The Bert Show: Vault - How Do You Tell Your Employee to Go Out More?

Episode Date: March 26, 2026
Featured Hosts: Aaron (Host), Bert (Co-host), Melissa (Co-host), and multiple callers

Episode Overview

In this lively episode, The Bert Show tackles a highly unusual workplace dilemma: a boss calls in seeking advice on how to address a drastic change in an employee’s performance—an employee who used to be high-performing while living a party lifestyle, but whose work has declined significantly since giving up partying. The hosts and callers debate the ethics, legality, and practicality of wanting your employee to "go out more," diving into the workplace dynamics, personal well-being, and the fine (and sometimes hilarious) lines between professional concern and personal choices.

Key Discussion Points and Insights

1. The Dilemma: Performance Declines With Sobriety

• Scenario:
  • The boss explains (02:01) that her star employee—always reliable, fun, and productive—has decided to stop partying for personal and relationship reasons.
  • Since then, he’s become late, grumpy, less productive, and less enjoyable to work with:

    "He's awful now. He's not fun to be around... People don't want to be around him. He's slow with getting stuff done. It's awful. It's a nightmare." (Caller/Boss, 02:18)

2. The Team Reacts: Ethics and HR Quandaries

• The hosts grapple with whether it's even legal or ethical to desire an employee resume "unhealthy" behaviors for company benefit:
  • “Basically what you're saying, as the boss, is I wanna do what's unhealthy for my employees for the good of the company.” (Aaron, 01:29)
• They consider approaching it through job performance rather than lifestyle:
  • “You have to start the conversation… and say, what's different? Why you didn't used to be this way?” (Bert, 04:01)

3. Approaching the Conversation

• Hosts suggest a tactful approach, focusing on observable changes:
  • “As a boss, you can only point out to him as a boss, what he's doing wrong at work… then, I think ask the question, what's different? Because you've never done this before.” (Bert, 09:39)
• The show rejects any suggestion of directly advising unhealthy habits.

4. Was It About the Girlfriend?

• A caller suggests the girlfriend might be the source of stress, but the boss clarifies it’s the same girlfriend; the lifestyle change is the only new factor (05:29–05:45).

5. Living Vicariously?

• Another caller speculates the boss just misses living vicariously through the employee’s stories:
  • “I want to say that I think she needs to get a life. Her life is boring. And she was living vicariously through him because when he was partying, she was like, oh, he comes in late, but we know he has long weekends. But not in his lifestyle exchange.” (Deborah, 06:35)
• The boss pushes back, insisting the real problem is performance, not her own sense of fun (06:57).

6. Could It Be Depression?

• The possibility that the employee is unhappy or even clinically depressed after making a major lifestyle change is raised:
  • “He’s just clinically depressed. I mean, I think he probably needs, like, serious help, like Prozac or something.” (Deborah, 10:03)

7. The Consensus: Guide, Don’t Dictate

• The team universally agrees that suggesting a return to partying is out of bounds, but guiding the employee to reflect on why their performance has changed is responsible management:
  • “Good managers and good leaders don't dictate what you do, but they ask you questions that sort of lead you into exactly the point that they're trying to make.” (Aaron, 09:19)
  • “Any boss that would even think or suggest that an employee harm themselves in order to improve the company's bottom line… you need to take a hard look at yourself, too.” (Melissa, 11:01)

8. The Show’s Signature Humor

• The hosts and callers keep things light with running gags about office bars, Jager Bombs, and margarita parties:
  • “Invite him into your office and have a couple beers on the desk. Let's do a Jager Bomb.” (Melissa, 04:16)
  • "Have an office party. Like, have an office party... Some margaritas and Mexican food and just make it all office." (Guest/Caller, 06:17–06:23)
• The conversation pokes fun at improbable solutions, ultimately underscoring the seriousness of workplace health.

Notable Quotes & Memorable Moments

• On the Spirit of the Problem:
  “He was more likable with his wild stories, but… now he's late, now his job performance is bad, and now he's grumpy around people.”
  (Caller/Boss, 07:31)

• On Management Tactics:
  “Maybe just ask, well, why, when you were partying, were you more reliable than when you’re not... Is something else going on that I need to know about?”
  (Bert, 04:41)

• On Drawing the Line:
  “Any boss that would even think or suggest that an employee harm themselves in order to improve the company's bottom line... I think you need to take a hard look at yourself, too.”
  (Melissa, 11:01)

• Injecting Humor:
  “Full serve bar in the lobby.”
  (Aaron, 06:30)

• On Perspective:
  “You have lost your employee, even though he's still in the office.”
  (Aaron, 07:46)

Timestamps for Important Segments

• 00:45 – Call-in begins; dilemma introduced
• 02:01 – Boss describes dramatic change in employee’s work and attitude
• 03:44 – Host raises HR and legal questions about discussing personal habits
• 04:01–04:41 – Advice: Focus on job performance, ask guiding questions
• 05:29–05:45 – Discussion of the girlfriend’s possible role
• 06:35–06:57 – Debate: living vicariously or real performance concern?
• 08:18–08:58 – Caller relates similar real-life scenario post-lifestyle change
• 10:01–10:14 – Caller suggests potential depression; shift to seriousness
• 11:00–11:13 – Final consensus: never cross the line into suggesting self-harm or unhealthy habits

Takeaways

• Work performance and personal habits can sometimes be intertwined, but it's never appropriate for a manager to encourage unhealthy behavior.
• Good managers focus on observable changes and create space for employees to self-reflect, rather than dictating their personal lives.
• Sometimes, dramatic lifestyle changes lead to unexpected workplace challenges; empathy and honest dialogue are key.
• The Bert Show uses humor to address a tricky topic, but ultimately lands on responsibility and workplace well-being.