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Courageous Conversations: The Time is NOW!
By Libby Wagner, Founder of Professional Leadership Results


When was the last time you felt like you had to summon all your courage, your heart thumping in your chest, butterflies in your stomach and mouth suddenly gone dry? Or instead, you were steeling yourself up for something big, all-business with your game-face on? Chances are, unless you’re a professional athlete or dragon-slayer, you were considering a Courageous Conversation of sorts, a face-to-face with someone important to you — a boss, challenging employee, discerning client or stakeholder, or even someone you love.

How can a simple conversation, an interpersonal interaction, evoke such fear, anxiety or excitement? It’s not rocket science, after all . . . what’s the big deal? It matters. It’s the risk, or at least the perceived risk, that helps to create this sense of awe, dread or even avoidance. The stakes feel high, and we’re never really sure of the outcome. But, it’s not as if the fate of humankind is at question . . . or is it?

I love poet and author David Whyte’s recollection of his understanding of the significance of conversation in the development of human beings. He shares that as a young man newly in love, he was more than uncomfortable with the realization that the object of his love wanted to talk about the relationship. Finally, after this painful conversation was over, he was relieved to have passed that milestone and would never have to have that interaction again. Except . . . she showed up the following week, and he found that the conversation seemed familiar: hadn’t we already covered this terrain? Was this déjà vu? And so, because he was a young man, he mentioned that they had already had this conversation . . . Everyone who’s passed 30 knows what happened next! Finally, he relates that his true realization would come much later: we are not having conversations about our relationships; the relationship is the conversation.

In the workplace, we are not having conversations with our employees, customers, peers and bosses about the issues at hand—the very way we engage, interact, resolve and solve problems is our business. Indeed, the Courageous Conversation is so vitally important precisely because the fate of your business—your fate—is at stake.

Consider these real conversations in business that need to be had, but aren’t.

  • Members of a leadership team who have “history” and therefore allow grudges, assumptions and distrust to impede every meeting and project.
  • Business owners who are siblings who aren’t sure how to approach the topic of their aging parents, still in the business.
  • Two competing factions of a non-profit organization, one whose numbers have always been in the red, the other always profitable and supports the first. Every executive decision leaves one feeling defensive and the other superior because no one will address the “elephant” in the room.
  • A business owner whose largest client is abusive, disrespectful, disruptive and self-righteous, so much so that the owner wonders if the money is even worth it because their values don’t match up.
  • An employee whose boss is inconsistent in his decisions and actions, which causes her to be overly cautious, uncreative and fearful that she’ll make a mistake.
  • Business partners who feel an increasing sense of dissatisfaction and inequality in terms of workload.
  • An organization undergoing significant changes in the past two years, including an acquisition, reorganization, and elimination of programs. Employees are just keeping their heads down, trying not to make waves, doing the minimal to get by.

Last winter, when I set out for a Saturday morning run around Green Lake in Seattle, I noticed a headline as I passed the newspaper box: “Infighting Distracted WaMu’s Regulators.” (Seattle Times, April 2010) Wonder what those conversations would’ve been worth? After the demise of Washington Mutual, which resulted in an estimated loss of $7 billion dollars in wealth and thousands of lost jobs and residual effects to the economy, it’s easy to see why having those Courageous Conversations is essential. Perhaps, even, the fate of human kind is at stake.

Knowing that you need to have the conversation and actually doing it are two different things. How can you ensure that you can remain calm and confident? How can you be poised, assertive and respectful? Practice the Three P’s for Courageous Conversations:

  1. Prepare: Identify what you want and be specific. Jot down notes, get really clear and even translate what you don’t want or like into what you do so that the chances of communicating clearly are better for you.
  2. Practice: Plan out what you will say, how you will say it, and how you anticipate the person’s response. Know how you might counter, where you have room to negotiate and what your “deal breakers” are. Utilize a confidant or someone you trust and practice your conversation with them. Ask for feedback.
  3. Plexi-Glass. Imagine you have a clear plexi-glass shield that protects you from anyone pushing your buttons or getting you off-track. Get really clear about your goal or desired outcome and identify phrases that can help you stay focused. If you can, Presume Good Intent as you prepare for the conversation, which can help you detach from emotionally responding or taking something personally.
  4. The time is now for you to step up and have that Courageous Conversation. What will it cost you if you don’t?