We know teams serve as the cornerstone of any successful organization. Yet all too often, the relational and emotional aspects of teamwork end up sidelined in favor of performance metrics alone — which ironically doesn’t always improve team performance.

Recently, I was invited to share insights on this on the ATD Talent Development Leader podcast (sponsored by Randstad Risesmart) where I discussed the team habits approach to the nexus of performance and belonging.

This was a conversation about what really matters to and on a team — why trust, belonging, and well-being aren’t just nice-to-haves but are the essentials we need to have productivity and impact.

What we see again and again is strong interpersonal bonds as the defining trait of high-performing teams. When there’s psychological safety, and people feel connected and understood, teams come alive. On the flip side, the absence of these bonds can be just as damaging as their presence is powerful. Without trust and open communication, even the most skilled teams struggle to make progress.

Throughout the conversation, I share practical strategies for embedding the eight essential team habits — guiding principles that any leader or team member can put into action.

If you’re looking to build a culture grounded in trust and purpose, I hope you’ll find this episode helpful — as we continue the ongoing work of reinstating the human side of teamwork at the center of team performance.

Topics We Explored

* Why work is fundamentally about relationships, not just outputs

* The evidence for high-performing teams being characterized by strong interpersonal bonds

* How belonging and trust are essential for maintaining healthy team relationships and driving performance

* Ways emotional and social components can be integrated into team decision-making, rather than just rational/strategic factors

* Why large-scale change initiatives often fail due to top-down approaches that lack buy-in — and democratic, bottom-up change is more effective

* That building an environment of trust and articulating a clear vision are critical leadership responsibilities

* The reasons many individual contributors end up feeling disempowered and disconnected from improving team dynamics

* Practical strategies for enhancing specific team habits that can lead to significant performance improvements

If Productive Flourishing adds value to your inbox, consider upgrading to a paid or pro subscription to access to the full archive, monthly community coaching calls, and more.

Episode Timestamps

[00:00] Introduction to the ATD podcast.

[01:24] Exploring the fundamental importance of relationships, not just outputs, in high-performing teams. Belonging and trust as essential glue for healthy team dynamics and performance.

[06:02] Why there’s a need to integrate emotional and social components, not just rational/strategic factors, into team decision-making. Avoiding the mistake of trying to extract these more human elements.

[10:07] We discuss the high failure rates of top-down, under-resourced change initiatives, and I explain why a democratic, bottom-up change management that addresses team pain points and creates a sense of urgency works better.

[16:43] Employee disengagement is a major challenge, which can best be addressed by making work more personal, relational, and empowering team members to improve their own circumstances.

[19:32] Overview of the 8 key team habits (belonging, decision-making, goal-setting, planning, communication, collaboration, meetings, core habits) as a scorecard for high-performance teams.

[28:13] Specific examples of enhancing team habits around meetings, such as reducing unnecessary updates and clarifying commitments for information-sharing.

[34:54] Recognition that many individual contributors feel disempowered and disconnected from improving team dynamics.

[35:47] Insights from Rutger Bregman's "Humankind" debunking myths about human nature, and how it relates to the need to emphasize relational elements in team habits.

[41:44] Upcoming project focused on the importance of trust and vision in leadership, as key questions teams are always asking.

[43:09] Invitation for listeners to connect.

[43:37] Conclusion and gratitude for the insightful conversation.

In this special anniversary episode, Charlie Gilkey and Maghan Haggerty reflect on the five-year milestone of Start Finishing, diving deep into its impact on their lives, the lives of their community, and Productive Flourishing’s evolution over the past 17 years. They explore how doing your best work transforms you as an individual and creates ripple effects for leaders and their entire teams.

Topics We Explored:

* The deeper paradox of productivity: Why do we often end up putting off the things we really want to do in life to some later date? (When that means we may not ever start, let alone finish, those projects.)

* The origins of Start Finishing as a book, and the driving force behind it, namely to argue for doing the work that matters and treating one’s "best work" as priority — and what that changes in how we approach meaningful projects.

* All the ways in which personal and team success are interconnected, and how Charlie’s third book Team Habits built on the foundations of Start Finishing.

* The multitude of “best work” stories we’ve heard from people around the world who, as a result of finding Start Finishing, have finished the projects that matter.

* Embracing life and work simultaneously by living and working with purpose, and finding joy in the process.

* Charlie's vision for the future of "Productive Flourishing", inviting people to embrace the "get to" mindset (“getting to” do the work we’ve dreamed of doing.)

Links and Resources Mentioned in This Episode:

CHARLIE’S BOOKS

* Start Finishing: How to Go From Idea to Done

* The Start Finishing Field Guide

* Team Habits: How Small Actions Lead to Extraordinary Results

* The Small Business Life Cycle

BLOG POSTS MENTIONED IN THIS EPISODE

* Yet Another Blog on Time Management?!

* Stand Tall, Creative Giants

* The Air Sandwich: Why Your Big Picture and Day-to-Day Reality Don’t Link Up

* A Frog a Day Keeps Your Anchors Aweigh

* Success Often Comes When You're Not Searching for It

OTHER RESOURCES MENTIONED IN THIS EPISODE

* Finite and Infinite Games by James P Carse

* Give to Grow by Mo Bunnell (Episode 254)

* Stumbling on Happiness by Daniel Gilbert

* PF Productivity Coaching

If this podcast episode — and PF in your inbox in general — benefit you, consider how much you might flourish with access to the full archive of writing, monthly coaching calls & e-courses with a paid subscription.

Thanks for Listening!

We’d love to hear your stories of what you’ve started and finished thanks to Start Finishing. Share your best work moments with us!

Subscribe to the Productive Flourishing Podcast on Apple Podcasts or your favorite platform so you never miss an episode. Plus, if this episode resonated with you, leave a review to help others find the show.

Episode Timestamps

[0:00] Re-introduction to the podcast and the 5-year anniversary of Start Finishing.

[2:15] Maghan discusses her personal journey with "Productive Flourishing" and the impact of Start Finishing on her life, work, and career.

[7:48] Charlie shares the origins of Start Finishing and how it connects to Productive Flourishing’s broader mission.

[15:30] The importance of “best work” and why focusing on it and keeping it a priority leads to our thriving.

[20:58] The transition from Start Finishing to Team Habits and how personal and team success intertwine.

[32:46] Further reflection on how Productive Flourishing has evolved over 17 years and what’s next.

[40:30] Maghan shares some Start Finishing reader stories about the power of finishing our most meaningful projects.

[47:20] Charlie and Maghan dive into ideas about thriving in both work and life, by following a sense of purpose in both.

Coming Soon: Limited, Signed Start Finishing

To celebrate the 5th anniversary, Charlie’s gone into the vault and found a small number of first edition hardcovers of Start Finishing he’ll sign (and personalize, with whatever message you’d like) and make available for sale.

If you’re interested in getting your own hands on this piece of PF history, or giving a one-of-a-kind gift to that person you know could benefit from Start Finishing, hit the button to sign up, and you’ll be the first to know when we have these available for sale.

Topics We Explored:

* Mo Bunnell’s new book Give to Grow and why it makes sense to focus on relationships and a giving mindset as the foundation for long-term business success.

* How to define business development and distinguish it from pure sales, as well as the importance of strategic helpfulness in developing a business or career.

* The logic behind providing value upfront through small projects or advice to build trust and increase the likelihood of future business and engagement.

* Strategies for making effective recommendations and managing client expectations, including the use of social proof and escalating commitments.

Links and Resources Mentioned in This Episode:

* Mo Bunnell: Website | Podcast

* Give to Grow Supplemental Materials: Downloadable resources, including the Give to Grow Team Launch Guide, top lead generation methods worksheet, meeting prep questions, research citations, and an exclusive secret chapter.

* Find Your Business Flow: PF’s new cohort program to help entrepreneurs focus on (among other things) growth — building relationships, scaling your business, and winning the work that matters.

Perspectives like those in this episode can help you grow your business. By upgrading to a paid subscription, you gain access to exclusive content, monthly coaching calls & e-courses.

About Mo Bunnell:

Mo Bunnell helps complex organizations grow by scaling business development skills and creating a growth-oriented culture. He’s the founder of Bunnell Idea Group (BIG) and the author of The Snowball System. BIG has trained tens of thousands of professionals at hundreds of organizations. Mo lives in Atlanta, Georgia.

Thanks for Listening!

Subscribe to Productive Flourishing on Apple Podcasts to get all the latest episodes delivered straight to your preferred mobile device. This is the perfect option for listening to the show in the car, on the subway, or while you’re working out. Plus, you won’t have to fuss with figuring out how you’re going to listen.

Episode Timestamps

[0:01:46] Charlie Gilkey introduces Mo Bunnell and discusses why he's excited about the Give to Grow book.

[0:05:02] Discussion of the broader definition of business development and how it differs from sales.

[0:07:34] Mo Bunnell explains the importance of balancing altruistic and economic success in business.

[0:11:41] Importance of selling the problem and the solution, not just the expertise.

[0:13:26] Discussion of the differences between the skills needed for "doing the work" versus "winning the work".

[0:18:30] Explanation of the concept of "certainty" versus "possibility" in business development.

[0:22:05] Explanation of the "give to grow" strategy and providing value upfront to build trust.

[0:26:52] Discussion of how to make effective recommendations and manage client expectations.

[0:31:14] Advice on naming programs and offerings to focus on outcomes, not just processes.

[0:35:47] Importance of providing options and allowing clients to choose.

[0:41:44] Addressing the challenge of transitioning from free to paid content.

[0:47:59] Practical tips for committing to and testing new business development strategies.

[0:52:54] Discussion of the importance of casting possibility and helping clients see their best version.

[1:06:51] Final thoughts on the emotion and inspiration of winning the work.

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.

If Productive Flourishing adds value to your inbox, consider a paid or pro subscription for access to the full archive, monthly community coaching calls, and more.

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 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.

Earlier this month Leadership Beyond Borders re-released an episode I did with them a while back, alongside host Kimberli J. Lewis. The conversation centered on how team habits apply in international, remote, and diverse organizations, and to change management. We discussed the need for clear communication as a team habit, with specific channels and protocols, especially on remote and geographically dispersed teams — as well as how to remove bottlenecks and strike a balance between providing enough information and too much detail. Our discussion touched further on the importance of personal connection, trust, and empathy in teams, and how this sense of belonging (another major team habit) ultimately paves the way for high performance. 

Leadership Beyond Borders looks at the impact constant change is having on our organizations and how these changes affect the kind of leadership we need to drive long-term success in today’s global economy. The idea of the podcast is to explore the opportunities and challenges of different kinds of organizations (including remote first) and what kind of leadership skills and values are needed to ensure engagement, retention, and ultimately great performance.

Topics We Explored: 

* Why in order to function within the global business environment, your business needs to constantly change and adapt to a variety of new constants

* The power of team habits and dynamics to drive success in today's fast paced business landscape

* How to figure out this new way of working with each other,  and putting it all back together when everything's broken. (Much in the way it was for so many organizations during the COVID-19 pandemic.)

* Why effective communication, collaboration, and interpersonal team leadership improve work outcomes.

If you and/or your team benefit from these posts, consider a paid or pro subscription for even more support in terms of monthly community leadership coaching, access to the planning system, and full archive of content.

Episode Timestamps

[0:05] Team habits and dynamics for business success. Host Kimberli Lewis discusses globalization, digital transition, and leadership impact with listeners worldwide. Charlie shares insights on team habits for success in a fast-paced business landscape.

[4:00] Forging a path in leadership, teams, and productivity consulting. Charlie argues that individuals in organizations are (usually) not the problem, but rather how they come together as a team and create systems that either work or don't work. We all play a part in the construction of our team’s habits, for better or for worse, and that’s important to acknowledge. He emphasizes high standards and compassion in leadership, and the potential for heroes to emerge in unexpected ways.

[11:46] Teamwork, inclusivity, and productivity. Charlie’s upbringing and complex childhood experience informs his approach to work communication management. He prioritizes lifting up those with least privilege and power in organizations. 

[17:09] Creating a baseline of trust and mutual respect. Overview of the eight habits of high-performing teams, including belonging, decision making, and goal setting. Meetings are a key area where team habits play out, and poor habits can lead to poor meeting culture. Belonging is especially crucial in virtual teams. Language of trust and relationship often beats out task-based language.

[25:17] Team collaboration and motivation. Understanding individual goals and motivations can help drive team collaboration. Rather than pushing team members towards a goal, it's more effective to help them find their own motivation and support them in achieving it. This requires finding common ground and aligning goals. 

[35:05] Decision-making habits for teams, including leveling decisions and addressing bottlenecks. Charlie discusses decision-making as a habit in teams, and explains the three levels of decisions. Decision-making habits (and knowing the decision levels) can transform other team habits and increase trust and belonging. Transparency and enrolling team members in decision-making removes bottlenecks and increases productivity. 

 [40:58] Effective communication in diverse teams. Communication in diverse teams requires specific channels for urgent vs non-urgent messages. Team members ought to commit to using agreed-upon channels to avoid confusion and ensure clarity. Communication often hinges on providing the right amount of detail. Brief explanation of how women and men communicate differently due to socialization and power dynamics.

[45:33] Productivity, team habits, and getting buy-in. After analyzing a team’s habits a roadmap can be created to improve specific habits. An easy fix on meetings might be leaving five minutes at the end of every call for next actions. Charlie encourages listeners to invite others into the changes they want to make together.

I had the pleasure of joining forces recently with Andy Kaufman, current host of The People and Projects Podcast, to discuss team habits — specifically, the high cost of ignoring them — and how and why team habits ultimately shape team culture and performance.

Our conversation touched on a variety of generative topics, including offering some practical approaches to: 

* enhancing team dynamics

* instilling a sense of belonging

* improving decision-making

* and addressing everyday ‘broken printers’ in professional and family life 

My thinking was that the touchpoints in this episode would be of interest to our Better Team Habits audience since they offer a similar level of depth to the analysis we offer in BTH Office Hours coaching (Paid and Pro subscribers) and Quarterly Planning sessions (Pro subscribers).

If you want to uplevel your leadership or team dynamics, I encourage you to upgrade your subscription to gain access to monthly coaching and our full planning system.

Sound Bites from the Episode

* “‘Time in’ erodes ‘awareness of’.”

* “Be the teammate you want your teammates to be.”

* “Belonging is a macro word that includes feeling appreciated at work, feeling like your contributions and perspective matter, that you have moral and functional trust.”

* “We do it because it’s the right thing and because this is how we want to be together and, oh by the way, it has these amazing other benefits.”

* “I would rather over-index on caring.”

* “So many families have a daily ‘broken printer’ that’s called the ‘getting to school runaround’.”

* “None of us show up at work and opt-in to the CC thread from hell.”

Episode Timestamps

* [00:00] Introduction

* [01:44] Start of Interview

* [05:36] The Broken Printer Metaphor

* [08:43] How We Encourage the CC Thread from Hell

* [12:21] Team Dynamics

* [14:56] What If You're Not a Senior Leader?

* [19:27] Number One Rule of Being a Great Teammate

* [21:18] Building Belonging Habits

* [30:14] The Importance of Small Gestures

* [38:34] Applying Team Habits to Families

* [44:48] Wrap-up

* [45:24] Andy Comments After the Interview

* [50:17] Outtakes

Gary Bertwistle (of Mojo Sessions fame) and I had this meeting of minds back in February — truly jamming together over substantial territory: from the need to acknowledge change and challenges in the modern workplace, to building trust and autonomy in teams, and techniques for aligning habits, communication, and belonging. I hope you’ll get as much out of it as I did. 

Topics We Explored: 

* The need for trust, personal responsibility, and sometimes dissent, to create productive forward-moving team dynamics

* Strategies for improving teamwork, such as rotating the role of red cell thinker and eliminating the least valuable meetings and habits. 

* Considering emotional and social data in decision-making, and asking specific questions to gather this data from your team.

* Challenges involved with leadership, such as prioritization, health and wellness in a busy work life, plus practical advice for overcoming some of those obstacles

If you want to gain access to more exclusive content, community coaching calls, and the full archive of our worksheets and resources, consider a paid subscription.

Episode Timestamps

[0:15] The role of teamwork in productivity with the impact of AI on jobs. Teamwork and collaboration are vital to productivity and leadership, especially in a moment when we’re facing changes to the nature of work after COVID and now, with emergent shifts in AI.

[3:41] Consequences of the pandemic, and paradoxes we run into with teams. Some of the consequences of the pandemic have gone ignored, including cumulative burnout and fatigue on teams. Many leaders continue to pretend this isn’t happening. Teams often struggle due to evolutionary wiring for people pleasing & goal orientation. Even individuals who may think they're personally being productive are not necessarily finishing tasks competently with teammates.

[10:42] Team dynamics, productivity, and emotional intelligence. Individual productivity differs from team productivity partly as a result of the social and collective overhead involved. Charlie highlights the disconnect that can emerge between leaders and team members around productivity and goals. Leaders and team members can have different perspectives on what constitutes productive work, leading to tension and misalignment. 

[17:40] Social and emotional factors in decision-making — and their impact on your team. As leaders, we ought to be considering social and emotional factors in decision-making, and actively gathering information in this area from our teams. Taking a more holistic approach can lead to better business outcomes. Charlie offers three questions to help teams understand each other's perspectives on change initiatives, and explains why we need a team-based approach to change. Plus why viewing each other as teammates fosters a collaborative and human-centered work model. 

[24:35] Trust and its impact on team productivity, belonging, and performance. Trust is highly key to employee productivity according to research. It’s an essential for high-performing teams, as it enables members to take risks and rely on each other. Belonging is the first category of team habits, as it fosters trust and ensures team members feel supported and valued — and are therefore more interested and invested in contributing. 

[28:59] Workplace dynamics, trust, and autonomy. In many cases, people have given up on leaning on their teammates enough in the workplace — and that obsession with autonomy leads to burnout and stress. Trust and autonomy must work together when it comes to creating great teamwork. When team members feel safe and supported, they are more likely to do their best work. Gary suggests there’s a connection between giving each other that space and developing trust. For example, when individuals have more control over their schedules, they tend to feel trusted and safe in their work.

[34:37] Trust and autonomy in remote work. Issues of trust are particularly key in remote work but there’s a need to set clear goals and expectations. Leaders should give employees the autonomy to figure out how to meet those goals, while employees agree to do their best to make it happen. Trust teams to figure out how to work best, extend responsibility to tell the org what's working/not working. Autonomy of schedule, trust, and responsibility signal trust to teams, leading to better outcomes.

[39:16] Father's life experiences, military service, and overcoming obstacles. Charlie reflects on his father’s resourcefulness and standards-driven approach to work, and the challenges he faced as a black man in the South in the 1960s. His dad used creative discipline and training methods to help his own kids meet his high standards. While high standards and toughness are important to leadership, being able to show compassion and gentleness is just as vital. He credits his mother for playing a significant role in shaping his perspective on leadership and life. 

[47:07] Prioritizing health and wellness is a personal project — it requires time, energy, and attention. Health and wellness are a project, just like building a team and using productivity habits. There’s good reason to prioritize health, even over creative or business goals.

[51:27] Prioritize health and wellness by scheduling time for it. Prioritize your calendar to align with your priorities, not just your tasks. Individuals should focus on doing the activities that are tied to what they want to be, rather than simply wanting to be something. That’s one starting approach to making progress on any goal.

[55:35] Combine the team’s personal goals with team goals for high performance. Personal importance is often neglected in scheduling, leading to imbalance. Build Goldilocks-level cadence for weekly goal discussions to boost accountability. That’s part of how you build teamwork in a way that leads to accountability. 

[1:02:09] Why dissent in teams makes for better decision-making and greater success. Gary highlights the importance of dissension in teams, citing Charlaine Nimeth's book on the topic. Charlie agrees on the need for rotating the role of “red cell team thinker” to maintain team engagement. “Red cell thinkers” identify potential risks and develop solutions.

[1:08:56] Improve team productivity by identifying and addressing broken systems and habits. Analyze the "broken printer" causing the most pain and frustration to your team. Start with easy wins to improve team dynamics and build discipline. Growing the team’s capacity for personal responsibility is the best approach to fixing team problems and helping folks work better together. Another first step is to fix your meetings and eliminate those meetings that are terrible for everybody.  

[1:16:16] Productivity, teamwork, and the right prioritization. Aristotle’s idea of thriving was that thriving is unique to each individual — but to reach a state of flourishing always requires principled action. Gary suggests sometimes it makes sense to prioritize execution over planning, and that burnout happens when we trade time and focus for other things. Examine your schedules and priorities, to decide if you’re making a good trade of your time and focus. 

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.

Productive Flourishing is a reader-supported publication. For exclusive insights, access to the archive, and group coaching calls for leaders and managers upgrade to a paid subscription.

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.

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 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.

Key Takeaways:

[3:24] Charlie’s background and why he decided to become an entrepreneur.

[9:16] It typically takes 18 months to 36 months just to figure out what you're doing as an entrepreneur.

[13:13] Mark talks about his career journey from going to film school to going to a corporate company at a franchise company making videos. There, he started to look at which projects he enjoyed the most and which ones had the highest profit margins that he could deliver.

[14:01] The lowest point in Mark’s business and how it changed.

[16:13] Mark’s story of using his high intelligence, talent, and energy in a way that served himself and others.

[23:47] Asking for help is one of the greatest things we could do.

[24:15] When you accept the gift of not knowing, it opens up all these possibilities.

[24:20] It’s okay that you don’t know, and you don’t have to fight that.

[31:42] What path will get your message in front of the people you want to speak to, and then once you are there, how do you build an experience better than your competitors?

[33:16] The principles of marketing and sales haven’t really changed since 2000 years ago. We’ve just gotten better at implementing those principles.

[45:28] Mark’s decision to stop running his business.

[1:04:11] Doing our best work requires us to center ourselves on our dreams and our passions.

[1:11:05] Ask yourself: what’s the smartest thing you can do next, and then, what’s the most courageous next step you can take on that project?

[1:19:38] Mark’s Challenge: Let him help you.

Mentioned:

Mark Drager: Website | Podcast

Richard Branson

Fast Company

Breakthrough Advertising

Key Takeaways:

[2:57] Ruby and Eric discuss some of the unique delights and challenges of being part of a writing trio.

[7:45] What is the bridge between this book and Morag’s book Cultivate: The Power of Winning Relationship?

[8:05] What are the intentional choices you can make to build ally relationships?

[12:44] Ruby and Eric break down the five components of an ally mindset:

• abundance and generosity
• connection and compassion
• courage and vulnerability
• candor and debate
• action and accountability

[13:23] In order to get more allies, you have to be one yourself.

[25:43] How can we start with small ripples of joy in our own lives and have that branch out to help others?

[28:12] Are two-hour staff meetings really necessary? And if so, how do we make them more efficient and profitable for everyone involved?

[34:13] If you’ve invested in your relationship, it’s going to withstand weird moments. In the meantime, what should we do when a sideways moment occurs?

[59:54] Challenge: lean into having the hard conversations. Keeping your head down isn’t going to change a damn thing. And, check out the Ally Mindset Profile to give you some insights into what comes naturally to you, as it relates to the five practices.

Mentioned:

You, Me, We: Why We All Need a Friend at Work

Ally Mindset Profile

John Gottman