Brad Stevens discusses the biggest challenge he faced in transitioning to a front office role.

Brad Stevens served as the head coach of the Boston Celtics for eight seasons, from the 2013-14 season through the 2020-21 campaign. During that time, he led the Celtics to seven playoff appearances and three appearances in the Eastern Conference Finals.

However, while the Celtics consistently made deep runs in the playoffs under Stevens, Boston was never able to get over the hump and win a title with the 47-year-old leading the team from the sidelines.

But that all changed when Stevens’ role with the Celtics switched from being the squad’s head coach to its president of basketball operations ahead of the 2021-22 season. He replaced Danny Ainge, who stepped down from the position after nearly two decades.

In his three seasons in his current role, the franchise has won one title and reached the NBA Finals twice.

But despite all the success that the Celtics have enjoyed with Stevens as the team’s president of basketball operations, he admitted that the job isn’t without its challenges. More specifically, he cited his biggest challenge in making the jump from a head coach to an executive.

“The front office has been so solid and been there a while, and we’ve all been there together,” Stevens told the Boston Globe’s Adam Himmelsbach. “So that’s really helped. The things I’m not as good at, we have so many people that are really good at. So it’s been a really fun place to be, a fun place to work. I’ve been thrilled to watch some of our coaches get opportunities elsewhere and been thrilled for our team and our coaches and front office that have put in so much time to get to taste a championship run this year.

“But it never stops. People ask me what the difference is. When you’re a coach you’re on an eight-month sprint and you’re in charge of leading the team or navigating the team and then you’re in charge of your staff. In this job it’s much more of a 12-month job with the cadence of the entire basketball operations. The roster building is such a small part of it that I probably would have underestimated that. I’d say it’s 10 percent of the job, if that, and that’s all anybody talks about.”

Stevens was named the 2023-24 Executive of the Year after Boston finished the regular season with the best record in the NBA at 64-18. In the 2023 offseason, Stevens orchestrated trades that landed Boston Kristaps Porzingis and Jrue Holiday.