Confessions of an Implementer – S2E44

Episode: My Employees Weren’t the Problem: I Was, with Hurricane Ken Dewitt

Host: Ryan Hogan
Date: April 9, 2026

Episode Overview

This episode of “Confessions of an Implementer” dives deep into the personal journey of EOS Implementer Ken DeWitt, famously known as “Hurricane Ken.” Host Ryan Hogan explores how Ken went from an intense, sometimes overbearing leader to someone who recognizes and works on his own management flaws. The candid discussion is rich with stories, hard-earned lessons, and actionable advice for leaders struggling with team performance and self-awareness. The focus is on leadership development, vulnerability, and embracing change to transform organizations and oneself.

Key Discussion Points & Insights

The Origins of “Hurricane Ken”

• Ken’s Reputation: Early in his career, Ken was nicknamed "Hurricane" due to his intense management style—a driven, demanding boss who unintentionally created a culture of fear among employees.

  • Quote: “Hurricane Ken is not somebody I’m proud of. He was a young 35 year old guy with about 30 employees...driven…But being driven, when you own an accounting firm, is one thing.” (05:13, Ken)

• The Blind Spot: Ken’s struggles with staff turnover and performance led him to hire a workplace psychologist. The core discovery was a shock: he was the root of the problem, not his employees.

  • Quote: “He said, ‘Yeah, man, I found exactly what's wrong with these people. You're just not, you're not going to believe it, you're not going to like it. It's you, you're an intense SOB.’” (07:05, Ken)

The Flag System (06:54)

• To help Ken recognize his own intensity, a “flag system” was put in place, inspired by beach warning flags:

  • Yellow: Ken’s baseline—already “blowing.”
  • Orange: A warning that Ken had overstepped; he needed to reflect on his recent behavior.
  • Red with Black Square: Full storm—Ken should leave the office.
  • Double Red: The team evacuates, leaving him to “blow around inside.”

• Key Insight: Most employees are “steady” or “compliant” by nature and are reluctant to confront overbearing behavior. Tools are needed to provide non-confrontational feedback.

Lessons in Vulnerability and Change

Owning the Problem

• The Painful Realization: Ken recounts the embarrassment and pain caused by his old style. “Your greatest strength is often your greatest weakness.” (07:27, Ken)
• Vulnerability as a Leader: By sharing his own mistakes, Ken realized he could help others—sometimes even seeing past employees come back to work after seeing genuine change.

On-Stage All the Time

• Constant Visibility: Leaders are “on stage 100% of the time”—employees interpret their moods and actions, sometimes reading silence as a storm warning.
  • Quote: “Whenever…you normally walk in the office past the receptionist and four or five times out of five…you don’t say anything to her…the first thing she's going to do is gather everybody at the water cooler and say, wait, storm is blowing. What's going on?” (12:50, Ken)

Being Called Out: The Grumpy Pill Story (22:12)

• Anecdote: A fearless employee gave Ken a literal “anti-grumpy pill”—a prop as large as a jawbreaker—promising to use it if the flag system failed.
  • Quote: “She said, 'I'll give you this pill.' I said, 'Donna, that's a single pill.' She said, 'Yeah, that's it.' I said, 'I don't think I can swallow a pill that big.' She said, 'Ain't for swallowing, buddy.'” (22:37, Ken)

The Mechanics of Change and Self-Leadership

Tools and Techniques

• Behavioral Profiling: Ken uses the DISC profile and other tools to understand and adapt to different working styles.
• Practice and Coaching: He highlights the need for continual coaching, referencing spiritual, personal, and sales coaches, as well as training like the Black Swan Group by Chris Voss.
  • “If it starts becoming about me, it's probably not a good time coming up.” (25:46, Ken)

Horseback Riding as Leadership Training (26:51)

• Ken took up horseback riding at 65 to practice calm, present leadership—horses, as sensitive animals, mirror emotional states and force the rider to lead decisively yet gently.
  • Quote: “I reasoned that I would take horseback riding lessons…to control my demeanor…less embarrassing to practice on a horse than with people.” (27:17, Ken)

Can People Change? (29:28)

• Hogan asks directly if fundamental change is possible.
• Ken’s View: Change is possible, but only if someone wants to change. It often takes hitting “rock bottom” or experiencing deep loss.
  • Quote: “If you want to change, I know you can. …Change starts with a desire that you recognize that's not good. …You have to want to.” (29:46, Ken)
• He shares personal background—his father found sobriety through AA, reinforcing the necessity of personal motivation for real change.

Apology and Repair (39:00)

• Real Apologies Matter: Ken emphasizes that genuine apologies are hard, emotional, and necessary for real trust repair.
  • Tree and Nails Analogy: Apologies might pull out the “nail,” but the scar remains—true healing must acknowledge this.

Team Health & Psychological Safety

Leadership Mindset

• Everything is My Fault (43:25)
  • Leaders must accept ultimate accountability: “Everything is my fault. I must manage others, and I must manage myself.” (43:54, Ken)
• Promoting Technical vs. Leadership Skills: Technical expertise does not equate to good management. Most leaders are untrained in people leadership.
• Growth Mindset and Failure (52:36): Embrace failure as part of growth—perfection is not the goal; excellence is.

Practical Exercises

• Annual Team Health: Candid exercises, such as “one thing to start/stop,” discussed as essential but vulnerable moments for teams, with new members sometimes (rarely) allowed to observe.
• Modeling Vulnerability: Leaders must be open to real feedback, show willingness to learn, and set the tone for the team’s culture.

Investing in Leaders and Teams

• Training is Non-Optional: Even without big budgets, start small—invest in workshops (such as EOS’s Great Boss), cohorts, or learning management systems. “One retention is worth more than the cost of training.” (68:03, Ken)
• Delegate and Elevate: Leaders must move from “player” to “player-coach,” then to “coach,” and eventually to mentor.

Selecting Clients and Values Alignment (72:13)

• Best Client Fit: Chemistry is paramount; Ken looks for clients open to self-accountability, learning, and treating staff well. Core values must align.
  • Quote: “If I sense there’s a lot of blame on others…this is going to be something where I’m going to tell you that everything’s your fault. I’m kind of unforgiving about that.” (75:03, Ken)
• Warning Against Compromise: Early in business, it’s tempting to take any client, but lack of value-alignment hurts everyone, especially your own team.

Notable Quotes (with Timestamps)

• On Blindspots:
  • “Your greatest strength is often your greatest weakness.” (07:27, Ken)
• On Vulnerability and Repair:
  • “Saying you’re sorry…it’s easier than it used to be, but it points to a failure. …You can beat yourself up over that failure or you can forgive yourself and you got to forgive yourself for the failure so that you can genuinely apologize…” (41:01, Ken)
• On Fundamental Change:
  • “Change starts with a desire that you recognize that's not good. I mean, I'm hurting that person, and I don't want to be that way.” (31:12, Ken)
• On Leadership Accountability:
  • “Everything is my fault. I must manage others, and I must manage myself.” (43:54, Ken)
• On Team Health:
  • “The first dysfunction [of a team] is always insufficient trust to confront a problem.” (54:23, Ken)
• On Training:
  • “While people don't have money up front…I started out with, you know, $500 or $1,000 in my training budget and over time I could afford better training. So we've got to become a learning organization.” (70:12, Ken)
• On Client Selection:
  • “Can I see a desire to do better? Do I see a genuine care for their employees?” (75:15, Ken)

Memorable Moments & Stories

• The Johnny Cash Blackout: Ken shows up to a meeting in a black cowboy outfit for a group prank—left as the lone participant (“They left me out to dry” – 02:36, Ken).
• Flag System Story: Color-coded flags as non-verbal feedback for his intensity—an innovative (and humorous) solution to a real problem.
• Horseback Riding Analogy: Learning leadership through horse training at age 65—a surprising but insightful metaphor for calm, gentle influence.
• Anti-Grumpy Pill Anecdote: A team member presents him with an unwieldy “pill” if even flags can’t change his behavior—blending humor with honest feedback.
• Apology & the Wounded Tree: Powerful metaphor on the lasting impact of leadership mistakes and the importance of repair.

Timestamps for Important Segments

• Hurricane Ken Origin Story: 05:13–09:50
• Flag System Explanation: 08:51–12:00
• On-Stage As a Leader: 12:00–15:43
• Vulnerability and Repair: 16:59–22:12
• Behavioral Tools & Preparation: 22:12–25:46
• Horseback Riding Analogy: 26:51–29:02
• Can People Change? 29:28–34:27
• Effect of Triggers and Apologizing: 36:22–41:01
• Everything Is My Fault: 43:25–50:48
• Failure and Growth Mindset: 52:36–54:18
• Team Health, Psychological Safety: 54:18–62:06
• Investing in Training: 67:00–70:12
• Selecting Clients & Values Alignment: 72:13–77:23

Final Thoughts

This episode is a masterclass in leadership humility, self-coaching, and the necessity of vulnerability for personal and organizational growth. Ken DeWitt’s stories—infused with honesty, humor, and hard lessons—make the case for deep self-reflection. The practical tools and perspectives shared are invaluable to any leader looking to break through their own “hurricane” moments and build healthier, high-performing teams.

Ken’s journey is a testament to the fact that transformation is possible when a leader is willing to see—and own—their blind spots. The holistic view of leadership, balancing accountability, empathy, and personal development, makes this a foundational listen for anyone on the path to becoming not just a better boss, but a better human.

To connect with Ken: Email kdwetosworldwide.com or google “Ken DeWitt EOS.”