Proactive Coaching: The Key to Unlocking Exceptional Sales Performance

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 ongoing development rather than merely correcting errors. This proactive coaching involves setting strategic goals with sales teams and using performance reviews—not as a critique but as a platform for growth and future planning. This method mirrors practices from top professionals in various fields who, regardless of their success, regularly receive coaching to enhance their performance.

Applying a coaching mindset to sales involves recognizing each team member’s individual needs and strengths. This personalized approach ensures that all team members, from the highest performers to those who might be struggling, receive the guidance they need to improve. The dialogue between a sales leader and their team shifts from what went wrong to what can be optimized, fostering a culture of continuous learning and adaptation.

An important part of this coaching process is the practical application of strategic planning, such as using quarterly business reviews (QBRs) to assess past performance and set proactive goals for future achievements. These sessions provide a structured framework for both leaders and salespeople to reflect on successes, learn from challenges, and plan actionable steps for ongoing improvement.

Leadership in sales also extends beyond internal team dynamics to personal development. Sales leaders are encouraged to invest in their own skills and capabilities to better serve their teams. This commitment to personal growth is crucial as it models the importance of lifelong learning to their teams, thereby instilling a similar mindset in their salespeople.

Effective sales leadership thus requires a dual focus: enhancing the team’s capabilities while simultaneously improving one’s own leadership skills. This approach not only achieves better sales outcomes but also builds a more resilient and adaptive sales organization, where both leaders and team members are committed to continuous improvement and excellence in their craft.

The role of a sales leader today is not just about managing a team but about actively participating in and fostering an environment of growth and excellence. By adopting a coaching mentality and focusing on both team and personal development, sales leaders can create dynamic teams that meet their current sales targets and are equipped to handle future challenges, ensuring sustained success and growth in the competitive market.

Here are a few actionable suggestions that a sales leader can do today!

  1. Schedule a Strategic Coaching Session: Identify a sales team member who could benefit from targeted coaching. Set up a one-to-one meeting for this week, focusing not on past shortcomings but on potential growth areas and setting actionable goals.
  2. Review and Refine Sales Metrics: Take a closer look at the metrics currently used to evaluate your team’s performance. Consider whether these truly capture the critical drivers of success or if they need adjustment to better reflect and promote your sales organization’s strategic goals.
  3. Initiate a Personal Development Plan: Reflect on your own leadership skills and identify areas for personal growth. Commit to a specific action, such as enrolling in a leadership workshop, starting a new book on advanced sales strategies, or scheduling regular check-ins with a mentor to enhance your leadership effectiveness.
Two Tall Guys Talking Sales Podcast – Empowered by ESOP: Enhancing Sales Management in Employee-Owned Firms with Wisdom by Marc Metz – E83

Two Tall Guys Talking Sales Podcast – Empowered by ESOP: Enhancing Sales Management in Employee-Owned Firms with Wisdom by Marc Metz – E83

In this enlightening episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey continue their engaging dialogue with Marc Metz, a seasoned expert in the sales and business transition arena. Building on the momentum of their previous conversation, they delve into the intricacies of transitioning a business through an Employee Stock Ownership Plan (ESOP). Marc shares firsthand experiences and practical insights, making this a must-listen for business owners contemplating a transition that rewards employees and preserves the company’s legacy.

Key Topics Discussed

  • The ESOP Transition Model: An exploration of the ESOP as a unique strategy for business transition, focusing on its structure, benefits, and challenges. Marc shares a compelling case study of a construction company making this significant shift.
  • Management and Structural Challenges: Discusses the critical need for a clear management structure post-transition, emphasizing the importance of placing the right people in the right positions and avoiding the pitfalls of rapid corporatization.
  • Preparation and Strategy: Offers valuable advice on preparing for an ESOP transition, including the slow and deliberate evaluation of candidates for leadership roles within the new ownership structure.
  • Sales Team Dynamics Post-Transition: Examines the sales team’s role during and after the transition to employee ownership, highlighting strategies to rejuvenate and realign sales efforts with the company’s new direction.

Key Quotes

  • Kevin: “It’s interesting that we talk about helping people avoid landmines. So Sean and I use a lot of our past experience to talk about where we skinned our knees so that others don’t have to.”
  • Sean: “I’m a big believer in three salespeople become four, four become five, five becomes six. And you use that existing run rate that you got from the first three, first four, first five to pay for that next one. And you grow profitably by doing that.”
  • Marc: “Go slow. I’ll tell you one thing is if the owner can do it three to five years before they’re actually ready to sell, it’s going to provide dividends to them and they’re going to have a better multiple more money in their pocket.”

Additional Resources

  • Traction by Gino Wickman: Recommended reading for listeners interested in understanding the EOS model and the GWC concept (Get it, Want it, Capacity to do it) that Marc references during the discussion.


For any business owner pondering the path to employee ownership, this episode offers a wealth of knowledge, cautionary tales, and strategic advice. Through Marc Metz’s experienced lens, listeners gain an understanding of the ESOP model’s complexities, the importance of careful planning and execution, and the pivotal role of sales leadership in navigating a business’s transition. Whether you’re in the early stages of considering an ESOP or looking to optimize your sales team post-transition, this episode of Two Tall Guys Talking Sales is invaluable. Tune in to equip yourself with the insights needed to ensure a smooth and successful transition to employee ownership.

Two Tall Guys Talking Sales Podcast – Mastering the Art of Business Transition: Insights from Marc Metz – E82

Two Tall Guys Talking Sales Podcast – Mastering the Art of Business Transition: Insights from Marc Metz – E82

In this riveting episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome a special guest, Marc Metz, President of Optimus Sales Group. Together, they delve into the critical yet often overlooked topic of business transitions, providing invaluable insights and strategies for companies navigating the journey from generation to generation. This episode is a treasure trove of knowledge for business owners, sales leaders, and anyone involved in the business’s lifecycle.

Key Topics Discussed

  • Business Transition Strategies: Marc Metz shares his expertise on the three main ways businesses transition: selling to an outsider, passing on to family members, and employee stock ownership programs. Each method comes with its unique set of challenges and opportunities.
  • Overcoming Overvaluation and Sales Dependencies: A common stumbling block for pre-sale businesses is the company’s overvaluation and the heavy reliance on the owner for sales. Metz discusses strategies to realign expectations and decentralize sales efforts.
  • The Importance of Building a Business to Sell: Metz emphasizes the critical nature of preparing a business for sale from day one. This involves creating robust systems and processes that ensure the business can thrive independently of the current owner.
  • Sales Team Dynamics in Transitions: The discussion highlights the potential pitfalls and strategies around managing key sales personnel during a transition, ensuring their loyalty, and maintaining sales momentum under new ownership.

Key Quotes

  • Kevin: “How do they, get ready to get ready to sell? If they wake up tomorrow and say, I want to sell by April, they might be, might be challenged. But if they wake up and say in a few Aprils, in a few years from now. What might the recipe be that you would prescribe because you’ve been there done that?”
  • Sean: “So I want to build on this topic a little bit more. Let’s play the scenario out. … It’s just a good employee. Been around, been very loyal to the company. … And now you’re trying to sell that. So I’m, I’m foreseeing a problem of if I’m a buyer of that business, I’m saying, well, how loyal is that one salesperson?”
  • Marc: “The first exercise I recommend to these guys and gals is hey, look what happens if you get hit by a bus tomorrow? What’s going to happen to your business? Think about that and start putting things in place That’ll mitigate that risk because that’s the very very first thing and I’m talking all aspects operations sales financial, all of those things, look at everything.”


Whether you’re a business owner contemplating the future, a sales leader navigating changes, or simply interested in the dynamics of business transitions, this episode is a must-listen. Kevin, Sean, and Marc provide a rich discussion filled with actionable advice, real-world experiences, and strategic insights designed to equip you with the tools you need to navigate the complex landscape of business transitions. Don’t miss this opportunity to learn from the experts and ensure the legacy and longevity of your business. Tune into this episode of Two Tall Guys Talking Sales for a deep dive into preparing your business for the next chapter.

The Art of Sales Compensation: Balancing Motivation and Goals

The Art of Sales Compensation: Balancing Motivation and Goals

Few topics in sales stir as much discussion and attention as compensation plans. The proper compensation structure can ignite a team’s performance, attract top talent, and drive a company toward its strategic goals. Conversely, a poorly conceived plan can lead to demotivation, high turnover, and missed targets. This discussion delves into the intricacies of designing compensation plans that motivate and align with a company’s broader objectives, offering insights for salespeople, sales managers, and CEOs alike.

Compensation in sales is not just about rewarding past successes; it’s a strategic tool that shapes future behavior. The fundamental premise is straightforward: sales professionals are motivated by earnings potential. Yet, applying this premise within compensation plans can be complex, nuanced, and sometimes contentious. It’s essential to balance base salary and variable compensation, ensuring sales representatives are adequately supported and incentivized to pursue new business aggressively.

The debate between 100% commission versus a guaranteed salary represents the spectrum of risk and reward in sales compensation. On one end, a 100% commission plan offers unlimited earning potential but lacks security, potentially leading to a high-stress culture and a short-term focus. It also makes it much more difficult to recruit younger sales superstars who may not have the financial security to afford a 100% commission compensation plan. Conversely, a guaranteed salary provides stability but might dampen the urgency and hunger that drive sales excellence. The consensus among seasoned sales leaders points to a balanced approach, often epitomized by a 50/50 split between base salary and variable compensation. This structure aims to provide a safety net while ensuring sales efforts directly impact earnings.

Understanding the market potential within a sales representative’s territory is critical when setting quotas and compensation. For larger teams, the ability to average performance across the group can help smooth out individual variances. However, in smaller teams or founder-led sales organizations, each member’s contribution is magnified, demanding a more nuanced approach to quota setting. Regardless of team size, aligning individual quotas with company objectives requires a blend of data analysis, market insight, and an appreciation for each territory’s unique challenges and opportunities.

Beyond the structure of compensation plans, the timing and criteria for payouts are pivotal. Monthly payouts can incentivize immediate results and help maintain momentum, whereas quarterly payouts may lead to strategic deal timing but can also introduce cash flow challenges for sales professionals. Moreover, compensation plans should evolve in tandem with a company’s strategic goals, ensuring that sales efforts are aligned with the organization’s overarching priorities.

Crafting effective sales compensation plans is both an art and a science. It demands a deep understanding of human motivation, a clear vision of company objectives, and a commitment to fairness and transparency. By carefully designing compensation structures that reward performance, foster team collaboration, and support long-term strategic goals, companies can create a sales culture that not only meets targets but exceeds them, driving growth and success in the competitive world of B2B sales.

Immediate Action Item 1: Evaluate and Adjust Your Compensation Structure

Assessment of Current Plans: Begin by thoroughly assessing your current sales compensation plan. This involves evaluating how well the existing structure supports your company’s strategic goals and motivates your sales team. Are your sales representatives meeting their targets? Do they feel motivated and supported? These questions can uncover valuable insights into the effectiveness of your compensation plan.

Balanced Compensation Review: Reflect on the balance between your organization’s base salary and variable compensation. Does it align with the 50/50 split recommended by seasoned sales leaders? If not, consider adjusting this balance to provide both security and incentive to your sales team. This balance is crucial for motivating your team while ensuring they are adequately supported.

Action Steps:

  • Survey your sales team to gather feedback on the current compensation plan.
  • Analyze sales performance data to identify patterns or areas for improvement.
  • Consult with HR or compensation specialists to explore potential adjustments.
  • Implement a pilot program for a new compensation structure in a small team or region to measure its impact before a company-wide rollout.

Immediate Action Item 2: Align Compensation with Strategic Goals and Territory Potential

Quota Setting and Territory Analysis: It’s essential to align individual quotas with the sales territory’s potential and the overarching company objectives. This alignment ensures that sales efforts are directed towards strategic goals, optimizing both individual and team performance.

Compensation Plan Evolution: Regularly review and update your compensation plans to align with your company’s strategic goals. This might mean adjusting the payout criteria, the balance between base and variable compensation, or the targets set for sales representatives.

Action Steps:

  • Conduct a territory analysis to ensure realistic quotas align with market potential.
  • Set up a quarterly review process for the compensation plan to ensure it remains aligned with company objectives and market conditions.
  • Engage sales managers in discussions about territory potential and strategic goals to ensure their input is considered in compensation planning.
  • Communicate changes in compensation plans clearly and effectively to the entire sales team, ensuring they understand how these changes benefit both them and the company.

Implementing these action items can lead to a more motivated sales team, better alignment with strategic goals, and improved sales performance. Remember, the key to successful sales compensation is not just in the design but in the ongoing evaluation and adjustment to meet the evolving needs of both your sales team and your company.

Two Tall Guys Talking Sales Podcast – Scoring Big in Sales: Lessons from March Madness – E79

Two Tall Guys Talking Sales Podcast – Scoring Big in Sales: Lessons from March Madness – E79

In this sports-oriented episode of “Two Tall Guys Talking Sales,” hosts Kevin Lawson and Sean O’Shaughnessey dive into the fascinating parallels between March Madness NCAA basketball tournaments and sales strategies. Kevin and Sean take this opportunity to explore how the tournament’s structure and the season leading up to it offer valuable lessons for developing winning sales strategies.

Key Topics Discussed:

  1. Preseason Preparation and Regular Season: The significance of constant improvement and team synergy throughout the sales season to refine strategies, similar to a basketball team’s journey to the NCAA tournament.
  2. Tournament Strategy and Sales Planning: Drawing analogies from the NCAA’s regional competitions and seed rankings to sales approaches, market positioning, and competitive analysis.
  3. Winning the Customer Relationship: Identifying the final sales deal as the ‘national championship game,’ focusing on strategic planning and execution to win customer trust and secure business.
  4. Overcoming Adversity and Learning from Losses: The importance of analyzing lost sales opportunities (akin to unexpected tournament upsets) to understand and improve future sales tactics.
  5. Sales Team Dynamics and Individual Growth: Encouraging personal development and adapting roles within the sales team for optimal performance, paralleled with a basketball team’s adjustment to injuries and game dynamics.

Key Quotes:

  • “The trophy in sales is the customer relationship.” – Kevin Lawson
  • “Only one team ends the season with a victory; similarly, in sales, there’s only one winner.” – Sean O’Shaughnessey
  • “It’s important to win through better execution of the plan… and hard work.” – Sean O’Shaughnessey
  • “We’ve got to figure out our place in the market… It’s the same progression in business.” – Kevin Lawson

Additional Resources:

MEDDPICCC for sales strategy and the importance of opportunity qualification –


This episode is a masterclass for sales professionals and leaders looking to elevate their game by drawing inspiration from March Madness’s structure, strategy, and spirit. Kevin and Sean’s dialogue reminds us of the importance of preparation, strategy, resilience, and continuous learning in the quest to win in sales. As the NCAA tournament captivates basketball fans, let it also inspire sales teams to strive for excellence, adapt to challenges, and ultimately clinch their championship trophy: a successful and lasting customer relationship