Paul Lieberstein reflects on the beloved role of Toby Flenderson, 20 years after ‘The Office’ premiered

The Office turns 20 on Mar. 25, so obviously we wanted to celebrate with Paul Lieberstein, who was not only a writer and showrunner on the sitcom, but played Toby Flenderson, the hated, yet beloved, HR head at Dunder Mifflin, Scranton.

In a recent interview with HR Brew, he reflected on his character and the connection he’s built with the HR community, thanks, in part, to the show's millions of fans.

Before The Office. Lieberstein didn’t originally set out to be a television writer, but he always loved comedy.

“That’s not one of the jobs that is presented to you in Connecticut,” he told HR Brew. “So I kind of acted as if it was never really a possibility.”

Lieberstein earned an economics degree from Hamilton College in Central NY before a brief stint as an auditor in corporate America. During that time, he didn’t have many interactions with the function with which he’d someday become synonymous.

“I had an interview and an exit interview, and paperwork to fill out and maybe a seminar, [but] that was it for my formal HR experience,” Lieberstein told HR Brew.

As it turned out, corporate life wasn’t the right fit for Lieberstein, who found his work “unfulfilling.” He decided to pursue his passion and moved to Los Angeles to pursue television writing. He wasn’t an overnight success, but before long, his talent and new connections landed him a job writing for the ’90s sitcom Weird Science.

Toby as a stop-gap. After writing for comedies like Clarissa Explains it All and King of the Hill, he got a gig writing for a show that would eventually become the American version of The Office. But the character he would end up playing came about later, and almost by accident.

“I had one line and it wasn’t supposed to be anything more than that...It wasn’t [until] after a while that we called it ‘HR.’”

That one line was in Season 1, Episode 2, “Diversity Day.”

“Hey, we’re not all going to sit in a circle Indian style, are we?” he remarked, setting the tone for the character who would become Toby Flenderson as the Dunder Mifflin staff walked into a conference room for diversity training.

Lieberstein had never acted, but he said the creators knew he was Toby after watching his delivery.

But it might’ve been Michael Scott, regional manager, played by Steve Carrell, who, in Season 2, Episode 2, “Sexual Harassment,” summed up his character best: “Toby is in HR, which technically means he works for corporate, so he’s not really a part of our family. Also, he’s divorced, so he's really not a part of his family.” Michael and Toby’s relationship was characterized by a feud lasting seven of the show’s nine seasons. But without Toby, there might not have been a Michael.

“It became clear that [Dunder Mifflin] wanted Michael to work there, and HR was just a means of allowing that to happen,” Lieberstein said. He compared Toby to a tattle phone that a teacher might put in their classroom so students can gripe about each other. The catch, at Dunder Mifflin, was that the phone didn’t really do anything. “That's what Toby was, in a way; just a tattle telephone that people could come and complain about Michael, or feel like complaints were registered.”

Lieberstein went on to have many more memorable moments as Toby, from getting hurt on the first day of his new, laid-back life in Costa Rica (Season 5) to (awkwardly) celebrating Movember (Season 9). Fans identified with his endless search for connection and validation—which his coworkers almost never gave—and belly-laughed at scenes of Michael bullying Toby for simply existing, as the battle between boss and HR took center stage.

Lieberstein also wrote some of the show’s most cringeworthy episodes, including “The Client” (Season 2), “Money” (Season 4), “Gossip” (Season 6), and “Sex Ed” (Season 7).

Standing the test of time. In “Diversity Day,” a sensitivity trainer, played by Larry Willmore, is brought into the office after Michael is reported to HR for his offensive Chris Rock impersonation. Michael quickly takes over the meeting, using traditionally sexist and racist stereotypes.

Even two decades later, this episode feels particularly timely, Lieberstein acknowledged, given the current climate around DEI initiatives.

“I don’t think we knew we were doing something poignant or prescient at all,” Lieberstein said, later adding, “I haven’t seen that episode in a while, but it does feel like that would be impossible to do today.”

Lieberstein feels differently about HR now than he did during those early days of The Office, when he and the show’s other writers were making up jokes between NBC-mandated HR seminars.

“I have a special connection to those fans who come up to me and say they’re in HR,” he said. “Certainly Toby had no power at all, even though Michael thought he did, so, I have a kinship for what they [HR leaders] are going through.”

The Office has gained a new generation of fans since it went off the air after nine seasons in 2013—especially during the Covid-19 pandemic, when it was still available to stream on Netflix—and remains one of the most beloved comedies of all time, that fans repeatedly rewatch. But Lieberstein hadn’t rewatched the show until a couple of months ago.

“I’ve been watching with [my son], and it’s been kind of fascinating. What feels good, what feels honest, what doesn’t feel old or dated,” he said. What feels the same, however, is how he feels about the experience of working on the show. “It was just a remarkable experience that I can’t believe I got to do. I don’t think there’s anything else that comes close to it, bringing that kind of group of talented people together,” he said.

Toby today. While fans of the show may still be wondering if Toby is the Scranton Strangler, we wanted to know what he would’ve thought of HR today. Take AI, for example.

“I think he would be all for it. He would probably be disappointed that his company won’t pay for it,” Lieberstein said. “I think the fact that so much of what he did could be done by a computer would make him feel a bit useless.”

And that sentiment may, in part, be how the world got one of Toby’s most famous lines.

“HR is a joke. I can’t do anything about anything.”