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Preparing for Difficult Conversations: A Simple Strategy for Success


Have you ever walked into a difficult conversation only to find yourself losing focus, caught off guard by an unexpected turn, or leaving without making your key points? These moments can be some of the most challenging in our professional and personal lives. As lawyers, we know the power of words, but when conversations are difficult and we aren’t prepared, even the best intentions can fall short. Yet, with the right preparation, these moments can become opportunities for connection, growth, and progress.

Over my years as a General Counsel and now as a coach, I’ve learned that preparation is the key to transforming tough conversations from stressful to impactful. One of the most effective tools I’ve used is a simple, old-fashioned triangle.


Why Use a Triangle?

A triangle can be more effective than a traditional list of bullet points. It’s not just a visual aid—it’s a mental map that reinforces balance and focus during challenging discussions:


  • Three Points: People naturally remember things in threes. At each point of the triangle, write down one of the three most important messages you want to convey.

  • Stability: A triangle’s balanced structure helps you stay grounded, even when the conversation takes an unexpected turn.

  • Clarity: Unlike a long list of bullets, a triangle provides instant clarity—if you feel off course, glancing at it, or picturing it in your mind, can quickly refocus your thoughts.

  • Direction: Its shape naturally encourages flow, helping you connect your ideas and see how they relate to one another.


How to Use the Triangle

The triangle is not only useful for preparation but also serves as a tool during the conversation itself. Here’s how:


  • Prepare: Before the conversation, draw a triangle and assign one key message to each point.

  • Anchor: Use it to guide your focus if the discussion becomes emotional or takes an unexpected turn.

  • Reflect: Refer back to it after the conversation to evaluate whether you communicated your core points effectively.


The Power of Preparation

During a difficult conversation, it is easy to become sidetracked or overwhelmed. While you can’t control how others approach or react, you can control your own preparation and responses. A triangle helps you to clarify your goals, remain calm throughout the discussion and bring the conversation back to your core points.


Beyond the Triangle: Finding What Works for You

While the triangle is a simple and effective method, it may not resonate with everyone. You can consider exploring resources like:


  • Difficult Conversations by Sheila Heen, Douglas Stone and Bruce Patton

  • Supercommunicators by Charles Duhigg

  • Podcasts like The Art of Difficult Conversations with Chris Wong and Lucie Tesarova


The key is to find a tool or approach that aligns with your communication style and helps you navigate tough conversations.


Difficult conversations will always be challenging, but with thoughtful preparation, they can also lead to growth and meaningful progress. Whether you use the triangle or another method, taking time to prepare allows you to  approach these discussions with focus and confidence.


What tools or techniques have helped you in tough conversations? I’d love to hear what works for you.


Co-Chair, Ready Set GC Advisory Board

Founder, JK Leadership Advisors, LLC


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