Maintaining a Strategic Lens Amidst the Time Pressures of a Pandemic School Year

Jonathan Weiss, Board Chair, Hillel Torah, Skokie, Illinois

This school year has been like none other, constantly grappling with new questions:


A confirmed COVID case in the first grade: Who’s been exposed and how long must the class quarantine?

New state guidelines have been released: Does this impact our travel policy?

A snowstorm is on the way: Can we proactively prepare for a digital learning day?

The in-school demands and protocols make staff communication more challenging: Is there a way to carve out additional meeting time for them?


Even in a typical year, it’s hard to balance the need for thinking strategically and longer term while in the throes of the day-to-day questions, twists and turns that come up at day schools. All the more so this year, when our time and energy are being stretched to the limit with myriad new questions.


At Hillel Torah, we’ve made it a point this year, when tackling the urgent issues, to also weigh the impact and progress our efforts will have on our bigger picture. For instance, when looking for ways to combat the challenge of remote staff communication, we decided to creatively carve out more dedicated professional development for teachers, solving a near-term need while also enabling teachers to grow and feel motivated during a challenging year. Similarly, even as the realities of quarantines precluding full in-person schooling nudged us to prioritize the technological innovation needed for digital learning now, it also led us to discuss how Zoom, digital assignments and a combination of asynchronous and real-time learning might play a role in the future of our school and the educational system at large.


Despite the demands on our time being daunting, it is our obligation, as members of the board and administration partnership, to carve out the time and focus on furthering our strategic thinking. In The Seven Habits of Highly Effective People, Steven Covey modeled his time management matrix as a 2-by-2 crossing of Urgency (tasks requiring immediate attention) with Importance (tasks with greater significance in achieving your goals). The most underserviced of quadrants—the Non-Urgent but Important ventures—runs the risk of getting squeezed even further amidst the pressures of the pandemic.


As such, here are a few proactive steps that helped us this year, for how to keep longer- term planning at the forefront during these hectic times.


Plan ahead. Create a workplan for your strategic endeavors, with clear guidelines about what you wish to accomplish by various points throughout the year. Avoid just “winging it.”


Schedule strategic sessions in advance. By placing meetings on the calendar in advance, you commit to having these discussions, rather than just “waiting for things to calm down” (which may never happen).


Trust your committees. Ensure committees meet regularly and feel empowered to make important decisions without layers of bureaucracy. Digital meetings tend to be more effective when limited to a smaller group of topic experts.


Effective meetings. Send agenda items and pre-read materials in advance, then manage your meeting to ensure all items get appropriate time, leaving space at the end to review and agree upon action steps. Following the session, send a timely recap about the decisions made and who is responsible for what moving forward.


Stay flexible. Inevitably, though, urgent items may sometimes end up needing precedence anyway. When this occurs, go ahead and press “pause.” But simultaneously adjust your workplan, reschedule your meetings and commit to carrying forward with your revised plan.

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HaYidion Leading Together
Leading Together
Spring 2021