Traditional Strategic Planning Must Shift to Embrace Less Certainty and More Insights

Winter 2023

By Greg Bamford, Crystal Land

This article appeared as "Control Alt Delete" in the Winter 2023 issue of Independent School.

When you hear the words “strategic planning,” what do you think? Data terror? Workload hell? Dullsville? Or do you think: Joyful? Creative? Insightful? Do you fear a top-down strategy that doesn’t relate to the real work schools do every day? Or do you visualize a plan to help your school see the path ahead more clearly—and create new possibilities for the future? 

The strategic planning processes we participated in 15 or 20 years ago are examples of a traditional strategic planning process—one that still exists in many schools. Following a SWOT analysis, a large team quickly formed groups tasked with preset goals. Each goal area had a single word or phrase to direct their work: faculty, finance, physical plant, fundraising. While team members debated the initiatives and action steps long and hard, the final strategic plan read more like a menu at the Cheesecake Factory than an inspired strategy for change. 

Creating detailed action plans around predetermined areas of focus is a regular part of school leaders’ work—it’s how they take care of daily business. But a problem arises when we bring that mindset to the strategic-planning level. The result is often an overly controlled process, producing a strategy that’s too brittle to navigate the twists and turns of school life. In a world that’s full of surprises and unanticipated events, schools urgently need less certainty and more insight. The “best”—most visionary and most impactful—plans come from shifting your mindset from finding the “answer” to exploring a wide array of possibilities. 

The link between process and product is central. To gain the insight necessary to thrive in the face of uncertainty, schools need to shift from traditional strategic planning to an experience that centers curiosity, begins with human experience, embraces ambiguity, challenges assumptions, and sparks hope.

Why We’re Stuck

As with so many things in life, the central obstacle to embracing a better strategic process is our desire for control in an uncertain world. When it comes to forming strategy, this desire shows up in four key ways.

The want to communicate certainty. The unpredictability of a VUCA (volatile, uncertain, complex, and ambiguous) world can feel scary and threaten our feelings of competence. Communities often look to leaders to express certainty about the school’s future. 

Confirmatory thinking. Surprisingly, we often meet with potential clients who say they already know what they want to focus on in their plan. In their minds, a strategic planning process is designed only to flesh out the details of implementation—or to get the community to ratify a predetermined direction, often developed by a small group of board members or administrators. 

A legislative mindset. In many schools, strategic planning teams are formed as quasi-legislative bodies—membership is designed to ensure each constituency has representation, and members arrive to meetings prepared to advocate for what they see as “their” needs and to advance a specific agenda. 

A lack of confidence in the capacity of others. Most school leaders have had an experience where they shared power with others and things went south. And, in truth, sometimes school leaders, teachers, parents, and alumni can be short-sighted. A reluctance to share control is often rooted in fear of what might happen. 

Embracing Ambiguity

It’s human nature to try to control processes and outcomes. In their book Navigating Ambiguity: Creating Opportunity in a World of Unknowns, Andrea Small and Kelly Schmutte name both the challenges with not knowing and the benefits of embracing ambiguity: “Difficult challenges in a complex, changing world require creativity to tackle, and ambiguity is a natural part of that creative work. You simply can’t have one without the other.” They also note that our relationship with ambiguity can change depending on the circumstances. We often move, depending on the topic, between “enduring, engaging, or embracing” ambiguity. 

In the strategic planning process, school leaders who are responsible for the future of their schools may lean toward enduring the process when they could—and perhaps should—move to engaging and embracing the questions to open up creative thinking and options. 

In our work with schools, we emphasize the language of “compasses over maps”—the idea that a strategic plan should choose a clear direction without attempting to anticipate a detailed sequence of action steps over several years. With this lens—which we learned from Whiplash: How to Survive Our Faster Future by Joi Ito and Jeff Howe—schools can adjust their tactics to respond to a changing landscape while still heading in a direction that serves their missions and values. 

To embrace ambiguity:

  • Let go of preconceived notions about what the process should be and what the plan should look like. Remind yourself: Don’t anticipate the answers. 
  • Listen, listen, listen. And try to not just listen from your particular seat at school (“I’m on the board so I should…”). Use phrases like “Tell me more” and “Can you share a story that highlights that for me?”
  • Expect to feel really uncomfortable, challenged, and not certain at points of the process. Discuss at the beginning of the process so that folks aren’t surprised if they feel the same. (We like the Gartner hype cycle to visualize what this work may feel like.)
  • Think about the stages of navigating ambiguity. Are you merely “enduring” ambiguity? Can you consider “engaging” or “embracing” topics and issues that make you uncomfortable? How might you actively reframe your approach to ambiguity by formally naming it and making it a part of each stage of the process? 

The Importance of Needfinding

In our work, we’ve found that most schools start talking about “what to do” too early. We suspect that’s because we live in a pragmatic culture, and talking about what we’re going to do has an appealing, let’s-cut-to-the-chase ring to it. After all, isn’t that the point? Aren’t we here to decide what to do?

It can also happen because people come with ideas they’re already excited about. They may see the process as an opportunity to advocate for that idea or to represent a constituency that needs a voice.

We’ve found that when groups focus on solutions too early, they get stuck. They can’t agree on a set of solutions because they don’t agree on a set of problems or opportunities. Or, just as bad, they reach consensus too early, ratifying—rather than challenging—the conventional wisdom within the community. 

The mantra we’ve taken up is “needs before solutions.” Does your team understand the needs that are present in the community? Do they understand the possible opportunities for the school? Before you seek answers, have you found the right questions?

Our recommendation is to break the process into two phases: Spend roughly half the time exploring what’s needed and what’s possible (the “opportunity space”), and spend the other half deciding what to do (the “solution space”). 

To put needs before solutions:

  • Dedicate half of your process to defining the needs, opportunities, and problems that are most critical for your school to address in the next strategic plan. This will feel like a long time! However, ensuring that you have gotten clarity on where to focus will make alignment around future directions more efficient.
  • Take time to observe and listen through methods that capture stories and nuance, such as stakeholder interviews, student shadows, and campus observations.
  • Go beyond the doors of your school for inspiration. What else is happening in the outside world that you can use to inspire and shape your thinking? How can you bring in outside voices and outside models?

Thinking Like a Futurist

We all know that we need to be ready for the future. We’ve witnessed changes in our markets and our communities. We’ve heard countless times that today’s students are likely to have jobs that haven’t even been invented yet. 

Despite this, most people in schools—including trustees, despite their strategic and generative roles—tend to use their own experiences in schools as a mental model for imagining possible futures. As a result, it’s easy to lose sight of emerging ideas and trends that may disrupt the experience we’ve grown attached to, as well as possibilities that are infrequent or difficult to anticipate but highly impactful—like a global pandemic. 

To be ready for a range of possible futures, strategic planning teams need to think like a futurist. This allows teams to consider a longer-term direction that is more likely to shape the future rather than simply react to it. Futurists do not predict the future; they aren’t telepathic, they have no crystal balls, and they don’t rely entirely on quantitative data to envision the future. They use scenario planning to understand what’s possible, probable, and eventually, what is preferable. By keeping all scenarios alive, you increase the odds that your plan will set the conditions for your success under multiple scenarios. You may also have greater agency in the final outcome.

How can school leaders imagine what’s possible? The first step is to examine what’s already happening at the margins—as a niche practice, from immature technology, or in other markets. Often, signals about the future are visible: New behaviors are emerging but countercultural; new technologies are present in other industries but not yet implemented well in schools; new markets are emerging but not yet profitable. Like Kodak once upon a time, a school’s current market may be dying but still too profitable to let go of.

In her book Imaginable: How to See the Future Coming and Feel Ready for Anything—Even Things That Seem Impossible Today, the futurist Jane McGonigal emphasizes the power of cultivating our imagination about the future. Doing so offers a microdose of shock now so that we experience less anxiety (and more preparation) when contexts change in the future.

To make your strategy more future-ready:

  • Encourage your team to time travel. We often lead school teams through an exercise in which we ask them to describe a student’s day—from waking up to going to bed—20, 40, 60, and 80 years ago. What is the student doing before school? What do they do at school? What happens after school? Often, this reveals rapid changes in the environment young people are growing up in (parenting style, access to media, culture), even if schools are often slow to catch up. The exercise helps teams understand that big shifts can happen in a decade or two. 
  • Listen for the “signals in the noise.” We borrow this language from the futurist Amy Webb’s work, The Signals Are Talking: Why Today’s Fringe Is Tomorrow’s Mainstream. She suggests looking for trends that are currently on the margins of education, like virtual reality or artificial intelligence, and understanding the implications for their school if they move to the center. Online instruction was only happening on the margins a decade ago—it was an option that was largely used by students in special situations. We all have experience with it today.

Sharing with the Community

Once a school makes it to the final stage—agreeing on the goals, initiatives, and action steps—strategic planning is not over. Schools need to actively plan for successful implementation. It’s not enough to complete the plan, create a glossy brochure, and assign team members a to-do list. That is a sure-fire way to lose enthusiasm—as well as the opportunity to share the process and the product with the larger community. 

A key step is to take those ambitious and visionary goals and make them part of the drinking water at school through media, storytelling, shared vocabulary, and repetition. Schools need both top-down and bottom-up approaches to implementation. In our experience, the best strategic plans don’t sit on the shelf but become part of the annual and day-to-day experience for the board, the head, administrators, and faculty—they should lead with their strategic plan every day. 

While each community may have a different “way in” to implementation, it’s important to remember that it all doesn’t and shouldn’t happen in the first two years. In fact, for sustained change to happen, it may take several years to achieve the ultimate goal. 

To effectively implement ideas:

  • Hack the plan. Ask faculty and staff to each “hack” the strategic plan. Each person finds one way to bring it to life, incorporating the hack into their teaching or year’s plans. Use these hacks to tell stories and promote success. Report out and celebrate in division and department meetings as well as at the end of the year.
  • Be a storyteller. School communications can include short and informative features on students and teachers who are bringing aspects of the plan to life. The head of school uses the strategic plan as talking points and writing points in her internal and external communication. 
  • Use task forces. Consider creating short-term (one-year) task forces to work toward specific action steps. Led by teacher leaders and administrators, task forces allow people other than the head and leadership team to move an agenda forward through prototyping, feedback, and iteration. 

Imagine the Possibilities 

Strategic planning is a unique opportunity to gather your community in a conversation about the future. It’s a chance to build a stronger capacity to think creatively and approach problems in human-centered ways. It’s a moment where you can make stronger connections with your community and with other schools grappling with similar issues. 

If we seek to control the outcome rather than to learn as much as we can, challenge our preconceptions, and see what the process teaches us, we forfeit all of those advantages. And in a world that’s changing so quickly, control is an illusion anyway. Curiosity is the currency that opens up new possibilities as everything shifts around you.

A New Process at Work

Crystal Land was most recently at Head-Royce School (CA) where she served for more than 30 years as the head of school, senior administrator, and teacher-leader. She participated in and led several strategic planning processes. “I believe that if my school’s plan had evolved as I had initially imagined,” she says, “it would have looked like a detailed checklist rather than a strategic direction. We ended up creating a plan that lifted up the entire community and provided the school with a future-oriented compass that is still at work today.” 

During the 2016 strategic planning process, the team started with the needs-before-solutions approach. One pressing issue was student mental health. A quick-fix approach leads to tactics like “hire more school counselors,” but this path doesn’t start with assessing the needs of the community. We began with finding out more about the K–12 student experience. The strategic planning team members shadowed students, interviewed parents and school employees, assessed homework policies, researched curriculum and programs from schools (some of which were very different from Head-Royce), visited classes, reviewed survey data from Challenge Success, and even checked in on how young alumni were experiencing their work worlds and futures. 

The insights gained helped the team frame the overarching strategic plan goal: “Commit to and sustain a culture of balance and well-being,” which led to a multitiered set of initiatives and action steps implemented over the course of the five-year plan. It included sunsetting the Advanced Placement program; creating teacher-designed advanced seminar courses; adopting a new middle and upper school schedule with longer learning blocks; reexamining and understanding assignments, workload and homework; increasing mental health resources; building a mental health parent education program; creating wellness and community days; providing faculty and staff lunches, yoga and wellness options, and creating extensive outdoor spaces to support the critical connection between mental health and the natural world.

By focusing on understanding human needs before jumping to solutions, the strategic planning team ultimately created a more generative—and truly strategic—goal that allows the school to continue to iterate and adjust over the course of the strategic plan. The generative process of observing student and community needs allowed the school to assess many paths forward instead creating preset “answers.” 

As the school approached the formal end of the five-year plan, Bridge to 2022, the board and administrative team decided to extend the current plan’s five core goals with new initiatives as a new head began. The staying power of a strong strategic plan was evident as the school reviewed the implementation and the accomplishments and acknowledged the ongoing needs of the school community.

Greg Bamford

Greg Bamford is senior partner and co-founder at Leadership + Design, a nonprofit organization that partners with schools to support positive change. Bamford was previously head of school at Watershed School in Boulder, Colorado, and the associate head of school for strategy and innovation at Charles Wright Academy in Tacoma, Washington.

Crystal Land

Crystal Land is a partner at Leadership + Design, a nonprofit organization that partners with schools to support positive change, and a former head of school.