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EP 83 Judgement Day

The Bad Boss Brief Podcast · 2026-06-03 · 31 min

0:00--:--

Key moments - from our scoring

Substance score

27 / 100

Five dimensions, 20 points each

Insight Density6 / 20
Originality6 / 20
Guest Caliber4 / 20
Specificity & Evidence5 / 20
Conversational Craft6 / 20

Judgment has become culturally stigmatized, but hosts Stephanie Pirillo and Eugene S. Robinson argue it's essential for protecting yourself and making sound decisions in work and personal relationships. They distinguish between fair judgment based on observable behavior and unfair prejudice, exploring how judgment relates to forgiveness, boundaries, and professional boundaries. The conversation challenges the narrative that judgment is spiritually or morally wrong - what they call 'spiritual gaslighting' - particularly as it affects women in power imbalances. They examine how bad judgment cascades through organizations not because it's contagious but because dissenting voices are suppressed by fear of retaliation, using examples from their experience at Ozy Media and discussing how to assess others' judgment as a hiring or dating criterion. This episode will resonate with leaders, HR professionals, and anyone navigating toxic workplace dynamics or relationship red flags.

Key takeaways

  • →Good judgment is a necessary life skill, not a character flaw, and should be used to set boundaries and make decisions about relationships and professional engagements.
  • →The cultural narrative against judgment often prevents people from challenging bad decisions in leadership, allowing poor judgment to cascade through organizations unopposed rather than spread.
  • →Assessing whether people around you - colleagues, partners, potential employers - demonstrate good or bad judgment is a critical filter for decisions about trust and commitment.
  • →When facing workplace conflict over texting concerns to coworkers, the effective approach is to reframe the conversation around the legitimate business problem rather than defending the communication method.
  • →Forgiveness does not require continuing engagement or exposure to someone's harmful behavior; you can forgive someone while maintaining firm boundaries against future interaction.

In this episode

  1. 1The Nature and Value of Judgment
  2. 2Judgment vs. Forgiveness in Relationships
  3. 3Real-World Examples: Ozy and Carlos Watson
  4. 4Assessing Good Judgment in Others
  5. 5Bad Judgment and Workplace Culture
  6. 6Fire Me Now: Texting About Your Boss

Mentioned

Stephanie PirilloEugene S. RobinsonBill BurrCarlos WatsonClaire KeeganDan SavageFacebookOzyBerlin Zoo

Guests

Eugene S. Robinson

Topics in this episode

Ozy MediaCarlos WatsonCouples TherapySpiritual gaslightingDan SavageClaire KeeganClockwork OrangeFacebook hiring processHR escalation procedures

Questions this episode answers

What's the difference between judgment and forgiveness according to this episode?

Forgiveness means letting go of emotional attachment to wrongs done to you and can include compassion, but it doesn't require staying in contact with or trusting someone again. You can forgive someone while still acknowledging who they are and maintaining firm boundaries, like not letting them drive your grandchildren.

How does bad judgment spread in workplace cultures?

Bad judgment doesn't spread because it's contagious, but because employees learn not to challenge it due to fear of retaliation or knowing they won't be heard. When leaders make poor decisions unopposed, those decisions cascade unchecked through the organization, not because others lost their judgment but because speaking up became unsafe.

What should you do if your boss confronts you about complaining in a text to a coworker?

Walk in with the legitimate concerns you raised rather than defending yourself for venting. Frame it as protecting the company's interests, acknowledge you should have come directly to the boss, and propose new ways of working together going forward.

What signs of bad judgment should disqualify someone from hiring or dating?

Bad judgment in hiring includes lengthy interview processes (16+ rounds), asking candidates to do free work, or general poor decision-making. In dating, examples include sending unsolicited explicit photos or other behaviors showing lack of consideration for the other person's perspective.

Is it okay to judge people based on their past behavior?

Yes - people generally don't change much after adulthood, so past behavior is a reliable indicator of future actions. The hosts argue using judgment to assess how you want to interact with someone and what boundaries to set is mature and self-protective.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

6 / 20

The episode is mostly personal anecdote and philosophical meandering about judgment as a concept. The one genuinely substantive B2B observation - that bad leadership decisions cascade because dissent is culturally suppressed, not because judgment is contagious - is quickly abandoned, and the 'fire me' scenario offers surface-level advice. Filler and tangents dominate the runtime.

I think the problem to solve is that people are not listening to dissension. Usually I have seen many, many, many circumstances where there is a bad judgment by someone in leadership... the bad judgment is unopposed for cultural reasons. It doesn't spread.
I would go for brazen. I would brazen it out and say... do you want to talk about the concerns that I raised in the email? I mean, in the text exchange?

Originality

6 / 20

The reframe of forgiveness as emotional detachment rather than restored trust is mildly interesting, and the point about dissent-suppression vs. judgment-contagion is a small step beyond the obvious. Otherwise, the takes - past behaviour predicts future behaviour, bad bosses create bad cultures - are thoroughly recycled.

forgiveness is letting go of my emotional attachment to wrongs done me by another person... You can forgive somebody and still acknowledge fully who they are.
she gave me a second chance, but there was no coming back from that

Guest Caliber

4 / 20

There are no guests - this is a two-host format. One host is an executive coach, the other a writer and former Ozy employee. Neither is a senior B2B operator or practitioner who has run a company or function at scale, and the conversation reflects that; it stays at the level of personal philosophy and anecdote rather than operational experience.

I'm the executive coach
I worked in Silicon Valley since 19, like 85

Specificity & Evidence

5 / 20

Named references exist - Carlos Watson, Ozy Media, Facebook's interview process, Dan Savage - but these are illustrative anecdotes with zero data, metrics, timelines, or dollar figures. The 'fire me' scenario is concrete in setup but the advice stays vague. No numbers of any kind appear in a B2B-relevant context.

Convicted felon Carlos Watson
I went through nine at Facebook, and I think it got to 16 before they finally figured out, I think you're too senior for this job.

Conversational Craft

6 / 20

The hosts have genuine chemistry and the 'fire me' segment shows some structure, but questions are broad and leading, claims go entirely unchallenged, and tangents (painkillers, polar bear enclosure, Irish short stories) are indulged rather than redirected. There is no productive disagreement or probing follow-up on any substantive claim.

Do you think that bad judgment is contagious in a professional setting? Like a snowball?
Hold on. Do you think that bad judgment is contagious in a professional setting?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Stephanie Pirillohost59%
  • Eugene S. Robinsonguest41%

Most-used words

judgment51boss12judging12wrong9different9problem9relationship9saying8didn8conversation7ways7fire7carlos7forgiveness7back7somebody6

Episode notes

In this episode of The Bad Boss Brief, we discuss: - how judgement can help you set good boundaries - can judgement and forgiveness co-exist - why you want your bosses and partners to have good judgement and more And, no, we’re not choosing topics based on Eugene’s tattoos but if the shoe fits... Watch, listen, share with your friends! As always, send us show ideas, comments or thoughts to wtf@badbossbrief.com . This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit badbossbrief.substack.com/subscribe

Full transcript

31 min

Transcribed and scored by The B2B Podcast Index.

Stephanie Pirillo: Foreign. Welcome to the Bad Boss Brief. I am Stephanie Pirillo.

Eugene S. Robinson: I'm, um, Eugene S. Robinson.

Stephanie Pirillo: And we are at episode 83, and we are calling this one Judgment Day.

Eugene S. Robinson: I'm actually, I think, the only one in this conversation that has that word tattooed on their body. Judgment. And, uh, there's a. There's some kind of confusion with it because, as you know, or maybe not, there are two ways to spell judgment.

Stephanie Pirillo: Which way do you spell it with the E in the middle or not?

Eugene S. Robinson: Well, you know, that's sad. I have to look, um. With the e in the middle. Yes.

Stephanie Pirillo: Okay. So just so you know, because I looked it up when I was writing this. Um, it is. Either way is correct.

Eugene S. Robinson: Yes.

Stephanie Pirillo: One is a little more American. One is a little more British. I think the more British one has

Eugene S. Robinson: the E. Yes, I went for traditional.

Stephanie Pirillo: Yeah, exactly. So we are talking about Judgment Day, and it is up to your judgment as to whether you use the middle E or not. But what we wanted to talk about today is the notion of judgment. I feel like there is a very strong cultural message against judgment, that it is bad to judge another person. It is unkind. It is not progressive. It is, you know, not spiritual. There's, like, all this judgment about judgment, and I thought it would be interesting to talk about. So just to start out with, do you think judgment is bad?

Eugene S. Robinson: No, no, no. I'm a New Yorker. I spent the grip. I remember one point, my kids said something to me about judgment. That's my role. I'm m. A. I'm a semiotician. I applied meaning. I'm. I'm judging every single. That is a pejorative sense where you're. Well, what the assumption is. What you're saying is I'm unfairly judging somebody. But it's rare that, you know, I'm unfair. I remember getting to a screaming argument with an ex, and she goes, well, she just said something really asinine, and this is an ex that, you know. And she said, well, that's just my opinion. I go, opinions can be wrong. You know, I could be of the opinion that that oxygen is fire. It's not, you know, so, um, no, I'm perfectly happy and comfortable in my judginess. And. And it works both ways. I'm, you know, if you see me coming and based on something other than maybe the color of my skin, you know, tone, timbre, you know, cut of my jib, choose. You don't like me. I can understand that completely. I'm sure I'm giving off signs One, nature's warning signs, they're to be used. They're there for a reason. I'm okay with judgment.

Stephanie Pirillo: Yeah. And I, so that's what I wanted to talk about is where is it appropriate? Where are kind of the risky areas? You know, is it different at work or at home? Personally? And the things that I think are important about judgment, I think there's a couple of things. So one is I believe that there is right and there is wrong and there's. Obviously there's circumstances where there's gray areas, but generally there's a right and there's a wrong and I think it's useful to name it. And so judgment to me also is. It has an ethical framework. Right. So if I am judging whether or not a kind of behavior is ethical. Wait, why are you laughing?

Eugene S. Robinson: Because I once said to a friend he had some extra painkillers left over from surgery, they'll give him to me. He goes, what do you need them for? I go, I'm a 47 year old MMA fighter. That's what I need him for. He goes, uh, no. I go, well, you have an ethical problem with this? He goes, yes. I go, funny. I don't have any friends with ethics. And I didn't talk to him for like a year after that. I was so irked. You know, I'm not going to get addicted to four tablets. But anyway, sorry to interrupt, but I

Stephanie Pirillo: would also say I'm sorry, I have lots of ethics.

Eugene S. Robinson: Okay, you have lots of ethical friends. Oh, you have lots of ethics.

Stephanie Pirillo: I have both.

Eugene S. Robinson: If you had four tablets and I asked you for, would you give them to me? You know, answer carefully.

Stephanie Pirillo: That's a good question. I don't,

Eugene S. Robinson: I've never had a problem with addiction. Never, Never.

Stephanie Pirillo: I know, and I'm aware of that. And I think if it was a question of like giving them to you or throwing them in the trash, I would probably give them to you because you don't have a problem with addiction and otherwise they just go in the trash. And I do have a problem with addiction, so I don't want them in my house.

Eugene S. Robinson: Yes, correct. So, yeah, and I wouldn't offer them to you. Precisely. That's good ethical behavior. Just saying no, because I might possibly. That's not good ethical behavior. That's just kind of granny stating, I don't know, but whatever.

Stephanie Pirillo: You're judging his judgment.

Eugene S. Robinson: I'm judging his judgment. But we are still friends. So it's fine. That's fine. I got, I got over.

Stephanie Pirillo: But I think that the Idea. Because one of the things that's frustrating to me is I feel like the, uh, the concern people have about not appearing to be judgmental caused them to over index on excuses. Well, she had a tough childhood. He, you know, didn't realize that there would be repercussions down the road and that, you know, some things are just wrong. Right? They're just wrong. And I don't think we need to continue to have discussions about them. And I think we get to make decisions about who we want to interact with based on our judgment of their choices. Because that's where I really feel like the judgment comes in is how do I want to interact with another person and what boundaries do I want to set around another person? Right.

Eugene S. Robinson: Uh, yeah, there's a guy, his name is A.C. i did an article on him and he used to have this thing called Crime Faces, which is amazingly funny. He ended up being kind of one of Bill Burr's favorite online comedians for a period of time. And I guess he ran to copyright issues. He would take fights online and he would, he would, uh, he uh, would commentate them like they were sporting events. And he did this one about. He found some video of a guy in Thailand who was running down the street shoeless, you know, shirtless, and does a flying drop kick on some guy. And he sets a. You know, you try to give him, you try to give him some space. You know, you held him at the end of a long spoon. He says he's all right now, he's a married man, he's got a kid at home. And he goes. By the end of the evening, the same thing happened. The guy is wrecked on Fireball kicking down. And it was a very funny piece. But I was like, yeah, there's a certain point at uh, which nature has judgment built into its process so that you can avoid things like that. When you're 40, you're not babysitting a drunken friend or you're not saying, well, I guess it's okay for them to drive. You don't do that shit. After a certain age, you just stop. Because judgment serves you well, you know, and in a professional sense as well. I mean, people kept saying, why did you work at Ozy for so long? I said, well, it's hard to get another job. And did I know something was wrong? Yeah, I knew something was wrong, but my judgment was fully engaged. I was not blind about anything that was happening except for the particulars of the criminal behavior. But I knew it was a messed up place from the, from the Beginning. So judgment helps.

Stephanie Pirillo: Well, and talking about work judgment, I mean, we both worked for Ozzie. We both worked for Carlos, me, for a much shorter period of time.

Eugene S. Robinson: But I think what's interesting, Convicted felon Carlos Watson.

Stephanie Pirillo: Convicted felon Carlos Watson. But I think, you know, if. If you or I were to hear of someone that we knew who was investing in Carlos now, if Carlos was starting a new enterprise and they said, hey, I think this is great, I'm going to put money or time or effort, or I'm going to go to work there, we would judge swiftly and summarily. And if that person came to us for advice, would probably give them an advice to go in the. In the other direction. Right. And I think that the judgment part of it is also, you know, it's part of that the maturity of recognizing people generally are who they are going to be by the time they're adults. Right. Very few people change. And you can look to past behavior to indicate future actions.

Eugene S. Robinson: That, uh, this is where you cut to the philosophical underpinnings of judgment. That really is like a sin qua non. This is a really important thing.

Stephanie Pirillo: How.

Eugene S. Robinson: How does your judgment sit with forgiveness? I mean, because the common perception is that by judging person, you are removing them from the shadow of possible forgiveness. And, and. And I think that's sometimes. Okay. Is that what we're saying?

Stephanie Pirillo: Well, I, uh, think it's complex, so I think there's a couple of pieces to that. It's. What is forgiveness mean? Right. So forgiveness and forgiveness means a lot of different things to a lot of different people. So let's use the. You know, we've talked about addiction a couple of different times. So let's use the example of someone who is a recovering addict and relapses. Um, Right. I can see that person as someone who is ill. I can have compassion for them. I can forgive them for unskillful choices that they make in the grips of addiction. So in a sense, I have forgiven them. I have compassion for them. I am exercising spiritual principles and my engagement with them. But there's no way that my grandkids are getting in a car that they're driving.

Eugene S. Robinson: Uh, would you go to work for convicted felon Carlos Watson again? No. Okay. Yeah. Okay.

Stephanie Pirillo: And again, I think the question is, what is forgiveness? For me, forgiveness is letting go of my emotional attachment to wrongs done me by another person.

Eugene S. Robinson: Yeah, got it.

Stephanie Pirillo: Right. It's not. And I think you can do that. You can forgive somebody and still acknowledge fully who they are. I mean, there are People who have wronged me significantly, who I have forgiven, I can even sometimes exercise some compassion for, but they will never darken my doorstep again. Yeah, right.

Eugene S. Robinson: Yeah. I'm wondering if I've been that intractable about. About any. Yeah. Sometimes in rare occasions, I've been like, you have crossed a line that this. There's no coming back from this, so there's no point. So. Yep.

Stephanie Pirillo: I, um, I've been reading a lot of, um, work by Claire Keegan and she's an Irish writer, mostly short stories, some novellas, um, just amazing, amazing. And I read, um, in her short story collection, I think it's called Dark Horses, and it is a story of a man reminiscing a relationship. And he's in Ireland, rural Ireland, and he is getting drunk in the day and he's missing a woman that he loved. And a friend sitting next to him at the bar says, whatever happened? And this woman. And he said, I came home and I threatened to let her horses out onto the road.

Eugene S. Robinson: Mhm.

Stephanie Pirillo: And his friend says, had you had a wee drop? And he said, yeah, I'd had a wee drop. And he takes her beloved horses open, drunk, opens up the gates and drives the horses onto the road, of course putting them in great danger. And there's.

Eugene S. Robinson: Oh, he actually does this.

Stephanie Pirillo: He does this. And there's this really haunting line where he says to. He says to his friend, she gave me a second chance, but there was no coming back from that. And I mean, her work is beautiful. And you don't know until the end of the story why she left him. You just know that he's devastated by it. But this idea of like, she gave me a second chance, but we both knew there was no coming back from it. I do think there are moments in a relationship, whether it's a work relationship or a romantic relationship or a family relationship where you can't come back. And even if you give that person a second chance, you can't. And so I, uh, think the idea of judging where you are in your.

Eugene S. Robinson: Sorry, you can't. If you're expecting anything other than the similar outcome.

Stephanie Pirillo: Exactly.

Eugene S. Robinson: If you expect the same outcome, go ahead. You know, I'm writing a piece now and I quote, it was such a German quote, with a woman, if you remember, climbed into the polar bear enclosure, uh, in the Berlin Zoo and was attacked. I don't think she was killed. I think they rescued her in time. And they go to a German official who said, in a very Jerry way, said, well, we have noticed in the past that, uh, when you jump in the polar bear enclosure, this tends to happen. That was it. That was it. It tends to happen. I mean, yeah. If you go back in expecting the exact same thing. Well, okay, You'll. You'll be fine. So. Right.

Stephanie Pirillo: And so I think that, I mean, one of the concerns that I have is that this, this sort of, um, the cultural narratives around judgment and I think in particular, like the spiritual narratives, like I wrote a substack called where I talked about spiritual gaslighting. The ways in which I liked it. Yeah, yeah, thanks. The way that. Which, you know, and I mean, use spiritual reality, spirituality writ large. Right. It's not necessarily religion. It could be a mindfulness practice that you're doing something wrong in judging. And I think that that really, um. I think that really damages people. Like, you know, I do not watch the show Couples Therapy, but I get served up clips about it all the time on social media. And couples therapy is, I guess it's marriage therapy or couples therapy where you go in and you agree to air your journey living in public, and then they put clips on it. And often it is one partner, usually the man who is behaving very badly. And what's interesting is that it seems to be, um, like somebody made a comment on social media that the show is just all about how women put up with horrible shit, basically.

Eugene S. Robinson: Yep.

Stephanie Pirillo: Sorry, I have to cough for a second. Um, and. And that's one of the things that I think about is that by saying there's something wrong with judging another person, what we are also saying is don't get angry, don't push back in power dynamics. And I do think, and you know, men can be in a horrible relationship with women. There's no question there are terrible women in the world who treat their male partners or male family members horribly. But I do think there is a cultural understanding that women in opposite sex relationships are supposed to do a lot of enduring. They're supposed to not be judgmental and forgive and give. I don't know. Do you think that's true?

Eugene S. Robinson: Uh, no, I don't. I don't really. And I mean, because when you say this whole nobody likes to be judged, that's why this anti judging thing has caught some purchase. But the reality of it is, you may not like it, but you should expect it. There was somebody who I knew whose marital fidelity hinged on that one plate too many. There's like one plate too. Like, you know, empty nesters, kids gone from the house, talked to the husband several times about, hey, could you, you Know, get the plate from the table. Don't put it on top of the counter. Put it in the dishwasher. You know, I don't need to see a sink full of dishes. Uh, yeah, listen. And he was pretty good for a while, and then one day came down, and for like three days in a row, there was just one plate on the counter right over the dishwasher. And that's when she made a decision to have an affair. Because clearly you were trying to bring me her attitude. I think she actually said it. Trying to bring me to heal using a plate. You. I'm judging. And you will pay for this judgment. So I. I don't think that, uh, uh, you know, and I've had situations where I've been in and I, you know, it's clear as a. As a bell or Unmuddied Lake, to borrow from Clockwork Orange, when it's over, because it's not. Uh, you know, I'm not out to subject you to the tyranny of my expectations, but I'm not a fool, and I'm not going to stick around to substandard behavior. And if women are being sold that narrative, as far as I'm concerned, that's some Connie Francis 1950 shit. I advise all my daughters get out. Statistically speaking, this can't be the best. So sorry. Go. You know.

Stephanie Pirillo: Well, and even if it is the best, right? Like, even if. I mean, I would say to friends, if your choice is miserable and partnered or sane and single, go for single every time.

Eugene S. Robinson: Yeah. You get more stuff done and, uh, your misery quotient is lower.

Stephanie Pirillo: Exactly. Well, let's talk about where I mean. Oh, and one more thing, too, about judgment is one of the things that I think is useful to look at, particularly in a work context, but in any context is do the people around you have good judgment

Eugene S. Robinson: that ties into our fire, Melanie. So good. Perfect.

Stephanie Pirillo: And so do the people around you have good judgment is a question of, like, Dan Savage, who I. I love his podcast. Savage Love talks and really, uh, gives relationship advice. And he says, you want to have. You want to see good judgment in the people that you are dating or considering dating. You know, like some. Some straight guy who starts sending a woman who he's just exchanged messages with unsolicited as dick pics, has bad judgment.

Eugene S. Robinson: That depends.

Stephanie Pirillo: You know, most. Most straight women are not interested in that as the second. Hey, here's a picture, right?

Eugene S. Robinson: And I think what I'm saying is, if you've been asked to do so.

Stephanie Pirillo: Yeah, I think it's unsolicited being the key. The key point.

Eugene S. Robinson: But thank you. Yes.

Stephanie Pirillo: That we are always looking for. For as we are assessing any kind of relationship demonstrates of good judgment. Right. And I think that's important. You know, also in terms of work, if you are going through an interview process and it takes, you know, 16 rounds, you've talked to 20 people, and they. That they've asked you to do work for free, yes, they're demonstrating many things, but also bad judgment.

Eugene S. Robinson: I went through nine at Facebook, and I think it got to 16 before they finally figured out, I think you're too senior for this job. It's like, you guys couldn't have figured that out 15 fucking interviews ago. Unbelievable.

Stephanie Pirillo: Right? So assessing for other people's good judgment and being mindful of if they show bad judgment, like, you don't need that. Like, that is a. That is a disqualifying. That is a disqualifying event. Do you want to. I mean, I've got some other.

Eugene S. Robinson: Hold on. Do you think that bad judgment is contagious in a professional setting? Like a snowball? Like, the boss makes one, and then you make one, and then it just becomes the culture. Bad judgment becomes a culture.

Stephanie Pirillo: I don't think that the problem to solve there is bad judgment. I think the problem to solve is that people are not listening to dissension. Um, so usually I have seen many, many, many circumstances where there is a bad judgment by someone in leadership. And depending on the culture, they are either not challenged at all because they're never gonna change. It risks retaliation. You know, there's a lot of reasons why people won't challenge a leader's bad judgment or bad decisions. And the leader may be a bully. They may know that they're going to get retaliation, um, or they just might not be listened to. Like, it takes a certain amount of energy to say to a leader, I think this is going to be a problem. You're risking social capital. And so I think when a leader makes a bad decision, that bad decision snowballs and cascades. Not because everyone else was removed, like, didn't got their judgment snatched out of their head, but because they have been taught that speaking back, telling the truth, pointing out flaws, is never going to work out well for them. So they just won't say it. So the bad judgment is unopposed for cultural reasons. It doesn't spread.

Eugene S. Robinson: Here we go. Politics in America. Good for you to cap that.

Stephanie Pirillo: What's your. Let's see your fire me now. What's your fire me for?

Eugene S. Robinson: Uh, the Fire me. Is, um, this woman, um, has a slightly problematical boss. Um, and she has kind of covered for him. And, you know, I mean, she's been a good employee. Right. Uh, not complaining. But the boss came in and asked something. Reason unreasonable, she felt, given how helpful and generally supportive she's been and, you know, as now is the law of the land in many, uh, places where you're still forced to go to the office. She's texting with a co worker. I can't believe he's asking me to do this thing. It's like, oh, sure, I covered for him before I did this other thing. Well, unbeknownst to her, for some reason, the person that she assumed was a workplace friend decided to play this for advantage and presumably said, oh, I accidentally. Sorry, forwarded your text to the boss. And so now she's got a Monday morning meeting coming up where she has to face the boss over. She didn't use anything pejorative. Didn't use any. He's not a dumb son of a bitch. None of that. Just said that she thought that the workplace situation was uncomfortable, unfair. But she's been outed by a person that she assumed. She goes, I'm frozen with fear. I don't know how to. What. What do I. What do I. Am I got to lose what was happening here? And, uh, what should I do? And so I thought, that's an interesting. Well, I mean, for me, it's easy. You never trust anybody you work with, so that's easy. How would you make that mistake? But I'm not out to punish the victim here. I was trying to think, well, what. What would you do in this situation?

Stephanie Pirillo: I mean, I would go for brazen. I would brazen it out and say, um. I would just say, you know, do you want to talk about the concerns that I raised in the email? I mean, in the text exchange?

Eugene S. Robinson: Nice.

Stephanie Pirillo: Because it sounds like they're. It sounds like they're valid concerns. And so this is one where I think if you walk in and you decide, what's the conversation I want to have right now? And if the conversation you. If I were talking to this woman right now, I'd be like, the conversation you want to have is, why is your boss doing the unskillful thing that he did?

Eugene S. Robinson: Yep.

Stephanie Pirillo: Right. And that's the problem.

Eugene S. Robinson: It's not me protecting you. It's not me protecting me. It's me protecting the health. The financial health of this company.

Stephanie Pirillo: Right. You know, and that, like. And then, you know, if. If your boss wants to get into like, well, you were texting this person or you were doing whatever to say. I certainly know now not to text with this individual again.

Eugene S. Robinson: Text. Yep.

Stephanie Pirillo: Clearly I'm never texting this person again. And then to maybe even admit like, you are right. I should probably have come to you directly with this concern. Which is why I'm glad that we can discuss this now because it would be great if we could come up with a couple with new ways of interacting so that this doesn't happen again.

Eugene S. Robinson: That's why you deserve the big money. There you go. That's fucking perfect.

Stephanie Pirillo: That's why I'm the executive coach. But I think what's important is to recognize, you know, it's. We're all. I always talk about narratives. We're always doing dueling narratives. Right. And so the narrative that this boss may come in and she's, you know, what she's concerned about is the boss is going to come in and be like, you were, you know, texting trash about me to, you know, a coworker.

Eugene S. Robinson: Yeah.

Stephanie Pirillo: And again, I think it's useful if he does come down hard on that, to try to be like, can we involve hr? Yep. Right. And then I was expressing some frustration. I would use minimizing words like venting, blowing off steam, some emotions that I had. I was not talking about anything confidential. I, um, probably would have been more skillful if I could have addressed these with you directly. But hopefully we can today talk about ways in which I think we could work together more skillfully. I didn't do anything, you know, I didn't do anything unethical. Yeah.

Eugene S. Robinson: And I would actually like to try to see somebody write a pip off of that, you know.

Stephanie Pirillo: Right. And the reality is, you know, I mean, I don't see how she can get fired for this. Like, you know, it would be like, how is that different than, than the boss walking in on a conversation that she's having and overhearing her say, I can't believe he asked me to do this thing again. So, but, so, so that's a good. I like that. Fire me. So let's just go ahead and finish up with where. Because there are examples where judgment is a problem. Right. So let's just talk about where that is. And we've kind of, we've kind of already talked about this, but I think that it's. If you are trying to use your judgment as a way to control or manipulate others.

Eugene S. Robinson: Mhm.

Stephanie Pirillo: That's bad. Right. So for example, everybody says, say again?

Eugene S. Robinson: Everybody says, well, or if you think

Stephanie Pirillo: about it like, one of the things I talk about, a lot of my friends are grandparents, and so we talk about the third rail of parenting adult children, which is keep your opinions about child rearing to yourself.

Eugene S. Robinson: Right?

Stephanie Pirillo: Like, kids are raised differently than when, you know, our, uh, certainly your oldest. Our oldest were like, being raised. Right. So, like, potty training in the early 90s was a different deal than potty training in the 2025, 2026 era. They read different books, they have different resources. You know what? It doesn't matter. The kids are going to end up using the toilet. And so I think that there's a lot of ways in which parents of adult children will try to control or manipulate their. The child rearing of their, you know, said grandchildren in ways that are not helpful, that are based in judgment, that really don't matter. You know, like, what difference does it make if a. If a three year old little boy runs around in a dress because his sister has a dress, you know, and that parents may have issues with that. They may have feelings about it. They need to just keep their mouth shut. So I think the idea of, like, always having an assessment of, like, how important is that this. Right. Like, if a parent. If a. If a, uh, parent is going to tell their grown child something about how to raise their kids, it needs to be either A, invited or B, like life threatening.

Eugene S. Robinson: Yeah, Correct. Otherwise you can draw from the Big Lebowski. Second time he's come over the show, just say, hey, that's your opinion, man. You know, you don't like dresses. It's your opinion. Good. I'm, um, glad you have it. We are fine with dresses on boys here, so. Yeah, right.

Stephanie Pirillo: And it doesn't, you know, and it doesn't matter. And then I think also, you know, one of the things is people who are making a judgment based on authority they don't have or knowledge they don't have. So I had someone interact with me in an unskillful way, and he was mansplaining artificial intelligence to me. And, you know, it's like, I also had.

Eugene S. Robinson: Did you read the Sad Wives of the AI in the New Yorker?

Stephanie Pirillo: No. No. I'll, um, have to look that up.

Eugene S. Robinson: Oh, my God. You got it. Before next show, please try to be okay.

Stephanie Pirillo: Maybe that's something we can talk about on the next show. But. And even a different example is somebody, um, not in a work context, was explaining team, uh, dynamics and organizational development to me, and I really was, like, with a lot of judgment, like, that I wasn't getting it. And I wanted to be like, please, I have a master's degree in this. I have been doing this for a dozen years. People pay me coin.

Eugene S. Robinson: What you should have done, what you should have done is just got the exact opposite way. Really? What happens then?

Stephanie Pirillo: Well, no, because they. That this was such a judgment laden missive that it was actually for me it was relationship ending. I was like, yep, and I'm done. And I'm done. And so I think the idea is like if your judgment is based on something you know very little of, either you have no personal experience, no lived experience, no educational experience, then, and the person to whom you are speaking, the one you are judging, has the degree, the experience, the lived experience, then you need to just shut the fuck up.

Eugene S. Robinson: You know, I had a delightful thing I called, you know, I've learned a few things from the convicted felon Carlos Watson. And one of the things he did really well was he just talked to people that he was into. If he, if they had, he didn't. It was not an ask. I'd like to spend a few minutes to pick your brain. And so I called this lady at a record label in la, of course, pursuant to maybe signing one of the bands I'm in, but I want to talk to you about music. And uh, we talked about music and she spent 20 minutes of a conversation lecturing me m on the value of social media. Right. I've been doing music since 1980 and I worked in Silicon Valley since 19, like 85. And I just listened patiently and it was with great, great satisfaction and delight that within six months of this conversation she got me to ed out of the industry. Her female artist on her record label, um, turned their backs on her, you know, left the company, left her eye and dry. She had to leave the company to save the company. And I was like, sometimes the right things happen to the right people. So I never complained at the time. I just took it on the chin and thank you for your input and spending the time and that was the end of that. But it was really delightful to see on the other side.

Stephanie Pirillo: Yes. And I hope that that um, karma circles around to these, this particular individual that I am talking about as well. So. All right, well that's what, that's what we have time for today. If you have comments, suggestions, ideas for stories or something you want us to talk about on fire me. WTF badboss brief.com WTF badboss brief.com I promise I read every single one and respond to anyone who isn't trying to sell us something. All right, that's it. See you soon. Thank you. Bye.

Eugene S. Robinson: Adios. Bye.

Stephanie Pirillo: Thanks for joining us for another episode of the Bad Boss Brief with Eugene S. Robinson and Stephanie Pierollo. You can find Stephanie on substack@spayrolo.substack.com and you can find Eugene on substack at Eugene S. Robinson Substack, as well as over on Instagram @mrsleep3. That's the number three. If you've got a workplace question, situation, or story you'd like us to discuss, send it to me. Stephanie tfadbossbrief.com Be sure to join us every other Wednesday at, uh, badboss brief.substack.com for new episodes. Until next time, don't be an asshole at work. Thanks for listening.

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