Win Now, Win Later: What the 2017 Boston Celtics Can Teach Schools About Strategic Planning

Jimmy Kelley
Triple Threat Storytelling
3 min readMay 24, 2017
Photo by Eric Kilby/Graphic by Jimmy Kelley

When schools enter into the strategic planning process, the goal is to chart a course for the future of school that has both short- and long-term deliverables. The ultimate goal of a new building or increased endowment will take the length of the plan — somewhere between five and 10 years — to bear fruit, so in order to show progress in the early parts of a strategic plan campaign schools must put points on the board by placing emphasis on innovative programs or thinking about how current assets an be leveraged to move the program forward. Win now, then win later — just like the 2017 Boston Celtics.

The Celtics have, for the last few years, been in the unique position of competing in the NBA Playoffs while simultaneously owning picks at the top of the NBA Draft typically reserved for teams with the worst records in the league. Celtics President Danny Ainge has been able to play in both ends of the NBA sandbox thanks, in large part, to a 2013 trade that saw the Celtics send the backbone of the 2007–08 NBA Championship team to the Brooklyn Nets in exchange for assets that have continued to pay dividends today. By swapping a great deal of salary for low-cost young players and draft picks, the Celtics were able to build a new backbone for a roster that earned the №1 seed in the Eastern Conference and a spot in the Eastern Conference Finals.

What the Celtics have achieved is the aforementioned “Win now, then win later” strategy that many independent schools employ in strategic planning. By winning 53 games during the regular season and making a run in the NBA Playoffs, the Celtics have proven they are capable of achieving excellence in the present while the draft picks — including the №1 overall pick in this June’s NBA Draft — represent an eye towards and emphasis on a future that hopefully includes the franchise’s 18th NBA Championship.

Meanwhile, one independent school in the midst of a strategic plan has made great strides in interdisciplinary studies and experiential learning over the last two years while, at the same time, taking steps towards a significant overhaul of the physical plant. This school is “winning” now by expanding and deepening its academic program and will continue to “win” later when the new academic facility allows that program the space to grow and flourish.

The Boston Celtics’ 2017 season will likely come to an end later this week at the hands of LeBron James and the Cleveland Cavaliers. Now, four years into this “strategic plan”, fans are getting anxious to see the fruits of this plan while the team is young, financially flexible, and has assets that, if invested properly, could help the franchise make the jump to championship contenders.

This summer, “win later” officially becomes “win now.”

Navigating that transition is what reveals effective leadership behind the strategic planning process. Only time will tell if the Celtics have the leadership capable of delivering on the ultimate goal of winning an NBA Championship, but school leadership teams can look at the example the Celtics have set over the last four years and see that is possible to maintain excellence in the present without giving up the promise of the future.

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Jimmy Kelley
Triple Threat Storytelling

Storyteller, Coach, Advisor @TheRiversSchool, Springfield College ’13, Bancroft School ‘09