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Courageous Communications, Part 3: Preparing for the Tough Conversations


Actor and director Stephen Moyer says, “Conflict is drama, and how people deal with conflict shows you the kind of people they are.”

Having worked with and observed thousands of leaders over the years, how they deal with the conflict inherent in difficult conversations is one of the critical distinguishing characteristics that separates average leaders from great leaders.

But how do you go about holding the uncomfortable conversations that are likely to produce conflict and drama, in the interest of moving your organization forward? How do great leaders handle what we call Courageous Communications differently from other leaders?

In this post, we’ll discuss how the most effective leaders prepare for their Courageous Communications. In our next post, we’ll discuss how to handle those conversations as effectively as possible.

As you read this post, it might be helpful to think of a real issue you might be facing with someone you work with – your manager, a peer or someone who reports to you. At the end of this post, there will be a few questions to help you think through how well you are prepared to tackle the courageous communication that is necessary.


The most effective leaders prepare on at least two levels for their courageous communications.

Thinking Differently about Conflict

First, they “think” (their assumptions, beliefs, perceptions, etc.) differently about taking on conflict than less effective leaders do. They know they will need to hold the difficult conversations and are fully comfortable with that responsibility…even if the conversations themselves might be extremely uncomfortable. Previously, we’ve discussed the Thinking-Action-Outcomes model. Effective leaders’ “thinking” recognizes that conflict, handled well, is a positive force, not something that should be avoided at all costs. When choosing to act, they also recognize that they ultimately are trying to engage people in the journey.

Less effective leaders shy away from the conflict. They may “think” that “conflict is bad.” Or, they want to be liked and are afraid that holding the difficult conversations will erode their “likability.” Hence, they avoid it, which paradoxically creates more of the disruption they were trying to avoid in the first place.

Effective leaders also create trusting environments in which effective conflict can occur.  One of the best performing senior executives I’ve had the opportunity to work with operates by what he describes as the Hippocratic Oath for Leaders: “I mean you no harm.” He feels his role as leader is to help the organization and every individual be the best they can be. So, his team – including managers, peers and direct reports –get tough feedback, but always from a caring/trusting perspective. They know he has their best interest, and that of their organization, at heart. (And, is the living embodiment of what we think is one of the great paradoxes of great leaders: Tough AND Caring. More on that in some future post.)

It’s no coincidence that organizations that deal with conflict and courageous communications most effectively, also have higher levels of trust and trustworthiness. They treat tough conversations as a natural part of who they are and not something to be avoided.

And, because the environment is positive, and non-respectful behavior isn’t tolerated, you see less of the horrific behavior representing years of systemic abuse that have been so prevalent in the news the last few weeks. In strong cultures, people know that disrespectful behavior by anyone at any level will be dealt with and not covered up. And, senior leaders embrace their roles as stewards of the organization’s values, not the worst offenders.

Acting Differently

The second level of preparedness is about how more effective leaders act as they prepare for a courageous communication. More effective leaders prepare for difficult conversations by addressing three questions:

1. Does this conflict need to be addressed?

A colleague of mine once worked for a manager whose catch phrase was, “That’s not a battleground we want to die on.” The problem was that there were NO battlegrounds he ever wanted to die on. Or, even suffer a minor wound. As a result, the guests his team was responsible for servicing didn’t get the best of what the resort could offer. People on his team didn’t get the feedback they needed to be their best. His team felt unsupported. Team members weren’t held accountable for results. Ultimately, they under-performed.

On the other hand, not every issue needs to be confronted. Early in my career, I worked for one of the worst bosses ever. We could do a full book chapter, maybe even a full book, on his efforts at wreaking havoc within his organization. He would absolutely fit the definition of “asshole” as Stanford University professor Bob Sutton described in his classic book, “The No Asshole Rule.”

The bad bosses’ catch phrase was, “You just need to go kick more ass” which he did on a regular and frequent basis. No issue was too small for him to confront. While he rarely turned his ire – bordering on insanity – toward me, he regularly wore out my peers about trivial details. As a result, everyone avoided him as much as possible, and did what they could to just get by. No one was even close to fully engaged in the effort to drive the division forward.

So, when do you choose to confront? It’s hard to give an explicit list, but here are a few questions to provide a starting point:

  • Is someone behaving outside your organizations values?

  • Is performance below an acceptable level, or below what someone is capable of?

  • Is someone’s behavior disrupting the ability of the team to perform their best?

  • How would you feel if a story about the situation appeared on the evening news, or the front page of the newspaper, and you were portrayed as not taking action to intercede?

2. What issue do we need to confront?

Better leaders focus their attention on the issue that creates the most leverage or is the most critical to address. And they recognize that the issue that needs to be addressed may change over time, even within a single conversation. Here’s the classic example: you’ve got somebody on your team who has shown up late for work a few times recently. As a result, he’s under-preforming and other team mates have expressed their concerns about it.

You address it with him. He owns his behavior and promises it won’t happen again. All good.

Then, two or three weeks later he shows up late again. What issue do you address?

If you thought, “Talk to him again about being late,” raise your hands.

Yeah, I thought that’s what you might say!

You have a new problem to confront: now it’s not about his tardiness, it’s the much deeper and more complex issue involving his commitment to you to “not be late again.” The critical issue has shifted to his failure to honor his commitment to you – an integrity-related issue, not whether or not he makes it to work on time.

3. How do we create a safe environment in which to confront the issue?

As noted above, creating a safe environment for Courageous Communications actually starts well before the conversation itself. It’s difficult to have a truly effective, tough conversation with someone if you haven’t built an environment of trust and respect or if you no relationship with the other person.

Presuming you’ve built the proper foundation, then, generally establishing a safe environment means finding a place to have the most productive conversation possible. The old adage, “Praise in public, criticize in private” generally holds true.

A few questions to spur your thinking and reflection:

  • To what extent are you holding all the courageous conversations you need to be holding with others?

  • Have you been avoiding any? If so, why? What would it take to hold the conversation?

  • How well have you created an environment in which difficult communications can take place?

  • If you think you’ve been holding courageous communications with others, but not getting the results you intended, why do you think that gap exists?

I’d love your thoughts and feedback.

In our next post, we’ll discuss how to make those conversations go well.

Intrigued by what you’re reading? Download our white paper on converting strategy into execution and learn more about us by visiting our website. WhiteWater International Consulting, Inc. helps organizations understand the challenges they face and helps enterprises achieve and sustain outstanding performance through unleashing the passion and capabilities of its people. Because an organization is only as good at the people who power it.

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