Podcast Summary: EEC 368 – 8 Stories for Personal Transformation at Work and at Large, with Bob Kaplan

Podcast: Excellent Executive Coaching: Growing Your Business and Enhancing Your Craft
Host: Dr. Katrina Burrus, PhD, MCC
Guest: Bob Kaplan, Author of Grappling
Date: February 10, 2025

Episode Overview

This episode centers on personal transformation in leadership, specifically the struggles and growth that accompany overcoming imposter syndrome, humility, defensiveness, and self-doubt among leaders. Bob Kaplan, experienced consultant, coach, and author of Grappling — a short story collection based on real leadership development journeys — joins Dr. Katrina Burrus for an insightful conversation on what truly holds leaders back, how guides and coaches can help, and why stories can foster self-awareness and improvement.

Key Discussion Points & Insights

1. Why Write Leadership Stories? (00:47)

• Bob Kaplan discusses his transition from nonfiction to fiction rooted in real events and people, aiming to render leadership growth more relatable.
  • “There are eight stories of people working on themselves, trying to raise their game with the help of a guide — in most cases a coach.” (Kaplan, 00:55)
  • Not all stories are about success; some explore failure and defensiveness.

2. Understanding Imposter Syndrome (01:58)

• Kaplan defines imposter syndrome as a tendency to underestimate oneself, which can manifest as either withdrawal or overcompensation.
  • “People will tell me, I’ve got the imposter syndrome. I think it’s that the person is better than they think.” (Kaplan, 02:13)
  • Underestimation may lead to people working harder or, paradoxically, to overcompensating by dominating conversations.

Effects in the Workplace (03:49)

• The underestimator may stay reserved, while the overcompensator “won’t shut up, who’s very obviously trying to demonstrate to us that she’s smart” (Kaplan, 03:27).

3. The Role of Feedback (04:08)

• Despite the thirst for positive feedback, many leaders focus on negative comments, often due to learned humility or fear of arrogance.
  • “Practically every leader...is drawn to the negative feedback like a moth to a flame.” (Kaplan, 04:31)
• Cultural factors play a role in attitudes toward self-promotion, as highlighted by Dr. Burrus’ comparison of Swiss and US work cultures. (07:36)

4. Humility as a Blocker (09:10)

• Through storytelling, Kaplan illustrates that humility can become a barrier to internalizing positive feedback.
  • Example: A high-performing executive labels humility as “the down player,” which exerts “downward pressure on his sense of self-worth” (Kaplan, 09:27) but, with persistent coaching, ultimately grows in confidence over time. (10:27)

5. The Sparring Partner/Coach’s Role (10:27)

• Naming issues (like excessive humility) can transform them into handleable “objects.”
  • “If it’s an object, then you can handle it.” (Kaplan, 11:05)
• Key coaching technique: More asking, less telling. Facilitating self-discovery leads to deeper, sustained change.
  • “When people discover things for themselves...it means more than if they’re told something.” (Kaplan, 11:47)

Practical Coaching Examples (12:16)

• Role-play and direct questioning help leaders recognize their own competence and overcome self-imposed barriers.
• 360-feedback tools reveal not just strengths and weaknesses but strengths taken too far.

6. Balancing Values: Directness and Kindness (14:00)

• Some leaders hesitate to hold people accountable for fear of violating deeply held values about kindness.
  • “He discovered that holding people accountable is not incompatible...with treating them well.” (Kaplan, 14:00)
• The “yin-yang” duality recurs in balancing toughness and empathy.

7. Overcoming Self-doubt and Unrealistic Expectations (14:28)

• A leader’s mental model—what they believe leadership fundamentally is—influences behavior and blind spots.
  • “You’re not going to get any better at relationships unless you place more value on relationships.” (Kaplan, 15:20)

8. Diagnosing Blockers to Change (15:42)

• Tools like the Inventory of Personal Functioning help leaders self-assess how they handle rejection, failure, or emotions.
  • “So the person’s filled out that tool on themselves...let’s talk about how you can do a better job of taking things in stride.” (Kaplan, 16:44)

9. The Power of Story in Coaching (16:54)

• Grappling’s eight stories animate the nuanced, erratic process of leadership growth.
  • “It’s like two steps forward, one step back...if you keep at it, you can make strides, you can improve.” (Kaplan, 17:13)
  • The book avoids explicit lessons, encouraging readers to reach their own insights, though themes are summarized at the end.

Notable Quotes & Memorable Moments

• On underestimation and overcompensation:
  “She might not speak up in meetings for fear that she’d be, what? Stupid?...But…someone who won’t shut up, who’s trying to demonstrate…she’s smart.” (Kaplan, 02:41–03:27)
• On humility as a blocker:
  “That blocks the uptake of the positive reinforcement.” (Kaplan, 06:31)
• On coaching philosophy:
  “When people discover things for themselves…self-directed, it means more than if they’re told something.” (Kaplan, 11:47)
• On finding balance as a leader:
  “He discovered that holding people accountable is not incompatible…with treating them well.” (Kaplan, 14:00)
• On optimism and growth:
  “If you keep at it, if you’re committed, you can make strides, you can improve, you can be happier.” (Kaplan, 17:13)

Timestamps for Key Segments

• 00:47 – Why write fiction for leadership development?
• 01:58 – Defining and unpacking imposter syndrome
• 04:08 – The challenge of accepting positive feedback
• 07:36 – Cultural effects on humility and self-promotion
• 09:10/10:27 – Humility as a self-esteem block; story of the “down player”
• 11:47 – Coaching method: asking vs. telling
• 12:16 – Role-play example to overcome barriers to praise
• 14:00 – Balancing accountability with compassion
• 14:28/15:20 – The mental models that shape leadership
• 15:42–16:44 – Tools for diagnosing and addressing blockers
• 16:54–17:13 – The value of stories; progress and optimism

Useful Links

• Contact Bob Kaplan: bkaplan@kaplandevries.com
• Book, Grappling: Available via Kaplan Devries website

Bob Kaplan’s insights make a strong case for the power of self-awareness, the value of patient and inquisitive coaching, and the truth that leadership growth is rarely linear, but always possible with the right support and mindset. Dr. Katrina Burrus’s thoughtful facilitation highlights the subtle cultural and personal layers that all coaches and leaders must navigate.