EXTREME LEADERSHIP - Behind the Boardroom with Managers and Sales Teams
by Keith Rosen
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From 11 epsHost
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Recent episodes
Training or Coaching. What Is The Difference?
Jun 24, 2026
Unknown duration
Your People Don’t Need More Answers. They Need Better Sales Coaching
May 19, 2026
53m 08s
Stop Training_ Start Coaching_ The Mindset Shift That Turns Sales Teams Into Champions with Keith Rosen
May 6, 2026
54m 55s
Sales Coaching and Personal Development Session with Keith Keith Rosen and Microsoft
Dec 11, 2025
1h 24m 01s
Transforming Sales through Coaching and Care Microsoft Live Event
Dec 4, 2025
3m 20s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/24/26 | ![]() Training or Coaching. What Is The Difference? | One of the common questions I hear from managers is, "When do I train them and when do I coach them? In this five minute conversation, learn the difference between training and coaching, and the questions you can use to assess whether the coachee needs training, coaching or both to unlock and sustain greater performance. | — | ||||||
| 5/19/26 | ![]() Your People Don’t Need More Answers. They Need Better Sales Coaching✨ | sales coachingleadership+3 | — | — | — | sales coachingleadership+5 | — | 53m 08s | |
| 5/6/26 | Stop Training_ Start Coaching_ The Mindset Shift That Turns Sales Teams Into Champions with Keith Rosen✨ | coachingsales teams+3 | — | — | — | coachingsales+5 | — | 54m 55s | |
| 12/11/25 | ![]() Sales Coaching and Personal Development Session with Keith Keith Rosen and Microsoft✨ | sales coachingpersonal development+3 | — | Microsoft | — | sales championcoaching+5 | — | 1h 24m 01s | |
| 12/4/25 | ![]() Transforming Sales through Coaching and Care Microsoft Live Event✨ | sales coachingsales transformation+3 | — | Microsoft | — | sales championcoaching+3 | — | 3m 20s | |
| 6/5/25 | ![]() The Toxic Trap Impacting Managers that Sabotages Your Coaching - Coaching In Your Own Image✨ | coachingmanagement+4 | — | — | — | toxic coachingdependency+5 | — | 1m 48s | |
| 5/6/25 | ![]() How Managers Navigate Their Team to Perform Through Fear and Uncertain Times✨ | leadershipempathy+4 | — | LinkedIn | — | leadershipempathy+5 | — | 1h 01m 20s | |
| 4/21/25 | ![]() How Great Leaders Communicate, Connect and Coach Up to Their Boss to Enroll Them In Change✨ | leadershipcommunication+4 | — | — | — | leadershipcommunication+4 | — | 3m 37s | |
| 12/19/24 | ![]() New Book! The Seven Killer Sales Coaching Questions✨ | sales coachingquestioning techniques+3 | — | keithrosen.comThe Seven Killer Sales Coaching Questions | — | sales coachingcoaching questions+5 | — | 2m 26s | |
| 11/26/24 | ![]() How Great Sales Leaders Manage Difficult Conversations✨ | sales leadershipdifficult conversations+3 | — | — | — | sales leadersdifficult conversations+3 | — | 57m 46s | |
Want analysis for the episodes below?Free for Pro Submit a request, we'll have your selected episodes analyzed within an hour. Free, at no cost to you, for Pro users. | |||||||||
| 11/10/24 | ![]() How to Coach Your Manager✨ | coachingmanagement+3 | — | — | — | coachingmanagement style+3 | — | 4m 17s | |
| 11/5/24 | ![]() The Role Of Human Connection In Sales✨ | human connectionsales strategy+3 | — | — | — | saleshuman connection+3 | — | 3m 55s | |
| 10/29/24 | ![]() Developing the Attitude and Mindset of Top Sales Leaders | Written by AI: Coaching is one thing, the coaching mindset is another. Beliefs precede experiences and how you think is what you get. What you focus on grows. These are just some of the fundamental, and transformational mindsets leaders need to adopt so they can then align how they think with what they do. Not the other way around. This creates a healthy, happy, sustainable coaching culture and transforms you into the leader and coach you want to be. The Leadership and Coaching Discussion meeting, led by Keith Rosen, emphasized the need for a transformational approach to leadership in the hybrid workplace following Covid, highlighting the alarming levels of employee disengagement and the necessity for deeper personal connections in coaching. Key topics included the importance of empathy, effective communication, and understanding team members' individual purposes to foster a supportive environment. Rosen advocated for a change in traditional performance improvement strategies, proposing a four-week turnaround plan for underperformers while encouraging managers to prioritize team member well-being amidst external pressures. He underscored the integral role of authenticity in leadership, drawing parallels between music and managing teams, and concluded by urging leaders to be proactive in enhancing their team's value and engaging in meaningful conversations about core values and priorities. Action items were established to ensure managers take concrete steps towards implementing these principles. Notes ️ Introduction and Leadership Mindset (00:00 - 11:25) Keith Rosen discusses transition to hybrid workplace post-Covid Highest level of employee disengagement and attrition Importance of tapping into people's individuality in coaching Only 1 in 20 managers trained in coaching Opportunity to reconnect with people on a human level Need for deeper personal connection in sales and leadership 76% of companies changed buying processes, only 17% changed selling processes Importance of putting people over profit Coaching and Connection (11:25 - 22:44) Challenges of managing diverse teams and high performers Need for empathy and skills to deal with personal issues Importance of setting positive intent in conversations Questions managers should ask to support team members Self-care as a crucial aspect often overlooked Managers need to push back against pressure from top leadership Importance of insulating team from excessive pressure Coaching as a Language (22:44 - 32:40) Coaching is not an event but a language Need for a universal coaching methodology Importance of uncovering people's sense of purpose Top intrinsic motivators: making a difference, collaboration, impact, life balance Need for managers to wake up thinking about making their team more valuable Mindset and Coaching Approach (32:41 - 41:51) Importance of exploring opportunities to make people more effective Setting positive intent in conversations with team members Questions to ask team members about their values and priorities Need for regular conversations about what's important to team members Importance of developing relationships and caring for team members Performance Improvement and Legacy (41:51 - 51:08) Criticism of traditional Performance Improvement Plans (PIPs) Proposal for a 4-week turnaround strategy for underperformers Importance of collecting evidence of change Concept of people self-selecting in or out based on their commitments Focus on creating a positive legacy as a leader Personal Interests and Leadership Lessons (51:09 - 01:00:01) Keith's passion for music and concerts Conversion of old garage into music studio Recent concert experiences Importance of authenticity and connection in both music and leadership | — | ||||||
| 10/24/24 | ![]() The Art and Science of the Complex Sale | In the recent discussion on Sales Leadership and Coaching featuring Keith Rosen, a seasoned expert with extensive global experience, the importance of transforming salespeople into top performers was emphasized through the lens of core values such as connection, selflessness, and the significance of cultural understanding in sales. Rosen highlighted the necessity of adopting a growth mindset, stressing self-leadership and accountability, while addressing common time management challenges for leaders. The conversation shifted to leveraging growth through supportive leadership that aligns personal goals with business objectives, advocating for a coaching approach that prioritizes questioning over telling to foster deeper engagement. Effective coaching techniques were discussed, showcasing success stories that demonstrate improved team performance and reduced attrition, underscoring the necessity for managers to take full responsibility for their team's outcomes. Key action items included identifying personal core values, developing self-accountability routines, enhancing coaching skills, and embracing managerial responsibility for team success. | — | ||||||
| 10/16/24 | ![]() Beyond the Numbers: The Power of Process-Driven Sales with Keith Rosen | Beyond the Numbers: The Power of Process-Driven Sales with Keith Rosen by Keith Rosen | — | ||||||
| 9/27/24 | ![]() Own Your Day - Time Management for Sales Leaders to Create a Great Life | Jason Cooper and I had a powerful conversation that most people either shy away from or simply forget about. Self Management. Bottom line, you can't create a thriving career while honoring your priorities and core values without owning your day and protecting your time. In this episode, discover how to: * Reduce your daily workload and protect your time. * Obliterate your never-ending to-do list and get more done in less time. * Identify and manage the unplanned events that distract you from your priorities, cause stress, and waste time. * Coach your direct reports on how they can improve their daily productivity, performance, and personal accountability. “If You Want a Great Life, Then Schedule One.” | — | ||||||
| 9/26/24 | The One Minute Sales Coach - Why Sales Managers Prevent Their Team from Doing Their Job | In one minute, discover how managers are actually preventing their team from performing. | — | ||||||
| 9/18/24 | ![]() Creating a Thriving Sales Culture | We can talk strategy all day long, but if leaders don't change the way they think then nothing will change. In this conversation with Jason Cooper, discover how leaders are communicating in a way that drives engagement. In addition, learn the inner game of leadership and the mindset of care that every manager needs to adopt including the power of being present. Finally, learn how to leverage people's core values to drive motivation and greater results. | — | ||||||
| 8/30/24 | ![]() How to Become a Better Listener in 45 Seconds | In the latest episode of Mastering Modern Selling, we discuss the transformation that salespeople and managers need to make to reconnect with buyers and customers in a new and deeper way in order to develop more meaningful, authentic relationships that drive more sales. The predominant sales and leadership strategy today is - CARE. | — | ||||||
| 8/19/24 | ![]() Mastering Modern Selling - Transforming Sales Leadership With Keith Rosen | In the latest episode of Mastering Modern Selling, we discuss the transformation that salespeople and managers need to make to reconnect with buyers and customers in a new and deeper way in order to develop more meaningful, authentic relationships that drive more sales. The predominant sales and leadership strategy today is - CARE. | — | ||||||
| 8/15/24 | ![]() How to Coach Someone in 60 Seconds or Less | COACHING TAKES TOO LONG! If you believe this, you're not coaching. Are you interrogating your team or collaborating with them? Here's how to coach someone in 60 seconds or less. | — | ||||||
| 8/1/24 | ![]() Why CARE is the New Sales and Leadership Strategy to Achieve Selling Success | Here's part of the powerful conversation I had with Jason Cooper, as we discuss the new superpower of selling and leadership - CARE. It's something we all want and need, especially our customers. Once salespeople shift from making the sales process about them and what you want to get, to what you have to give, care and coaching become your new competitive edge. What do you think? | — | ||||||
| 7/9/24 | ![]() The Rural Sales Show Sales Management Masterclass | I had a the pleasure of being a guest on the Rural Sales Show last week. In this episode we discuss: - Why you can't scale dependency - Why sales managers deflect and prefer to focus on their teams instead of themselves (what I call a global epidemic) - How to manage low performers and coach for accountability - How to use questions to open up possibilities in coaching conversations - The top traits of the most successful sales managers - How to run effective sales meetings - The importance of taking time to self-reflect to improve self-awareness | — | ||||||
| 4/2/24 | ![]() Interview at the Salesforce VIP Event for Sales Executives | Out of the archives! Here's a never before published video VIP event hosted by Salesforce, where Jason Jordan and I discuss with a group of senior sales leaders what top companies are doing to transform their sales organization to sell the way customers want to buy today, while creating a culture where coaching is the foundation of growth and people transformation. | — | ||||||
| 1/29/24 | ![]() The Art of Coaching: A New Perspective on Leadership | EVENT DESCRIPTION: Ever wondered how some managers consistently lead their teams to achieve unprecedented success? Keith Rosen, CEO of Profit Builders, joins us to share the secret: mastering the language of coaching. You'll learn how coaching transcends traditional problem-solving, fostering new possibilities and cultivating accountability within your team. Whether you're leading a sales team or running clinical operations, this session gives you tools to aid your employees in developing critical thinking skills, enabling them to become self-reliant problem solvers. But not all coaching is created equal. The one-size-fits-all approach is a trap that many managers fall into, leading to inefficiencies and disconnection within the team. Keith helps us navigate around this pitfall, discussing the importance of understanding each individual’s unique coaching style, motivation, and accountability methods. Moreover, we delve into the role of confidence in leadership and its direct correlation to sales performance. If you've ever been in a sales slump, this information is a game-changer that will help you intentionally cultivate confidence. Through this conversation, we hope to have provided insights that will guide you in transforming your leadership style and, ultimately, your team's performance. Join us on the CHAPcast for more empowering conversations like this. | — | ||||||
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