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strategic planning

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!


Sales Management with AI: Chat Interfaces vs. Automation Workflows

Sales organizations today face a critical decision: should they rely on interactive chat interfaces like ChatGPT, Claude, or Gemini, or should they focus on automation workflows? The answer isn’t either/or. Each approach has unique strengths, and choosing the right one directly impacts sales processes, productivity, and revenue generation.

The problem many sales teams encounter is “random implementation.” They hear about a new AI tool, adopt it quickly, and use it for the wrong purpose. The result? Chat interfaces get bogged down with repetitive work, and automation gets tasked with jobs that require creativity and nuance. Misuse not only reduces efficiency but also frustrates teams and erodes trust in artificial intelligence altogether.

So how do you know when chat is the right fit? The decision comes down to task complexity and uniqueness. Chat excels in situations that require creativity, flexibility, and human judgment. Four categories consistently stand out:

  • Creative and strategic tasks: proposals, executive messaging, strategic planning, and competitive positioning.
  • Complex problem-solving: sales opportunity strategy sessions, unique customer needs, and crisis management.
  • Learning and development: role-playing objection handling, skill coaching, and competitive intelligence training.
  • Research and analysis: prospect research, market analysis, and strategic planning.
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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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Two Tall Guys Talking Sales Podcast – The Art of Targeting: How Small Sales Teams Can Win Big in Expansive Territories – E111

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the challenges and strategies of managing large sales territories, especially for teams with fewer than five sellers. Reflecting on their extensive sales careers, they explore the intricacies of balancing time, travel, and targeting the right clients when facing expansive regions. Kevin and Sean share actionable insights on refining the ideal client profile (ICP) and discuss how small business… Two Tall Guys Talking Sales Podcast – The Art of Targeting: How Small Sales Teams Can Win Big in Expansive Territories – E111

Proactive Coaching: The Key to Unlocking Exceptional Sales Performance

A shift is occurring away from simply correcting problems after they’ve happened toward a more proactive and developmental approach to coaching sales teams. This evolution in strategy empowers sales leaders, CEOs, and managers to not only meet but also exceed their targets through effective team management and personal development. The concept of continuous improvement in sales begins with a focus on coaching. Unlike traditional reactive methods, modern sales leadership emphasizes coaching as a tool for… Proactive Coaching: The Key to Unlocking Exceptional Sales Performance

Boosting Business Performance: Integrating Sales and Marketing Efforts

The symbiotic relationship between sales and marketing is more crucial than ever. This dynamic duo drives the revenue generation engine, which is especially crucial when businesses are keen to set a positive trajectory. Marketing’s influence cannot be understated. It often shapes the business’s success months in advance. Strategies implemented by marketing today can significantly impact revenue streams later in the year. Therefore, it’s essential for sales and marketing to align and integrate their processes to… Boosting Business Performance: Integrating Sales and Marketing Efforts

Optimizing Sales Territories for Growth and Efficiency

Territory design is critical for ensuring efficient revenue generation and optimal team performance. Sales leaders, especially those at the helm of small—to mid-sized companies, must revisit and potentially recalibrate their territory strategies to accommodate growth and maintain competitiveness. Effective territory management starts with a clear understanding of the business landscape. Ensuring that each salesperson has a viable area with ample opportunity is crucial. This may sound straightforward but involves a delicate balance of geographic and… Optimizing Sales Territories for Growth and Efficiency

Competitive Edge in Crowded Waters: Mastering Red Ocean Strategies for B2B Growth

In the lexicon of strategic business planning, the concepts of “Red Ocean” and “Blue Ocean” serve as metaphors to distinguish between different market dynamics characterized by the degree of competition. A Red Ocean symbolizes sectors with fierce competition, saturated markets, and businesses clash over a finite demand pool. The landscape is marked by aggressive price wars and incremental innovations as companies struggle to carve out and defend their market share. These are arenas where the… Competitive Edge in Crowded Waters: Mastering Red Ocean Strategies for B2B Growth

Beyond Numbers: The Leadership Behind Effective Quota Management

In B2B sales, mastering the art of quota setting and management is a critical factor driving sales teams’ success across various industries. Whether you’re navigating the complexities of software sales, the intricacies of service offerings, or the demands of manufacturing and distribution, the ability to set realistic yet challenging quotas can significantly impact your team’s performance and, ultimately, your company’s bottom line. This article delves into the essential aspects of quota management, offering valuable insights… Beyond Numbers: The Leadership Behind Effective Quota Management

Crafting Your Path to Success: Strategic Sales Planning for Small Businesses

The foundation of success in B2B sales lies in the ability to close deals and the strategic planning and objective setting that precedes any sales activity. This article offers a roadmap for salespeople, sales managers, and CEOs of small companies keen on refining their sales strategies and bolstering their management capabilities. Connecting your sales objectives with your company’s long-term goals is central to developing an effective sales strategy. Sales leaders should cast a vision for… Crafting Your Path to Success: Strategic Sales Planning for Small Businesses