Improv, Not Knowing & the Power of Yes with Jeff Ash
Most people would rather do almost anything than get on stage and improvise in front of strangers.
But what if that's exactly where the growth lives?
In this week's episode of Fearful Giants, I sat down with Jeff Ash - owner and artistic director of Westside Improv, Second City alumnus, and professional sales and leadership coach - for a conversation about fear, failure, and what happens when you stop performing and start connecting.
I met Jeff when I took his Level 1 improv class this past quarter. Out of all the improv instructors I've worked with over the years, Jeff is hands down my favorite. He creates a space where people feel safe enough to be silly, vulnerable, and wildly creative - and he does it with humor, authenticity, and very little ego.
Jeff has spent his career helping people embrace the very thing most of us run from: not knowing what comes next. He's taught and performed improv all over the world, and along the way, he's discovered that the principles of improv - yes and, active listening, presence, letting go of judgment - are exactly what great leaders need.
“It’s hard to be nervous when your heart is on service.”
In This Episode, We Talk About:
Why most people are terrified of improv (and why that fear is the whole point)
How "yes, and" transforms the way you show up in conversations and relationships
The difference between performing for applause and connecting with people
Why struggle is where the real learning happens
What Jeff learned from bombing on stage (and why he's grateful for it now)
How to shift from a sales mindset to a service mindset
The simple truth that helps Jeff rise when fear drags him down
My Key Takeaways from this conversation with Jeff:
1. Improv isn't about being funny. It's about being present.
Jeff said something early in our conversation that stuck with me: "When you're really succeeding, when you're crushing it at anything, you're not learning anything." Improv forces you into the struggle - and that's where the growth is. It's not about landing the perfect joke. It's about showing up, listening, and being willing to look foolish.
2. "Yes, and" is a leadership superpower.
Most of us were taught to say "yes, but." We acknowledge someone's idea, then immediately shut it down with our own. "Yes, and" changes everything. It says: I hear you, I'm building with you, and we're creating something together. That shift transforms meetings, relationships, and entire team cultures.
3. People matter more than outcomes.
When I asked Jeff what truth he'd whisper into every leader's ear, he didn't hesitate: "People matter." Not results, not metrics, not performance - people. If you can show up with that as your North Star, everything else changes.
4. Service kills fear.
Jeff shared a saying that's become one of his anchors: "It's hard to be nervous when your heart is on service." When you make it about them instead of you, the fear loses its grip. Whether you're on stage, in a sales call, or leading a team - when your focus is on serving, there's nothing to be afraid of.
5. You don't have to be perfect. You just have to show up.
Jeff has bombed on stage. He's made shitty comments. He's lost audiences, and he's learned that none of that defines him. What matters is that he keeps showing up, keeps serving, and keeps creating space for people to grow. That's leadership.
This conversation with Jeff reminded me that the best leaders aren't the ones who have it all figured out. They're the ones willing to step into the unknown, embrace the struggle, and trust that the process will reveal what needs to emerge.
Whether you're a founder, a sales leader, or just someone trying to navigate difficult conversations with more grace, there's something in this episode for you.
Listen to the full conversation:
Connect with Jeff Ash:
Website: https://westsideimprov.com
Email: contact@westsideimprov.com or jeff@westsideimprov.com
Connect with Clay stelzer:
Website: https://15sixty.com/
LinkedIn: linkedin.com/in/claystelzer
Email: clay@15sixty.com
Resources Mentioned:
If you have a topic or guest you'd love to see on Fearful Giants, reach out to me at info@15sixty.com
Clay
#Leadership #Improv #YesAnd #BusinessLeadership #SalesLeadership #ActiveListening #EmotionalIntelligence #FearfulGiants