Mastering Tough Conversations
- JM Ryerson
- 11 hours ago
- 5 min read

Leadership is a journey full of challenges and growth, and few stories illustrate this better than Jeff Hancher’s. Rising from humble beginnings to corporate leadership and then boldly stepping out to start his own business, Jeff’s experience offers invaluable lessons on leadership, feedback, and personal transformation. In this article, inspired by a conversation with JM Ryerson, we delve into Jeff’s powerful insights on giving firm feedback in today’s fragile world, the fears leaders face, and the mindset shifts that can unlock true impact.
The Power of Firm Feedback in a Fragile World
Jeff Hancher’s upcoming book, Firm Feedback in a Fragile World, addresses a fundamental challenge in leadership: how to have tough conversations that are necessary for growth but often avoided. The title itself captures the tension leaders face today—delivering honest, sometimes uncomfortable feedback in a world where emotions and sensitivities run high.
Jeff’s journey to writing this book began during the early days of the pandemic, after he left a 20-year Fortune 500 corporate career to pursue his passion for developing leaders. Drawing from his corporate experience, particularly in succession planning and leadership development, he identified two main barriers that hold leaders back:
Lack of emotional intelligence
Inability to engage in challenging discussions or be a challenging leader
While emotional intelligence has been widely discussed, Jeff saw a gap in practical, actionable guidance on how to effectively deliver challenging feedback. This realization led him to create a performance management workshop that sold out repeatedly, and ultimately to write a book aimed at equipping leaders with a framework to earn the right to give firm feedback that transforms both business outcomes and lives.
Why Leaders Avoid Tough Conversations
One of the most compelling parts of Jeff’s message is his exploration of feedback avoidance. He breaks down the fear leaders experience when considering tough conversations into a memorable acronym: FEAR.
Fallout – Worry about damaging relationships or reputation.
Emotion – Concern that the conversation will lead to tears or anger.
Amateur – Feeling unequipped or inexperienced to handle the discussion.
Retaliation – Fear that the employee might report or retaliate, risking the leader’s standing.
Jeff emphasizes that these fears often keep leaders from addressing issues that, if left unspoken, can cause far greater harm. His antidote? A mindset shift: instead of asking, “What if I have this conversation?” ask, “What if I don’t?” The cost of silence can be far greater than the discomfort of honest dialogue.
Personal Story: How Firm Feedback Changed Jeff’s Life
Jeff’s own life is a testament to the power of firm, caring feedback. Growing up in poverty with sick parents, he started working as a truck driver at Cintas to support his family. Despite early struggles, a sales leader saw potential in Jeff and invested deeply in his development—teaching him sales skills, professional appearance, and leadership habits.
During a particularly difficult time after his mother’s passing, Jeff’s motivation plummeted. His manager confronted him with a hard truth: Jeff needed to decide what kind of man he wanted to be and warned that continued poor performance would cost him his place on the team. Although Jeff initially wanted to rebel, the trust and care his manager had built earned him the right to give this tough feedback. That moment sparked a dramatic turnaround—Jeff earned nine promotions, won numerous awards, and built a successful career.
“If you have a young Jeff Hampshire or a Jeff Hampshire on your team that is begging you to show up and lead, they might not like the firm feedback, but they need it, whether they’re telling you that or not.” – Jeff Hampshire
Balancing Care and Candor in Leadership
Jeff and JM discuss the common leadership dilemma: wanting to be liked but needing to be respected. Jeff warns against both extremes—the “aggressive leader” who bulldozes without earning trust, and the “passive leader” who avoids accountability to stay popular.
The key lies in earning the right to give feedback by setting clear expectations, providing frequent feedback, and holding people accountable. This balance creates an environment where tough conversations are received as acts of care rather than criticism.
Jeff illustrates this with a simple but powerful analogy involving breath odor. If a trusted friend offers a mint and kindly points out something you didn’t know about yourself, you’re grateful. But if a stranger bluntly insults you in public, you react defensively. The difference is the relationship and trust built beforehand.
Seizing Opportunities: The Role of Network and Courage
Jeff’s rise from truck driver to recognized leadership expert also highlights the importance of seizing opportunities and building a network. A pivotal moment came when he reached out to Tim Elmore, a prominent leadership mentor, with a heartfelt LinkedIn video message—a rare and bold move that led to a meaningful connection and opened doors to industry giants like Ken Blanchard and John Maxwell.
Jeff encourages leaders to be intentional about their growth, to push past impostor syndrome, and to surround themselves with mentors who have been where they want to go. His advice:
Don’t wait to be discovered—reach out and take the shot.
Be willing to fail and learn from it.
Invest time and resources in your personal development.
The Hardest Decision: Leaving a Corporate Career for Purpose
Despite his success at Cintas, Jeff faced a profound internal struggle about leaving the security of a Fortune 500 company to start his own business focused on leadership development. The stress of this decision literally caused him to pass out on a plane due to overwhelming anxiety.
What helped him decide was a “funeral test” — imagining his life at 80 and whether he would regret not pursuing his passion. With support from his wife, who believed deeply in his calling, Jeff took the leap.
He stresses that this kind of leap is not for the faint of heart and requires careful planning, mentorship, and self-belief. But ultimately, living without regret is worth the risk.
Firm Feedback Workshop: Transforming Leadership Culture
Jeff’s Performance Management Workshop is an immersive experience designed to equip leaders with practical skills to give firm feedback. It’s not a dry training session—it’s interactive, emotional, and transformative, featuring:
Role-playing exercises
Breakout discussions
Tools like workbooks, templates, and accountability structures
Real-life stories and practical strategies
The workshop has consistently sold out, reflecting a deep hunger in the leadership community for authentic, actionable guidance on feedback that drives both business success and personal growth.
Conclusion: Embrace Feedback to Build a Lasting Leadership Legacy
Jeff Hancher’s story and teachings remind us that leadership is not about being liked—it’s about being courageous enough to have the hard conversations that help others grow. By understanding the fears that hold us back and adopting a mindset that prioritizes care and commitment, leaders can transform their teams, organizations, and lives.
Whether you’re a seasoned leader or just starting out, embracing firm feedback in a fragile world is a powerful step toward reaching your fullest potential. As Jeff says, “If we genuinely love people, we will give them the hard feedback.”
To learn more about Jeff’s work, his upcoming book Firm Feedback in a Fragile World, and his workshops, visit his website and connect on LinkedIn. Take the leap, seek mentorship, and start making deposits in the lives of those you lead.
Watch this full episode of the Let's Go Win podcast on YouTube.