Business Conversation

We’ve all experienced having one of those cringe-worthy moments where we know we have to have a conversation we’d much rather not have.

Why do we avoid having tough conversations? What makes them so frightening? How do you have a tough conversation? Should we have them? At some point in life, we’ve all had to step up and have tough conversations.  Maybe it was with your boss, family, partner, friend, etc.  Maybe it involved speaking up to own your value, maybe it involved cheating, a break-up, changing company policy, or voicing a contrary opinion.  We all know that tough conversations are a necessary part of life, so why aren’t we having them?  They represent change and we’re not always ready or open to that change. 

In this interview, David Wood, Joel Bower, and I talk about having tough conversations. David Wood is a life coach who teaches others how to have tough conversations.  He helps others find and speak their truth. My co-host for this interview is Joel Bower.  He is a Master Mind expert and founder at Owning The Edge.  Together we’ll face tough conversations, discuss how we react when faced with these situations, our flight or fight responses and we can either rise to the occasion that’s potentially daring or cling to what we know in fear.

A former Consulting Actuary to Fortune 100 companies, David left his cushy Park Avenue job 20 years ago to build the world’s largest coaching business. He became #1 on Google for “life coaching”, serving an audience of 150,000 coaches, and coaching thousands of hours across 12 countries. He is the author of “Get Paid For Who You Are,” David believes that the tough conversations we avoid are our doorways to confidence, success, and love. They become defining moments that shape our world. He coaches high performing entrepreneurs, executives and teams, and now prison inmates to create amazing results and deep connection, one tough conversation at a time.

Opening Up About the Tough Conversations

If you’ve struggled to have those tough conversations you’ve likely wondered. How do people do things they find hard or uncomfortable? How can we go from clinging to our fears to choosing to go through the danger, through the pain again and again in the hopes of an upside? 

We suggest that you start by confronting those tough conversations head-on. We’re not talking about running in and saying the first thing that comes to mind but rather, take the time to break down each conversation. What are the positives? What are the negatives? If you persevere through this discussion, what will you get out of it? What will you have actually accomplished by working through this topic? If we figure this out early on, then the next steps will only be easier. 

Be self-reflective: Ask yourself, why are you nervous about this conversation? How can you improve your situation, your nervousness? Walkthrough the possible negative consequences. For a moment ignore all positive outcomes, what would happen if only the negative outcomes came to be? Can anything positive come from the negative? 

Our Experience with Negatives that Turned Into Positives

It’s no secret that we’ve all been through a few sour experiences. I’ve fallen off a mountain breaking almost every bone in my face. David was paragliding over the Bali Ocean at 300ft when a wing collapsed and he fractured his spine! Willingly taking these trips put us at risk where we had to face every negative possibility, including injuries and even potentially death. How did we make these risk assessments…courage! 

But know this: Courage is subjective. Tough conversations can be the same as jumping off a mountain or free climbing, your brain doesn’t know the difference! 

Training, Practice, and Commitment

How can you tell when the risks outweigh the reward? There is no substitute for training and practice. Without experience, it can be impossible to know when to not have a tough conversation. Without experience, it can be difficult to say what’s negative and what’s positive. Commitment can be the only thing between you and success. Without commitment, you can’t be willing to take the risks regardless of the negatives or positives. 

Struggling to Push Through the Tough Moments

Many people struggle with facing those tough situations. How can you overcome these moments? Try a few things from David’s worksheet! Ask yourself what are you afraid of? What are you really hoping for? 

My request… give yourself permission to be vulnerable. Give yourself permission to benefit from the negatives. Put intention behind your decisions. Working through the tough decisions and facing danger is nothing if there isn’t a reward or benefit to your risks. More importantly, ask permission first. Tough conversations aren’t one-sided. You’ve got to have shared permission, shared responsibility, and shared openness. Nothing will happen if only one party is open to overcoming the tough topic.  

How do you start the conversation? Start simply! ‘Can we talk?’ ‘Are you open to this…?’

How can you open communication? Share your hopes. ‘We can meet this quota.’ ‘This strategy will optimize everything.’ Share your fears. ‘My concern is…’ ‘I’m aware this is a risky, edgy conversation…’

Next, share the responsibility. Acknowledge that you or your actions were part of the problem and offer a solution. Make a request. ‘Consider this..’ ‘Give me 30 days to prove it can do better.’ 

Stay curious and listen. Listen in closely to their response, stay tuned in for their suggestions, their hopes, and their fears. ‘How is this for you.’ ‘Do you have a better suggestion.’ ‘I want to hear your thoughts.’ 

Monologues are never the way to work through tough conversations. Courage must come from both parties if the topic is going to be overcome. 

Consider how you can add to the conversation. What do you bring to the table? How can your experiences, your hopes, and fears steer the conversation and how can your courage help both parties push through tough topics? 

With gratitude,

Dov Baron, Expert on Leadership, presents his Authentic Leadership Matrix!

Dov Baron is first and foremost “The Dragonist”. As The Dragonist, he teaches us how to recognize, find, retain and nurture dragons (top talent) hidden within our organizations. Want to learn more about what Dov has to offer, and how you too can become a Dragonist in your realm? If you and your leadership team are dedicated to getting the result you set out to achieve in the most meaningful manner, bring Dov in to speak to your organization about the strategic advantages of Dragon Leadership. Go here to get started. Copyright: Dov Baron International 2020


  • @TheDovBaron

    Inc Magazine top 100 leadership speaker, Inc #1 Podcast for Fortune 500 Executives, Entrepreneur Mag contributor, Leadership Strategist, Storyteller.

    Dov Baron

    Dov Baron is “The Dragonist”, guiding us in how to recognize and nurture dragons (the top talent) hidden in our organizations. A Dragon Leader is not a position; it’s someone who is always pushing to improve and wants those they serve to reach their full potential.   Dov’s humour and no-BS style is contagious. As a master storyteller, he is considered to be the leading authority on actualized leadership. Actualized leadership means getting the result you set out to achieve in the most meaningful manner.   Working with diverse leaders and executive teams, Dov filters common bonds to create Fiercely Loyal cultures. You can’t achieve loyalty without “meaning”, and talent only stays when they feel they are a part of something larger than themselves.    Besides being a bestselling author of One Red Thread and Fiercely Loyal: How High Performing Companies Develop and Retain Top Talent, Dov has been named one of Inc. Magazine’s Top 100 Leadership Speakers to Hire and as one of the Top 30 Global Leadership Gurus. He has spoken to the United Nations, The World Management Forum (Iran), The New York National Speakers Association, and The Servant Leadership Institute.    In June 1990, while free rock climbing, Dov fell approximately 120 feet and landed on his face. The impact shattered most of the bone structure of his face. After ten reconstructive surgeries, no external evidence remains; however, this experience wasn’t just life-changing, it was completely transformational. Dov shares how Dragons are born in fire. Experiences that could potentially destroy you can, instead, birth purpose, passion, and the hunger to champion others. We can learn to nurture the Dragon Fire in ourselves, our families, our communities, and our companies.    Dov believes the world needs more "Dragon Leaders" committed to living their purpose, standing in their truth, and empowering others to find their fire and do the same.