Wicked Conversations

personal development Jul 14, 2018
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How to Disagree Without Being Disagreeable

Wicked Conversations tackle Wicked Problems and help lead to Wicked Results.

The use of "Wicked" indicates challenging, interesting, and worth it, not evil or done with malicious intent.

What’s Are Wicked Conversations For?

Wicked Conversations provides an approach for engaging in challenging discussions that lead to a deeper understanding of topics that defy easy resolution and positions you don’t share.

Wicked Conversations tackle difficult subjects with curiosity and courage. In Wicked Conversations attachment to assumptions and agendas melt away and transformation and truth become accessible. 

Who Are Wicked Conversations For?

Wicked Conversations are for those who seek to engage in meaningful dialogue that embraces empathy and mutual respect, even when they do not reach consensus or mutual appreciation.

What Promise Is Wicked Conversations Making?

Applying the Wicked Conversation approach to challenging debates enhances the feelings of equanimity and well-being for everyone engaged in them. Whatever the result, all parties joined in a Wicked conversation feel more exhilarated than exhausted and more included and appreciated than excluded and condemned when its over.

“I used to avoid discussions about important subjects and often got frustrated when I did have them. Then I started applying the Wicked Conversation approach. Now I feel excited and exhilarated after wrestling with tough issues with people who have a position different from mine.”

What Does a Successful Wicked Conversation Look & Feel Like?

Participants approach conversations with greater curiosity and courage and less over-confidence and certainty, especially on nuanced topics that defy clear resolution and easy “answers.” They apply assertions instead of assumptions. They leave self-serving agendas at the door. They seek to enhance and elevate the dialogue.

Disagreements are approached as collaborations seeking truth rather than competitions to be “right.” In Wicked Conversations, all parties align their words and purpose with their values instead of making them serve beliefs that are suspicious or suspect.

Where to Begin

Start where you are. You are already enough and at the same time, you are a work in progress seeking to tap your potential and realize your promise.

"We are what we repeatedly do. Excellence, then, is not an act, but a habit." ― Aristotle

A regular practice of engaging in Wicked Conversations refines your ideas and develops your voice. 

Gratitude Vs. Entitlement

You can get a handle on your emotional response to things you disagree with when you approach challenging subjects with gratitude. Wicked Conversations are not the conversations you have to do, they’re the ones you get to have.

"You have a right to your labor, but not to the fruits of your labor." ― Krishna

You are entitled to your opinion, but not to have the world agree with it. This doesn't have to be a source of frustration. Wicked Conversations are invitations to grow.

Embracing Failure

Wicked Conversations are conversations worth having. Conversations that matter. However, challenging yourselves and others will not always work out as you might wish. You must enter a Wicked Conversation knowing "This might not work." 

“Success is not final, failure is not fatal: it is the courage to continue that counts." ― Winston Churchill

A "failed" Wicked Conversation is not a death sentence, It's an opportunity to learn, to grow, to practice acceptance and humility. Embracing failure cultivates resilience and encourages a tenacity for veracity.

Empathy Is an Essential Step, But Not the Final One

The road to compassion, actively enhancing the experience of others by sharing your excellence, starts with the effort of empathy. Empathy is simply extending kindness toward others by seeking to understand their experience.

“If you can learn a simple trick, Scout, you’ll get along a lot better with all kinds of folks. You never really understand a person until you consider things from his point of view, until you climb inside of his skin and walk around in it.” ― Atticus Finch in To Kill a Mockingbird

The first Wicked Conversation is the one you must have with yourself. How can you possibly express kindness and extend understanding for another if you are unable to do the same with and for yourself?

Eudaemonia (AKA Human Flourishing)

Why are you here? For as long as human beings have strode the earth, they have asked important and perennial questions like, "What does it mean to be human?" "What does it mean to be happy?" And, "How can I be more of both?"

"Love the humble art you have learned and take rest in it." ― Marcus Aurelius

You're born with the capacity for reason, creativity, communication, and collaboration. Cultivating these human impulses serves your interests and those with whom you connect. Wicked Conversations nurture greater well-being for us all. 

Embracing Fear

Wicked Conversations require us to be generous and vulnerable and that's all the invitation Fear needs to come calling. The voice in your head that keeps you humble and hiding has served its evolutionary imperative, but it's not going anywhere anytime soon.

“There is nothing with which every man is so afraid as getting to know how enormously much he is capable of doing and becoming.” ― Søren Kierkegaard

Reframe Fear to become a compass and a friend. Fear's arrival is a sign that you're pointing toward something worth exploring. Thank Fear, and then step into what's next.

Values Vs. Beliefs

Beliefs are nothing more than opinion or conviction. An internal feeling that something is true without proof and without making holding it up to scrutiny.

Values are guiding principles that speak to what you deem worthy and important. You can hide behind your beliefs, but your values accurately reflect who we really are.

Too often, beliefs are oppositional. They divide us. Values, more often, are shared. Even when they don't unite us, values help us understand each other.

“We're all human, aren't we? Every human life is worth the same, and worth saving.” ― J.K. Rowling

Wicked conversations are based on values. Beliefs are too often bogus. Values-based discussions encourage greater elasticity and flexibility in our beliefs which enables happier and healthier discussions, even when they're challenging.

Assertions Vs. Assumptions & Agendas

You can't change someone else's worldview, even with facts and figures. Humans are born with a rational capacity, but rationalization is our default setting. Assertions provide a path for transforming arguments into Wicked Conversations.

“No one can make you feel inferior without your consent.” ― Eleanor Roosevelt

Here are a few assertions about assertions.

Assertions are ideas you hold true based on your observation and experience. When you put them forth to be “tested” you not only open the door to empathetically engage and understand someone else’s observation and experience but you are afforded the opportunity to iterate and improve your good ideas and abandon your bad ones.

Assertions employ your curiosity and courage and help you avoid the pitfalls of certainty and over-confidence. Assertions help you stop talking at, to, over, past, around, and through others and instead engage in collaborative conversation with others.

Collaboration Vs. Competition

A Wicked Conversation is not a life or death enterprise. Working with others is far more efficient than working alone or, worse, working against others. Collaboration can be exhilarating and exhausting, but this is true of any activity worth your time and effort.

"Alone we can do so little; together we can do so much." — Helen Keller

Selfishness and ego-gratification might yield short-term wins, but lead to long-term suffering. Wicked Conversations happen with and for others, not to or at them.

Presence Vs. Attachment

Attachment to results that are beyond your determination is not just unhealthy, it’s a path to suffering.

"If you are depressed you are living in the past. If you are anxious you are living in the future. If you are at peace you are living in the present." ― Lao Tzu

Attaching the value of your work (or yourself), to results is a path to unhappiness. Focus on the reasons for your Wicked Conversation (What’s it for? Who’s it for? What change do you seek to make?). In doing this you create not only the best chance to influence the results you seek but, far more important, the best chance to flourish, even when you fail.

Purpose Vs. Passion

Struggling conversations are driven by passion. Meaningful conversations are driven by purpose.

"What man actually needs is not a tensionless state but rather the striving and struggling for some goal worthy of him." ― Viktor Frankl

Before you launch into a Wicked Conversation, know the goal. What does shared "success" look and feel like? Make sure your strategy aligns with your values and talents and engage with a clear and properly motivated intention.

Ends & Means

Wicked Conversations are a winning strategy for living, working, and relationships where you can thrive more and stress less.

"In the final analysis, means and ends must cohere because the end is preexistent in the means, and, ultimately, destructive means cannot bring about constructive ends." ― Martin Luther King, Jr.

The goal of a Wicked Conversation is understanding and deeper truth. The tactics you employ need to be organized by a Wicked Conversations strategy built upon thoughtful intentions, generous motivations, and deliberate aspirations.

Compass Vs. Roadmap

In an age rewarding certainty and confidence, it's tempting to look for a map. The shortest, fastest, and easiest way to get where you want to go (or worse, where others want you to go).

The problem with maps is they only lead you where others have already been. They can't reveal the best course forward now. A compass can do that.

Maps require obedience. Compasses cultivate empowerment.

"I am free to wander. Heading in the right direction. Not all those who wander are lost." ― J.R.R. Tolkein 

Wicked Conversations employ a compass. A willingness to learn as you go. Allows for course correction and tacking. The compass invites adventure and fellow travelers.

"What's Next?"

The way forward involves leaning in and leaping into Wicked Conversations more often. Assertions made with curiosity and courage are the antidote to the pitfalls, dead ends, and misfortunes of arguments made with certainty and confidence.

"First, do nothing inconsiderately or without a purpose. Second, make your acts refer to nothing else but a social end." ― Marcus Aurelius

Wicked Conversations aren't based on assumptions and agendas. They are invitations to develop each other's potential so that we can all deliver on our promise.

Engage and embrace more Wicked Conversations. We need you so that we can all fly higher together!


Scott Perry, Chief Difference-Maker at Creative on Purpose.

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