How to Hire Someone and Be a Good Boss

Summary

How To! with Mike Pesca

Episode: How to Hire Someone and Be a Good Boss

Date: July 14, 2026
Host: Mike Pesca (Peach Fish Projects)
Guests: Paula Poundstone (comedian, podcaster), Nedra Glover Tawwab (licensed therapist, boundaries expert)

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Episode Overview

This episode tackles the highly relatable, often fraught challenge of hiring—and more crucially, how to be a good boss. With Paula Poundstone’s comedic candor as both case study and comic relief, and therapist-author Nedra Glover Tawwab offering practical, empathetic expert advice, the conversation explores the awkwardness, pitfalls, and aspirations of bosshood—especially in personal or home-grown work environments.

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Key Discussion Points & Insights

1. The Awkwardness of Bossing at Home

• Paula’s Dilemma: Paula describes herself as a "terrible boss" who dislikes exerting authority, talking about money, or confronting employees—even though she relies heavily on them for both personal and professional logistics.
  • "I don't like to tell anyone anything. I can't stand talking about money." (Paula, 02:55)
• Blurring Boundaries: Most of her staff work out of her home, some being friends-turned-employees (like her longtime assistant, formerly her handyman).
• Emotional Complexity: Paula feels affection when she hears her assistant call her "my boss," underscoring her conflict between collegiality and authority.
  • “If I hear him say that, my heart just fills with warmth. I’m like, he knows I’m his boss. That’s fantastic.” (Paula, 03:13)

2. Stories of Hiring & Pet Sitter Fiascoes

• Unique Hiring Needs: A critical staff need is a reliable pet/house-sitter—a role once held for 32 years by the same person, now difficult to fill due to high expectations and the messy realities of many animals.
  • “There’s a lot of animal waste involved... I just feel awkward about it.” (Paula, 10:28)
• Friction With Technology: Paula despises hiring through apps or websites, finding dropdown menus inadequate and online processes impersonal.

3. When Employees Don’t Mesh

• Incompatibility: She relays the comedic but frustrating experience of hiring someone recommended by her accountant—only to find the new assistant wore overwhelming perfume (triggering allergies) and loud shoes, both intolerable in Paula’s small home.
  • “She would come slathered in perfume... she had like clacky shoes... There was a lot of clacking.” (Paula, 12:55)
• Avoidance Tactics: Rather than confront, Paula tends to evade problematic employees—sometimes literally moving house.

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Expert Guidance: Setting Boundaries & Being Clear

4. Nedra Glover Tawwab—Therapist’s Take

• Be Clear From the Start: Articulate needs (e.g., no scents, quiet shoes) upfront in the interview or job description.
  • “If you know that you have some smell sensitivity, if you know that loud clacking is a problem, those could be things that you talk about on the first day... That’s important to say up front.” (Nedra, 18:20)
• Ongoing Communication: Continually articulate updated expectations as needs or environments change.
  • “Being very clear around what the new rules are and that they apply to everybody, and here's why, is really important.” (Nedra, 20:17)
• Model Boundaries: Bosses set the tone for work-life balance and must honor their own stated boundaries.
  • “If you honor what work life balance and you have to allow people to have it... you can put a send later on [emails] instead of, you know, maybe bothering people on their personal time.” (Nedra, 21:26)

5. Addressing Mistakes Swiftly

• Immediate Feedback Beats Delayed Correction: Nedra advocates for prompt feedback when expectations aren’t met which prevents problematic patterns.
  • “It's also helpful to quickly follow up with them so they don't establish a pattern of doing it the wrong way.” (Nedra, 24:15)

6. Accommodating Personal Challenges

• Openness About OCD: Paula’s perfectionism and cleaning standards arise from diagnosed OCD, which should be addressed candidly with applicants.
  • “Even mentioning, I have OCD, so I realize my cleaning standard may be higher than others... here is my expectation.” (Nedra, 24:17)
• Delegating HR Functions: Consider hiring a staffer or consultant to mediate staffing decisions if direct management proves difficult or draining.
  • “Is it something that you can go to a company and have done for you so that they are managing?” (Nedra, 25:43)

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Hiring & Firing Practicalities

7. Clarify Job Expectations & Assessments

• Make the Implicit Explicit: Spell out details many take for granted (e.g., number of times to clean a litter box, no unauthorized credit card use).
  • “Do you do any sort of hiring assessment when you’re hiring new employees?... Having some sort of questions that help you figure out which type of person actually fits this job.” (Nedra, 30:30)
• Trial Workdays: Offer paid, trial periods to assess actual competence before full hiring.

8. Letting People Go

• Direct, Evidence-Based Approach: Use specific examples of unmet expectations; conversations about performance should precede termination, so no one’s surprised.
  • "People shouldn’t be shocked when they’re fired. There should be some conversations before about them not doing their job well..." (Nedra, 37:25)

9. On Hiring Social Media Help

• Beware of Scams: Many "gurus" overpromise and underdeliver. Seek referrals from trusted peers for proven social media managers.
  • “They’ve tried with me—‘We’ll put you here, we’ll put you there’... it’s really important to figure out which of your colleagues they’re using and what their success rate has been.” (Nedra, 35:02)

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Notable Quotes & Memorable Moments

• Paula on delegation avoidance:
  “I think I moved. That’s usually how I get rid of an employee. I just move and then they don’t know where I am.” (Paula, 13:07)
• The philosophy of boundaries:
  “Sometimes we think it is being mean. We think it's unfair... ultimately it sets us up for lots of issues in the future when we're not upfront with what the job actually is.” (Nedra, 39:50)
• Comedy relief—on the universal fantasy of dodging boss conflict:
  “Part of me still does lean towards just moving. Really worked well in the past. I have some publicists that still haven’t found me and that’s good.” (Paula, 39:20)

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Timestamps for Important Segments

• [02:15] – Paula introduces herself, self-identifies bossing weaknesses
• [04:02] – Discussing Paula’s unique assistant/handyman relationship
• [08:16] – Staffing needs: the elusive perfect pet (and child) sitter, challenges of hiring online
• [12:55] – The perfume and clacky shoe debacle, avoidance as a firing technique
• [18:20] – Nedra’s first expert intervention: clear upfront expectations, especially about sensitive triggers
• [24:15] – Discussion of how Paula’s OCD plays into expectations; importance of swift, clear feedback
• [25:43] – Should Paula offload HR/hiring functions to an external person or company?
• [30:30] – On practical assessments and hiring questions—testing for real fit
• [35:02] – Social media hiring warning; word-of-mouth trumps flashy sales pitches
• [37:25] – How to fire someone compassionately but firmly, giving advance notice and correction
• [39:46] – Paula’s summary, takeaways, and perennial urge to escape management issues via moving house

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Actionable Takeaways

• State boundaries and non-negotiables clearly at the outset
• Give direct, swift feedback—late corrections are less effective
• Conduct practical hiring assessments (including trial runs)
• Consider separating ‘boss’ and ‘HR’ roles if possible, via delegation
• Address unique expectations (from OCD or personal quirks) openly
• Don’t just hire to “do someone a favor”—prioritize true fit
• When firing, refer to specific prior conversations and unmet expectations

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Final Thoughts

The episode blends Paula’s endearing awkwardness as a boss (and her real-world misadventures) with Nedra Glover Tawwab’s firm-but-kind boundaries wisdom. The critical thread is clarity: clear communication, clear roles, and self-insight can transform even the most fraught boss-employee relationships. For anyone managing a home-based team, or just feeling overwhelmed by the messiness of leadership, this episode offers both laughter and a real roadmap.

Transcript

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[Paula Poundstone]

Hey, it's Ryan Reynolds here for Mint Mobile.

[Nedra Glover Tawwab]

Now.

[Mike Pesca]

I was looking for fun ways to tell you that Mint's offer of unlimited Premium Wireless for $15 a month is back. So I thought it would be fun if we made $15 bills. But it turns out that's very illegal. So there goes my big idea for the commercial. Give it a [e-mail] Switch upfront payment

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[Paula Poundstone]

You know, he takes that thing apart and looks at it, he's okay. It's so full of cat hair that it like burned up inside.

[Mike Pesca]

Hello and welcome to how to. So everyone hates their boss, right? I don't think so. The institution of the Boss itself. Maybe not specific bosses, but the institution is valorized right at the end of video games. There's the big Boss, there's acting like a boss. There's Boss Baby. That's a franchise that people hearken to. Springsteen is the Boss and in a good way. So I've come to believe that the question is how to have a good boss, but more appropriately, how to be a good boss. One of those bosses that we like. And I think the answer might be as the quote that gets attributed to Gandhi or Hillary Clinton or maybe the Boss baby himself. Be the change you want to see in the world. And today we have a brilliant guest who needs some assistance being her funny, engaging, crowd pleasing self. She's a great stand up, one of the mainstays of Wait, wait, don't tell me. The NPR News quiz and host of the Nobody Listens to Paula Poundstone podcast. I may have given away the reveal.

[Paula Poundstone]

Hey Mike, great. Good to see you. It's just me, Paula Poundstone. And who am I? What am I I'm a stand up comic.

[Mike Pesca]

Now you say great, but let's be honest, you have a terrible cough. You always have a cough. I have a cough. I don't know if this is getting in the way of our bossing.

[Paula Poundstone]

Oh yeah, well, it gives me a little, you know what it gives me? That it covers that pathetic plank. Sometimes as a boss, I do think maybe if they just feel sorry for me, that'll work. Maybe not. Maybe not the right approach. Maybe, I don't know.

[Mike Pesca]

That's an all the Harvard Business Review studies, you know, to roll over and show your belly and have big doleful eyes so they take pity on you.

[Paula Poundstone]

I am a terrible boss for a variety of reasons, not the least of which is that I don't like to tell anyone anything. I can't stand talking about money. I very rarely come at something from a perspective of like, I'm the boss and so you have to do this. I'm not running a factory or a store. I don't have like tons and tons of employees. I have a handful. Sometimes I hear my assistant will be on the phone with somebody and say, well, my boss, I'm doing this for my boss, or I need this for my boss. And if I hear him say that, my heart just fills with warmth. I'm like, he knows I'm his boss. That's fantastic.

[Mike Pesca]

And that's the only indication you get when he, when he affirms that to third parties.

[Nedra Glover Tawwab]

Yeah.

[Paula Poundstone]

And part of it I think too is A, we work out of my home together and B, we have done that for, I don't know, seven, 28 years. And so, you know, I think there's maybe some boundary issues sometimes.

[Mike Pesca]

Huh. Is, is this assistant, has he been your assistant for those 20 something years?

[Paula Poundstone]

You know what? We've had kind of a funny trajectory. No, he was my handyman for a while and. But he was like my handyman like on a daily basis. And then, you know, my, my life kind of fell apart. I had no money and so I, you know, I couldn't have a handyman at that point. And then a little bit. And then he, and then he became my friend who fixed things sometimes. And then at some point he became my, my assistant. I've sort of forgotten how long each thing was. But anyways, you know, enough years that, you know, we have a good deal of history together. And he's, you know, he's fun and funny.

[Mike Pesca]

By the way, was he hired as an assistant because of his skill with a ratchet set? What did you See in him as a handyman that said to you he'd be a good assistant. Or was it more? Well, he's kind of fixing things for free. Now that I have some more money, I'm going to actually pay him.

[Paula Poundstone]

No, he had. He has worked as both. Not just for me, he's worked for other people as an assistant. And he's extremely good with computers. And in this world, that's very important, particularly when you're me, because I'm extremely not good with computers. I'll just give you one example, which is a few days ago, my computer began to make a crackling sound before it went dark and not good. And I'm making a couple of daily video series that I'm very invested in making sure they come out each day. And in addition to the fact that I do a weekly podcast called Nobody Listens to Paula Poundstone. And so there's a lot depending on that computer working. And I was, you know, horrified when this thing happened. It was probably the middle of the night. I've forgotten now. But, you know, I contact him. He comes and he, you know, takes the thing apart and looks at it. He's okay. It's so full of cat hair that it, like burned up inside. I have a lot of cats.

[Mike Pesca]

So he cleared the cache of cat hair.

[Paula Poundstone]

Well, the computer became useless. We couldn't recover that. Well, he couldn't. Not me. Yeah, he couldn't recover that computer. But then the issue became so, like,

[Mike Pesca]

when you go, when you click on that little icon where it says storage, it just said, you know, Persian, Mongolian. It just listed the breeds instead of the bites.

[Paula Poundstone]

Yes, exactly. So my podcasting partners, they all were trying to weigh in and be helpful. And so there was the one scenario where I could run out and buy a brand new computer that I can't really afford. But also I wouldn't know how to work it because mine was very old. So that's like moving. That's like saying, well, you know, I have to. I have to go out of town in a day, but let me move first. Right. So anyways, all these ideas were floated and no, you should do this and no, you should do that. And he's the kind of guy who goes on Craigslist and finds something for cheap, which often drives me crazy, quite honestly. Cause time is money and he's salaried. But he says, he says, well, let me go. His idea was, let's get a computer that's very much the same as the one that I already had. And I got to Tell you for a couple of hundred bucks. Within less than 24 hours, I was back up and running. I got to say that was damned impressive. And then he transferred the stuff. None of which could I do. So he has a lot of. He has a lot of really good skills.

[Mike Pesca]

So first of all, let me offer a, an observation which is that I find I'm like you. I'm not great with computers. But I have learned not to say I'm not good with computers. I say I'm not great with digital technology. That at least elevates me into the last 15 years of not being good with computers. Yes, that's very important.

[Paula Poundstone]

Yeah.

[Mike Pesca]

If you say I'm not good with computers, I don't even know if people who are under 45 know what we're talking about. So. But my main question is, could we just set the scene or could you describe all your employees? What does Paula Poundstone Inc. In general look like? Who do you employ and who would you like to employ?

[Paula Poundstone]

Well, okay, a big component. And this sounds sort of petty, but it's not actually at all, which is I have to have somebody house and pet sit while I'm out of town. And then years ago I also had to have a nanny and my nanny obviously stayed at the house with the kids while I was gone and also took care of the pets and which we've had a variety of numbers of pets and a variety of species of pets over the years. So that was a big job. And I had the same woman in that role for 32 years. And a little while ago she got very ill and had to quit like that and getting a new person to do that job because I have a lot of pets and, and there's you know, rogue peeing and you know, pets are disgusting. And that has been just kind of a nightmare finding somebody to do that job. And that's where too like I, even though I'm hiring somebody from a pool of like now when you go to hire somebody, oftentimes, and I try to avoid this like the plague, oftentimes it's on some God damned, what do you call it, an app or like a website of some sort.

[Mike Pesca]

It's like a smaller computer. Yes, yes.

[Paula Poundstone]

Yeah, you have to do it off a website. You don't get to talk to people. And there's like a. Everything is a dropdown menu. You know what pets do you have? And they'll see stuff on those sites, like what are their names? What breed are they? Like anybody really cares about that. But the dropdown Menus often don't have a selection for my circumstance. And to type everything into the computer over and over again for these sites is just a tedious waste of time. So I have tried really hard to just sort of use word of mouth and put out the twilight bark from 101 Dalmatians and get what I need, but that hasn't been working either. And I was in. As I said, she had to quit really quickly. I had to get that position filled very quickly, and it hasn't gone well.

[Mike Pesca]

It is odd to imagine someone who would say, I will pet sit for a pet named Otis, but not for a pet named Mrs. Spangles.

[Paula Poundstone]

Well, precisely. And even when I get as far as someone coming to the house and me showing them what to do, even though it's a person who pet sits, this is their plan. This is what they want to do. They posted their name and that's how I got them. I always still feel kind of horrible demonstrating sifting a litter box. There's a lot of animal waste involved. And again, anybody doing that job should be well apprised of that already. But I just feel awkward about it.

[Mike Pesca]

Yeah, well, that, that's the job.

[Paula Poundstone]

And the only thing I feel more awkward about is talking about the money.

[Mike Pesca]

Yeah, I, you know. Okay, so. So you have your personal assistant. You have your pet sitting position. The podcast, which is excellent. I've been on. Nobody listen to Paula Poundstone. That is staffed independently. Am I right about this?

[Paula Poundstone]

Yeah.

[Mike Pesca]

Okay. Any other positions that need filling besides the two you've mentioned?

[Nedra Glover Tawwab]

No.

[Paula Poundstone]

I mean, and then, you know, of course I have accountants. I don't know if they're called my employees. Certainly they don't think so. But after I. After many years, I have like a great bookkeeper at my accountants who I really, I'm particularly pathetic around. And I would love it if she would just come run my whole life. She's so good. It's funny because when you get somebody in any role that is really good at their job, it is just manna from heaven. I've had a couple of different assistants over the years. At one point, I hired a woman because my accountant actually had recommended her, thought she would be good, and it was a disastrous pairing. For example, as you know, I have a chronic cough. I'm allergic to anything with a scent. And we're working in my home. And she would come slathered in perfume, and I'm like, it's not like we're in an office setting where there's other people. She's Gonna meet where? Like who is she coming onto with this perfume? Not me, but I same thing. I can't remember if I even was ever able to tell her that. And she had like clacky shoes, like Dr. Scholl kind of shoes or clogs or something. They would just like clack, you know, I live in a small house. There was a lot of clacking. She presented as if once she started working for me, man, my life was gonna get easier. And then the disappointment of those two things not matching up. I got rid of her. I can't remember how it's easier anymore. I think I moved. That's usually how I get rid of an employee. I just move and then they don't know where I am.

[Mike Pesca]

Change your name, right?

[Paula Poundstone]

Yeah.

[Mike Pesca]

So, Paula, it does seem if I could diagnose from afar. It does seem. First of all, sympathies on the person who invoked your misophonia and also your Ms. Osmia, I believe is the name for when you have either a heightened sensitivity to smell or sensitivity to smell that drives you up a wall. I identify with that. But it does seem like there is perhaps a.

[Paula Poundstone]

What's misfortunia?

[Mike Pesca]

Misphonia is. Is the sounds. It's the clacking. Yes, that's. That's a big one. It often shows up with people chewing, you know, so it sounds like there is perhaps a constellation of problems to be solved. And we are both adults, but I can guarantee you that our next guest is not going to say more of an adult, but someone who has spent her life in gathering expertise to correct and solve every single one of your problems. I guarantee you after the next 15 minutes of conversation. All right, maybe I'm guaranteeing you too much and describing the job that I want, not the job I can do. But in a moment on how to Paula Poundstone's deliverance will present herself. Stick around. The fastest growing businesses aren't doing more, aren't spinning their wheels more. They're doing things smarter. And smarter is usually delegating. Which brings us to upwork. They help you bring in expert freelance help fast so that you can delegate so that you can be that fast moving business that is a growth hack. Upwork is a one stop platform to find, hire and pay expert freelancers across the web in software development, data and analytics, marketing, business operations and more. You can browse profiles, review past work and get help skills, scoping the roles so you can hire with confidence and get started quickly. Upwork also cuts down operational hassle by handling things like contracts and payments in one place so you could spend more time running the business. It's free to sign up. Posting a job is easy. Visit Upwork.com right now and post your job for free. That is Upwork.com to connect with talent ready to help your business grow. That's up w o r k.com upwork.com

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[Nedra Glover Tawwab]

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[Mike Pesca]

we're back with how to We've been talking with Paula Poundstone and what a life she leads. In fact, she'll be appearing at Jonathan's in Ogunquit, Maine this Friday and next weekend in Albany at the Egg. Now to get back to the Egg and other places, she does need some support back home. All her cats and dogs need to be sat for and sifted through in Los Angeles. So now I would like to introduce us all to someone who has a fair amount, in fact a great deal amount of expertise in the specific area of hiring and bossing. And I just know she's going to be able to meet Paula Poundstone where she is.

[Nedra Glover Tawwab]

Yes, I'm Nedra Glover to wab, licensed therapist and author.

[Mike Pesca]

So, Nedra, you one of your books? I think the first one, the best selling, Set Boundaries, Find Peace, A guide to Reclaiming yourself. I think a lot of those things would help. Paula, what do you think?

[Nedra Glover Tawwab]

Yes, as I was listening, one thing that, especially with the last assistant and the perfume, one thing that could be really helpful when hiring people is to be very clear up front. Front. So if you know that you have some smell sensitivity, if you know that loud clacking is a problem, those could be things that you talk about on the first day. So this person isn't continuing to do this annoying thing and wearing down our patients. I've seen these sort of things when I've worked with different professionals. They'll, you know, have someone let you know, like, you know, this person. They can't smell a lot of different things. So please don't wear anything that's too strong. I think that's important to say up front.

[Mike Pesca]

Paula, did you, could I ask, did you do that interview online or was the interview in person?

[Paula Poundstone]

No, it was in person, but I don't think I noticed the perfume until she was actually here working.

[Mike Pesca]

And maybe she wore slippers, ballet slippers.

[Paula Poundstone]

And it was also, you know, I don't know, it's like the environment, it's my home and it's not fancy. It just seemed like such a strange setting for somebody to be so slathered in perfume one way or the other anyway. So. But all right. But it's, you're right. If I had established that up front, that would have been, that would have been helpful. There were things after that incident of hiring that person and it going so colossally badly where I realized, yeah, you know what? In an interview, because I'm also a compulsive talker in an interview, the person applying for the job knows much more about me by the time the interview is over than I do about them. All I knew about her was that she was a woman. Okay. That's all I knew about her.

[Mike Pesca]

So, nedrab, thank you for starting with a specific, but let's even go backwards and go more global. What would you say, having heard, Paula, maybe you were getting some insight as you listened in, as you eavesdrop, what was occurring to you?

[Nedra Glover Tawwab]

Yeah, clear boundaries are really important when we're starting the job or even as we're in the job Communicating as the needs of the environment shift. Because, you know, maybe you started your job 10 years ago and some things weren't a thing. You know, I can imagine that, you know, employers are now having to institute new things with AI or with working from home. Like, as you're in a work environment, things will shift. So being very clear around what the new rules are and that they apply to everybody, and here's why is really important. Also demonstrating some, some boundaries as a boss, because people often complain that they work in these environments where it's like, we, we honor work life balance. We love for you to enjoy your time off, but then they have a boss who's calling them all evening, calling them while on vacation. So it's really important for bosses to respect the boundaries that they're saying are really important. If you honor what work life balance and you have to allow people to have it, you have to encourage them to take that vacation time and respect it by not reaching out to them. You know, we do live in a, in an age where you can save those emails and have them send out a week later. So it's, you know, you can put a sin later on it instead of, you know, maybe bothering people on their personal time. And, you know, ultimately, I think you have to be under Nedra.

[Paula Poundstone]

I don't know how to do send later. So I would have to call Wendell on his vacation to have him explain to me how to do send later so that I don't bother him on his vacation.

[Nedra Glover Tawwab]

Well, you have to talk to him about that before he goes on vacation. Right? You know, we're having this conversation now,

[Paula Poundstone]

so until you said it, I didn't know it existed.

[Nedra Glover Tawwab]

Well, now you know, and I just saved Wendell some hours on his vacation to help you have some things in place, even if it's, you need to be picked up from the airport. Like, who else can do it if I'm out of town or if I'm away on vacation? You know, for, for bosses, I think it's very important to be understandable but firm. And because we're working with other people, sometimes there's this scariness around a rule being a rule or things needing to be done because it's a function of your job. And we dance around that thing is like, oh, maybe. Well, you don't have to. We'll see. You know, kind of like we do with kids. And it's like, this is the job. I have a question for you. When you have an issue with an employee, how swiftly do you address the issue? Like, when you notice today this person did not empty the litter box. Do you let it, like, oh, we'll see if they do it tomorrow, or, you know, do you wait for them to do it, like, a third time? Or is it, like, immediate at the end of that day you send the email?

[Paula Poundstone]

No, I would say the former. Yeah, I don't. Because I really don't like conflict either. Or I'm just like, a lot of times when I get home, I have to clean for like, three hours because so little has been done. And then I'm like, well, okay, it's. It's resolved now. We're starting fresh again. Yeah. Yeah. It's very frustrating.

[Mike Pesca]

Nedra, there's something else that you should know. And I think maybe it showed up in the last couple anecdotes Paula gave, which is that she does have ocd, so maybe that explains something about she'd come home and work for three hours, and it doesn't. Well, it does drive her a little crazy. She knows it's not right. But I don't know how to factor that into. Well, I don't know. Maybe. I guess that if you're honest with the hiree, the potential hire upfront, and you are, and here's the word I wanted to get to, and I want you to expound upon it if you can offer maximum clarity, that will probably pay dividends down the road. Is that a big part of your boundaries discussion?

[Nedra Glover Tawwab]

Absolutely. I love that you. You mentioned that, even mentioning I have ocd. And so I realized that my cleaning standard may be higher than others. And here is my expectation when a person does not meet that expectation. It's also helpful to quickly follow up with them so they don't establish a pattern of doing it the wrong way. Because sometimes we'll let people get into a pattern of doing it their own way or not doing it at all. And then a week or two later is when we finally say something and they're like, well, I've done it ten times this way. What's the problem? And even with some of our old employees, and we start to see this shift in how they're managing things quickly, having that conversation with them. You know, bosses are human, too. I get it. Like, not liking conversation. Some of us are like that. And it's also something we can work through. Is it room for you to maybe hire? And this could be temporary. I don't even think you have to do this. Like, there are companies, there are people who can do this. But to almost hire, like a staffer, like, if you don't have the skills to staff people and you need them to be highly trained and you don't want to have these conversations. Is it something that your assistant could do? Is it something that you can go to a company and have done for you so that they are managing?

[Paula Poundstone]

Oh, that's interesting.

[Nedra Glover Tawwab]

It's kind of like you just get to tell on them and somebody else corrects those things. Like that could be a HR consultant. Like you can. Yeah, I mean, you can.

[Paula Poundstone]

I love the idea of having hr. Well, I'll tell you the irony. The irony about having my assistant to it, which, trust me, I've thought of, is that I know his response. It'll be, I'm not doing that. And then I have to get somebody to tell him that he has to do that.

[Mike Pesca]

Maybe it wouldn't be. It's not optimal that you have to sell your assistant on doing his job. But there is a logical argument there, which is that, Wendell, this will pay off. Not even in the long term, in the medium term, how much of your job is making up for these other hirees that aren't doing their job? Maybe he'll see, because, you know, he's a logical guy and a handyman, former handyman, that he will see the logic of that.

[Paula Poundstone]

It might work. You know, the majority of people who work for me do it while I'm gone, but they talk to one another. And he can't stand being the conduit. And maybe he would feel better about the conduit if he did the hiring. I don't know. That's a good point. I sort of like the HR idea, but the only problem with that is it's kind of chicken shit, if you don't mind me saying so, in that the idea that I sort of pretend I didn't have anything to do with it, you know.

[Nedra Glover Tawwab]

Well, they know you had something to do with it. It's your business. I mean, any company, the company exec is not the person who's hiring the. The cashiers and the, you know, it's like, yeah, I know that they're not doing their job and they'll get fired for it, but I don't have to be the person to do it. Like there's someone else to do that to keep that role sort of going. And I think it allows you to work on the other areas where you're really. And not this hiring and firing part. Like, you can do your podcast, you can focus on your tour, creating material. It's, you know, it's a blind spot almost like, is there another person who needs to be on the team to manage this thing that's not managed well?

[Mike Pesca]

Yeah.

[Paula Poundstone]

Gosh, I'm tearing up right now. The idea of being able to work on my podcast or create material that's. That's such a. That sounds like paradise to me.

[Mike Pesca]

I also think that it would be very funny for you to give, and you like to be funny. Sentences like, well, listen, it's out of my hands. The suits in corporate have decreed. Like, this is not. This is not. If it was up to me. Also, there was an episode of Cheers where Norm, who is this well loved figure, invented a Persona named Kreitzer, and Kreitzer became his executive function or his boss, and Kreitzer was. Would give all the bad news to people. People literally thought Kreitzer existed, and this was just a way for Norm to be the good guy and Kreitzer would be the bad guy. And for a time before this was all exposed because it's a half hour sitcom, it worked very well for Norm. So maybe you could invent some sort of Kreutzer type figure.

[Paula Poundstone]

Yeah.

[Mike Pesca]

All right. This is Kreutzer. Now listen up, you bunch of gutless, sniveling little wimps. I don't care what Peterson said, that

[Paula Poundstone]

low life does not lay down the rules.

[Mike Pesca]

Nedra, do you think that the big problem here, to get to the root of the problem, is it a philosophy of hiring the wrong people or is it more a management problem? It's a little bit of each. But if she had to really attack one with real bullet points, with real items that are achievable, what should Paula concentrate on?

[Nedra Glover Tawwab]

I agree with you, Mike. I do think it's a little bit of both. It could be hiring the wrong people. It sounds like you, with the one employee, you knew a lot about all of their personal stories. She's a grandmother. She does this, she does that. And sometimes that can cloud our judgment around who to hire. It's like, this person needs a job. Here's a job is not necessarily based on their ability to do the job, but on our desire to be a good person. Right. And help them in the world, which is great. Right. But it doesn't make for a great employee. And so being very clear around things that are specifically needed for this job and even allowing people to have, like a trial day, you don't even really hire them, but I'll pay you for your time. Let's see how you do, especially in this role where you've had a lot of turnover. The other Thing that I think is really important is being super clear up front about what the job is and making sure that you are managing those expectations directly in the beginning. Not allowing people to go too long or too far without the correction of what the role should look like. Do you do any sort of hiring assessment when you're hiring new employees?

[Paula Poundstone]

What does that mean? I probably don't.

[Nedra Glover Tawwab]

Then like, you know, I'm thinking of some sort of questionnaire that is suited for the role that they'll be taking. So if it's someone who, who is a pet sit sitter, how many times a day should you clean the litter box? Asking them if they're like, one time, it's like, whoa, okay, if you, if you interview somebody and they're like, I think at least three or four times, that person might be a better match. Having some sort of questions that help you figure out which type of person actually fits this job. I'm not training them to be a better person in this job. They already have the skills. This is Bethenny Frankel from Just be with Bethenny Frankel. Let me be blunt. Most dog food is junk. It just is. And I'm not feeding junk to Biggie and Smalls. That is why they eat just food for dogs. It's real, 100% human grade food with ingredients I actually recognize. Not mystery pellets pretending to be healthy. And once I switched, the difference was obvious. Better digestion, better skin, more energy. Dogs who actually feel good instead of just surviving dinner. And here's the thing, you care about quality. You make an intentional choice to be healthy. So why are you gambling with your dog's health? So let's think about our furry babies. Go to justfood4dogs.com right now and get 50% off your first box. No code. Just try it. Because once you see the difference, you're not going back.

[Mike Pesca]

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[Nedra Glover Tawwab]

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[Nedra Glover Tawwab]

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[Paula Poundstone]

I had a. I had someone that worked for me at one point that was using my credit card. So I could have asked the question, is it okay for you to use my credit card?

[Mike Pesca]

Yeah. Embezzlement, yay or nay?

[Nedra Glover Tawwab]

And by the way, what is their credit like? You know, like when people work at banks, they have to have a certain credit score to be. I mean, that's how they used to do it. I don't know if they still do it that way, but there was some sort of checking of what is your financial picture. You're going to be handling money. We want to see if you have credibility yourself. So if you can't handle your own money, do we want to put you in the vault?

[Paula Poundstone]

Yeah. Right. Okay. So self promotion. I loathe. I have to do it, but I really bloody loathe it. And a lot of it is this, you know, sort of online with the social networking. And I'm going to be here and I'm going to be there and telling people that. And for me, everything kind of depends on it because my number one income is people coming to see me in a theater. If they don't know I'm in the theater, then guess what? It doesn't go very well. So this is a big thing. And so a few times now, I have hired people that were sort of social. I don't know what they call themselves like, but sort of, you know, supposed social networking kind of, you know, gurus that are going to take over, and you give them all your passwords and you give them access and you make them, you know, they're the people who can, you know, go in and post. I've hired these teams of people that sell themselves brilliantly and then do nothing. And I think it's this sort of unspoken thing between people. I think that. I think they're con artists.

[Mike Pesca]

Well, you're talking to Nedra, someone with, I think, 1.8 million Instagram followers. So she's pretty good at this. She probably has some insight.

[Nedra Glover Tawwab]

Yes. I don't use any of those teams, though. I do it myself. And I will say part of the reason I do it myself is based on what you said that I have some colleagues and friends who've used these massive company. Sometimes they're taking other people's content and putting it on your page as your own words. So that gets you in trouble or they are not doing the job in they. In the way that they, they say they will be able to, to do it and deliver. However, there are some people who have great results with social media managers. Everyone is not swindling and scamming in that arena. And it's really important to figure out which of your colleagues who, who they're using and what their success rate has been. That's a great place to use some word of mouth because you do want to make sure that you're finding a trustworthy person to do the job. So if you have friends who, who have actually used someone and seen results, that is the best way to find a social media manager.

[Paula Poundstone]

Oh, that's a really good point because, boy, these people can sell themselves.

[Nedra Glover Tawwab]

Yes, they do. They do. They've tried. They've tried with me. We'll put you here. We'll put you there. Yeah.

[Mike Pesca]

So let me just also say this, that you might know this, not know this about Paula. She is a nurturer. She has fostered many, many animals, many children, many relationships. And I think that fostering instinct is showing up in the hiring process. And it's oftentimes the enemy of the boss employee relationship. And I don't want to commit her to more expenditures than she is able to expend. But the idea of having someone essentially be HR or the hiring manager or some taking that task from her might in fact be the best way to do it.

[Paula Poundstone]

Yeah.

[Nedra Glover Tawwab]

Just because we're great at business doesn't mean that we need to manage the business. And sometimes our greatest work is on task and not the hiring and managing of employees. And finding someone who can do that job well is really important for your business.

[Paula Poundstone]

Is there a technique, Nedra, to firing?

[Nedra Glover Tawwab]

Oh, great question. I say clear and straight. You know, here, here are, you know, some instances where you've been told X, Y and Z. That was not done. So I'm going to have to let you go. Um, it's not time for conversation. That should have already happened. Um, you know, I once heard someone say that people shouldn't be shocked when they're fired. Like there should be some conversations before about them not doing their job well, whether they want to listen to it or not. Some people, they have clear indications that they're not doing their job well, and they're shocked when they're fired. We're not talking about those folks. We're talking about people you've never said anything to. In your first line of defense is firing them. So, you know, have some conversation. Make sure you're talking about the issues before and giving people time for correction. And if they don't correct, then the next step is you've been asked this and we've talked about it, and I will have to release you. You cannot work with me anymore.

[Paula Poundstone]

Oh, gosh. I, you know what? I have this task to do and it just, I don't know if I'll recover. It's going to cause digestive problems for me.

[Mike Pesca]

But you have these, I think now you have some tools, you have some insight. It's a lot. Do you think you're going to follow up on any of these ideas? And how are you going to do that, Paula?

[Paula Poundstone]

Yeah. Okay. Well, for one thing, this laying out the, the expectations, you know, better in the beginning. That's my number one downfall. I'll have to look into the thing about using staffers. It's funny you mentioned earlier, if you're a really good business person. I'm a lousy business person. I'm the worst business person. So I don't have a lot of money, but it might be worth the investment of doing that to make things go smoother. Although on the other hand, what if I. What if. Because technically they're sort of an employee, too. And what if I'm not good with them either and they all mutiny. But yeah, yeah, I think those are the, you know, two, two things that I, I most take away. Part of me still does lean towards just moving. Really worked well in the past. I have, I, I have some publicists that still haven't found me and that's good.

[Mike Pesca]

And Nedra, do you have any last pieces of advice?

[Nedra Glover Tawwab]

Last piece of advice. I'd like to go back to what Paula said about your expectations. Sometimes we think it is being mean. We think it's unfair. We're trying to play good cop by not being clear. And ultimately it sets us up for lots of issues in the future when we're not upfront with what the job actually is. They can decide in the beginning if they want to be there, if it's something they can actually do.

[Paula Poundstone]

Yeah, yeah. Maybe I stressed the vacation plan too much.

[Mike Pesca]

Well, this was an excellent conversation and please stay tuned for our next show, how to Work for Paula Poundstone. Episode 14, the Definitive Guide to Non Clacky Shoes. Our guests today have been Nedra Glover to Wab, who's a licensed therapist, a relationship expert. Among her best selling books are Set Boundaries, Find Peace, A Guide to Reclaiming Yourself. Nedra, thank you so much.

[Nedra Glover Tawwab]

Thank you for having me.

[Mike Pesca]

And Paula Poundstone, who's frequently on Wait Wait, Don't Tell Me and has her own excellent podcast which is a lie right in the name. Nobody listens to Paula Poundstone. Paula, thank you and good luck. Best of luck, Paula.

[Paula Poundstone]

Thanks Mike. And you know what, you can leave your application with my staffer. Let me get you her number.

[Mike Pesca]

If you like what you heard today, please give us a rating and a review. And we do need your questions that start with the words How to. Email [e-mail] how to is produced by Jeff Craig and Cory Wara. Michelle Pesca puts the can do in How To. Charles Duhigg founded the show as a best selling author, a business consultant, a nationally ranked kayaker and a quilting influencer. Which is why he says when filling out online forms that ask for occupation,

[Paula Poundstone]

the drop down menu is often don't have a selection for my circumstance.

[Mike Pesca]

I'm Mike Pesca, back every week. Answering your questions of how to

[Commercial Narrator]

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[Mike Pesca]

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