Office Ladies – "Second Drink: The Job Part 1" with Paul Lieberstein

Podcast Date: October 20, 2025
Hosts: Jenna Fischer & Angela Kinsey
Guest: Paul Lieberstein (Writer, Actor—Toby Flenderson)

Episode Overview

In this special "Second Drink" episode, Jenna and Angela welcome Paul Lieberstein, writer, showrunner, and the actor behind Toby Flenderson, to break down the pivotal season 3 finale of The Office, "The Job Part 1." The episode dives deep into the storylines, production process, and behind-the-scenes context of this major transition episode, with laughter, insights, and exclusive recollections from the set. With anecdotes from Paul, memories of casting decisions, deleted scenes, and thoughtful analysis of Jim and Pam’s emotional arcs, this episode uncovers the creative forces that shaped one of The Office’s most beloved finales.

Key Discussion Points & Insights

1. Episode Context & Superfan Edition

• The original broadcast of "The Job" was a special, hour-long episode (really 40 mins with commercials) that served as the season 3 finale (02:32).
• The "Superfan" edition, now available, runs over an hour and includes additional/deleted scenes, notably an extended cold open with Jim and Pam at the beach, restoring moments that illuminate Pam’s character evolution (03:02–04:14).

2. Restored and Deleted Scenes Highlighted

• Pam and Jim Beach Flashback: Originally intended as the cold open, this restored scene shows a "new, direct" Pam communicating unapologetically (04:14).

  • Quote:
    Pam (Jenna): "You know what's interesting? I don't feel embarrassed at all. I just feel good. Good. If you don't have anything to say, you don't have to say anything—or I take that back. You have to say something." (04:26)
  • Dave Rogers (editor) calls this one of his favorite moments, synonymous with the “creative freedom” of the show’s docu-style editing (05:28).

• Dwight Interviews Andy: The Superfan cut restores a long, hilarious sequence of Dwight grilling Andy to be his number two, featuring wild questions and on-the-fly writer jokes (07:24).

  • Sample Q&A:
    • Dwight: "What is 879 times 413.7?"
    • Andy: "2401.647, repeating."
    • ...
    • Dwight: "What is the Dharma Initiative?"
    • Andy: "It is the source of all energy on this planet. It is a corporation formed by aliens." (07:24–08:23)

3. Jim, Pam, and Karen: Relationship Dynamics

• Listener letter explores Jim's emotional detachment from Karen and hints on how the cracks in their relationship become clear during the finale (08:45).
  • Quote:
    Jenna: "...when I rewatched this episode... They are just, like—they are not a match. It was so clear to me when I rewatched this episode." (09:58)

4. Paul Lieberstein: Becoming Toby & The Writer-Actor Experiment

On How He Became Toby

• Greg Daniels intentionally blurred the writer/actor divide, giving small roles to writers so they could inform their scripts from an acting perspective (16:09–17:50).
• Paul was cast rather casually:
  • Paul: "I left the [writers'] room and I came back and they said, 'You're going to play this part.' And it was one line in Diversity Day…" (16:51)

Early Table Reads & Unexpected Longevity

• At first, Toby was not meant to recur; he was cast to deliver one line and get kicked out by Michael (18:47, 19:15).
• The organic and very funny interaction between Paul’s deadpan and Steve Carell’s antagonism helped the character stick.

“Acting School” for Writers

• Paul shares how logistical acting tips (like moving water bottles for continuity) became his earliest acting lessons (20:09).
• Brian Baumgartner helped him “break through” by explaining practical acting adjustments for sound—enlightening Paul on what actors must do to stay “real” on camera (21:05).
  • Quote:
    Paul: “They have to justify anything that needs to be done and make it feel real.” (21:54)

Impact on Show’s Culture

• The blending of writers and cast fostered creative trust and gave The Office its unique collaborative energy (22:05–22:55).

5. The Writing and Production of "The Job"

• Paul and Mike Schur co-wrote the episode, collaborating closely and dividing scenes between themselves and small writer groups (23:14–24:45).
• The process was flexible: sometimes a sole vision, often highly collaborative, always dialogue-driven (24:45).

Storylines Origin & Jan’s “Boob Job”

• The "Jan gets a boob job" idea lived on a card in the writers' room for months, waiting for the right moment (25:26).
  • Jan’s spiral into self-destruction was discovered during her solo talking head in “Cocktails,” clarifying her future narrative arc (25:49).
  • Paul: “Once we got that, this was like a stage in her spiral.” (26:00)
• Melora and Steve’s chemistry in Jan and Michael’s scenes was repeatedly praised (26:17–26:57).

Iconic Running Gags:

• Creed Thoughts Blog: Mike Schur wrote the "Creed thoughts" talking head; Jason Kessler, the show’s writer’s assistant, ran the associated NBC.com blog in Creed's voice (27:11).
• Schrute Bucks: Likely credited to Justin Spitzer, these "currency" props proliferated around set and inspired a deleted subplot about Creed trying to “flood the market” (27:49–28:44).

Fan-Favorite Writing

• Paul loved writing for Creed, Kevin, Michael (“His voice is just so clear in my head”), but found every character fun and inspiring in their own ways (29:36–30:17).

Favorite Moments

• • Paul: "I really laughed out loud when [Michael says to Hunter about Jan], 'Tell her I want to squeeze them. She'll know what I mean.'" (30:27)
  • He also loved the framing and tension of Jan’s firing, David Wallace’s strength, and Michael hiding behind the doorframe—a masterclass in balancing awkwardness and character truth (30:56).

6. Inside Writer Motivations: Ryan, Karen, and Corporate

• Fans ask: Why did Ryan, not Karen, get the corporate job—Ryan didn’t meet the sales experience requirement?
  • Paul: The real-life reason was to shake up character dynamics by putting Ryan (B.J. Novak) in charge; he’s a “good bullshitter but incompetent,” making for rich story potential (32:37).
  • It also opened doors for Jim/Pam storylines and fun status reversals between Michael and Ryan (33:40).

Abandoned Card: The Lost Double Date Episode

• A “double date” card sat on the writers’ wall for years (Jim+Pam & Dwight+Angela), but was never produced.
  • Jenna: “It haunts me.” (34:38)

Additional Behind-the-Scenes Stories

The Writer-Actor Bond

• Angela and Jenna reflect on the culture crafted on The Office, where actors frequented the writers’ room, fostering an atmosphere of safety, collaboration, and trust uncharacteristic of most TV sets (22:55).

Character Ownership by Writers

• Some writers had favorite characters—Mike Schur enjoyed “Angela Martin falling apart,” Justin Spitzer championed “Dwight stuff,” and the team routinely redistributed storylines so all writers had “their” moments (29:17–29:41).

Memorable Quotes & Moments (with Timestamps)

• Jenna Fischer: "Pam just says, ‘Jim was nice, told me that he missed our friendship too.’ And then they kind of hug and walk off... Even the way it was in the original broadcast really illuminated the creative freedom that the documentary filmmakers have when they are deciding what they want to show and when." (05:27)
• Paul Lieberstein (on acting): "Imagine going into acting knowing nothing about acting, and the first thing you're being taught is take your water bottle off your desk and put it underneath your desk… It was like, things like that that made up my acting school." (20:11)
• Angela Kinsey: "It was so fun to have you guys on set. It’s hard for me to imagine other shows now without that creative collaboration and that feeling of safety and trust." (22:55)
• Paul Lieberstein (on Jan’s storyline): "Once we got that, this was like a stage in her spiral." (26:09)
• Paul Lieberstein (on favorite moment): "I really laughed out loud when Hunter... Tell her I want to squeeze them. She'll know what I mean." (30:27)
• Jenna Fischer (on Ryan’s promotion): "It’s almost Shakespearean, you know, it’s like Michael thinks of himself as the king and this like lowly peasant just went right past him." (33:59)

Notable Timestamps for Key Topics

• Pam & Jim Beach Scene Superfan Flashback: 03:44–05:27
• Extra Andy/Dwight Interview Questions: 07:09–08:23
• Listener Letter on Jim/Karen/Pam: 08:44–09:55
• Paul Lieberstein’s Interview Begins: 14:28
• On the Writer-Actor Experiment: 16:09–21:54
• Writing The Job with Mike Schur: 23:05–24:45
• Jan’s Augmentation Storyline: 25:26–26:09
• Schrute Bucks & Creed Thoughts Blog: 27:11–28:44
• Fan Question: Why Ryan, Not Karen?: 32:22–33:40
• Unmade Jim/Dwight & Angela/Pam Double Date: 34:38–35:41

The Show’s Emotional Arc and Thematic Takeaways

• The episode is about transition: leadership at Dunder Mifflin, relationship crossroads, personal metamorphosis.
• Pam’s new confidence and Anna Karenina "all or nothing" honesty is both cringe-inducing and cathartic.
• The series’ docu-style editing, as discussed by Dave Rogers, is a creative playground that shapes both character and audience perception.

Final Thoughts

The "Second Drink" edition delivers everything an Office fan craves: inside jokes, honest reflections on character and craft, and the loving, comedic chemistry of the cast and crew. Paul’s guest spot is a highlight, revealing the calculated chaos and happy accidents that made The Office an enduring classic.

Next Week:
The breakdown continues with "The Job Part 2": all the drama in New York, Dwight as regional manager, Pam’s secret new role, and more exclusive stories.

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