The Impossible Conversations Podcast
A podcast about how real breakthroughs actually happen
Most leadership podcasts focus on outcomes—the polished strategy, the clean success story, the lesson learned in hindsight.
The Impossible Conversations goes upstream.
Hosted by innovation strategist and author Melissa Dinwiddie, this podcast features thoughtful, peer-level conversations with senior leaders about the thinking behind meaningful breakthroughs: the moments of uncertainty, misjudgment, course correction, and learning that rarely make it into case studies or keynote slides.
This is not a “failure story” podcast.
And it’s not performative vulnerability.
It’s a space for leaders to talk candidly about:
- Decisions made without full information
- Early ideas that didn’t quite work—and what they revealed
- Where a trusted playbook fell short
- How learning reshaped the way they lead
Grounded in the Create the Impossible™ framework—Play Hard, Make Crap, Learn Fast—the show reframes imperfection as a strategic advantage, not a liability.
The Impossible Conversations is designed for Directors, VPs, and senior leaders in tech, HR, innovation, and regulated industries who are navigating complexity, risk, and real-world constraints—and who are willing to think out loud about what they’ve learned along the way.
Interested in Being a Guest?
I primarily invite guests directly.
That said, if this conversation resonates and you believe you’d be a strong fit, you’re welcome to raise your hand below.
This show is best suited for leaders who:
- Have led through ambiguity, not just growth
- Are thoughtful about how their judgment has evolved
- Value learning over polish
- Are open to reflective, unscripted conversation
- Submitting this form doesn’t guarantee an invitation—but it does start a conversation.
