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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!

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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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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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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Building a Zero-Cost AI Sales Stack: How to Validate Value Before You Spend a Dollar

Most sales leaders today feel the tension between innovation and fiscal responsibility. You know artificial intelligence can accelerate productivity, clarify messaging, and drive revenue generation. You also know your competitors are implementing AI-driven sales processes and reaping the benefits. Yet you are expected to somehow produce results without the budget to experiment, test, or validate new technology.

This pressure creates the classic chicken-and-egg dilemma. You cannot get budget approval without demonstrating value, but you cannot demonstrate value without access to capable tools. That tension often leaves sales leaders paralyzed, observing advancements but unable to participate. It is an exhausting cycle that erodes confidence and slows down organizational progress.

The good news is that modern software economics have shifted. You no longer need an enterprise-level budget to run meaningful AI pilots. Instead, today’s freemium models allow teams to build real workflows, automate real processes, and create real sales success with no financial risk. These free tiers exist because vendors want you to become reliant on the workflow, meaning you can use that dynamic to your advantage as you design early-stage pilots.

A practical approach for sales management is to treat free AI tools as validation engines rather than long-term solutions. You begin with lightweight experimentation, focusing on a single friction point that slows your team. Whether the issue involves pre-call research, drafting follow-up emails, or scoring inbound leads, AI can automate repetitive tasks, freeing your sellers to focus on value selling. The goal is not perfection; it is measurement.

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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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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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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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Turning Around Sales Performance: Strategies for CEOs and Sales Managers to Foster Internal Alignment

Navigating a sales turnaround isn’t just about fixing numbers; it’s about transforming the business. It’s about realigning expectations, rebuilding internal trust, and creating a structured, sustainable path forward. 

If you’re a CEO, sales manager, or a key salesperson in your organization, the pressure to reverse a sales slump can feel overwhelming. However, the truth is that turnarounds aren’t made in a sprint; they’re built through clarity, consistency, and effective communication.

Too often, sales leaders make the mistake of focusing only on the downward trend. They get caught up in the urgency of the numbers and forget that the real challenge lies in managing upward, setting expectations with executive leadership, and aligning them with reality. 

If your sales team is underperforming, your internal stakeholders are your new audience. Just as with external prospects, you need to manage their expectations with a clear, actionable plan.

The process starts with a shift in mindset. 

Instead of viewing upper management as critics, think of them as clients. What do they need to believe in this turnaround? What information do they need to trust your leadership? Start by building a high-level outline. Avoid over-engineering the details in the early stages. Focus on where you want to go, then reverse-engineer the steps to get there.

Every turnaround starts from a rear position. That means your first job is to stop the downward momentum. Before you can scale revenue, you need to stabilize it. That requires a clear definition of success, agreed upon by everyone involved. 

  • Are you trying to double revenue in 12 months? 
  • Or just return to last year’s baseline? 
  • Is that goal realistic given your market, team, and resources? 

If not, revise it. A stretch goal is fine. A fantasy is not.

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From Reporting to Coaching: Elevate Your One-on-One Sales Meetings to Drive Performance and Trust

A one-on-one sales meeting is not a reporting meeting. It’s not about reviewing what already happened. And it’s definitely not about the manager doing most of the talking. The purpose of a one-on-one pipeline review is to develop the salesperson, surface challenges, and accelerate opportunities. If your one-on-ones are anything less, you’re leaving performance on the table.

Sales leaders often default to micromanagement. 

Especially when the rep is new or struggling. But that approach backfires. It creates dependency and stifles problem-solving. The goal is to coach your reps into leading the meeting. That shift changes everything. When reps own the agenda and bring forward deal-level insights, they’re forced to think critically. That’s where growth happens.

If you’re leading a sales team or are a CEO playing the role of sales manager, you need to establish a clear structure. But the rep does the prep. You define the meeting cadence and format. Weekly or bi-weekly, depending on your velocity. You outline the sections: committed deals, stalled deals, and at-risk deals. 

But the rep fills in the content. They come to the meeting ready to walk you through each opportunity, with specific updates and clear asks.

Preparation is non-negotiable. For both sides. 

The salesperson should have updated their CRM before the meeting. The manager should have reviewed that data in advance. If either party shows up unprepared, the meeting becomes reactive. 

A waste of time. And it erodes trust quickly. 

Reps notice when you haven’t read the notes. They know when you’re winging it. And if they feel their effort isn’t valued, they’ll stop putting in the effort.

You want to create a culture where preparation is expected and rewarded. 

The fastest way to management failure is to ask questions that could have been answered by reading the CRM. Instead, use that time: 

  • To probe deeper. 
  • Ask about the deal strategy. 
  • Challenge assumptions. 
  • Help salespeople spot gaps they missed. 

That’s where your experience has real value.

It’s tempting to jump in and solve the problem. Especially when you see the red flags before the rep does. But resist the urge. Let them talk it through. Coach them toward the insight. Your job isn’t to close the deal; it’s to build someone who can. That means teaching them how to identify weak spots, how to pressure test a deal, and how to re-engage a stalled buyer. The real value of one-on-ones is in that development.

Think about how you coach. 

Are you diagnosing for them? Or are you helping them diagnose for themselves? When a rep says “this deal is solid, no issues,” that’s a red flag. Every deal has risk. Your job is to help them uncover it. Ask: “What’s the biggest thing that could derail this?” Or “What’s the last thing the buyer said that gave you pause?” These questions surface the truth. And they teach reps to self-assess more effectively.

There’s a fine line between coaching and grading. You want reps to be honest about their pipeline without fear of judgment. 

If a deal is weak, that’s not a character flaw. It’s a coaching moment. 

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