How to Have Hard Conversations: Managing Up, Family Traditions, and Boundaries

Some of the most important conversations in our lives don’t happen often. But when they do, they change everything.

In this episode of Diversity Conversations, Eric Ellis and Tommie Lewis explore what they call rare but consequential conversations. The kind of conversations we avoid, delay, or don’t know how to navigate, yet they shape our relationships, leadership, peace, and future.

From learning how to respectfully end a conversation with a boss, to unpacking family traditions that lost their original meaning, to defining what real friendship actually requires, this episode invites listeners to slow down and reflect on how they show up in the conversations that matter most.

You’ll hear powerful real-life stories, honest reflections, and thoughtful distinctions around:

• How to have hard conversations without burning bridges
• Managing up and setting boundaries with authority figures
• Family patterns we normalize but never question
• The difference between having friends and being one
• Forgiveness versus allowing yourself to be used
• How to evaluate where your time, energy, and care truly belong

This conversation is not about perfection.
 It’s about courage, clarity, and choosing intention over avoidance.

If you’ve ever struggled with knowing what to say, when to say it, or whether to say it at all, this episode will meet you exactly where you are.

🎧 Listen in, reflect deeply, and join the conversation.

Interested in joining the conversation as a guest?
Diversity Conversations welcomes leaders, thinkers, and community voices who value honest dialogue and meaningful impact. If you’d like to be considered, reach out and tell us why this conversation matters to you. 

Leadership, Difficult Conversations, Personal Growth, Communication Skills, Boundaries, Emotional Intelligence, Relationships, Friendship, Forgiveness, Diversity and Inclusion, Diversity Conversations

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