Advertise on podcast: EXTREME LEADERSHIP - Behind the Boardroom with Managers and Sales Teams

In this episode of Behind the Boardroom, host Jason Cooper welcomes back globally recognized sales leadership authority Keith Rosen for an insightful conversation about humanizing leadership in the modern business era. Drawing from his latest book, *Crucial Coaching Conversations*, Rosen breaks down how managers must shift from simply managing activity to adopting coaching as a language of intentional communication. The discussion navigates the fast-paced evolution of AI and technology, emphasizing that while tools can surface performance data, they lack the "heart" and empathy required to truly connect and mitigate employee fear. Key takeaways from the episode include exploring the "art of enrollment" to align personal priorities with business objectives, understanding how to coach through mindset assumptions rather than managing future-based fears, moving away from the toxic habit of being a "chief problem solver" to scale team independence, and implementing a holistic 360-degree coaching culture where everyone—from the CEO down to cross-functional peers—remains coachable.

Leaders regularly ask about performance, priorities, and results. But when was the last time you asked someone how well they are taking care of themselves, setting boundaries, or being fully present with their family? In this two-minute video, I explore the Conversation of Care—the personal leadership conversation most managers were never taught to have, yet their people may need most.

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.

In this conversation, Keith Rosen challenges the way most sales leaders think about coaching, training, accountability, hiring, and performance. The hard truth is that your people don’t need more answers from you. They need better coaching that helps them think, own their decisions, build confidence, and grow beyond dependency. Keith shares why coaching is no longer a management technique, but the language of modern leadership, especially in a world shaped by hybrid work, AI, burnout, low engagement, and constant pressure to perform. This episode is for every leader who wants stronger salespeople, healthier teams, better conversations, and results that do not depend on the manager solving every problem.

If you want the secret to becoming a sales champion, stop changing what you do, and start changing how you think. Top salespeople upgraded their thinking from pitching to partnering, selling to serving, closing to caring, convincing to collaborating, fixing to facilitating, and pressure to creating possibilities. Check out this session with the sales champions at Microsoft.

If you want the secret to becoming a sales champion, stop changing what you do, and start changing how you think. Top salespeople upgraded their thinking from pitching to partnering, selling to serving, closing to caring, convincing to collaborating, fixing to facilitating, and pressure to creating possibilities. Check out this excerpt from my session with the sales champions at Microsoft.

The Toxic Coaching Trap Every Manager Falls Into that Sabotages Your Coaching ☠️ Coaching In Your Own Image. 🚨 “This worked for me.” 🚨 “This is what I would do, so you should too.” 🚨 “This is how I like to be managed/motivated/held accountable.” Coaching in your own image isn’t coaching - it’s projecting your perspective, ideas, and solutions to control the outcome, instead of having your team create the solutions or come to the revelation themselves. This a fast track to dependency, and eroded trust, engagement, coaching and performance. Great managers don’t guide/manipulate people to take on their agenda and answer, and try and control the conversation. They coach the individual, without judgement, by uncovering and respecting their unique goals, opinions, personal values, priorities, skills, challenges, personality, how they do things to achieve results, where they are in their life and career, and where they want to go, based on what they want, not you. So: ⚡Drop the ego. ⚡Stop assuming you know the answer and ask more questions to uncover the truth. ⚡Start uncovering their ideas first and what people really want and need. ⚡Don’t "should" on people. (A "Should" is the excrement of your agenda and makes people wrong 😕) Let them self-assess and arrive at their opinion on how to do things to build confidence and a growth mindset. Lead them, not your reflection. 🔥

Overview - AI Generated Keith Rosen's Journey: Keith, with 35 years in sales and leadership, evolved from life coaching inspired by a newspaper article. He has coached in 76 countries, emphasizing support for leaders amidst uncertainty. AI Impact on Authenticity: Concern over AI-generated content overtaking human authenticity, with 56% of LinkedIn posts being AI-written. Technology can enhance efficiency but cannot replace essential human connections in leadership and sales. Shifting Leadership Focus: Pandemic highlighted the need for empathy in leadership; 92% of employees contemplate job changes, emphasizing a people-over-profit culture. Coaching should foster mindset development alongside skill enhancement—shifting from traditional metric focus. The pandemic has underscored the importance of empathy in leadership, prompting leaders to prioritize emotional intelligence and understanding in their interactions with employees. With 92% of employees considering job changes, organizations must cultivate a people-over-profit culture to retain talent and enhance employee satisfaction. Effective coaching should focus on developing a growth mindset in addition to enhancing skills, moving away from a sole emphasis on metrics and performance targets.

You walk into a meeting and before you finish your first sentence, you see the crossed arms. The raised brows. The silent resistance. You’re not in a conversation. You’re in a standoff. That's why the best leaders communicate differently. The Art of Enrollment is a practical, real-world guide to help you communicate in a way that gets people to lean in, not push back. It shows you how to move from explaining and convincing… to enrolling people in the bigger vision — so they take action not because they’re told to, but because they believe in it. Whether you’re resetting expectations, or building buy-in around a new direction, The Art of Enrollment gives you a step-by-step approach that removes the fear from confrontation and the tension from hard conversations.

Here's the link to download the book and audio version: https://keithrosen.com/seven-types-of-coaching-questions/ “I don’t know what questions to ask when I’m coaching,” is the most common challenge I hear. Sure, managers tell me they’re coaching their team by asking questions. However, not every question is the right question, and poor, leading and manipulative questions will lead to coaching failure, and the erosion of trust. The fact is, every manager struggles with coaching. That’s why I’ve condensed 32 years of real-world sales coaching experience into a 40 page, daily sales coaching playbook. This isn’t just another book on the methodology of coaching; it’s the final coaching resource you’ll ever need to help guide people to crafting their own success strategy so you don’t have to. It’s everything you need to know around asking the 7 types of questions that create breakthroughs and results, and when to ask them. The 7 Killer Sales Coaching Questions is your daily coaching playbook, providing you not only with WHAT questions to ask, but WHY you’re asking them so coaching becomes a normal part of your daily communication, regardless of the situation you’re in. Instead of a random list of questions, this book will help you simplify the coaching process, making you a powerful, influential communicator and leader. You’ll learn how to: Build trust and break through obstacles. Inspire positive change, self-accountability and action using the right questions. Close more sales faster than ever before. Get your time back. Create breakthroughs in results, attitude and performance using one question. Avoid self-serving, manipulative questions that erode trust, relationships, performance, and confidence. Coach skill-set, and mindset to ensure long term results.

How Great Sales Leaders Manage Difficult Conversations by Keith Rosen

If you don't like the way you're being managed, it's your responsibility to tell your manager, “This is how I’d like to be managed and held accountable.” 🤯 Take charge of making the rules and how you want to be managed. Here's the Coaching Up talk track that will engage them to #maKEITHappen 🙂

Your prospects and customers are human too, not just a sales quota. The most effective selling strategy that drives more sales and accelerates personal evolution is care and developing authentic, personal connections. Where is this step in your sales process? 🤭 When it comes to selling and coaching, who you are and how you show up is always more important than what you do. Here's how to make this transformation to master this "new step" in your sales process.

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

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.