Do Good To Lead Well with Craig Dowden

When was the last time you paused before taking action to ask, “What problem am I really trying to solve?” In this episode, I sit down with Kendra MacDonald, CEO of Canada’s Ocean Supercluster, to unravel what it means to lead with purpose in a rapidly changing world. The conversation starts with her daring career move from a global role at Deloitte to building a new organization from the ground up, which was fueled by a passion for meaningful innovation.

If you’ve ever questioned your own courage to change course or felt the tug-of-war between personal boundaries and professional expectations, Kendra offers practical wisdom. She talks through her steps to manage risk when taking on something new, using self-reflection rather than bravado to guide decision-making. Facing imposter syndrome? She’s been there too, and her advice is grounded and honest: focus on your unique contributions and let curiosity lead, especially when you’re the newcomer in the room.

For leaders building teams, or founders starting with just a vision, the conversation surfaces actionable insights such as the crucial role of constant communication, the importance of recognizing and rewarding small acts of courage in teams, and the need to set and protect personal boundaries to stave off burnout. Kendra is transparent about the challenges of remote work and the ongoing experiment to keep her own organization connected across digital distance.

True leadership is about the quality of the questions we ask ourselves and others. Tune in for an inspiring conversation about how we can do both.

What You’ll Learn
- Strategies for overcoming the fear of career pivots.
- How to motivate teams to embrace innovation… without being annoying!
- Balance operational realities with purpose-driven missions.
- Build a thriving remote team culture.
- Overcoming imposter syndrome and leading as an introvert.

Podcast Timestamps
(00:00) – Career Journey: From Deloitte to Ocean Economy
(07:06) – Innovating with Purpose: Framing the Right Problem
(09:45) – Courage to Change: Navigating Career Transitions
(12:29) – Building Organizations from the Ground Up
(15:17) – Setting Boundaries & Personal Clarity in Leadership
(18:13) – Leading as an Introvert: Speaking, Visibility & Energy
(24:28) – Top Leadership Qualities for Today’s World
(28:15) – Motivating Teams & Driving Innovation
(39:09) – Leading in AI & Tech-Driven Times

KEYWORDS
Positive Leadership, Innovation, Purpose-Driven Leadership, Career Transition, Technology Adoption, Artificial Intelligence, Continuous Learning, Remote Work Culture, Organizational Culture, Psychological Safety, Courage, Resilience, Authenticity, Global Mindset, Diversity in Leadership, Work-Life Boundaries, Imposter Syndrome, Trust, Team-Building, Ethics in AI, Burnout Prevention, Curiosity, Change Management, Mentoring, CEO Success

Do you ever wonder if the quietest voice in the room can truly lead—and win—in a world built for extroverts? This episode of Do Good to Lead Well is a refreshing, insightful journey into that very question, as I sit down with Benjamin Friedman, author of “Silent Strength: The Introvert’s Guide to Building Successful Startups.”

The conversation opens with Benjamin’s “me-search;” his personal and professional quest to understand how introverts can succeed when the business world often favors extroverted traits. Can an introvert be authentic and ambitious, all while driving top-tier results? Absolutely, says Benjamin, but it’s all about leveraging your way of being, rather than trying to fit someone else’s mold.

Listeners will come away with practical advice for managing meetings, leveraging networks, and navigating self-doubt. He also shares tools for raising our self-awareness, the power of a “challenge network,” and the importance of aligning values with the people you build alongside. When fear or imposter syndrome strikes, Friedman reframes those moments as evidence you care and offers ways to harness uncertainty as fuel for growth.

The common thread throughout this episode is one of curiosity and vulnerability. It is about questioning our assumptions and beliefs while building a roadmap to authentic success.

What You’ll Learn
- The power of the quiet leader.
- Self-awareness as a foundation.
- Leveraging a Challenge Network.
- How to harness fear and navigate uncertainty.
- Reframing networking.
- The secret sauce of vulnerability.

Podcast Timestamps
(00:00) – Silent Strength: The Origin Story
(06:01) - The Universal Value of Introvert Insights
(11:42) - Self-Awareness as a Foundation for Success
(18:44) - Reframing Imposter Syndrome & Building Presence
(22:29) - Empowering Introverted Voices in Meetings
(28:56) - The Power of a Challenge Network
(36:15) - Getting Useful Feedback
(40:29) - Navigating Fear, Uncertainty & Opportunity
(45:32) - Thriving as an Introvert in Sales & Networking
(50:25) - Co-Founders, Relationships & Final Insights

KEYWORDS
Positive Leadership, Self-Awareness, Feedback, Personal Growth, Vulnerability, Leading with Intention, Curiosity, Startup Founders, Introverts in Leadership, Challenge Network, Networking Strategies, Sales (for Introverts), Eustress vs Distress, Leveraging Strengths, Authenticity, Managing Meetings, Inclusive Environments, Managing Fear, CEO Success

I’m excited to share Part 2 of my 2025 yearend retrospective, which highlights the most impactful insights shared by our amazing guests, as determined by you, the listener. The goal of this special 2-part episode is to lay the foundation such that 2026 is your best year yet!

What is incredible to me is how similar the core themes were across the different guests who joined us on the program. Not surprisingly, curiosity was a major area of emphasis. In a world of constant change, being curious about ourselves and others is vitally important to unlock our individual and collective potential.

We also touched on the importance of community and belonging to create cultures of peak performance. Emotions were also discussed in depth, not as a distractor, but more as a navigational compass. Becoming friends with our inner worlds and listening intently to the lessons our emotions are trying to teach us was a crucial takeaway from this past year.

Last but not least, and building on the past thread, in a world of AI, it is essential not to delegate our thinking to technology. While it is an invaluable and powerful thought partner, we, the user, needs to continue to be the thought leader. Being more mindful and intentional about the questions we ask is the key to our success!

I hope these episodes provide some actionable insights you can leverage in 2026 and beyond!

What You’ll Learn
- Curiosity: A superpower in leadership and in life
- Social sensitivity and team success
- The 3 C’s of meaningful work: Community, contribution, challenge
- AI as a leadership tool: The CRIT Framework
- Cognitive diversity and team innovation
- Unleashing creativity and problem finding
- Embracing emotions in leadership
- The power of mattering

KEYWORDS
Positive Leadership, Personal growth, Professional Development, Uncomfortable Conversations, Team Dynamics, Individual/Collective Excellence, Mindfulness, Navigating Uncertainty, Embracing Curiosity, Asking Questions, Building Resiliency, Authentic Leadership, Psychological Safety, Positive Change, Managing Stress, Success Principles

Happy New Year! I’m so excited to connect with you as we kick off 2026. This year marks a special milestone for us, as we’re rapidly approaching our 200th episode of the Do Good to Lead Well podcast! Your incredible support and engagement are truly why we continue to attract such amazing guests, and for that, I am profoundly grateful.

Instead of a typical goal-setting episode to start the year, I wanted to do something a little different. I thought it would be wonderful to look back at 2025 and highlight some of the most memorable “mic drop” moments from our extraordinary guests. These are the insights that resonated most with you, based on your comments and messages.

I hope they serve as a powerful playbook for your personal and professional growth in the year ahead!

What You’ll Learn
- The importance of leaning into uncomfortable conversations
- Why uncertainty is not the exception, it’s the rule
- How minimizing our smartphones may maximize resilience
- Using AI to spark our curiosity
- You can leverage the power of purpose everywhere
- The importance of replacing failure with learning moments
- How to use evidence to drive better decisions and make work fair
- The secret to being a Likeable Badass
- Why You Want to Ask Yourself: “Who Am I When No One Is Watching?

KEYWORDS
Positive Leadership, Personal growth, Professional development, Uncomfortable Conversations, Alignment on Purpose, Individual/Collective Excellence, Mindfulness, Navigating Uncertainty, Embracing Curiosity, Asking Questions, Building Resiliency, Authentic Leadership, Learning Moments, Psychological Safety, Likable Badass, Make Work Fair, Evidence-based insights, Positive change, Managing Stress, Success Principles

Welcome to a special holiday installment of the Do Good to Lead Well podcast, where I explore how to embrace the festive spirit without feeling overwhelmed by stress. This episode compiles scientific and anecdotal evidence, providing actionable advice for achieving genuine disconnection from work as well as authentic connection with our friends and family. Understand the necessity of truly stepping away from work to allow for restoration, enabling you to start the new year with renewed vigor.

The episode also delves into the importance of being mindful of conversational topics during holiday gatherings. Learn strategies for navigating discussions to maintain a positive and constructive environment, safeguarding your relationships from unnecessary tension.

We will also highlight the perils of pursuing perfection, highlighting that the true essence of the holidays lies in connection and shared moments. Explore the concept of giving experiences as gifts, which create lasting psychological and emotional benefits. I close by sharing perhaps the most meaningful gift we can give those we care about. It is simpler and more powerful than you may think.

What You’ll Learn
- How can we maintain the season’s magic without losing our peace?
- The importance of disconnection for reconnection
- Why we need to set boundaries to show up at our best
- The perils of chasing perfection
- Give the gift of experience
- The power of being intentional about our attention

KEYWORDS
Positive Leadership, Holiday Stress, Relaxation and Recovery, Recharging, Self-Care, Setting Boundaries, The Power of a Positive No, Perfectionism, Nurturing Relationships, Digital Detox, Happiness, Meaningful Life, Well-Being, Interpersonal Connection, Positive Conversations, Positive Communication, Attention Economy, Family Dynamics, Mental Health, Managing Stress, Success Principles