Serious Playfulness | Team and Culture

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.

Get practical tools for healthier teams: https://teemwork.ca/#contact

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

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.

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.

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.

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.

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.

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

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.