Fixing the Plane While We Fly It with Kate Tyson

Note to the reader: Team Habits, my most recent book, was released one year ago this week. You might also be aware of Productive Flourishing’s sister publication, Better Team Habits, a spin-off of the book.

We’ve had incredible moments over on BTH in the past year. For those not subscribed to both publications I’d like to celebrate the book’s anniversary by sharing with you a singular podcast episode I sat down to do with my friend Kate Tyson on “fixing the plane while we fly it.” I think it will prove fruitful for PF readers too — for your current or future teams.

— Charlie

Many of us would likely agree on the fact that the dominant, central power structures that make up our system need some reform. That goes for institutions large and small, whether we’re talking about a particular startup company or the global economy.

But what is change supposed to look like, and how does it come about?

If I could offer one of the basic tenets from Team Habits, it’s that we start the change process by first shifting the way we relate to each other — in our teams and at work. 

This episode originally aired on Kate Tyson’s podcast Boss Talks: Whiskey Fridays, in which she and I dive into how cultural change is a long-term play, and why better team habits are a critical component of the process.

Topics We Explored

* The challenges of leading and effecting change in businesses, particularly in the context of social and economic change, and the importance of engaging with the 'messy middle'.

* Looking for 'subversive simplicity' in our lives, business, and management decisions — which often challenges conventional wisdom on growth and productivity.

* The disconnect between workplace culture and the caretaking reality at home of many team members.

* How to address these and other issues of power and balance in the workplace we’ll need as a whole a more collaborative approach to decision-making and team bonding

* Leading and forming teams is never easy.

* Why by acknowledging issues and addressing power dynamics head-on, we have a chance to avoid conflicts or deal with them effectively.

* How prioritizing relationship-building with our teammates ultimately creates change and trust

This episode touches on many topics I explore at length in my book, Team Habits: How Small Actions Lead to Extraordinary Results.

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About Kate Tyson

Kate Tyson is a multi-disciplinary business owner and rebellious spirit, and the owner and director of Wanderwell, a consulting and bookkeeping practice that grows thriving small businesses, while investigating new models for being in business. Wanderwell integrates financial expertise with an empathic, vision-forward approach, and leads with the belief that businesses can help create a more just world that centers people, community, and the environment.

Episode Timestamps

[0:00] Leadership, power sharing, and social change. What does it take to shift from a single-leader model to a democratic leadership approach? Many companies and leaders struggle with the challenge of moving towards shared leadership without losing direction. Businesses can be platforms for social and economic change, and as a result, grapple with the complexities of dismantling oppressive structures within capitalist frameworks. How do we foster collaboration and ensure respect within the workplace while striving for excellence?

[5:28] Cultural norms in the workplace. The workplace can be a site of systems change and social justice, given the growth of decentralized micro-capitalist businesses in the 2000s. Leaders need to prioritize team well-being to avoid perpetuating negative aspects of the dominant culture. Charlie shares how to recognize and dismantle harmful cultural norms — and how leaders can become