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D!D Leadership Conference Agenda 

Welcome to Do It Differently: Rethinking How We Work and Lead.

Today's experience combines keynote conversations, leadership breakouts, community
discussions, reflection opportunities, and interactive experiences designed to help you explore new ideas, challenge assumptions, and connect with others.

Use this guide to learn more about the speakers, sessions, partners, and ways to continue the conversation throughout the day and after the event.

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Schedule

Do It Differently!
Rethinking How We Work and Lead

Our day is designed to spark new ways of thinking, leading, and connecting. You’ll dive into keynotes and interactive sessions.

Lead with Play
Donavan Robinson | Pop Colab

This session kicks off the conference with one simple idea: we don't all play (perform) at work in the same way, and understanding that changes how you lead, collaborate, and connect.

 

You'll learn what play actually is, discover your dominant Play Personality from a framework developed by Dr. Stuart Brown of the National Institute for Play, and leave with a practical lens for spotting how the people around you are wired.

 

You'll get a short worksheet, a moment of honest self-reflection, and one thing to pay attention to for the rest of the day.

The Skill Beneath the Skills
Tamara Kroeker | Enneagram Aware

Discover the instinctual patterns and internal drivers that shape how leaders think, decide, communicate, and lead.

 

Strong leadership isn’t just about what we do, it’s about understanding what drives how we do it. This session explores what self-awareness actually means and why it is foundational to effective leadership. You will learn how instinctual patterns influence decision-making, delegation, communication, and stress responses. Through reflection, journaling, and small-group discussion, you will examine the forces beneath your leadership habits and develop practical insights you can apply immediately in your own leadership context.

Success That Sustains
Kate Hanson | Kate Hanson Co.

In a world where expectations are high and demands are constant, many leaders are not lacking strategy. They are carrying too much while trying to execute it.

 

Leadership today is not just demanding. It is becoming harder to sustain.

 

This session introduces a different approach. One where leaders strengthen how they think, decide and operate so they can lead with clarity, steadiness and confidence even as complexity increases. When leaders shift how they operate, performance improves without adding pressure or eroding capacity.

 

Through humour and relatable stories, Kate introduces a simple but powerful framework that helps leaders recognize the patterns driving their results and shows them how to shift toward a more sustainable way of leading.

 

This is not about doing more. It is about sustaining what you have already built.

The Game with No Rules*
Jordan Labelle | Evergreen Growth Collective

33 Minute Problem-Solving Sprint

 

Most leaders and business owners are already playing a game with no rules. Too many problems, competing priorities, and no clear way to decide what actually matters first.

 

In this high-energy, 33-minute breakout, you will step into a fast-paced collaborative sprint built around a realistic scenario: a stalled company, too many priorities, a burned-out founder. Working in small groups, you'll be guided through a three-part framework to cut through the noise: understand what's really going on, focus on the highest-leverage problem, and build an action plan that doesn't depend on the leader doing it all.

 

But here's the twist. The framework isn't handed to you. You build it. The rules emerge from the room, one at a time, as the game needs them.

 

You will leave with tools you can use immediately in your own organization and a fresh perspective on what good leadership actually looks like.

 

What you'll walk away with:

  • Clarity on what matters most. How to identify the real bottleneck in your business, not just the loudest or most visible problem.

  • A decision-making framework that fits you. A simple method for prioritizing based on what actually matters to you, not what you think should matter.

  • A new way to lead. How to stop carrying it all yourself and start building plans that use the right people, tools, and systems around you.

How to Lead with Play: Understanding Your Team Through Play
Donavan Robinson | Pop Colab

Using some familiar ideas companies use to introduce the idea of play at work, this breakout applies the Play Personality framework created by Dr. Stuart Brown and play-based insights to make "work" enjoyable for everyone. You will learn how each of the 8 play styles shows up on a team, what those people need to do their best work, and what happens when the environment isn't designed for them.

 

You will work through a real workplace challenge in a small group, with each person contributing through the lens of their play personality rather than their job title. The results tend to surprise people.

You will leave with a practical way to look at your team differently, a clearer sense of who you might be excluding from the conversation, and a few specific actions you can take when you get back.

 

This session is for anyone who leads people, runs meetings, builds teams, or wants to build a culture that nurtures their team using the things we naturally do. "Play"!

The Art of Doing it Differently
Jane Helbrecht | Uplift Engagement

As automation and AI continue to dominate discussions around how we work, we all have an opportunity to reconnect with the art of our work. The unique creativity, humanity and playfulness we and our teams bring to work continues to be a competitive advantage and is perhaps more important than ever.

 

In this keynote, we will share how work is changing and how leaders and team members can respond and experiment with how we get work done. We’re in a time of massive change and big changes bring big opportunities to impact the ‘how’ behind our work and get even better results.

 

 Outcomes:

  • Attendees will understand some of the current pressures on workplaces and teams, as well as trends in how the world of work is shifting.

  • Attendees will reflect on the art and creativity in their own work and how they can leverage that artfulness for a bigger impact.

  • Attendees will learn examples of how teams and workplaces are experimenting with how we work to drive not just performance but also well-being.

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Break The Ice

Start the day with energy and ease. Mix, mingle, and spark new connections in a relaxed environment designed to get conversations flowing from the very beginning.

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Open Exchange

Be part of the dialogue. Ask questions, share perspectives, and engage directly with speakers and peers in a dynamic, two-way exchange of ideas.

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Recess

Step away and dive in. Interactive activations throughout the day invite you to explore ideas, recharge your energy, and continue conversations in a playful way.

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Gather and Graze

It's more than lunch. It’s a shared experience. Enjoy great food while connecting with others, exploring activations, and building relationships in a vibrant, social setting.

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Experiment

Get hands-on with new ideas. Test, try, and explore tools, concepts, and approaches in an interactive space designed to spark curiosity and practical insight.

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Playground

End the day on a high note. Celebrate with music, conversation, and immersive experiences that help you unwind, connect, and carry the energy forward.

Explore the Experience

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Our Title Sponsor

This is the space to introduce the title sponsor and a brief description of their company. 

Thank You

Premier Partners

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Event Partners

Event Supporters

Media Partners

Do It Differently extends beyond the stage.

Throughout the day, you'll have opportunities to participate in reflection activities, connect with other attendees, engage in playful experiences, meet our partners, and continue conversations beyond the sessions.

The Event Includes

Keynotes and Leadership Breakouts

Reflection Experiences

Community Conversations

Interactive Activations

Music Bingo & Networking

Partner Experiences

Slack Community

Prizes & Draws

Awesome People

We encourage you to design your own experience, explore the spaces, meet someone new, and discover what resonates most with you.

 

Because sometimes the most meaningful learning happens between the sessions.

Event Spaces

Main Room

Welcome, Keynote sessions, Leadership Breakout, the Q&A Huddle, and Close.

Pop CoLab

Build a Bag, Leadership Breakouts, Play, and Creative Experiences.

RCC Tenant Lounge

Mix & Mingle, Lunch Pick-Up, Snacks and Refreshments, Leadership Breakouts, Conversations, and Play

Main Foyer

Interactive Activations, Partner Experiences, Reflection Activities, Music Bingo, Karaoke, and Networking

Washroom Access*

Washrooms are in the Richardson Concourse Foyer outside the RCC Tenant Lounge.

 

*Please note that an access key card is needed. A volunteer will let you in near the doors at high-peak times. Visit our Guest Event Hub for a key card.


A washroom is also available in the Pop CoLab space.

Join the Conversation

Connect with attendees, speakers, volunteers, and partners throughout the day. Share ideas, photos, and insights.

D!D Advisory Group

A curated group of professionals who contributed time, expertise, and insight to shape the event’s content and overall experience.

Pop CoLab
Uplift
Imva
KHCO
EnneagramAWARE
Evergreen_Growth_Collective

Premier Partners

This event would not be possible without the support of our amazing partners. 

StudioQ
BGO
RCC

Playground Partners

Media Partners

Land Acknowledgement

We are on Treaty land.

We acknowledge that our water is sourced from Shoal Lake 40 First Nation (Shoal Lake 39 is also impacted) in Treaty Three Territory, and that most of our hydro-electricity comes from Treaty Five Territory in northern Manitoba. Through the land, we recognize our connection and commitment to working with the Red River Métis, all First Nations Peoples across Turtle Island, and the Inuit of Canada.

Take the Play Quiz

We don't all play the same way, and that's the whole point.

Take our quick Play Personality quiz and find out how you're wired to play. Share it with your team, your friends, or that one coworker who definitely needs this. Compare results. Start a conversation. Have some fun with it.

Pop CoLab Winnipeg

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Get in Touch

Connect with us to learn how Pop CoLab can elevate your team. For inquiries, reach out via email or phone, and let's create something memorable together!

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