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New View EDU Episode 87: Making How Matter

April 14, 2026

Available April 14, 2026

Find New View EDU on Apple Podcasts, Spotify, and many other podcast apps.

Julie WilliamsonLeadership sometimes feels like a lonely job with lots of competing tasks but few clear guideposts. Even with the most meticulous planning, leaders can know conceptually what needs to happen but falter in articulating how all the pieces will come together. Author, strategist, and consultant/coach Julie Williamson joins host Debra P. Wilson to talk about the challenges and opportunities of leadership and what it means to make “how” matter in our work.

Julie and Debra start by discussing the challenges of turning a strategic plan into an actionable framework that sets an organization up for success. Julie points out that most leaders are comfortable with investing in a plan and the tools and resources needed to support the associated tasks, but falter in changing their leadership styles to create alignment across their team in a way that allows for sustainable change. 

Julie talks about the “failure gap,” which separates the 70% of transformation attempts that fail from the 30% that succeed. The leadership habits that form a bridge between a fine job and a transformational job fall in that gap, she says. The difference is in having the courage and clarity as a leader to ask, “what do I need to change about my habits to really help this team achieve what we have envisioned?” She and Debra agree that it’s easy to slide back into comfortable habits and routines, both for leaders and for the team members who support the vision, and that helping break less-optimal systems to replace them with new paths to success can be a daunting—but necessary—task.

How school leadership teams support the work of the head is a particular area of concern. Julie highlights the need for the board and head to be in strong alignment to enact any kind of cohesive, visionary plan for an independent school community. She underlines the fact that on many, perhaps most, independent school boards, there are members who are there more for the love of the school than for their understanding of their role. Julie recommends that board chairs work to clarify the roles, responsibilities, and norms of all board members to ensure the group is functioning optimally and in service of supporting the head. 

When that kind of alignment and support structure is absent, Julie says, there’s a greater propensity for loneliness and isolation and a greater likelihood of burnout or turnover for the head. The interplay between head and board should always be calibrated in a way that doesn’t add to the burden of headship. When a head of school is preoccupied with how they can navigate tension and board dynamics, rather than how they can work with the board to move the vision forward, the work will suffer and leadership becomes a much more difficult task. Julie notes that leaders are, first and foremost, humans, and the way they work together to support one another is critical to building community and cohesion that allows important work to advance.

Key Questions

Some of the key questions Debra and Julie explore in this episode include:

  • How can leaders find alignment with their teams? What do they commonly miss or overlook in that quest?
  • Where does the “failure gap” show up in day-to-day leadership behavior?
  • What systems and behaviors can help leaders engage cross-functional teams?
  • What are some common challenges and pitfalls when working with boards? How can boards and heads work more seamlessly together to ensure success?

Episode Highlights

  • “Changing how you lead means changing some deeply embedded habits about how you're showing up together as a leadership team. How you, as the head of the organization, how you're behaving and what you're doing in the organization to drive the strategy forward. If you're not transforming how you lead, you will not transform your organization, no matter how good the strategy is.” (7:31)
  • “The hard things that you want to work on, whether you're a CEO or a head of school, the hard things you want to work on is how do we be in better service to our students, to our families, to our customers, whatever that looks like for you. You don't want the hard things that you're working on to be, got to go wrangle the board again, or I've got to go convince my team that this is the right direction to go. Right? That's not what you want to spend your time on. And that will cause turnovers.” (27:11)
  • “So if a leader is feeling a real sense of anxiety or trepidation about meeting with the board in any way, in my mind, the board is failing. Because you should be creating an environment where whether it's good news or bad news, that person feels confident that they have a group of people who are there to support their success and that they are going to partner with them and hold them accountable, yes. You know, challenge them, yes, push them, yes, but make them feel small or make them feel anxious or make them feel unworthy of the role? No.” (31:53)

Resource List

Full Transcript

  • Read the full transcript here.

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About Our Guest

Julie Williamson, PhD, is the CEO and a managing partner of Karrikins Group, a global consulting firm that helps executive teams achieve alignment, lead transformation, and get aligned. A strategist, speaker, and bestselling author, Julie is recognized as a leading voice on how aligned leadership unlocks enterprise-wide progress.

She works with leadership teams around the world to turn strategy into impact by closing the gap between agreement and alignment. Her work blends business acumen, social science, and practical facilitation to help leaders shift how they lead together in pursuit of their most ambitious goals.

Julie is the author of the best-selling book Make HOW Matter and is a frequent contributor to Forbes Business Council and CEO Magazine, where she brings a clear, human, and pragmatic perspective to the challenges senior teams face today.