The Fast Track to Strategic Leadership

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Type: Article

Topics: Leadership Development, School Administrator Magazine

August 01, 2026

Appears in August 2026: School Administrator

Addressing key questions that force us to clarify what we鈥檙e trying to accomplish, why it matters and how to pursue it for impact

Smart questions are the superpower of successful leaders. My fascination with questions began during my decade in the Boston Public Schools, where I served as assistant superintendent of teaching and learning. Over the past 20 years, working with superintendents and leading the Aspen Institute鈥檚 Urban Superintendents Network, I鈥檝e seen the same pattern again and again: leaders doing too many things without enough purpose and strategy.

The pace of school systems is relentless. With issues constantly demanding attention, educators often move from one urgent matter to the next with their heads down. In that environment, it鈥檚 easy to react rather than reflect, to keep moving without pausing to gain perspective or think strategically. Yet the better system leaders become at critical and strategic thinking, the more likely their systems are to help students develop those same skills.

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Author

Rachel E. Curtis

Leadership and strategy consultant and executive coach

Boston, Mass.

Building Others鈥� Strategic Leadership Capacity

One of the most important roles of a school system leader is to build the capacity of the people around you. The four questions described in the accompanying article strengthen others鈥� strategic leadership by helping them explore complex work in a simple, manageable way. That, in turn, builds organizational capacity.

Make the questions part of everyday practice through these means.

Use them with direct reports. Ask leaders to apply the questions to the high-priority initiatives they lead. Focus one-on-one meetings on the questions that feel most important or hardest to answer. Listen closely and stay curious.

Model them publicly. Use the questions in school board meetings, leadership team meetings and principal meetings. Be explicit about why they matter. Share what you鈥檙e learning as you apply them to your own work, including what has been challenging.

Make them a system habit. Use the questions to guide leadership discussions and decision-making across the district and in schools. Encourage teams to use them when reflecting on and presenting their work. Notice and celebrate principals who adopt them to use with their leadership teams. Track progress in the use of the questions.

Supporting Tools

Two online resources (available at) expand on the four questions and help individuals and teams strengthen their strategic leadership.

Individual self-assessment: a short (5-7 minutes) reflection that highlights strategic leadership strengths and areas for growth. It can be completed individually, with peers or with a team. Sharing results and insights with colleagues builds new learning, trust and a culture of continuous improvement.

Team assessment: a tool that helps teams examine how strategically they operate. Three levels of assessment (think 101, 201, 301) provide entry points and opportunities for continued development for any team.

鈥� Rachel Curtis

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