This document summarizes a presentation about facilitating courageous conversations. The presentation covers topics such as interrupting with care, moving conversations from safe to brave, debunking myths, growing through iterations, and engaging across differences. It provides tools and examples for having difficult discussions, including being a DEAR (describe, explain, affirm, request), active witnessing, listening bravely, comparing dialogue to debate, and using polarity thinking. The goal is to have conversations that challenge participants but also make them feel safe and able to learn and grow.

1. The Roeper School
Rosetta Eun Ryong Lee
Seattle Girls’ School
Interrupting with Care and Facilitating
Courageous Conversations
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

2. About Seattle Girls’ School
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3. Agenda
 Safe Versus Brave
 Interrupting with Care
 Courageous Conversations
 Resources and Tools
 Questions and Answers
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

4. Engaging in Courageous
Conversations
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5. Safety Versus Comfort
Safety: I feel that, in this space, I can ask questions without
fear of judgment. I can voice my perspective and know that
I will be validated for the fact that that is my truth. Others
may challenge my ideas, but that challenge is in the spirit of
greater shared understanding and growth.
Comfort: I feel that, in this space, my reality will be agreed
with, validated, and unchallenged. I don’t have to explain
myself to be understood, and I don’t have to justify my
perspective, as everyone shares it.
True dialogue happens in an environment where everyone is
safe but not always comfortable...
SO THAT THEY CAN LEARN AND GROW.
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

6. Moving Conversations
from Safe to Brave
 Controversy with Civility
 Ownership of intent and impact
 Challenge by choice – with reflection
 Respect in all its multiplicity
 Pointed challenges, not personal attacks
 Mindfulness of the true source of emotions
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

7. Debunking Some Myths
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 All or None
 Mistakes
 Apologies
 “Tonsils” Theory
 Vulnerability

8. Growing Through Iterations
William Taylor’s Reflective Competence Model
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

9. Reflection: Courageous Conversations
What are some of your
challenges for authentic
dialogue? How might you
move into more
courageous
conversations?
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

10. Interrupting with Care
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11. Speaking From the Heart
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12. Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)
Can you lean on the
relationship?
Can you make it personal?
* Is your relationship
hierarchical? *

13. Being A DEAR
 Affirm the person or relationship
 Describe the behavior without judgment
 Explain the emotion/impact and your filters
 Assume positive intent
 Request or suggest different behavior
*** Key Points: timing, I statements, actions not
adjectives, inside feelings not outside feelings***
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

14. You are a good friend. I have so much fun
with you, and I can tell you anything. Earlier
today, when I got my math test back and I got
98%, I heard you say, “Well of course you got
a 98% - you’re Asian!” I was pretty hurt when I
heard that. I work hard in all my classes to get
good grades, but so many people assume it’s
because of my race. It’s sad that I don’t get to
own my accomplishments like everyone else.
I’m pretty sure you didn’t mean for me to feel
that way. Can I ask that you please don’t say
things like that anymore?
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)
Being A DEAR: An Example

15. Being A DEAR: An Example
I think you and I both agree we all have a
right to be respected and heard in this
community. When we were disagreeing
about budgets, you said, “You’re being
overdramatic,” and later, you called me a
“drama queen.” Statements like this make it
sound like I am being too emotional and
that my concerns are drama rather than real
issues. I am assuming you don’t intend to
police my tone or dismiss my concerns. I
would appreciate your not saying things
like this anymore. Thank you.
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

16. Being A Witness
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

17. Are you speaking to the agent or
the audience?
Do you want to minimize harm to
the target group?
Do you want to educate?
Do you want to challenge social
norms?
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

18. NCBI Effective
Interventions Model
 Reduce Defensiveness
– Tone
– Body Language
– Respect
 Keep the Conversation Going
– Hear Them Out
– Ask Open-Ended Questions
– Set Aside Your Feeling for the Moment
– Dialogue
 Build the Relationship
 Stop the Behavior
 Win an Ally
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

19. Active Witnessing: Examples
 Ask open ended questions
– “He looked suspicious”
– “How did he look? How was he acting? Why was that suspicious?”
 Find out the experience motivating the comment
– “Why can’t they just speak English around here?”
– “It must be hard not to understand what people are saying around you.”
– “I’m sick of my taxes paying for freeloaders”
– “Tell me more about about that.”
 Use exaggerated humor to highlight what’s going on
(use sparingly)
– “You’re gay – what do gay people think about this issue?”
– “I’m not sure – I’ll go ask. It may take me a while, since there are a million people.”
 Join the person and do not make yourself superior
– “She got that award because she’s Black and female.”
– “You know, I hear that a lot. I’ve been trying to figure out why we seem to think when a
Black woman gets recognized it must be because of ‘diversity’ or ‘affirmative action’
reasons rather than that she earned it.”
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

20. Listening to the Real Message
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21. Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)
Is this about what you did or
who you are (guilt or shame)?
What is your mindset voice
telling you?
Might this be an opportunity to
learn and grow?

22. Listening and Responding Bravely
 Listen with full attention
 Don’t try to defend or respond right away
– Take deep breaths
– Acknowledge your feelings
 Your mistakes don’t define you
– Be worthy of their trust and gift
 Prioritize the Impact over Intent
– Apologize for real
*** Moving through these moments with grace is
called shame resilience. It’s a vital skill***
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

23. Listening and Responding: Examples
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)
 “I really appreciate your telling me this.”
 “I’m so embarrassed that I did that.”
 “I’m so sorry my words and actions made you feel
that way. No matter what I intended, it hurt you.”
 “I’m pretty overwhelmed right now, and I don’t
want to respond in a way I’d regret. After I take a
few minutes, do you think you can help me come
up with a better way to handle that situation?”
 “I wanted to go back to a moment I don’t think I
handled very well… Can we talk?”

24. Process Break
How might you use
these tools in your
everyday life and more?
What questions or
concerns come up?
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

25. What About Group Conversations?
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26. Fears and Anxieties that Keep Us
from Having Conversations
 Offending
 Losing Face
 Tokenism
 Social Risk
 Bursting the Bubble
 Rocking the Boat
 Conflict
 Lack of “Authority”
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

27. Pitfalls and Obstacles that Keep Us
from Conversing Again
 Outbursts
 Silence
 Denial
 The Good Talk
 Teacher vs. Facilitator
 Personal Attacks
 The Quick Fix
 Leadership Oppression
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

28. Learning Zones
and Performing Zones
Learning Zone: You engage deeply in the areas of
weakness. You actively seek new information,
strategies, and feedback for adoption. You embrace
mistakes in this low-stakes environment.
Performing Zone: You showcase your areas of strength
(e.g. a competition routine). You engage in new
information, strategies, and feedback in relation to
your current thinking (e.g. PhD defense). You minimize
mistakes in this potentially high-stakes environment.
Make sure you know what zone you’re in SO THAT YOU
CAN MAXIMIZE THE BENEFITS OF THAT SPACE.
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

29. Comparing Dialogue and Debate
 Dialogue is collaborative. Debate is oppositional.
 In dialogue, one listens in order to understand and find
meaning. In debate, one listens in order to find flaws and
to counter arguments.
 Dialogue reveals assumptions for reevaluation. Debate
defends assumptions as truth.
 Dialogue calls for temporarily suspending one’s beliefs.
Debate calls for investing wholeheartedly into one’s
beliefs.
 In dialogue, one searches for basic agreements. In
debate, one searches for glaring differences.
 Dialogue remains open-ended. Debate implies a
conclusion.
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)
Adapted from Shelley Bennan, Dialogue Group, Boston Chapter, Educators for Social Responsibility

30. Singleton Compass
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31. Polarity Thinking
Cognition marked by flexibility and
elasticity that enables individuals to
recognize and navigate the countless
opposing yet interdependent energies
that manifest in all life. Polarity thinking
transforms ‘either/or’ contrasts into
‘both/and’ formulations that allow for
mutually-satisfying, stable, and
predictable gains in personal and
professional life.
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)
Caroline Blackwell, National Association of Independent Schools

32. Polarities, Not Binaries
 Equality and Equity
 Free Speech and Inclusive Speech
 Diversity and Inclusion
 Diversity and Unity
 Systems Work and Individual Work
 Calling Out and Calling In
 Heat (protests, disruption, opposition) and
Light (education, patience, collaboration)
 Safety and Bravery
 Accommodation and Assimilation
 Change and Tradition
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

33. Polarity Mapping
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Caroline Blackwell, National Association of Independent Schools

34. Engaging Across Differences
 Be willing to sit in the gray areas
 Be willing to be uncomfortable
 Be willing to be vulnerable
 Be willing to extend trust and earn trust
 Be willing to listen fully
 Be willing to continue the conversation
 Be willing to believe we need each other
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

35. Process Break
How might you use
these frameworks in your
everyday life and more?
What questions or
concerns come up?
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)

36. Inclusive Communities
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37. Presenter Information
Rosetta Eun Ryong Lee
6th Faculty and
Professional Outreach
Seattle Girls’ School
2706 S Jackson Street
Seattle WA 98144
(206) 805-6562
rlee@seattlegirlsschool.org
http://tiny.cc/rosettalee
Rosetta Eun Ryong Lee (http://tiny.cc/rosettalee)