Have Courage in Your Conversations

published2 months ago
1 min read

Howdy, Zack here.

Silence isn’t always golden, especially in the world of business. It can be the quiet before a storm of confusion, misunderstandings, and unresolved tensions.

While working on an illustration for this week’s letter, Jenna scribbled two smiling pens, happily signing the Contract. To me, it captured the essence of what happens when vital conversations are faced head-on and not avoided.

Flashback to the early 2010s with my marketing/ad agency, SWIRE. Mixing right-brained creatives with left-brained strategists, opinions collided often. The challenge wasn’t just about getting everyone on the same page; it was about ensuring the page even existed. Enter the Courageous Conversations Contract, our needed beacon in choppy communication waters.

Having challenging conversations doesn’t have to feel like a confrontational rap battle. It’s more like jazz, where each instrument, no matter how different, finds a way to harmonize. Yet, in our business rhythms, we often dance around issues instead of confronting them head-on.

Ever had that awkward moment when you wanted to address an issue with a colleague but weren’t sure how? Or perhaps you’ve been on the receiving end of feedback that felt more like a slap than a constructive nudge. That’s where our Courageous Conversations Contract came into play at SWIRE. It wasn’t just a document. It was our melody, our tune — setting the rhythm for a harmonious workspace.

It’s about understanding that sometimes, what’s left unsaid is more damaging than a challenging conversation. The essence? Address it directly, with respect, honesty, and openness.

How can you facilitate Courageous Conversations?


  • Be Direct, But Kind
    Address issues head-on but do it with empathy. Remember, it’s about the issue, not the person.
  • Seek Understanding
    Before diving into your perspective, seek to understand theirs. It makes all the difference.
  • Create & Use Your Contract
    To spark some ideas for your Contract, here's an artifact from my SWIRE days.

Just remember:
Conversations are bridges. Built right, they can connect the most diverse of thoughts and create avenues for unparalleled growth. But, like any bridge, they need a solid foundation and the right blueprint. The Courageous Conversations Contract is that blueprint. 📜


  1. Guinness 0.0 — The next best thing to Guinness when you're alcohol-free. For me, on 75 Hard.
  2. VidIQ — Just launched my first YouTube Channel & VidIQ is indispensable.
  3. SparkPaws — Got a pup? Wanna match?

Until next Wednesday, embrace the courage to converse meaningfully and watch your business achieve harmony. 🎶

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