Better Team Habits
Better Team Habits
Fixing the Plane While We Fly It with Kate Tyson

Fixing the Plane While We Fly It with Kate Tyson

Charlie talks Team Habits on this recent Boss Talks: Whiskey Fridays Episode

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

’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.

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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

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 aware of and shift away from perpetuating negative cultural patterns through reflection and awareness.

[11:58] Burnout & Team Dynamics. Charlie explains how burnout and revolving doors (of employees) can be symptoms of how white supremacy and toxic hierarchy affect businesses and our experience in the workplace. Common assumptions about productivity in the workplace are often deeply flawed. Cranking tasks out faster is only one dimension of productivity. Being a leader or owner may mean challenging norms about pressure and invisible expectations (especially for emotional and social labor). We want team members to take more ownership and yet we need to share the burden — with self-care and compassion. That means looking at system issues, rather than finding individual blame.

[20:53] Decision-making and mutual care. If we want to care for the humans in our businesses we need to think about things like language. But it can’t be words alone. We might want to look at team habits about how we approach one another — do we approach situations with empathy and avoid making assumptions? If there’s a wider collective issue on the team, those are things that training and clear communication can go far in addressing, especially when creating a new team. A central idea in Team Habits is about levels of decision-making for team members, and the importance of communication and context. 

[30:34] Democratizing leadership and employee ownership. Kate shares personal experience with Quaker organizations, highlighting consensus-driven decision-making and anti-authoritarianism. The discussion turns to deeper work of helping people decolonize themselves, including employee equity and ownership pathways. Open book management (OBM) is one approach to doing that. 

[36:11] Power dynamics in the workplace. Salaries are one challenge that come up in disrupting traditional power dynamics (and is a topic addressed by OBM.) Transparency is one approach to disrupting the secrecy and taboo around salaries — while it’s fair to acknowledge that power dynamics in organizations are complex, involving individual and institutional power.

[39:45] Interpersonal vs. Institutional Power. Interpersonal power is a hugely important topic for teams. Charlie emphasizes the need to put more care back into work relationships between teammates to build trust and support. If one person steps on another’s toe, it can lead to mistrust and friction, but also one individual might choose institutional power as a means to solve the problem, reinforcing the paradigm and creating a triangle of intervention.

[45:08] Care vs. institutional power, and difficult conversations. Teams at some point are forced to choose between institutional power or actual care. Team members must be willing to have difficult conversations. Inconsistent communication and delegation practices bring about tension. 

[51:22] Breeding respect and autonomy. Respect is crucial, for everyone on the team, but also those in leadership positions, even in anti-hierarchical organizations. Leaders need unscheduled time to think and make decisions, respecting their unique function and autonomy. Kate discusses the importance of intentionally designed structures in anarchist movements, citing the Goldilocks problem.

[58:06] Team habits, meeting and collaboration. Changing one type of team habit has ripple effects on others, like eliminating bad meetings. Relational work is not separate from business work, since often it's our relationships that are most important to us as humans.

Better Team Habits
Better Team Habits
Charlie Gilkey
Kate Tyson