a sustainable way to grow their business, and one effective strategy is to focus on buyer personas. Identifying and understanding these personas can streamline the sales process, making it easier to target the right customers and tailor your approach to meet their specific needs.

Consistency is key. When you consistently sell to profitable companies that see value in your solutions, you can standardize your sales processes and messaging. This consistency allows you to tweak and improve your methods incrementally, rather than making wild changes that may not lead to profitability. Many small companies don’t have the luxury of unlimited cash flow. They need to be mindful of their line of credit and ensure that their accounts receivable don’t get out of hand. By focusing on companies that are easy to sell to and where your product or service fits seamlessly, you can make your clients successful and maintain a steady growth trajectory.

The entrepreneurial operating system (EOS) is a valuable framework that helps businesses achieve consistency. By setting firm foundational corners, such as data, people, and core processes, businesses can create a structured environment where everyone can succeed. For sales departments, this means formalizing not only the messaging but also the reporting structure, job descriptions, core goals, and key behaviors. Consistency in these areas leads to reliable and repeatable results.

A repeatable sales process is crucial. If everything is custom, nothing is standardized, and this can lead to chaos. Sales leaders must set the standard for consistency, and both business owners and salespeople need to align themselves with these consistent behaviors. Standardizing the sales process enables better forecasting and a more predictable customer flow.

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What Kind of Sales Coach Are You?

Repeatable revenue comes from a coachable system, and a coachable system starts with clarity on “why” the salesperson wins.

Most sales managers try to scale results by cloning the top producer. That works only when the top producer is running a repeatable motion, with controls, standards, and decision points that the team can execute under pressure. When it’s personality-driven, you end up managing a talent show instead of a pipeline.

If the sales manager can’t explain why their cadence works, why they qualify the way they do, why they push back on certain requests, then they’re operating on instinct. Instinct can close deals, but it can’t be trained, forecasted, or improved.

Actionable takeaway: write the 5–7 moves that create forward motion, then add the one-sentence “why” behind each move. That becomes the start of a real operating system: something you can inspect in 1:1s, reinforce in pipeline reviews, and measure over time.

If you’re leading a team, the decision is simple: are you building a program that survives turnover, or rewarding heroics that disappear the moment the top rep changes seats?

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Why AI in B2B Sales Fails at the Last Mile and How to Fix It

Most conversations about AI in B2B sales focus on speed. Fewer focus on control. That is the blind spot.

AI can produce drafts, summaries, research, and follow-up frameworks in seconds. That part is real. But the final 20%, the last mile, is where revenue quality is either protected or destroyed. That final layer requires human judgment: context, timing, risk assessment, and the decision of what should happen next.

The central operating issue in sales today is not effort. It is an allocation. Too many high-value salespeople are spending prime hours on low-value administrative work. CRM cleanup. Internal updates. Document hunting. Manual transcription. Reformatting information that should already be structured. That is a sales management design flaw, not a rep discipline issue.

When sales organizations fix this, performance changes fast. More customer-facing time creates more trust-building interactions. More trust creates better access, stronger positioning, and better conversion outcomes. This is not theoretical. It is how revenue generation compounds in real markets.

The right model is not “AI only.” It is a hybrid model: deterministic automation for correctness, AI for speed and language quality, human oversight for business judgment.

Deterministic systems should control anything that must be exact: pricing, contract elements, offer logic, approval rules, and data integrity. AI should then layer natural language, personalization, and messaging refinement on top of verified inputs. This is how you scale value selling without introducing preventable errors.

If your team is still using AI as a standalone drafting tool, you are under-leveraging it. If your team is sending AI output without last-mile review, you are overexposing the business. The goal is not automation theater. The goal is repeatable, high-confidence sales processes that increase throughput without compromising trust.

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Hiring Your First Sales Leader? Build a Sales Machine, Not a Band-Aid

You are ready to hire your first sales leader when you are prepared to buy leverage, not relief. Titles do not grow revenue. A high-impact sales leader creates durable selling capability, reduces owner dependency, and raises standards through coaching, recruiting, and operating cadence. If what you really want is a second version of you to carry the number and keep deals moving, you are hiring a band-aid, and you will pay for it twice.

Most owners make this hire at precisely the wrong moment. The pressure is real, the pipeline feels fragile, and the business is starting to outgrow informal management. So the owner reaches for the obvious move: “We need a sales manager.” The problem is that the role is designed around short-term comfort rather than long-term capacity. The result is a well-paid administrative firefighter who inherits the chaos instead of fixing the system that creates it.

Before you post a job, clarify the objective. Do you want a revenue driver or a capability builder?

A revenue driver is a manager who helps you hit the number by conducting deal inspections, applying forecast pressure, and holding reps accountable. That can be valuable, but it is often a disguised need for personal production. A capability builder is a leader who creates repeatable performance by improving the quality of selling, tightening hiring standards, and building a coaching system that makes average reps better and good reps consistent. That is the role that changes enterprise value.

Here is the hard truth most owners avoid. If you design a role that combines selling and leading, selling will win. Always. When a leader has a quota, the business trains them to prioritize their own deals over the team’s development. They will “help” reps when a deal is in a late-stage, visible phase, then postpone coaching, recruiting, and onboarding because those activities do not pay this month. Over time, the team remains dependent, the pipeline remains uneven, and the owner remains in the middle.

Assessing readiness: leader or band aid

Readiness is not a revenue threshold. It is an operating decision. The question is whether you will let a sales leader lead.

The owner’s trap is hiring a leader while keeping day-to-day control: still running reviews, intervening in pricing, rewriting emails, jumping on calls, and closing important deals. In that environment, the new leader cannot build authority; they become an assistant with a title. You’ll be frustrated they’re “not taking enough off my plate,” while they’re frustrated at not being able to make decisions without you.

If you want a clean test, look for these warning signs:

  • You are still the primary deal closer and default problem solver.
  • You do not believe the company can make the number without your direct involvement.
  • You step into deals because you do not trust the process, the rep, or the forecast.
  • Your coaching is ad hoc, usually when something goes wrong.
  • Recruiting is episodic, triggered by pain, rather than continuous.
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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 – 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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