What does it take to lead a successful transformation when the road ahead is anything but predictable?

In this episode of The Failure Gap, Julie Williamson sits down with Dan Johnson, CEO of Innovation Federal Credit Union, to explore how leaders move beyond agreement and build the alignment needed to deliver on ambitious goals.

With more than 30 years in financial services and 15 years at Innovation, Dan has built his leadership career through deliberate moves across different roles, sometimes even taking a step backward to gain a broader perspective. That willingness to embrace discomfort has shaped his approach to leading major transformations, including Innovation's digital transformation and transition to becoming a federal credit union in Canada.

Dan shares candid lessons about building trust, embracing healthy conflict, and creating accountability that helps teams succeed rather than simply pointing out where they've fallen short.

Episode Takeaways

• Build trust before you need it. Successful transformations start with strong team relationships. Creating space for vulnerability, honest conversations, and healthy conflict helps leaders navigate challenges together when things get difficult.
• Alignment isn't a one-and-done event. Getting everyone on the same page at kickoff is important, but maintaining alignment requires ongoing attention. As Dan puts it, leaders need "defined curbs" that keep everyone moving in the same direction without requiring perfect lockstep.
• Clarity, commitment, and accountability go together. Leaders need more than agreement on priorities. They must establish shared understanding, make explicit commitments, and have the courage to address blockers and negotiate trade-offs along the way.
• Make meetings matter. The problem isn't always too many meetings. It's meetings that don't create value. Strong facilitation, meaningful participation, and clear takeaways turn conversations into opportunities to build alignment and accelerate action.
• Celebrate the wins and the misses. Transformation is rarely a straight line. A growth mindset means learning from mistakes, recognizing milestones, and occasionally finding humor in the unexpected detours. Sometimes a little laughter is exactly what a multi-year initiative needs.

Dan's challenge to leaders is to stop treating alignment as something you achieve once and preserve forever. It takes continuous conversation, curiosity, and courage to keep teams moving forward together. And when things don't go according to plan, as they inevitably won't, the goal isn't perfection. It's staying connected, making adjustments, and keeping the enterprise moving toward shared success.
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Dr. Julie Williamson wrote the book on how to Make HOW Matter. After working with hundreds of executives and leadership teams at Fortune 500 and S&P 500 companies, she created the Make HOW Matter Accelerator™ to bring the power of leadership alignment to more leaders at every level.

Grounded in both real-world business experience and social science, this virtual, self-paced program helps you turn the principles of Make HOW Matter into practical leadership skills you can use every day. Whether you’re a small business owner, leading a division, or simply looking to increase your influence and drive better results, you’ll learn how to close the gap between agreement and true alignment, and turn priorities into action. Ready to make HOW matter? Explore the Make HOW Matter Accelerator™.

Learn more about Julie and Karrikins Group:

• Connect with Julie on LinkedIn
• Follow Karrikins Group on LinkedIn
• Check out Julie's book, 'Make HOW Matter: Key Conversations for Leaders to Build Alignment and Accelerate Growth'
• Learn more about how Karrikins Group helps enterprise teams drive better results

Josh Kern’s leadership journey has taken him from Capitol Hill to marketing to the CEO seat, with plenty of restaurants along the way. Now CEO of Snooze, Josh brings a marketer’s curiosity to leading a beloved breakfast brand through its next stage of growth. His experience has taught him that leadership isn’t about arriving with a ready-made playbook. It’s about listening first, understanding what makes an organization special, and then getting clear about what needs to change.

For Josh, that meant starting at Snooze with a simple stop, start, continue exercise and listening closely to what people had to say. Those insights helped shape a focused “true north” for the organization while protecting the culture and magic that already existed. It also reinforced an important leadership lesson: when you’re the CEO, even a casual idea can suddenly become someone else’s priority. For an idea-generating marketer, that requires a little self-governance.

Episode Takeaways

• Listen before you lead change. Understanding what people value, where trust is lacking, and what makes the organization distinctive creates a stronger foundation for alignment.
• Prioritization starts at the top. Leaders need to recognize the weight their words carry. Too many ideas can create churn, disrupt priorities, and send teams running after every shiny penny.
• Build a team that challenges you. Josh intentionally surrounds himself with leaders who complement his strengths and welcomes healthy debate. Alignment doesn’t require everyone to think alike. It requires people to debate openly, decide, and then move forward together.
• Culture lives in everyday experiences. From long-tenured general managers to Snooze’s focus on hospitality and community, culture is reinforced through how people are treated, developed, and connected. Apparently, great pancakes don’t hurt either.
• Stay curious and be willing to fail. Whether testing a new menu item or pursuing a strategic priority, leaders need the courage to make smart bets, learn what works, and stick with an idea long enough to understand the results.

Josh closes with an idea bigger than breakfast: bringing people together to restore confidence in downtown Denver. It’s a fitting reminder that meaningful change requires more than agreement about what should happen. It requires people with different priorities and perspectives to align on HOW they will make it happen together.

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Dr. Julie Williamson wrote the book on how to Make HOW Matter. After working with hundreds of executives and leadership teams at Fortune 500 and S&P 500 companies, she created the Make HOW Matter Accelerator™ to bring the power of leadership alignment to more leaders at every level.

Grounded in both real-world business experience and social science, this virtual, self-paced program helps you turn the principles of Make HOW Matter into practical leadership skills you can use every day. Whether you’re a small business owner, leading a division, or simply looking to increase your influence and drive better results, you’ll learn how to close the gap between agreement and true alignment, and turn priorities into action. Ready to make HOW matter? Explore the Make HOW Matter Accelerator™.

Learn more about Julie and Karrikins Group:

• Connect with Julie on LinkedIn
• Follow Karrikins Group on LinkedIn
• Check out Julie's book, 'Make HOW Matter: Key Conversations for Leaders to Build Alignment and Accelerate Growth'
• Learn more about how Karrikins Group helps enterprise teams drive better results

Debra Wilson, president of the National Association of Independent Schools (NAIS), took an unconventional path into education leadership. After law school and a start at the Department of Justice, she staged what she calls a “self-intervention” and asked what work would truly fill her cup. The answer led her to NAIS, where she spent nearly 20 years moving from regulatory work into governance, risk management, and organizational leadership. After serving as president of the Southern Association of Independent Schools, including leading through the pandemic, Debra returned to NAIS as president.

Her journey offers a useful reminder that there may be no wrong step, just the next one. Sometimes the best leadership move is recognizing when it’s time to find a different trail.

Episode Takeaways

• Build strategy with people, not for them. Debra's team engaged staff and members throughout strategic planning, creating shared meaning before the polished plan ever appeared. Agreement is easier when people receive a strategy. Alignment gets stronger when they help build it.
• Going slow can help you go fast. Debra has a bias toward action, but she recognizes that transformation requires time to build clarity, common language, and commitment. Otherwise, leaders risk adding more initiatives while wondering why nothing moves.
• Acknowledge the messy middle. Transformation asks people to sustain existing work while building new capabilities. Leaders need to recognize that reality, provide resources, and make trade-offs rather than quietly piling more onto already-full plates.
• Treat boards as learning ecosystems. Healthy board alignment requires more than good governance hygiene. Board members need context, education, clear expectations, and meaningful opportunities to contribute strategically. Simply telling someone to “be strategic” is not much of a strategy.
• Lead with clarity, culture, and empathy. Debra encourages leaders to simplify communication, build shared language, pay attention to culture, and get curious when someone responds unexpectedly. Misalignment may be signaling something people believe is at risk.

Debra leaves us with an invitation to align around curiosity. Imagine bringing together people with dramatically different perspectives to explore how education works around the world, then asking a bigger question: If we could build education again from the ground up, what would we create? Alignment doesn’t require everyone to arrive with the same answer. It creates the context for people to wrestle with important questions together.
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Dr. Julie Williamson wrote the book on how to Make HOW Matter. After working with hundreds of executives and leadership teams at Fortune 500 and S&P 500 companies, she created the Make HOW Matter Accelerator™ to bring the power of leadership alignment to more leaders at every level.

Grounded in both real-world business experience and social science, this virtual, self-paced program helps you turn the principles of Make HOW Matter into practical leadership skills you can use every day. Whether you’re a small business owner, leading a division, or simply looking to increase your influence and drive better results, you’ll learn how to close the gap between agreement and true alignment, and turn priorities into action. Ready to make HOW matter? Explore the Make HOW Matter Accelerator™.

Learn more about Julie and Karrikins Group:

• Connect with Julie on LinkedIn
• Follow Karrikins Group on LinkedIn
• Check out Julie's book, 'Make HOW Matter: Key Conversations for Leaders to Build Alignment and Accelerate Growth'
• Learn more about how Karrikins Group helps enterprise teams drive better results