The Time Is Now: Mastering the Art of the Courageous Conversation

In the aftermath of the Challenger disaster in 1986, NASA found that the engineers working on the spacecraft had concerns about the O rings when exposed to extreme heat. But those engineers were afraid of sharing the information so they didn’t pass it up to their supervisors. 

That one missed conversation resulted in a 32-month hiatus in the shuttle program and tragically ended the lives of 7 Americans. 

Thankfully, unlike NASA, most of our day to day conversations rarely have life or death implications.

So, while our silence may not put lives at risk, 

silence can undermine our ability to lead ourselves and others well. 

Since the civil unrest in Minneapolis on Memorial Day, our nation has been wrestling with how to move forward in creating a country where respect and opportunity are available to all.

Our emotional wounds from the months of self quarantining, battling COVID 19 haven’t yet healed.

We are still exhausted from trying to teach our kids while we juggled our own workload.

We’re drained from worrying about protecting our families from a danger we can’t actually see.

And we’re tired by the still strong pressure to perform as usual at work, while we work to keep the family machine running smoothly at home.

If we don’t do something differently,

we will continue to be emotionally and physically spent.

We must learn how to master courageous conversations.    

In her book, Fierce Conversations, Susan Scott wrote, “While no one conversation is guaranteed to change the trajectory of your career or life, any single conversation can.” 

The conversations that take the most courage – those in which you speak candidly and listen openly – are those which make the biggest impact. Those are the conversations that create a pathway to building the relationships, influence and outcomes you desire.

At home, at work and in the world at large,

mastering these high-stake conversations is critical, and yet, for most of us,

deciding to have those conversations is extremely stressful. 

It’s no wonder why we avoid conversations like this. 

They feel risky.

We’re afraid of offending. 

We’re afraid of being judged. 

We don’t want to lose face. 

Some of us “don’t do vulnerability”. 

Many of us don’t want to rock the boat.

And finally, the optimistic among us hold out hope that it will go away on its own. 

BUT, the truth is, there’s too much at stake to avoid having these difficult talks.

As Kerry Paterson wrote, in the book, Crucial Conversations: Tools for Talking When Stakes Are High ,

“In perhaps the most revealing of all the health-related studies, a group of subjects who had contracted malignant melanoma received traditional treatment and then were divided into two groups. 

One group met weekly for only six weeks; the other did not. 

Facilitators taught the first group of recovering patients specific communication skills. (When it's your life that's at stake, could anything be more crucial?)

After meeting only six times and then dispersing for five years, the subjects who learned how to express themselves effectively, only 9 percent had succumbed as opposed to almost 30 percent in the untrained group.” 

This study indicates that our immune systems are at stake when we avoid courageous conversations.

However, our health isn’t the only thing that’s negatively affected when we avoid tough talks. 


Jobs, relationships, happy families

and the causes we’re most passionate about…

are all at risk when we stay silent.

So, at a time with so much unrest and unease, I’ve asked myself “Where in my life right now, is a courageous conversation needed?” 

As a life balance and leadership coach, I get to watch my clients transform their lives when they ask themselves good questions. You can do it, too.

With the summer here, is it time for a family meeting to set expectations about what everyone can do to keep the household running smoothly?

As a business leader, is now the time to check-in with each team member to discuss their current job satisfaction and what could be done to improve it?

With deep polarization in our country, this is the time you want to talk with your children about your core values of respect, responsibility and reason?

I’ve created a checklist so you can see where your dialogue skills might need to be shored up before you dive into a crucial conversation. 

With a little bit of practice, all of us can master the art of engaging in courageous conversations in a constructive way.

However, as with most things, a bit of preparation can really set the stage for a productive conversation.


PREPARE AHEAD:  Consider who you’re speaking with and think about their best time of day. And where would they be most comfortable? Decide on a non-threatening, neutral setting for your conversation. 

CHOOSE ONE TOPIC OF FOCUS:  Conversations have a way of getting sidetracked, especially those that are fraught with emotion. It’s your job to keep the conversation on track. To keep the focus, stick to only one topic. Choose a topic that benefits both of you. Even those who disagree with the “how” often agree on the “why”.

KEEP YOUR PARTNER’S PERSPECTIVE IN MIND DURING THE CONVERSATION: You can do this by asking yourself some questions about them prior to your conversation like, “What’s their backstory?” “What values might they hold close?” “What might be going on at home for them?” “How might they respond to what I have to share?” The point isn’t to assume you know what your partner’s thinking, but for you to try on different perspectives before you engage in a tough conversation.

KNOW WHAT YOU WANT AND WHAT YOU DON’T WANT: It’s important to have your intended outcome clear in your mind before you begin. It’s equally as important to know what you DON’T want to have happen. Knowing what you DO want and what you DON’T want are the guardrails for your conversation. 


After you’ve given time and thought in preparation, these are the 5 steps to keep in mind when you engage in your courageous conversation.

  1. Speak from your heart, don’t think from your head. (Share your hopes.)

  2. Focus on the facts and the future. (No opinions and steamrolling)

  3. Learn to look. (Observe emotions. Don’t just listen to words.)

  4. Make it safe. (You will be baited, Don’t take it.)

  5. Be curious and empathetic.

  6. Be grateful and request that the dialogue continue. 

Steven Covey said, “Most people do not listen with the intent to understand, they listen with the intent to reply. ” 

The need to be heard and understood runs deep in all of us.

The way we’re currently talking to one another is ineffective 

And it’s causing more entrenchment than understanding. 

Now is the time each of us needs to take responsibility to learn new ways to dialogue.



If you would like additional tools for those important conversations, schedule a complimentary 60 minute Strategy Session with me. During the call, you’ll receive strategies to lead yourself and others with compassion and courage. 





Lisa Bobyak, Life Balance Consultant, Leadership Coach and founder of Living Fully Balanced™, has been elevating the performance, perspective and peace of mind of high-achieving professionals on the brink of burnout for nearly a decade. Through her Living Fully Balanced™ methodology, she equips her clients with both the self-awareness and planning tools to thrive in our fast-paced, work-driven society. Her inspiring and educational presentations challenge the current hustle culture and offer strategies to prevent burnout and create balance. Lisa is the creator of the transformative  Love Your Life Again program. She’s also authored the ebook, 7 Days to Loving Your Life Again and the Living Fully Balanced Life Planner©. 

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