What if the real competitive advantage in an AI-saturated workplace isn’t more tools, but how human it still feels to build things together? In a world where “vibe coding” and AI copilots can translate almost any instruction into code, the leverage shifts to how clearly people communicate, how bravely they improvise in uncertainty, and how much imagination they are willing to bring into the room.Jessia Hoffman lives exactly at that intersection. As founder of On Deck Workshops and a Stanford instructor in applied improvisation, she’s spent years using improv, story, and play to help teams at companies like Google, Bloomberg, and Cisco become more connected, courageous, and creative. Her fully experiential sessions – connective games, shared rituals, and teachable moments – impactfully transform how people relate to risk, failure, creativity, and one another – which is exactly the humanness that AI can’t automate. We talk about:

Why improv is actually a trainable skill, not a personality trait
How teams that fail together build stronger bonds and better products than teams that just “win”
Why brainstorming fails in most companies (and how improv fixes it)
The real meaning of “Yes, And” and how it unlocks thriving team culture
How psychological safety is built in the body, not in slide decks
Why culture, not tools, is the real differentiator in an AI-saturated worldIf you’re a founder, manager, or builder navigating ambiguity, this episode will change how you think about communication, creativity, and leadership.

To follow Jessia Hoffman,

LinkedIn: https://www.linkedin.com/in/jessiahoffman/

Website: https://ondeckworkshops.com/

RESOURCES!
- Want to talk to Jessia or ask her a question? Connect with her at: linkedin.com/in/jessiahoffman/
- Could your team benefit from improv at your next offsite? Check out On Deck Workshops: ondeckworkshops.com
- And for improv magic in your inbox, sign up for their (every-other-month) newsletter: https://mailchi.mp/598b8d6ac148/ondeckworkshops

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About the host :

I’m Aishwarya, a product builder obsessed with turning raw ideas into real, working tools, especially with AI in the mix. Over the last 9+ years in SaaS, I’ve shipped zero-to-one products, scaled product marketing & GTM motions, and built across MarTech automation, real-time collaboration tools, and live event tech.

Today, I work hands-on as an AI-first builder & forward-deployed PM/Engineer, working closely with AI models, agents, and orchestration systems to shape next-gen AI products.

You can follow me here,

LinkedIn: https://www.linkedin.com/in/aishwarya-ashok/

Twitter: https://x.com/aishashok14

My product memos: https://aishashok.com/

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Timestamps:

00:00 - Trailer

01:09 - Intro

04:01 - What is improvisation, and how did you discover improv?

07:03 - From high school to starting On Deck: your journey

12:18 - Can improv be learned as a skill? The right mindset for beginners

21:34 - Is improv always a team activity? Can solo improv help personal growth?

29:17 - Tools & techniques used with teams at Google, Cisco, LinkedIn, etc.

37:25 - How improv naturally helps people loosen up and open up

41:25 - Do you use these tools in the first few minutes to make people feel at ease?

44:51 - Theatre & stand-up improv: practice vs reading the room

48:02 - Improv as a creative boundary to build on others’ ideas

01:02:05 - Parallels between improv and working with AI as a co-partner

01:06:10 - Tech is abundant, but creativity and execution still matter most

01:07:56 - Quick improv exercise: “Name three things” game

01:14:52 - Why human creativity is key to using AI effectively

01:17:08 - Outro