Leading Strategically

Amanda: Let’s talk about whole-life harmony. Asking leaders to keep an eye on current goals, honor their commitment to their educators, and plan for growth is a lot, and quite frankly, it sounds exhausting. How do you make it work?

Jonathan: It is a lot, which is why leaders have to be strategic. Leading strategically requires a vision and if you’re truly going to be aspirational and alter trajectories, you can’t just fiddle around the edges. To set a truly inspirational vision incorporating people, you likely need to engage in empathy work (deep listening via interviews, focus groups, shadows, etc.).

You need to be talking to people across your building or system about their lived experiences. This could look like shadowing students, spending time in focus groups with parents, and conversing with your staff. Depending on the audience, you might ask questions like:

  • What do you appreciate about our work?

  • Tell me about a time when you experienced _______.

  • What do you need help with? What makes it challenging? What obstacles are in the way?

  • How might we support you with ______?

Depending on people's role in your system, they may not be willing to tell you directly. In that case, you could recruit partners to help with your empathy and listening work. When The Liber Institute partners with a school or system, we will schedule Empathy Interviews, Focus Groups, and design surveys. These activities generate a lot of data, so we will have Liber team members comb through those stories, surveys, and conversations with leaders from our partner organizations, distilling what we learn into themes, insights, and meaningful vignettes. All those experiences, voices, and ideas inform and influence the creation of a vision.

If you’re not whole or well, this work will deplete you, and your product will suffer. The vicarious weight (that stress and trauma) leaders carry can become unbearable if it isn’t shared and processed, and that goes for district leaders as well as our leaders in the classroom.

At The Liber Institute, we’re a team of 5, including myself. At the end of 2023, I spent three days crafting our 2024 strategic plan with my coach and all the insight we had gathered. Imagine a teacher with 30 students in a class, maybe 120 students across the day; principals with hundreds of students; or superintendents with thousands of students - what does that strategic planning session demand? Who can you enlist to support your planning process, and what room can you create so you can give the task the focus it deserves?

Amanda: I never really thought about it like that. Planning for a classroom is hard enough, but preparing for thousands of students and potentially hundreds of educators must be exhausting. The mental load, that pressure - how do you manage it?

Jonathan: The best way to manage it is by taking preventative measures. Leaders have to be holistically well. I challenge all leaders, from classroom to district level, to step away and restore themselves occasionally. And not only after you begin to feel stressed. Plan quiet time proactively, even if it is a daily reminder to breathe and reflect. Block off time on your schedule, take that mental health day, or go on that retreat. Do what is necessary to preserve your mental health, and then return to the people you serve with a fresh mind and renewed energy. 

Not only do you need that energy and clarity for planning, but you also need it when grappling with heavy data. Qualitative data leaves so much room for personal experience, which allows for community-based planning and allows you to begin to know people on a vulnerable level, for better or worse. For example, while chronic absenteeism may be a hard data point to look at, the stories behind it can be devastating. Understanding those truths is the difference between a bandaid and a healing salve; we need that information to make meaningful changes for our students.

I haven’t always had this perspective. We live in a time and place where working 60, 70, or 80 hours a week is treated like a badge of honor, even at the expense of your health and time with family or friends. Couple that with the weight of educating students who have been overlooked for years, and the pressure to do everything all the time is overwhelming.

Amanda: I completely understand that - there’s always more work. What other advice do leaders have for trying to relieve that pressure?


Jonathan: Okay, in addition to creating space for yourself and adopting self-care habits, I want to challenge leaders to develop a healthy relationship with the “pause.” If you can’t say, “I don’t know, let me get back to you,” then you must practice today. You don’t always need to have an answer right away. Sometimes, taking a breath and thinking more deeply about a question is exactly what you need in order to offer the best response later. “No” is also an answer and, as I once heard it, “No” is a complete sentence. Equipping your toolkit with a “pause” and a “no” could go a long way!

Also, let’s start looking at how we manage relationships with a coaching lens. Coaching is superior to supervising in many ways, but for this conversation, the most significant benefit is realizing you don’t have to have all the answers. Think about the highest-paid coaches in the world. They don’t have every answer to every question. The most transformational relationships I have had with coaches rarely led to definitive answers from my coaches. Instead, they frequently asked ME questions and waited for MY answer! Great coaches can step back and see patterns, pause, and assess the situation before making a recommendation or asking the next question. They challenge their teams to be the best version of themselves. All of that requires them to be healthy, well, and refreshed, with the courage to pause and admit when they don't yet have an answer.


Amanda: Jonathan underscored the importance of strategic leadership in education, emphasizing the need for empathy-driven vision building, self-care, and embracing moments of pause. In our next post, we’ll keep the conversation flowing, diving into the ongoing process of developing leaders. Until then, you can check out our previous posts.

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