Throughout the 1950s and 60s, Sherman spent his life in Hyde Park, Massachusetts, the southernmost neighborhood in Boston.

His extended family members, who lived nearby, were devout Green Bay Packers fans and have dutifully followed Sherman's career.

Sherman was also raised in Northborough, Massachusetts, where he attended Algonquin Regional High School, playing for the football team.

Right after college, Sherman became an English teacher and an assistant football coach, serving at Stamford High School in Connecticut in 1978 and at Worcester Academy in Massachusetts from 1979 to 1980.

Sherman has been married to his wife Karen since 1982, and the couple have five children together (Sarah, Emily, Matthew, Benjamin and Selena).

Sherman is the father-in-law of Cincinnati Bengals head coach Zac Taylor, who is married to his oldest daughter.

A former reading and special education teacher, Karen is a very active member of the West Dennis Library Board of Trustees.

Sherman started his college coaching career as a graduate assistant at the University of Pittsburgh, where he was part of Jackie Sherrill's staff from 1981 to 1982.

In 1994, Sherman left Texas A&M to coach the UCLA offensive line, which included former Baltimore Ravens pro bowler Jonathan Ogden.

Additionally, he recruited Leeland McElroy, who would become one of the Aggies' top 10 all-time leading running backs.

[6] On December 20, 1996, A&M head coach R. C. Slocum promoted Sherman to offensive coordinator to replace dismissed Steve Ensminger.

Additionally, Green Bay and the Philadelphia Eagles were the only two teams to make the playoffs for four consecutive seasons from 2001 to 2004.

An offensive-minded coach, Sherman led the Packers to break franchise records for rushing in 2003 and passing in 2004.

In 2003, Packers quarterback Brett Favre led the NFL in touchdown passes, in addition to setting a franchise record for rushing yardage.

The Packers had lost pro bowlers Javon Walker, Bubba Franks and Ahman Green to injured reserve early in the season.

[21] In 2011, the Aggies began as a top 10 ranked team, but fell out of the polls after losing four games, three of which had double-digit half-time leads.

Five days later, on November 24, 2011, they would lose at home to the University of Texas 27–25 on a last-second field goal, in what would likely be the last game of the rivalry.