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Strategic Leadership: How Heads Can Add Value to Their Schools and Have Fun at the Same Time

Disgruntled parents, underperforming teachers, rogue trustees. Heads have a long list of headaches. But beyond those irritants is a creative and generative part of the job, challenging and satisfying. The world of strategic thinking, of focusing on adding value to the school can be that creative space beyond the daily grind. To my way of thinking, it’s the fun part of the job.

Creating value for independent schools has two meanings for a head, both of which come in the form of questions. First, how can I help the school do a better job of living its mission in a financially responsible way? Second, how can I create or enhance the capabilities of the school so that future school leaders will be able to do a better job of fulfilling the school’s mission? To answer these questions in a way that will create value requires deep integrative thinking, research, an understanding of context, an objective perspective of the school’s present capabilities, management practices that align with goals, courage, trust, talent, imagination, a competitive spirit and most importantly, a relentless commitment to learning. And that’s just the short list.

What must a new head do to avoid the trap of chief problem-solver and instead embrace the fun of being a strategic leader? The answer to this question would require a book-length response, but I want to focus on a handful of suggestions that derive from my work with heads of school as well as my own experience.

1. Create time to reflect and think.
Susan Cain, the author of Quiet, has written and tweeted about the unique attributes of introverts as effective leaders. It makes sense. Most heads could take a page from the leadership book of introverts. An introvert doesn’t mind being in her office, door closed, thinking deeply about the challenges the school faces. Now don’t get me wrong- there is clearly a need for heads to be out and about, to be the public face of the school, and there are certain problems heads must deal with because of their potential impact on the school. But in my experience most heads need to manage their time better and carve out periods during the day or week just to think. As Martin and Lafley have illustrated in Playing to Win, strategic thinking is hard. It requires focusing on key questions in a sequential process, but at the same time assessing the impact on the overall strategy. For example, a head can’t gravitate to a certain vision without thinking about the school’s capabilities and its ability to achieve the vision. Nor can she sustain momentum to create lasting change if she is not thinking about how to feed capabilities so that they remain the engine of change. Trusted senior administrators and maybe even thoughtful trustees might be able to check the reasoning behind a head’s thought process, but more often than not, they are not in a position to play a generative role. Only the head can do this because only the head has a deep and wide enough understanding of context to connect the dots. I once asked one of the most successful insurance executives in the world why he was so successful. His answer: “I know the business.” 

2. Never stop learning.
The Harvard Business Review in its “Daily Alert” has written extensively about why strategy fails. Many of the blog posts indicate the prevailing assumption that the strategy was right but “we just didn’t execute.” This is the equivalent of what I hear from trustees so often: “We need to do a better job of marketing.” It’s such an easy default solution but reflective of the superficial insights that drive strategy. In your role as head, you have to keep seeking new sources of information so that you can continually ask yourself, “Is my vision really a “winning aspiration” to use Martin and Lafley’s term?” You have to keep looking for evidence that your strategy for success continues to make sense. I know a lot of heads who use dashboards with their boards of trustees, and as a general indication of the health of the school, it makes sense. But I’d rather see heads use data that directly speaks to the assumptions behind their strategic plans, data that helps school leaders draw reasonable conclusions about the efficacy of the vision and the strategy to realize that vision. The best heads are constantly learning. Their competitive spirits drive them to find evidence to support the direction of their respective schools. At the same time, they are objective enough to realize that it may be time for a pivot when the numbers just don’t add up. 

3. Make your first year more than just avoiding mistakes.
It’s true that first-year heads should avoid big changes that question the traditions and culture of a school. Resource Group 175 consultant Bob Henderson advises new heads to think of schools as villages, not just businesses, and to take the time to learn their customs before introducing significant change in his blog Blunt Alerts for New Heads of School. This is sage advice for establishing lasting positive change. But this advice should not be an excuse to ignore the hard work of understanding the challenges the school faces as well as the limitations that school culture and capabilities inevitably impose on planning. Pete Upham, Executive Director of The Association of Boarding Schools, argues that one of the most important jobs of a head is to define reality. Observing school culture, studying statistics, asking thought-provoking questions, probing potential opportunities, examining the school through the respective lenses of different constituencies, thinking like a customer- these exercises in data and perception gathering allow the head to develop and refine current reality as a precursor to strategic planning. It is the antidote to heads unthinkingly inflicting their values on the school or just as bad, imitating the school down the street. When there is a common understanding of current reality, vision and strategy can logically follow. 

It’s true that being a strategic leader is hard work. It requires evidence gathering, analysis, a commitment to deep learning, the courage to execute, self-reflection and more. It also requires training because there are so many conceptual pieces to the puzzle, and like all puzzles, the pieces fit in certain ways. Institutes like The Leadership Lab at
Greenwich Leadership Partners can be extremely helpful in teaching new heads how to think strategically in the context of their respective schools. In addition, mentoring with an experienced consultant can help a new head gain valuable insights that will set the stage for establishing a strong foundation for change.

So, heads, don’t lose sight of your role as strategic leader; resist the temptation to let those everyday problems define your headship. Play in the world of strategy. And go have some fun!