Coaching for Leaders, Episode 750:

Six Questions Every Leader Should Ask Themselves — with Margaret Andrews

Date: September 22, 2025
Host: Dave Stachowiak
Guest: Margaret Andrews, Author and Harvard Instructor

Episode Overview

This episode explores the foundational principle that effective leadership begins with self-understanding. Dave Stachowiak and guest Margaret Andrews—author of Manage Yourself to Lead Others and creator of Harvard’s most popular professional development program—dive deep into six essential questions every leader should ask themselves. These questions are designed to foster self-awareness, enable growth, and ultimately enhance the ability to lead others. Margaret draws on extensive research, teaching experience, and practical exercises to offer listeners actionable insights on leadership development.

Key Discussion Points & Insights

The Importance of Self-Understanding in Leadership

• Self-Management as Leadership’s Foundation:
  • Almost all leadership development begins with self-understanding because “managing ourselves helps us lead others more effectively.” (A, 00:00)
• Interpersonal Skills Over Technical Skills:
  • Margaret introduces her “Best Boss Exercise,” where participants list qualities of their best boss.
    • 85% of noted qualities are interpersonal/emotional intelligence (“soft skills”), not technical skills or IQ.
    • “What makes a really great boss is not their intelligence and it’s not their technical or functional skills, it’s those interpersonal skills.” (B, 05:50)
  • Dave cites Daniel Goleman’s work, reinforcing that nearly 90% of leadership differences come down to emotional intelligence rather than cognitive ability. (A, 06:21)

The Six Core Questions for Leader Self-Reflection

Margaret’s six questions are designed to uncover what has shaped us, how we define success and values, and how we manage our emotions and respond to feedback. She recommends taking time—revisiting these questions over days, weeks, or years.

1. Who and whose thinking has shaped you as an individual?

• Purpose: To reflect on the people, events, and influences—positive and negative—that have formed your beliefs and identity.
• Includes: Parents, teachers, friends, enemies, books, movies, conversations.
• “These things shape us… sometimes people in your life can be on both sides of the ledger—as somebody that helped you but maybe also hurt you too.” (B, 13:00)
• Margaret suggests discussing with someone who knows you well for additional perspective.

2. What situations and events have helped shape your perspective?

• Purpose: To understand key “pivotal moments,” both positive (“lucky accidents”) and negative (“unlucky accidents”), that have influenced your worldview.
• Example: Meeting a spouse at a party you didn’t want to attend; a family tragedy; a job loss.
• “There are those things that we don’t have control over… but once you know where you’re starting from and where you want to go, there’s a much clearer path.” (B, 18:47)
• Invokes C.S. Lewis: “You can’t go back and change the beginning, but you can start where you are and change the ending.” (B, 18:47)

3. What does success look like for you?

• Purpose: To define personal and professional success—to differentiate your own goals from societal or inherited expectations.
• Margaret encourages probing further: "Why that title? Why that amount of money? That is oftentimes pointing to something else… understanding what success looks like for us helps us to peel off things that aren’t serving us.” (B, 21:19)
• Dave reinforces that clarity on the underlying “why” is crucial.

4. What are your core values, and how have these values changed throughout your life?

• Purpose: To clarify guiding principles and how values might evolve.
• Two Ways In:
  • Examine your calendar—where you spend your time signals real values versus stated values.
  • Notice what makes you angry (“what makes you angry is that one of your values has been stepped on”). (B, 24:55)
• Margaret: “Oftentimes people think this is the hardest question because we’re not really asked this question very often.” (B, 24:55)

5. To what extent are you aware of, and allow yourself to feel, your emotions?

• Purpose: To promote emotional self-awareness, which is fundamental for emotional regulation and effective leadership.
• Check on who notices your emotions first: “If you’re aware of your own emotions as you’re having them, you are the first one that is aware of that.” (B, 28:20)
• Leaders who aren't attuned to their emotions cannot manage them or their impact on others.

6. What feedback have you received over the years about how your actions and behaviors impact others?

• Purpose: To integrate external perspectives—both positive and negative—into your self-understanding.
• Sources: Family, friends, performance reviews.
• Margaret advocates: “On a certain level, all of it [feedback]… might be important for you to know. It doesn’t mean that you have to take all of it in and do what they say, but it might be important for you to know.” (B, 30:13)
• Don’t discount positive feedback: “Don’t forget the good stuff. That’s why you’re invited to the party.” (B, 32:42)

Notable Quotes & Memorable Moments

• On Emotional Intelligence:
  “What makes a really great boss is not their intelligence and it’s not their technical or functional skills, it’s those interpersonal skills.”
  —Margaret Andrews (05:50)

• On Pivotal Moments:
  “You can’t go back and change the beginning, but you can start where you are and change the ending.”
  —C.S. Lewis, quoted by Margaret (18:47)

• On Values:
  “Oftentimes people think this is the hardest question because we’re not really asked this question very often.”
  —Margaret Andrews (24:55)

• On Feedback:
  “Don’t forget the good stuff. That’s why you’re invited to the party… that is important. Otherwise they wouldn’t tell you that.”
  —Margaret Andrews (32:42)

• On Changing Leadership Beliefs:
  “When I was younger I thought the leader was the person that always had the answers, that they were very decisive, etc. And I think I’ve learned that that is not true.”
  —Margaret Andrews (34:29)

Timestamps for Key Segments

• 00:00–07:11: The necessity of self-understanding and the “Best Boss Exercise”
• 07:44–11:13: Why self-knowledge is the starting point for leadership, and intros to the six questions
• 12:21–16:52: Deep dive on Question 1 (Who/whose thinking shaped you)
• 17:15–20:17: Question 2 (Events/situations shaping perspective); the role of agency
• 21:19–23:53: Question 3 (What does success look like for you?)
• 24:25–27:20: Question 4 (Core values and how they manifest/shift)
• 28:20–29:53: Question 5 (Awareness of emotions and emotional intelligence)
• 30:13–32:53: Question 6 (What feedback have you received about your impact?)
• 33:55–34:29: The power of returning to the questions; building ongoing self-insight
• 34:29–35:44: Margaret shares how her thinking on leadership has changed
• 35:44–end: Closing gratitude and resources for further learning

Tone & Language

Throughout the episode, the tone is reflective, supportive, and practical. Margaret draws listeners in through illustrative exercises and relatable anecdotes, while Dave allows conversation to flow naturally, pressing for depth and clarity.

Final Takeaways

• Self-awareness is not a one-time project—it’s a practice that deepens and evolves over time.
• Leadership is grounded in understanding oneself and embracing interpersonal dynamics, not just technical skill or decisiveness.
• These six questions offer a roadmap for any leader seeking to grow and make a greater positive impact—starting with themselves.

For deeper exploration, listeners are encouraged to revisit the episode and check out related resources on CoachingforLeaders.com, including episode notes and Margaret’s full book.