A native New Yorker, Bolman was born in Brooklyn to parents who were products of Peoria, Illinois. Geographic alternation between the East Coast and Midwest was a regular theme early in his life - he lived in eight towns and five different states before heading to New Haven, Connecticut to attend Yale University.

After earning a B.A. in History, Bolman spent a year at Yale Law School working for the Yale Law Journal and a venerable Boston law firm. However, law was not his passion, and he opted to teach. Having taken a course in organizational behavior as a senior in college, Bolman decided to earn his Ph.D., at his Alma mater, in a newly developed organizational behavior program. After earning his degree, Bolman taught at the business school at Carnegie-Mellon University for five years before relocating to Boston and the Harvard Graduate School of Education, where he taught for more than 20 years. It was at Harvard where he met his long-time writing partner, Terrence Deal.

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