Serious Playfulness | Team and Culture

About Serious Playfulness | Team and Culture

For leaders who care deeply about people and outcomes. Hosted by Kyle Neilson and Stephanie Rivard, Serious Playfulness explores the tensions of leadership, team dynamics, and culture with warmth, clarity, and just enough humour. These are candid conversations on trust, self-doubt, team health, and what it means to lead well, without corporate fluff. If you're building something that matters and want to lead with integrity, you're in the right place.

Publisher

Teem Work Podcast

Category

business

Language

en

Explicit

No

First episode

22 Apr 2025

Latest episode

11 Sept 2026

Latest episodes

18 episodes in the feed.

1. 

   11 Sept 2026

   The Vocation of the Business Leader: Conversation with Roger Aguinaldo

   Catholic leaders are rethinking money, mission, and the future of faith‑driven business. In this episode, we explore how Catholic institutions can steward resources more boldly, invest with conviction, and build mission‑aligned businesses that actually thrive. And the big highlight: the upcoming Catholic Faith Investor Summit in New York! A gathering of leaders stewarding Catholic capital and reshaping how the Church engages the financial world. If you want to be part of this movement, the Summit is where it starts.

2. 

   7 Jul 2026

   Growing Leaders the Right Way

   In this episode of Serious Playfulness, Kyle and Stephanie dig into the challenges of fast growth, young managers, and multicultural teams. They talk about how to support new leaders, how to use working genius to depersonalize tension, and why mentorship matters when people are learning to manage for the first time. They share stories about communication gaps across countries, the risks of unclear expectations, and the simple tools that help leaders build confidence and clarity. You will learn: Why young managers need more support than most leaders assume How working genius helps teams understand each other What mentorship looks like in a growing organization How cultural differences shape communication Why clarity at the top affects everyone downstream If you want to grow your people while you grow your business, this conversation will give you practical steps to start. Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission driven organizations, or visit us at teemwork.ca. #teemwork #teamhealth #clarityincommunication

3. 

   22 Jun 2026

   For the Employees

   In this episode of Serious Playfulness, Kyle and Stephanie talk about what to do when you notice confusion or dysfunction at work but you are not the leader. They look at how to ask for clarity, how to define success when no one has written it down, and how to understand your real authority in a role. They share stories of employees who felt lost, the simple questions that unlock better communication, and the signs of a culture you may want to avoid before you ever accept the job. You will learn: How to ask for clarity without sounding confrontational What to do when your role has no clear measurements How to understand your real decision making authority What to look for when interviewing an employer When it might be time to move on If you want to feel more confident, more grounded, and more equipped to shape your workplace from the inside, this conversation will help you get there. Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission driven organizations, or visit us at teemwork.ca.

4. 

   9 Jun 2026

   Why Good People Walk Away

   In this episode of Serious Playfulness digs into the quiet forces that push strong employees out the door. Kyle and Stephanie unpack why toxic behavior spreads when it is not addressed, how isolation drains relational people, and why unclear goals make even great performers want to leave. They share stories of real workplaces, the cost of losing good people, and the simple habits that help leaders keep their best talent. It is a practical and honest look at culture, clarity, and what people need in order to thrive. You will learn: Why toxic behavior pushes out your best people How isolation affects relational employees Why clarity and measurement matter more than leaders think How value, feedback, and trust keep people engaged If you want to build a team that stays, grows, and actually enjoys working together, this conversation will help you get there. Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission driven organizations, or visit us at teemwork.ca.

5. 

   26 May 2026

   Beauty, Culture, and the Messy Work of Making Art

   In this episode of Serious Playfulness, Kyle talks with painter Laurel Dougan about the beauty hiding in everyday life, the pull of technology, and what it means to follow a creative calling. They share stories from the Napa conference, the shift from realism to abstraction, and the moment Laurel felt pushed to keep going. It’s a conversation about art, faith, and the courage to keep creating when the path isn’t clear. You will learn: How technology shapes our sense of beauty What it looks like to nurture a creative vocation Why value in art has nothing to do with price Perfect for anyone who loves art, has a creative streak, or needs a reminder that beauty still matters. Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission-driven organizations, or visit us at teemwork.ca.

6. 

   27 Apr 2026

   How to go on Vacation (for Real)

   In this episode of Serious Playfulness, Kyle and Stephanie dig into why so many leaders struggle to truly unplug, even when they know they need a break. They explore how unclear delegation, constant firefighting, and identity‑driven habits quietly keep leaders tethered to their phones, their inboxes, and their teams. They share stories of organizations where leaders became the bottleneck without realizing it, and how that dependency creates stress, confusion, and burnout for everyone involved. You’ll learn why healthy systems and clear authority aren’t just operational tools, they’re what make real rest possible. You’ll learn: Why leaders become “too needed” without meaning to How unclear roles and authority keep teams dependent Practical clarity steps that free you to actually step away If taking time off feels impossible, or if your team falls apart when you do, this conversation will help you build the clarity and trust you’ve been missing.

7. 

   13 Apr 2026

   Clarity Before Marketing: The Step Most Teams Skip

   In this episode of Serious Playfulness, Kyle and Stephanie tackle the mistake most teams make before launching a campaign: skipping internal clarity. They share stories of organizations that “spin out” trying to market without knowing who they are or why they exist, and how that confusion leads to vague messaging, wasted money, and team frustration. You’ll learn why clarity isn’t just about better copy, it’s about cohesion, confidence, and results. You’ll learn: Why unclear goals quietly sabotage campaigns How internal confusion shows up in external messaging Simple clarity questions that save time and money If your team’s marketing feels scattered or reactive, this conversation will help you refocus before your next big push. Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission-driven organizations - or visit us at teemwork.ca.

8. 

   31 Mar 2026

   Your Team Doesn’t Need More Goals, it Needs ONE That Matters

   In this episode of Serious Playfulness, Kyle and Stephanie challenge one of leadership’s most common habits: setting too many goals. Instead, they make a counter-intuitive case for choosing one clear, unifying priority, and why simplicity is often the key to momentum, morale, and real progress. Through practical examples and memorable analogies, they explore how multiple goals quietly fragment focus, slow teams down, and leave people pulling in different directions. Drawing on real-world team experience and proven frameworks, they show how clarity helps teams row in rhythm instead of spinning in circles. The conversation also connects this idea to their free DIY Team Assessment PDF, which helps leaders uncover whether their team is aligned, and includes a 90-minute team health meeting outline to help teams identify and rally around the one goal that matters most right now. You’ll learn: - Why multiple goals often reduce effectiveness instead of increasing it - How a single, shared priority improves focus, morale, and follow-through - How to identify and measure the one goal your team should rally around If you’re heading into a new season feeling overwhelmed by competing priorities, this episode offers a simpler, more sustainable way forward. Listen now and explore the free resources at www.teemwork.ca (http://www.teemwork.ca)

9. 

   16 Mar 2026

   Diagnosing Team Health: Warning Signs Leaders Shouldn’t Ignore

   In this episode of Serious Playfulness, hosts Kyle and Stephanie invite leaders to pause before planning for 2026 and take an honest look at what’s happening inside their team right now. They focus on the everyday issues that quietly derail teams: unproductive meetings, low morale, and misunderstanding roles. Through practical stories and clear examples, they unpack the “yellow flags” leaders often overlook and explain why these signals matter more than another strategy session. The conversation also introduces a free DIY Team Assessment PDF, (https://teemwork.ca/toolkit/)including a 90-minute team health meeting outline, designed to help leaders spark honest dialogue and make immediate, meaningful improvements. You’ll learn: - Why ineffective meetings and slow decisions are signs of deeper issues - How low morale and unclear roles undermine trust and collaboration - A simple way to assess team health and take action in one focused meeting Download the free PDF and explore more details at www.teemwork.ca (http://www.teemwork.ca)

10. 

    4 Feb 2026

    From Confusion to Clarity: Fixing What’s Really Holding Teams Back

    In this episode of Serious Playfulness, hosts Kyle and Stephanie dive into the often-overlooked practice of diagnostics in team dynamics. It’s not enough to spot the symptoms of dysfunction, real health comes from uncovering the root causes. Drawing on years of experience with nonprofit teams and purpose-driven organizations, Kyle and Stephanie share how subtle issues can quietly undermine cohesion, and why an external perspective can bring clarity leaders sometimes miss. Through real-life analogies and candid stories, they highlight how proper diagnostics can transform not just problem-solving, but the overall effectiveness of a team. You'll learn: Why surface-level fixes rarely solve deeper team challenges How subtle dynamics can mask the true source of dysfunction Practical ways to bring hidden issues into the light Why addressing root causes builds resilience and long-term effectiveness This episode is especially for nonprofit leaders, founders, and team leads who sense something is “off” but can’t quite name it. If you’ve ever felt stuck treating symptoms without progress, this conversation will resonate. Don’t let hidden issues quietly erode your team’s strength. Tune in for practical tools, honest insights, and a reminder that clarity is the foundation of healthy leadership. Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission-driven organizations - or visit us at www.teemwork.ca (http://www.teemwork.ca/).

11. 

    4 Aug 2025

    Diagnosing "Pretty Good": Tackling Mild Dysfunction Before It Hurts Your Team

    Get practical tools for healthier teams: https://teemwork.ca/#contact (https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbmVUdE5hSXg3T0ZQaVVJdWhYZk9NOTlkSFdHUXxBQ3Jtc0trX0VnMlN2dFZkMEdsb0x5Y054RVR6UGNielp1M084QWNHbEhmZHNEVWhqMHctd1kyVTlRS3p2RWdwZTEwZlhZQUtuZVFNdVlwaExlXzVuZVQya0VmUnBtQUZIMHExX3pIeWxRcWU2VEVvQmI0ZFpGWQ&q=https%3A%2F%2Fteemwork.ca%2F%23contact&v=gT_amqvUBms) In this episode of Serious Playfulness, Kyle and Stephanie dive into the overlooked problem of mild dysfunction—the “not bad” team dynamics that quietly drain clarity, cohesion, and performance. Drawing from real-world examples and leadership blind spots, they unpack why proactive leaders don’t wait for things to break before taking action.You’ll learn: Why “we’re doing fine” can be a red flag in disguise How low-level confusion grows into major misalignment A practical exercise to test clarity and buy-in on your team What hidden resentment and artificial harmony signal about team health How to avoid losing your best people by acting early

12. 

    15 Jul 2025

    Leading Volunteers with Clarity & Kindness

    Get practical tools for healthier teams: https://teemwork.ca/#contact In this episode of Serious Playfulness, Kyle and Stephanie unpack the art of leading volunteers in mission-driven organizations. Drawing on real-world stories, from turf wars over locked cupboards to greeter roles that unintentionally push people away, they explore how treating volunteers like valued team members can transform performance and commitment. You’ll learn: Why front-loading clear expectations prevents conflict and confusion How prompt, gracious feedback turns good intentions into great work When and how to have courageous conversations to uphold high standards The power of probationary roles and annual renewals in volunteer management How to foster a culture of serious playfulness that inspires excellence Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission-driven organizations.

13. 

    1 Jul 2025

    On Selling: How Rejection Fuels Success

    Get practical tools for healthier teams: www.teemwork.ca What if selling wasn’t about slick scripts or pushy tactics, but about genuine service and humble perseverance? In this episode of Serious Playfulness, Kyle and Stephanie unpack their journeys into the often misunderstood world of sales. With stories from consulting, client work, and a thousand “no’s,” they explore how reframing sales as an act of service can unlock courage, virtue, and surprising joy. You’ll learn: Why great sales begin with a mindset of service, not manipulation How reframing rejection as success leads to bolder, better outreach What it means to pursue “a thousand no’s” (and why it actually works) How humility, detachment, and Excel can help you grow a business you love Why even cold emails can be personal, purposeful, and effective Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission-driven organizations.

14. 

    17 Jun 2025

    A Blueprint for Human Flourishing with Andrew Abela

    Get practical tools for healthier teams: www.teemwork.ca What if the secret to lasting personal growth, and healthy team culture, isn’t ambition, but simplicity? In this episode of Serious Playfulness, Kyle Neilson interviews Dr. Andrew Abela, author of Superhabits, to explore how breaking big goals into small, repeatable steps can lead to lasting transformation. From cockpit decisions to classroom transformation, this conversation is a refreshing take on the power of virtue in real life. You’ll learn: Why “beginning is winning” and how to start small and actually stick with it How real virtue rewires your habits, not just your intentions Why Captain Sully’s miraculous landing wasn’t a fluke, but a lifetime of virtue at work How to build virtue into student life, business teams, and personal growth Why a simple habit done daily is more powerful than chasing perfection Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission-driven organizations.

15. 

    3 Jun 2025

    Is This Person Toxic… or Just Difficult? | Dealing With a Bad Apple on Your Team

    Get practical tools for healthier teams: teemwork.ca One bad apple really can ruin the whole bunch, but what if they’re subtle, charismatic, or just a little passive-aggressive? In this episode of Serious Playfulness, Kyle and Stephanie unpack the tricky reality of working with someone who quietly sabotages your team’s morale. From gaslighting to group manipulation, they share real consulting stories and practical tools for leaders stuck in the tension between performance and dysfunction. You’ll learn: Why one toxic teammate creates “emotional drag” for everyone else What manipulation and gaslighting can look like in the office How to know when it’s time to say goodbye (and how to do it well) Why team health is worth the hard conversation Subscribe for more conversations on team clarity, emotional intelligence, and the real dynamics of mission-driven work.

16. 

    20 May 2025

    Why Vague Values Hurt Your Team | Culture, Clarity & Organizational Integrity

    Get practical tools for healthier teams: www.teemwork.ca Too many organizations post values on the wall but never live them out. In this episode of Serious Playfulness, Kyle Neilson and Stephanie Rivard unpack the real problem with vague values, and why clarity, honesty, and self-awareness matter more than ambition or unity-speak. Whether you're leading a nonprofit, business, or faith-based team, this one’s for you. In this episode, you’ll learn: Why values should describe who you are, not who you wish you were How to define your organization's “smell” (yes, we explain) Why mixing morality, strategy, and personality leads to confusion How to fix mismatched values that no one really believes in When to edit your values vs. address behaviour Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission-driven organizations.

17. 

    6 May 2025

    Navigating Awkward Social Moments at Work: Boundaries, Feedback & Courageous Honesty

    In this episode of Serious Playfulness, hosts Kyle Neilson and Stephanie Rivard wade into the wonderfully weird world of awkward social moments — the ones that happen at work. From morning greetings that cross personal boundaries to belly-button hand placements in board meetings, nothing is off-limits.Drawing from real coaching scenarios and personal experiences (yes, even a long-mispronounced word on stage), Kyle and Stephanie explore why these small but strange moments matter — and how our responses can either strengthen or silently strain team dynamics. You'll learn: Why awkward behaviour, left unaddressed, erodes team clarity and trust How to give feedback that’s kind, direct, and actually helpful When to speak up (and why waiting too long makes it harder) How courage in small moments shapes team culture Why honesty — even about bad breath — is an act of love This episode is especially for nonprofit leaders, founders, and team leads navigating seasons of transition or scaling. If you’ve ever faked confidence, avoided asking for input, or held back from taking risks for fear of looking incompetent — this conversation will resonate.Tune in for stories, laughter, and practical wisdom on navigating the social quirks that come with working alongside other humans.Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission-driven organizations or visit us at www.teemwork.ca

18. 

    22 Apr 2025

    Imposter Syndrome in Leadership: What to Do When You Feel Like a Fraud

    In this episode of Serious Playfulness, hosts Kyle Neilson and Stephanie Rivard tackle a feeling many mission-driven leaders know too well ... imposter syndrome. That creeping fear of being "found out," the quiet question of “Who am I to be doing this?”, and the pressure to appear more capable than you feel, all of it is on the table. Drawing on years of experience working with nonprofit teams and purpose-driven organizations, Kyle and Stephanie explore how self-doubt and insecurity can silently undermine decision-making, team relationships, and leadership clarity. But they don’t stop at naming the problem, they offer a candid, compassionate conversation on how to move through it. You'll learn: Why imposter syndrome is a natural response to growth, not a sign of failure How overcompensation and false confidence can strain team dynamics Why clarity, honesty, and humility build real trust, not weakness Practical ways to assess if you’re the right leader for the next stage How bringing self-doubt into the light can free you... and your team This episode is especially for nonprofit leaders, founders, and team leads navigating seasons of transition or scaling. If you’ve ever faked confidence, avoided asking for input, or held back from taking risks for fear of looking incompetent, this conversation will resonate. Don’t let self-doubt quietly erode your leadership. Tune in for honest insights, practical tools, and a reminder that leading with humility is often the boldest move you can make. Subscribe for more conversations on team health, authentic leadership, and the real challenges facing mission-driven organizations.

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Spotify

5.0 / 5

3 ratings