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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!

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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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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Two Tall Guys Talking Sales – Winning Sales Strategies for Productive, High-Impact Pipeline Reviews – Episode 149

Pipeline reviews don’t need to feel like an ambush. In this episode, Kevin Lawson and Sean O’Shaughnessey break down how to turn pipeline meetings into high-value working sessions that improve sales management, strengthen sales processes, and accelerate revenue generation. The conversation focuses on preparation discipline, trust, and transparency, as well as a practical playbook for advancing complex deals through relationship mapping and peer-to-peer executive engagement. You’ll hear straightforward sales strategies you can implement immediately, whether… Two Tall Guys Talking Sales – Winning Sales Strategies for Productive, High-Impact Pipeline Reviews – Episode 149

The Three Pillars of Sales Success: Ideal Client Profiles, Effective Messaging, and Aspirational Offers

Let’s start this article with a rhetorical question to the sales professionals, sales managers, or CEOs: Have you ever found yourself guilty of sending messages to prospects without fully considering their specific needs or how your offer aligns with them?

If so, you’re not alone—this is a common pitfall in sales. The good news is, it’s entirely fixable by developing a straightforward, strategic approach.

An effective sales strategy hinges on three core components: defining your ideal client profile (ICP), crafting a resonant message, and presenting a compelling offer. These elements are interconnected. Mastering their alignment will significantly enhance your sales effectiveness.

Ideal Client Profile

Let’s start with the ideal client profile. How well do you know the companies you’re targeting? Identifying your ideal customer is foundational to your entire sales approach. It’s not enough to say that your market is “small businesses” or “tech companies.” Instead, think about your best clients—the ones you genuinely enjoy working with, who value your product, and who generate profitable, sustainable business. Think about companies that rarely devalue your product or service by asking for a discount. What do these clients have in common?

Now that you have your favorite customers from above, reflect on your top five or ten accounts. Are they in the same industry? Do they share similar challenges or company structures? Perhaps they all have common goals that your product consistently solves. Pinpoint these commonalities. This process will help you create a precise and actionable ideal client profile.

But don’t stop at company-level characteristics. Remember, even in B2B sales, you’re ultimately selling to individuals. Identify the specific roles or buyers within these organizations that are responsible for making buying decisions. Who are these decision-makers? What motivates them personally and professionally? Do they all have the same kind of college education? Do they all have similar career paths? Understanding the people behind the logo makes your outreach more personal, targeted, and effective.

What is your message?

Once you’ve developed a clear picture of your ideal client and the people within those companies, the next step is crafting a message that reflects your value-selling message. This message is how you communicate your value proposition—it’s the bridge between your product and your prospect’s needs. Too often, sales messaging falls flat because it focuses heavily on the seller rather than the buyer. Statements that emphasize “we,” “I,” or “our product” rarely resonate deeply. Instead, effective messaging highlights the customer’s perspective, clearly communicating the benefits they will experience.

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Maximizing Sales Team Productivity: The Importance of Effective Sales Meetings

Numerous factors can contribute to a sales team’s success or failure. Two key aspects that are often overlooked yet hold immense importance are the structure and content of sales meetings. These gatherings are not just about reporting numbers or discussing targets. They are platforms for learning, sharing, and strategizing that can significantly boost a sales team’s performance.

One of the fundamental principles of a productive sales meeting is having a clear plan. This doesn’t mean having a rigid agenda without room for spontaneity. On the contrary, it’s about having a framework that guides the discussion and ensures that the meeting stays focused on the key topics at hand. 

A common mistake many sales leaders make is covering too many topics in a single meeting. In an attempt to address every issue, they often skim the surface of each topic without delving deep into any. The result is a meeting lacking depth and tangible insights or solutions. Limiting the number of key topics to one or two per meeting is advisable to avoid this. This allows for a more in-depth discussion and a better understanding of the issues at hand.

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Maximizing Productivity in Sales Meetings: Key Principles and Best Practices

Sales meetings are the lifeblood of any sales-driven organization, providing an essential forum for communication, collaboration, and strategy development. Yet, despite their significance, many salespeople, managers, and CEOs struggle to conduct productive and efficient meetings. This issue often stems from a lack of understanding of key meeting principles and best practices, particularly in the areas of time management, content planning, and participant engagement.

The adage “time is money” holds especially true in sales. Every minute counts, and wasted time equates to lost opportunities. This is why punctuality is of the utmost importance. A meeting that starts late or runs over time is disrespectful to participants and detrimental to the team’s overall productivity. 

To avoid this pitfall, sales leaders should ensure they always arrive early to meetings and start them on time, without exception. This requires careful planning and preparation, as well as a commitment to respecting the time and schedules of others. The same principle applies to the end of the meeting. Sales leaders should always strive to conclude meetings on time, which requires careful meeting agenda management and a willingness to keep discussions focused and on track.

Content planning is another crucial aspect of effective meeting management. Just as a ship needs a compass to navigate the seas, a meeting needs an agenda to guide its proceedings. A well-crafted agenda provides a clear structure for the meeting and helps to keep discussions focused and productive. It also sets clear expectations for participants and helps to ensure that all relevant topics are covered.

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Enhancing Sales Performance Through Effective One-on-One Coaching Meetings

The effectiveness of sales management is paramount, particularly in how sales managers support their team members to enhance performance. The nuanced relationship between a salesperson and their manager can significantly influence their success, a topic that is gaining traction among CEOs and sales leaders seeking to maximize their team’s capabilities. One-on-one meetings between sales managers and salespeople are not just routine check-ins but pivotal moments that can define a sales team’s success trajectory. These interactions… Enhancing Sales Performance Through Effective One-on-One Coaching Meetings

King of Spades: Pre-Call Strategic Planning: Prepare in Advance to Present a United Front With Management During Sales Calls

Harmonizing Sales and Management: A Prelude to Success The intricate dance of a joint sales call, where the sales team and top management come together, can be likened to a finely tuned orchestra. Each member plays a distinct part, but harmony is only achieved when everyone is attuned to the same melody. As such, aligning the sales strategy with the expectations of top management is not just beneficial—it’s essential. Dissonance here can lead to a… King of Spades: Pre-Call Strategic Planning: Prepare in Advance to Present a United Front With Management During Sales Calls

Two Tall Guys Talking Sales Podcast – A Roadmap for Successful Sales: Strategy, Tactics and More – Episode 36

In this dynamic episode of the “Two Tall Guys Talking Sales” podcast, hosts Kevin Lawson and Sean O’Shaughnessey, delve into the importance of strategy in successful sales performance. Using a navigational analogy, the hosts discuss how just like using an app like Waze, successful sales also requires anticipation and understanding of the challenges on the way. Drawing parallels between navigation and sales, Kevin and Sean underscore the value of proactive strategic planning. From the importance… Two Tall Guys Talking Sales Podcast – A Roadmap for Successful Sales: Strategy, Tactics and More – Episode 36

Two Tall Guys Talking Sales Podcast – Focus on One or Two Key Topics in Your Weekly Sales Meeting – Episode 22

Your sales meeting should discuss the highest priority topics that require immediate attention. For broader issues, it is recommended to use other venues. To stay on point, it is important to control the agenda and flow of the meeting. Additionally, meeting minutes should be kept short and focused on action items to ensure that tasks are completed following the meeting. Discussing one or two topics deeply rather than many topics lightly is recommended to promote… Two Tall Guys Talking Sales Podcast – Focus on One or Two Key Topics in Your Weekly Sales Meeting – Episode 22