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

Emily Cates, Head of Go-to-Market Transformation and Operations at Zebra Technologies, has built a career by saying yes to opportunities before having every detail figured out. Starting in HR and talent development, she moved into the business through chief of staff, services operations, P&L leadership, and eventually enterprise transformation. Along the way, she experienced startups, hypergrowth, acquisitions, and a successful business turnaround. Her journey has given her a unique perspective on what it takes to move people from agreeing that change is necessary to aligning around HOW to make it happen together.

Episode Takeaways:

• Treat transformation like value selling. Enterprise leaders need a compelling reason to participate in change. Emily emphasizes understanding what matters to each stakeholder, investing in those relationships over time, and connecting transformation to the value they need to see.
• Build it together. Bringing leaders a fully baked solution can invite resistance. Emily prefers giving stakeholders something they can shape together, creating shared ownership instead of hoping everyone enthusiastically embraces someone else’s brilliant PowerPoint.
• Put the truth on the wall. During a professional services turnaround, Emily gathered candid feedback from customers, partners, and colleagues and created a literal “wall of truth.” Seeing the challenges together allowed the leadership team to identify themes, confront root causes, and align around what needed to change.
• Anchor transformation in shared meaning. Whether the goal is becoming more customer-first or changing a go-to-market model, leaders need clarity about what those ideas actually mean in behaviors and decisions. Connecting transformation to existing values and cultural expectations can make that alignment stronger.
• Use radical thinking to break groupthink. When teams get stuck, Emily deliberately introduces an idea far outside the current thinking. The team may never adopt the radical option, but exploring it can move everyone beyond the comfortable circle of familiar answers.

Emily leaves us with a timely challenge around AI. Its speed makes traditional, sequential approaches to alignment difficult. The opportunity is to figure out how to move far and fast without leaving alignment behind. That means treating alignment as iterative work, continuously learning, shaping, and adjusting together rather than waiting for the perfect answer before moving.

To connect with Emily Cates outside of this episode, connect with him on LinkedIn here.

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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