[MTM] The Courage to Speak Up: Mastering Tough Conversations

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Finding Confidence in Conflict:
A Guide to Navigating Difficult Conversations

October 29, 2024

We all face those moments when a tough conversation is inevitable. Have you ever felt your heart race just thinking about it? Whether it’s with a colleague, client, family member, or, in my case, a landlord, navigating these conversations can be nerve-wracking. But when handled with confidence and empathy, they often lead to unexpected growth.


Before I left Nashville, I was renting a beautiful home that had attracted me with its Zen-like backyard. I loved the space. The only thing I didn’t love about it was… my landlord.

He was a kind man, truly. But let’s just say he was particular—especially about how he wanted the hedges trimmed, down to the exact height.

Had I been the groundskeeper at his personal home, I’d have happily complied. But considering I was renting and living there, it felt a bit over the top. I didn’t want to be disrespectful, yet I also didn’t want to feel micromanaged in my own space.

Now, if you’ve read Mastering the Moments, you know I hate conflict. I avoided addressing this issue as long as I could. But eventually, I gathered the courage to share my perspective.

That conversation was uncomfortable for both of us, but it was worth it. I discovered something surprising: the fear I’d built up was worse than the actual conversation. Once I spoke up, there was an instant feeling of relief. Standing up for myself didn’t just get my point across—it strengthened our relationship. I felt more respected, and when it was time to leave, we parted ways on good terms.

When it comes to communication, Mastering the Moments is about learning how to listen, be authentic, and find solutions that honor both sides. This is true whether we’re dealing with personal issues or professional challenges.

Is there a difficult conversation you’ve been avoiding at home, at work, or somewhere else?

Follow this path to approach it with clarity and confidence, and maybe find that same relief waiting on the other side:

Four Steps to Approach Difficult Conversations with Confidence and Empathy

Difficult conversations have a way of finding us, and each one presents an opportunity for growth. Here are a few steps that have helped me over the years:

  1. Prepare with Clarity: Before entering the conversation, clarify your goal. Ask yourself, “What outcome do I truly want from this?” Write it down if it helps. Being clear on your own needs and objectives makes the discussion more productive and less emotional.
  2. Lead with Empathy: Remember that the other person has needs and concerns too. Start the conversation by acknowledging their perspective; something as simple as, “I understand this is important to you” can go a long way in creating mutual respect.
  3. Stay True to Your Values: Conversations are smoother when they align with your values. In that moment with my landlord, I knew I needed to stand up for my space but didn’t want to sacrifice respect. By anchoring in your values, you can speak with calm confidence.
  4. End on a Collaborative Note: After expressing your point of view, ask for feedback and invite a solution that works for both sides. This encourages a collaborative spirit, turning the conversation from a confrontation into a partnership.

These moments may seem small, but they add up, building resilience, confidence, and trust. In fact, if you’re navigating a change or challenge, my Rock the Reboot course goes deeper into these principles, providing tools for transformation and practical ways to handle life’s tricky moments.

Whether in leadership, sales, or personal relationships, difficult conversations don’t have to be dreaded moments. With a little preparation and a lot of empathy, we can turn them into stepping stones toward stronger connections and self-assured decisions.

Up we go—


Whenever you’re ready, there are 3 ways I can help you:

  1. Inspiring Keynotes: Looking for an energizing, empowering speaker to help your team rise above disruption and come back better than EVER? My "Adapt & Thrive" and "Beyond Resilience" keynotes are just what the doctor ordered. Call The Speakers Group at 615.526.6600 or click here to tell us about your program. I’d love to support you.
  2. Rock the Reboot: When you're feeling lost or uncertain in the midst of one of life's "reboots," my signature 5-week online intensive workshop will help you find your footing and get on the road to coming back better than EVER. Guaranteed.
  3. New Book! Mastering the Moments is a heartfelt and empowering book that challenges the modern belief that resilience is merely about bouncing back. By working with what is and letting go of what was, we can step into what can be to create a life filled with purpose and joy, even in the midst of adversity.

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Mastering the Moments

Resilience Strategist, Keynote Speaker, and author of Mastering the Moments: A Journey of Endings, Beginnings, and the Space in Between, Shawn Ellis is guiding a new wave of resilient leaders to adapt, grow, and emerge stronger from challenges, creating a more fulfilling, human-centric work environment. Shawn is the creator of The Reboot Roadmap, a transformative framework that helps individuals and organizations not only survive challenges, but go Beyond Resilience to thrive and come back better than ever.