Coach2Scale: How Modern Leaders Build A Coaching Culture – Details, episodes & analysis

Matt Benelli sits down with Mike Montague, sales and marketing expert at Avenue9 and host of the Human-First AI Marketing podcast, for a candid conversation about what sales managers are still getting wrong about coaching. From the myth that leaders need to have all the answers to the burnout caused by "super reps" turned managers, Mike breaks down why most 1:1s fail and how asking better questions can flip the script on team performance. If you're still equating pipeline reviews with coaching, this one’s for you.

They also unpack the critical gap between coaching and execution and why online learning and conversation intelligence tools fall short without behavior change. Mike shares his "Iron Man vs. Terminator" analogy to help sales leaders reframe their use of AI and makes the case for exposure therapy and tough love as the missing ingredients in most sales organizations. Whether you’re trying to scale performance or stop regrettable attrition, this episode gives frontline and senior leaders a roadmap for more effective, accountable teams.

Top Takeaways:

• Coaching is about asking questions, not giving answers. Managers who try to “know it all” become bottlenecks; real coaching empowers reps to think for themselves.
• The best leaders make themselves irrelevant. Like elite sports coaches, great sales leaders build systems and skills so teams can operate independently.
• AI won’t replace salespeople, but it will replace those who don’t use it. Sales leaders need to think like Ironman, using AI as an enhancement tool to increase awareness and execution, not as a replacement for human strategy.
• The frontline sales manager (FLM) role is the hardest in the company. FLMs are overwhelmed by tasks, undertrained in coaching, and lack the time or tools to develop their teams effectively.
• Selling someone what they need and can afford isn’t cheating—it’s your job. Sales should focus on qualified buyers with budget, authority, and urgency, not on convincing disinterested prospects.
• Coaching fails when it focuses only on deals, not skills. Most coaching sessions are just pipeline reviews; they don’t address the behaviors that improve performance in the long term.
• Exposure therapy is essential for growth. Managers need more reps, not more theory, to improve at hard conversations or high-stakes moments.
• Online learning is helpful but only if it’s paired with feedback and behavior change. Asynchronous learning tools often reinforce what reps already know; without coaching moments, they don’t close performance gaps.
• Managers who need approval frequently avoid necessary conversations. Leadership requires discomfort, and effective managers must overcome the urge to be liked to hold reps accountable.
• Coaching is different from managing—and most people don’t know how to do it. There's a widespread misunderstanding of coaching; most FLMs were never taught how to develop others, and it shows.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Every sales leader has heard the mantra: “Pipeline cures all.” But what if that’s only half the truth? In this episode, Matt Carey, SVP of Global Sales at FIS, breaks down why more pipeline isn’t always the answer—the right pipeline is. He shares hard-earned lessons from leading sales teams at Oracle, SAP, and FIS, explaining how top-performing organizations prioritize quality over quantity, measure pipeline health beyond raw coverage, and avoid common forecasting pitfalls.

Matt also explores the real role of frontline managers, not as super reps, but as force multipliers who elevate their teams. He discusses hiring strategies that separate true performers from resume fluff, the importance of post-mortem loss reviews, and why most companies still get coaching wrong. Whether you're a CRO, VP of Sales, or a frontline manager looking to level up, this conversation is packed with insights that will change the way you build and manage your pipeline.

Top Takeaways:

• Pipeline Quantity vs. Quality – More pipeline doesn’t guarantee success; leaders must focus on the right pipeline by assessing deal quality, aging, and true viability.
• The Problem with "Just Add More Pipeline" Thinking – Sales teams often flood CRMs with unqualified deals to meet coverage targets, leading to bloated and misleading forecasts.
• Why Frontline Managers Must Stop Being Super Reps – The best managers don’t just close deals for their teams; they enable reps to develop the skills to win consistently.
• Hiring Based on Past Performance, Not Promises – Great sales hires have a history of winning, regardless of industry or background; track record matters more than potential.
• Loss Reviews Are More Valuable Than Win Reviews – Studying why deals were lost provides deeper insights into messaging gaps, pricing misalignment, and product fit issues.
• How Sales Leaders Sell Internally – At higher levels, sales leaders spend as much time selling internally for budget, resources, and strategy alignment as they do selling to customers.
• Coaching Needs a System, Not Just Good Intentions – Too many one-on-ones are either deal reviews or therapy sessions; real coaching needs structure, accountability, and a focus on skill development.
• Managing a Global Sales Team Requires Cultural Awareness – Sales leaders must adapt their messaging and approach across markets, respecting regional differences in business etiquette and buying behavior.
• The Shift from Tactical to Strategic Leadership – Senior sales leaders must move beyond the day-to-day deal cycle and focus on long-term market positioning, competitive threats, and team scalability.
• Why Sales Leaders Must Track Trends, Not Just Deals – The best leaders analyze broader win-loss data, competitive shifts, and industry changes to refine strategy, not just react to individual deal outcomes.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Unlock the secrets of genuine connection in sales and leadership with our guest Lane Monson, an executive leader and coach who challenges the conventional wisdom of salesmanship. Do most salespeople really know how to connect deeply with others? Discover what Lane has to say as we unravel the five levels of connection, which many sales professionals only partially navigate. Through Lane's insightful anecdotes, including a transformative experience with a Navy chaplain, learn how asking the right questions can turn ordinary interactions into significant, life-changing connections.

Explore the seven keys to achieving 1% success as a sales leader, starting with the realization that great leaders are essentially great coaches. This episode promises to reshape your understanding of leadership from traditional motivators to empathetic guides. Using an analogy from organic chemistry, Lane illustrates the journey through challenging phases, emphasizing belief, desire, and the power of perseverance. By focusing on individualized coaching and understanding unique team motivations, listeners will gain insights into building belief through small wins, fostering a vision-driven approach to leadership that prioritizes personal growth alongside team success.

Exceptional sales leaders are more than just business savvy—they're compassionate coaches who build meaningful connections. Through captivating discussions about figures like Michelle Potter and Joey Green, we emphasize the evolution from motivational tactics to genuine empathy in sales leadership. Lane's journey from CEO to executive performance coach offers lessons in lifelong learning, mentorship, and curiosity, encouraging listeners to embrace unexpected career shifts. Tune in to uncover valuable insights into becoming not just a successful leader, but also a compassionate facilitator of growth and connection within your team.

Chapters:
(00:00) Myth Busting and Connection in Coaching
(09:18) Leadership Strategies and Personal Development
(26:51) Leadership and Connection
(36:03) Lessons Learned and Executive Performance Coaching
(51:48) Coaching Insights and Connection Building

Takeaways:

1. Salespeople Overestimate Connection: Many salespeople believe they connect well, but they fail to ask high-value questions, listen deeply, or build trust effectively.
2. The 7 Keys to 1% Success for Sales Leaders: Success comes from great coaching, fostering belief and desire, defining vision and purpose, building deep connections, asking high-value questions, and maintaining a growth-focused mindset.
3. Purpose Drives Perseverance: Understanding individual and organizational purpose helps leaders and teams navigate challenges and stay committed.
4. Accountability Requires Carefrontation: Balancing candor and care (“carefrontation”) helps leaders hold teams accountable while maintaining trust and respect.
5. Personalized Coaching is Essential: Tailoring coaching approaches to individual team members’ motivations, goals, and personalities fosters better alignment and outcomes.
6. A Growth-Focused Mindset is Key: Leaders must challenge old thought patterns and adopt accurate, supportive beliefs to inspire their teams.
7. True Connection Comes from Understanding: Leaders who deeply listen, empathize, and value their team members create stronger trust and engagement.
8. Encouragement and Structure Build Morale: Over-delivering encouragement and using structured coaching frameworks improve morale and ensure consistent performance.
9. Overcoming Resistance Requires Empathy: Resistance in teams often stems from fear, fatigue, or lack of clarity, and leaders must address these with active listening and care.
10. Leadership Transports People: Great leaders act like coaches, helping individuals move from where they are to where they need to be by providing guidance and direction.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

What if sales success wasn’t just about the money? Join us as we challenge this age-old myth with insights from Jim Gannon, SVP of Sales at Sysdig. Discover how autonomy, competition, and a genuine drive to impact the business play pivotal roles in achieving sales excellence. Jim reveals why curiosity and the willingness to learn from peers set top performers apart, shedding light on the motivations that propel seasoned pros and ambitious newcomers alike.

The episode further unpacks the essence of team dynamics with a spotlight on recognition and accountability. By celebrating the collective efforts of everyone from sales engineers to onboarding teams, we uncover how fostering an inclusive culture strengthens team cohesion. Jim dives into the balancing act leaders face in maintaining a positive yet accountable environment, emphasizing the critical role of enablement and data-driven insights in recognizing high-performing teams.

Leadership and mindset take center stage as Jim shares his experiences leading in Japan, offering valuable lessons on cultural awareness and scalable processes. Explore how a winning attitude, even against fierce competition, can be nurtured within sales teams. From strategies for private companies to tales of overcoming odds in the sports world, this conversation is your playbook for elevating sales performance and leadership prowess. Don't miss Jim's engaging stories and practical advice that promise to inspire and transform.

Chapters:
(00:00) Busting Sales Myths With Jim Gannon
(12:08) Fostering Team Recognition and Accountability
(19:05) Enhancing Sales Enablement Through Accountability
(28:01) Building a Winning Mindset in Sales
(33:51) Enhancing Customer Success in Sales
(38:55) Casting a Leadership Shadow
(42:53) Cultural Awareness and Training Stories

Takeaways:

1. Sales Motivation Beyond Money: Jim Gannon challenges the common myth that salespeople are primarily driven by monetary incentives. He emphasizes that autonomy, competition, and the desire to impact the business are key motivators. Understanding these can help CROs better tailor their leadership and incentive structures.
2. Curiosity as a Differentiator: Top-performing salespeople often exhibit a strong sense of curiosity and a willingness to learn. CROs should foster an environment that encourages intellectual engagement and peer learning to enhance team performance.
3. Recognition and Accountability: Building a cohesive sales team involves recognizing contributions from all team members, not just those who close deals. CROs should focus on fostering a culture of inclusivity and accountability, which aligns with company values and encourages collective success.
4. Sales Enablement and Data-Driven Coaching: Effective sales enablement requires moving beyond content overload to live training sessions and leveraging tools like Gong for data-driven coaching. CROs should ensure their teams have access to insights that can improve performance and identify areas for development.
5. Building a Winning Mindset: In challenging market conditions, CROs should inspire their teams by sharing stories of underdogs who have succeeded against the odds. This helps instill confidence and drive, encouraging teams to execute the basics with excellence.
6. Cultural Awareness in Global Leadership: For CROs overseeing international teams, understanding cultural nuances is crucial. Jim's experiences in Japan highlight the importance of cultural sensitivity and the concept of a "leadership shadow" in global contexts.
7. Leveraging Competitive Spirit: Salespeople who thrive often enjoy the challenge of competing against larger, better-branded competitors. CROs can harness this competitive spirit by encouraging strategies that focus on differentiation and value delivery.
8. Balancing Inspirational Leadership with Accountability: Jim emphasizes the need for CROs to balance inspirational leadership with creating a culture of accountability. This involves setting high standards while motivating teams to achieve them through clear, consistent expectations and support.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

What if the secret to exceptional coaching lies not in having all the answers, but in embracing authenticity and vulnerability? Join us as we chat with Chris Michelmore, the head of mid-market acquisition at Zoom, who brings his unique perspective on coaching both athletes and salespeople. Chris challenges the notion that great coaches must be the best performers, instead highlighting the power of meeting individuals where they are and guiding them toward their goals. Through compelling anecdotes, Chris underscores the significance of building trust and genuine connections, paving the way for both personal and team success.

Our conversation hits effective coaching techniques, contrasting the "peanut butter coaching" approach with more personalized methods. Chris advocates for tailored strategies that align with individual and collective aspirations, emphasizing that true improvement requires more than a one-size-fits-all mindset. By understanding the diverse needs of team members, coaches can foster an environment where each person thrives, creating a balanced dynamic that enhances performance across the board. The discussion also touches on the delicate balance of emotional investment, highlighting the pitfalls of overcoaching and the importance of wisely allocating resources.

Chris's insights extend to the importance of feedback and communication, sharing lessons learned from both positive and negative coaching experiences. Through personal stories, he illustrates how bad coaching can be as instructive as good coaching, contributing to a coach's growth and adaptability. With nods to renowned coaches like Michael Phelps' coach, Bob Bowman, and Bill Walsh, Chris emphasizes the value of focusing on process and community over outcomes. This episode promises to enrich your understanding of coaching, leaving you with actionable insights to apply within your own teams.

Chapters:
(00:00) Coaching Salespeople With Authenticity
(09:32) Effective Coaching Techniques and Strategies
(22:23) The Pitfalls of Overcoaching
(26:34) Building Trust and Effective Communication
(34:09) Unveiling Coaching Potential and Pitfalls

Takeaways:

1. Embrace Authenticity and Vulnerability: Chris emphasizes the importance of authenticity in coaching. CROs should not feel pressured to have all the answers or be the best in the room. Instead, being genuine and vulnerable can foster stronger relationships and build trust within the team.
2. Personalized Coaching Over One-Size-Fits-All: Tailoring coaching strategies to meet individual team members where they are is crucial. Personalized coaching that aligns with individual aspirations helps bridge the gap between where they are and where they want to be, driving better buy-in and improvement.
3. Balance Team and Personal Goals: Effective coaching involves balancing team-wide objectives with individual goals. This ensures that both the collective and personal aspirations are met, enhancing overall performance and team cohesion.
4. Allocate Emotional Capital Wisely: Emotional resources are finite, and CROs must allocate them wisely. Overinvesting in individuals who do not reciprocate the effort can lead to burnout. Focus on empowering those who show genuine drive and willingness to succeed.
5. Learn from All Coaching Experiences: Both positive and negative coaching experiences offer valuable lessons. Even controversial coaches can provide insights into different methodologies that may be effective. CROs should maintain a growth mindset and continuously learn from various coaching styles.
6. Focus on Process Over Outcomes: Inspired by renowned coaches like Bob Bowman and Bill Walsh, Chris advocates for focusing on the process and community rather than solely on outcomes. By improving processes, the desired results will naturally follow.
7. Encourage Feedback and Build Trust: Creating an environment where team members feel comfortable providing feedback is vital. Acting on this feedback helps build reliability and trust, essential components for a successful coaching culture.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

As we close the book on 2024, I want to take a moment to say THANK YOU. Whether you tuned in for one episode or all 52, you're part of a movement that believes coaching is the rocket fuel for performance. This year, Coach the Scale recorded over 65 episodes, reaching thousands of sales leaders. But this isn’t about vanity metrics—this is about impact. Each episode brought lessons that slapped us in the face and whispered, "Pay attention."

So, let's hit rewind on the top 10 lessons from 2024 that every sales leader needs tattooed (metaphorically) on their brain:

1. Coaching isn’t teaching—it’s training for battle.
Your reps don’t learn to box by watching YouTube. It’s role plays, feedback, and reps that build champions.

2. High performers are your blue-chip stocks.
Feed them or someone else will. Stop spending all your energy on the bottom 20%.

3. Focus on behaviors, not just outcomes.
Outcomes lag. Daily actions drive the engine. We are what we repeatedly do.

4. Active listening is a martial art.
As Colum at CoachEm says, curiosity is the currency that unlocks trust.

5. Feedback is love.
Frequent, honest feedback isn’t a luxury—it's oxygen for growth. (Thanks to Dr. Rachel Pacheco for the unforgettable underwear analogy. 😅)

6. Transparency and vulnerability are superpowers.
Admit mistakes. Wear your struggles. Trust follows authenticity.

7. Master the basics before getting fancy.
Tech is a tool, not a crutch. Fundamentals win championships.

8. Coach to the career, not the quarter.
Short-term wins are great, but long-term investment in your people pays compounding dividends.

9. Embrace AI or get left behind.
AI won’t replace salespeople. It will replace those who don’t use it.

10. Don’t rush to solutions.
Sales is like a carwash—the rinse cycle (discovery) is crucial. Skip it, and the dirt stays.

🔥 Every guest brought their A-game this year, and 2025 is already shaping up to be NEXT LEVEL. We’re kicking off with sales leaders from Zoom and Sysdig to answer the big questions:

• What makes a great sales leader?
• How do you create buy-in without being a dictator?
• How do you hold yourself (and your team) accountable?

Your voice matters. Keep the feedback, guest ideas, and tough questions coming.

Coaching isn’t a checkbox. It’s a craft, a mindset, and the only sustainable way to build teams that thrive. If you’re not coaching them, you’re losing them.

Here’s to an even stronger 2025.

Happy Holidays, and see you next year!

#SalesLeadership #CoachingCulture #EndOfYearReflections #CoachTheScale

What if your beliefs about feedback and coaching timelines are holding you back? Guest host Colum Lundt, CEO of CoachEm, takes the helm to interview our regular host, Matt Benelli! Both are co-founders of CoachEm and share the myths and misconceptions about coaching sales teams. Matt dismantles the notion that coaching yields immediate results, likening this misconception to expecting instant mastery in swimming. They advocate for feedback that strikes a balance, highlighting strengths while pinpointing areas for improvement, and the power of self-assessment that transforms coaching into a nurturing ground for growth.

Navigating the murky waters of management can be daunting for new leaders. Our discussion uncovers the universal struggle of setting expectations and the weight of maintaining accountability within teams. Through candid anecdotes, they uncover why some managers shy away from difficult conversations and the all-too-common trap of wanting to be liked. By modeling self-accountability and utilizing strategies like setting clear goals, holding regular one-on-one meetings, and providing timely feedback, managers can foster an environment of responsibility and success within their teams.

Finally, Matt explores the art of leadership through preparation and engagement. We highlight how leaders like Mike Myers and Bill Belichick exemplify humility, discipline, and adherence to team values. These seasoned mentors teach us the importance of thorough preparation, the strategic use of "commander's intent," and conveying messages from higher-ups in an inspiring way. Matt reflects on how building a team around shared values paves the way for long-term success.

Chapters:
(00:00) Building Coaching Cultures
(15:27) Accountability and Effective Management Strategies
(31:48) Effective Leadership Lessons Learned
(43:32) Coaching Lessons and Leadership Attributes

Takeaways:

• Long-term Investment in Coaching: Sales coaching is not about immediate results. It's a long-term investment in behavior change, similar to learning a new skill. Sales leaders should approach coaching with patience and commitment, focusing on gradual improvement over time.
• Balanced Feedback: Effective feedback should be balanced, highlighting both strengths and areas for improvement. Encouraging self-assessment among team members can create a more constructive and positive coaching environment, promoting growth and development.
• Accountability and Modeling Behavior: Sales leaders must hold themselves accountable before they can effectively hold their teams accountable. Modeling the behavior they wish to see in their teams is crucial for setting clear expectations and maintaining accountability.
• Structured Management Strategies: Implement structured strategies such as setting clear goals, tracking progress, and providing timely feedback. Address underperformance immediately to prevent issues from escalating, and maintain regular one-on-one meetings to reinforce accountability.
• Leadership Beyond Directing: Leadership involves preparation, engagement, and composure under pressure. Convey motivational messages effectively and focus on building inclusive environments. Use the "commander's intent" concept to guide teams towards common objectives.
• Learning from Notable Leaders: Emphasize humility, positivity, and adherence to team values as demonstrated by leaders like Mike Myers and Bill Belichick. Investing in managerial training and focusing on shared team values can lead to long-term success.
• Commitment to Self-Development and Curiosity: Encourage a commitment to self-development and foster a culture of curiosity within the team. These traits can be developed and are essential for continuous improvement and effective leadership.
• Effective One-on-One Meetings: Maintain the importance of one-on-one meetings with team members. Consistently holding these meetings demonstrates care for team members' success and fosters a culture of accountability and feedback.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

What if everything you thought you knew about leadership was turned on its head? Join us for an enlightening conversation with J.D. Sillion, a two-time CEO and three-time CRO, as he dissects the myths surrounding leadership and unveils a powerful framework for guiding teams through both high-growth and turnaround situations. Drawing inspiration from sports legends like Phil Jackson, J.D. emphasizes nurturing potential over wielding authority to foster an environment where teams can thrive. Our discussion traverses the challenges of sales accountability and the critical roles of strategy, structure, and culture in achieving team success.

Imagine a sales process so efficient that each deal feels like a win for your entire organization. J.D. Sillion discusses the pitfalls of low win rates and their impact on morale and scalability, advocating for a culture of accountability. But what does it mean to truly empower autonomy within your team? J.D. explores the nuances between kindness and niceness, emphasizing the need for honest conversations that help team members grow. Learn about the success contract framework and how maintaining high standards can transform your organization and align teams with a shared mission.

Reflecting on personal growth and the mentors who shape us, JD shares stories from his own journey, highlighting influential figures like Lisa Gallagher and Sal Sylvester. Through personal anecdotes, JD reveals how overcoming ego and embracing continuous learning can lead to profound transformation. Whether it's climbing metaphorical peaks in business or contemplating the art of giving a TED Talk, J.D.’s insights are a masterclass in leadership. As we wrap up, listeners are left inspired to challenge the status quo, driven by the insights of thought leaders such as Greg Popovich, Jim Collins, and Marshall Goldsmith.

Chapters:
(00:00) Building a Culture of Winning
(12:16) Achieving Sales Accountability and Empowering Autonomy
(27:26) Leadership Lessons for Success
(34:39) Continuous Transformation in Business and Sales
(41:56) Navigating Leadership and Coaches

Takeaways:

• Visionary Leadership and Team Success: JD emphasizes the importance of creating a compelling vision and fostering an environment that nurtures potential. CROs should focus on building a culture that supports team success rather than relying on authority or outperforming team members.
• Strategic Framework for Transformation: JD introduces a strategic framework centered on strategy, structure, and culture. CROs can use this framework to guide their organizations through high-growth and turnaround scenarios, ensuring alignment with a clear vision and purpose.
• Sales Accountability and Targeting: It is crucial for CROs to ensure sales accountability and target the right audience to enhance success rates. Focusing on product-market fit and maintaining high standards will boost win rates and morale within the sales team.
• The Importance of Difficult Conversations: True leadership involves having honest conversations that drive improvement and growth. CROs should distinguish between being kind and being nice, where kindness means caring enough to engage in challenging dialogues for the benefit of the team.
• Continuous Learning and Adaptation: JD underscores the value of continuous learning and adapting to new challenges, likening business obstacles to scaling Mount Everest. CROs should encourage a culture of perseverance, improvement, and embracing feedback.
• Role of Mentorship: Mentors and coaches play a vital role in shaping leadership journeys. CROs should seek guidance from influential figures to transform their leadership styles and inspire their teams.
• Autonomy and Accountability: Autonomy should be earned through accountability. CROs need to establish clear, non-negotiable KPIs and regularly review performance to foster a culture of responsibility and excellence.
• Global Perspective: For CROs leading international teams, understanding cultural nuances and decision-making processes is essential. Tailoring leadership and sales strategies to fit diverse cultural contexts can significantly enhance global business operations.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Keith Rabkin, the Chief Revenue Officer at PandaDoc, takes us on a journey through his unconventional path to sales leadership, revealing a fresh perspective on motivating sales teams that challenges the age-old myth of money being the sole motivator. Keith unpacks the art of understanding individual aspirations and leveraging them to enhance performance through his innovative two-by-three matrix approach. With an emphasis on setting personal goals and addressing team development needs, Keith provides actionable strategies for leaders committed to cultivating a robust coaching environment that inspires.

We rethink the sales process as a collective endeavor rather than a solitary pursuit, emphasizing the benefits of a customer-centric approach. Keith and I uncover the perils of the lone wolf mentality and highlight how collaboration and teamwork can elevate both sales outcomes and customer satisfaction. By involving multiple team members and building trust, sales professionals can foster long-term relationships that lead to repeat business and larger deals, proving that sales truly is a team sport.

Adapting to change in the sales landscape is no small feat, yet Keith shares his experiences and insights from the transition to value selling at PandaDoc. Drawing from the book "Switch" by Chip and Dan Heath, we discuss the role of enablement teams and consistent messaging in facilitating this shift. Keith’s reflections on mentorship and leadership reveal the importance of honest conversations, personal growth, and effective coaching in creating resilient and successful sales teams. Through his journey, Keith exemplifies how a focus on customer-centric values and strong mentorship can shape impactful leaders.

Chapters: 

• (00:00) - Modern Sales Leadership
• (10:31) - Sales as a Team Sport
• (13:52) - Navigating Difficult Conversations in Leadership
• (18:52) - Adapting to Change in Sales
• (33:23) - Coaching Influence on Leadership Success
• (36:34) - Coaching and Talent Development Strategies

Takeaways:

• Sales leadership is not solely about financial incentives. Keith Rabkin emphasizes understanding individual motivations beyond monetary goals. He introduces a structured two-by-three matrix framework to help leaders align personal aspirations with organizational needs, creating a more effective coaching environment.
• Sales should be approached as a collaborative, customer-centric effort rather than a solitary endeavor. Keith highlights the drawbacks of the lone wolf mentality and underscores the benefits of teamwork in building trust, improving close rates, and increasing deal sizes.
• Difficult conversations are crucial in sales leadership. Keith discusses the importance of honesty, data-driven feedback, and planning in managing expectations and improving team dynamics. These conversations, when handled well, foster transparency and opportunities for growth.
• Transitioning to value selling requires consistent reinforcement and support from enablement teams and managers. Keith shares insights on overcoming comfort zones and emphasizes the importance of repetition and planning in implementing change effectively.
• Mentorship plays a significant role in shaping effective leaders. Keith reflects on his career growth at PandaDoc, influenced by mentorship from industry leaders, and how a focus on customer-centric values can drive success and innovation.
• Effective coaching and leadership involve pushing team members to grow and excel. Drawing parallels to sports coaching, Keith emphasizes the importance of recruiting resilient individuals and fostering a challenging environment to promote critical thinking and development.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

In today’s episode, Matt interviews Ed Diller, Sales Leader at New Relic. They explore effective coaching practices and myths in sales leadership. They discuss the importance of strategic communication, creating win-win scenarios, and maintaining work-life balance in a post-COVID world. Ed shares valuable lessons from his extensive career, emphasizing the need for risk-taking, clear communication, and the benefits of focusing on strengths. He also highlights the role of coaching in career progression and how leaders can foster engagement and avoid burnout in hybrid work environments.

Takeaways:

• Ensure clear and concise communication, especially when working remotely. Utilize tools to mitigate grammatical errors and enhance the professionalism of communications.
• Use virtual face-to-face meetings (via Zoom or similar platforms) to maintain human connection and engagement within the team. Promote informal interactions to build camaraderie.
• Focus on being invited to higher-level discussions rather than bypassing immediate contacts. Build rapport and trust with initial points of contact before aiming for discussions with their superiors.
• Address the need for work-life balance in a remote work environment to prevent burnout among team members.
• Recommend that aspiring sales leaders read beyond typical sales books, exploring works that provide broader insights into leadership, strategy, and empathy.
• Focus on modeling the behaviors and strategies you want to see in your team. Provide constructive feedback aligned with their career aspirations, not just their current roles.

Quote of the Show:

• “Great salespeople don't just want a bigger paycheck for selling more. They want to take on more, they want to do more.” - Ed Diller

Links:

• LinkedIn: https://www.linkedin.com/in/edwardmdiller/ 
• Website: https://newrelic.com/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io