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This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, editor in chief of Entrepreneur magazine.
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And I'm money expert Nicole Lapin. On Tuesdays, Jason and I answer the.
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Helpline and help callers solve their work problems.
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And on Thursdays, I give you one way to improve your work and build a career or company you love.
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And it starts now.
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Oh, my God, you guys, I'm about to pull my hair out.
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Please don't do that. You have very lovely hair.
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Yeah, don't do that at all. Hello, you are Morgan, producer of this show.
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Hello.
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You have come to us today.
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Jason loves a very organized intro.
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Well, I like people knowing what the hell they're listening to. So they're listening to Morgan asking us a question. Hello, Morgan. You're here to ask us a question.
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I am, I am. I need to call the helpline. I need your help.
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You've done it.
C
So here's what's happening. So we work with a really lovely partner, and I don't want to give anything away about them, so I'm going to keep it pretty vague and use some hypotheticals, but let the record show, lovely partner, great to work with. Makes a lot of sense to work with them. There's a lot of really wonderful things about them.
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Great, wonderful people. You like working with them.
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I think you should say it and we will bleep it out.
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I don't think the name of the partners. Yeah, I don't, I don't want to be specific.
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I know. I just love an extraneous bleep. Feels like naughty.
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I think I need to keep it pretty vague or else they'll know. Okay, lovely to work with. Except, ooh, here's what happens. I, every couple of weeks have a meeting with them, and the meetings always devolve into these hour long conversations about the most granular processes for the smallest parts of the work that we do together. It makes me insane. And so I, I.
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To be fair, Morgan, you're already insane. But makes you more insane.
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More insane. This is right, this is feeling familiar. I've been in this world before. You get on, you're supposed to be talking about big things, and then they get caught up in the smallest, seemingly least important part of the conversation.
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A hundred percent. Like we should be talking about our goals for the partnership. Are we meeting them? What can we do to have greater success together? And normally, you know, on the calendar we have 30 minutes or so. We end up talking for an hour, screen sharing an Excel spreadsheet Oh, these line by line processes for these things that we do together, the three of us.
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Yeah.
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And don't have to talk through it. We just know what to do. And so it's as granular as like when you send an email with this type of update, if A scenario happens, forward the email and if B scenario happens, start a new email. Oh God, it's crazy.
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Awful.
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And I just feel especially because we're in startup mode and we have so many things that we're working on. I am just like buzzing on the other side of the zoom, watching my inbox stack up with, with like problems, questions, opportunities, like urgent things. And I'm on these call with these people being like, should we use Dropbox or Google Drive for this type of file? And I'm like, oh my God. And so I kind of want to know first and foremost, am I the asshole? Is this how people should be running their businesses? Do they know something I don't? Should I just be more patient? My take is that this is unnecessary and it's making it more complicated than it needs to be and adding in more friction.
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Do they redline your emails? Have you experienced that with anybody?
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Like for deal terms, for where people.
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Treat everyday emails as if they are contracts with deal terms and they will always reply by redlining the emails?
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Oh, actually, yes. They'll be like, see responses to your email below. Yes, they do.
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Is that a red line if they respond?
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Well, it depends. I've had multiple people do it with actual red lines. Like just imagine sending an email to someone with like, hey, I got a few things to discuss with you. And then you get an email back and it says, please see redline below. And then below is your email sort of torn to shreds as you think of the contract full of redlining. To me, that is a sign of someone I would not want to work with. And I have worked with those kinds of people and I want to run away as fast as possible because working with them takes too much time and too much energy for the actual ultimate output. And it drives me crazy. There's gotta be a good term for this that we should come up with right now. But like Morgan, you asked, are you the asshole? No, they are the process assholes. Maybe that's just they're the process assholes and it's gotta stop. I have no tolerance for it.
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I mean, I'm really surprised that they're a startup because when you first started explaining this, I thought it was like some big old boring, stuffy company that has A bunch of consultants in there, and they're, you know, all trying to cover their asses and not get fired. But a startup, I don't get that at all.
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I have a theory about why this happens. I think that if you work with someone and they get really granular about how things are supposed to happen, first it needs to happen this way, and then it should do this. And don't send an email like that and put it in this font and whatever. I think that these are people who simply do not understand what creates a good output. So let's just say, for example, that this partner. And we're keeping it really vague, so they're. But let's just say that the ultimate result of this partnership is a podcast or something, right? We make podcasts. It's a podcast. So if they're getting really granular about how emails should be sent, then I think that they don't actually understand what makes for a good podcast. And they think that the thing that makes for a good podcast is the thing that's right in front of them, which is the process that they can control in the same way as which. And I'm sure you have both heard this before where somebody will ask you, hey, I'm thinking about getting into podcasting. What equipment do you use, right? And what they really want to get into the microphone that you have, and you have like a mixing board, and it's like, no, no, no, no, no. That's not the thing that makes a good podcast. The thing that makes a good podcast is like, what do you have to say and who are you saying it to? And then get on a microphone. It doesn't matter what microphone. Get any microphone. Hot tip, friend Morgan, are you on.
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A microphone, by the way, right now.
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I have a voice note going, oh, great.
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A hot tip. Just in case anyone is wondering about microphones. Like, just go to Amazon right now and buy a Samson Q2U. It is $60. It has great audio. Don't think about a microphone ever again. Just buy the damn thing and then start making your podcast. Not sponsored but non sponsored. I reach out because I recommend that microphone all the time. I love it. So that is the problem. I think that people do not understand what creates a good output, and so they get obsessive over the input, the little process that they can control, and they think that if they just get the emails in the right order and if they get the spreadsheet in the right way, that it will produce a good result of a podcast or whatever the hell it is. And the problem is that that's not what makes the thing good. And I think that there's a misunderstanding there among all the people who are involved in this about what their role is in creating the good output. And so they just get obsessive over what they see as their role, which is to be a part of the process. That's my hypothesis.
C
That's so good.
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Unless, of course, their whole business was an email refinement business.
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Sure. This would be so appropriate. I gotta fire you because I'm not interested in email refinement. But, like, yeah, I think that's often the case. And I don't know how people get into that. Part of it feels like job justification. It's just like a lot of people trying to explain their existence. I remember the first magazine that I worked at was Boston Magazine. At Boston Magazine, we would pass around these page proofs. Like, every page of the magazine would get printed out at the very end of the process. And then it would get passed from person to person around the room. This is when magazines had staffs, so we would have a couple senior editors and junior editors. Every single one of them would have different things to say on these page. These people would be circling things, rewriting things, and it would turn to this mass chaos. Did that make the magazine better? The answer is no. I'm not even letting you answer. The answer is no. What it did do, however, is it justified the existence of everybody along the line. Everybody got a proof. Everybody's thinking, the last person to see this is going to be the editor in chief. I better have something to say on this page. Proof. So let me find some things to say. And all that did was it slowed everybody down and it did not increase the quality of the actual output.
C
Yeah, I think that that is such good framing. And I wish there was a way for me to tell them that.
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Yeah, I was just going to say, what have you.
C
No, I haven't said anything. And I do think again, they're lovely, great partners. I do think that if I said something, they would be very responsive to it. I don't think what I would be able to say is, I think you guys are focusing on the wrong thing. I think what I could say is before the next meeting. Hey, I have a hard out. Really need to keep this to 30 minutes. Here's the list of things on my side that I need to talk about. Feel free to jump in with your agenda items. If there's anything else that you as a team need to cover without me, I'll Just hop off and you guys.
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Can keep talking amongst yourselves.
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I have a possible solution. This is something I like.
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Jason doesn't like that approach.
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He goes, I don't think what that does is it removes you from a needless process, but it doesn't stop the needless process. And I would like to stop.
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But is she in charge of stopping the needless process? Well, somebody else's team.
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She has to engage with all the people who feel like they're a part of the needless process. And so in some way or another, unless Morgan, like crusaders. Yeah, like she will have to engage with it. She will still have to in some way or another. Remember whether or not. Yeah, exactly. The new email and the whatever. Right. Like this is crazy. They seem to think that people, human beings can absorb granular direction the way that a computer can. With a computer you go in and you can change the code and then the underlying code will then direct how the next things happen. You can build automations and then depending on how you write the automation, some complicated series of events will take place. But the problem is that humans just don't absorb automation tasks that way. So we, we have to stop treating people like automators and instead we have to understand what the hell they actually want to accomplish. And that is the thing that I think is missing here. So like Morgan, let me ask you, what do you think they are trying to accomplish? Give them the benefit of the doubt. They work with Money News Network. They want to do a good thing. Right. Like they have aspirations of good not going about it the right way. What are they trying to accomplish with this process? Madness. Stick around Help Wanted. We'll be right back. Welcome back to Help Wanted. Let's get to it.
C
I think that what you said about confusing process and output is definitely at play. I also get the sense that as a team, the work that they do is high intensity at times. And getting really granular about these processes gives them both a sense that they have control over this business. That is an industry that is changing a lot. But also I think that some of the people on the team are prone to some feelings of stress and feeling like everything there's no unknowns is giving them a sense of calm that does the complete opposite thing for me because that makes me stressed and wanting to pull my hair out.
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Yeah. Let me tell you a story. So come back around. It's going to sound unrelated. A couple days ago, me and my team at Entrepreneur magazine, we march into a media buying agency's office for a big meeting with A client. And we're there to pitch them all sorts of stuff that they could partner with Entrepreneur on. A lot of money on the line. And the meeting is supposed to begin like this. The head of sales at Entrepreneur is going to kick things off by just talking about the overall total addressable market of entrepreneurs. How many small business owners are there in America, et cetera, et cetera. This is a slide that he often uses to start meetings. I've seen it a million times. And then he's going to kick it to me, and I'm going to do this scene setting thing about Entrepreneur and blah, blah. Okay? So he gets to this first slide, does the first slide. It's like, the number of small businesses in America, America. And, like. And then unexpectedly, a woman in the room on the client side immediately interrupts him and, like, challenges that number. How exactly was that number reached? And, like, how does that number exactly break down? And, you know, like, what percentage of that number is? She just starts grilling him on these granular questions about this number on a slide that seems completely irrelevant. And at some point, the head of sales does not know how to answer her anymore. And so he just kicks it to me. He's like, jason, what do you have to say about this? Which is quite questionable strategy. So what I did was this thing that I have just learned to do in times in which I don't really understand why somebody is fixated on something, and that is that I asked her some version of. I was like, I hear you wanted to understand this particular number, but I assume that this is about something else that you're trying to drive to. I have a hypothesis that what you're really asking is how do we segment our audience so that we can reach exactly the segment of our audience that is the people that you want to reach. Is that why you're focusing on this number? And if not, what is it about this number that you're trying to understand? And that totally shifted the conversation. I was basically correct. Like, what she was doing was thinking. You're telling me that there are, like, millions of people out there, but we want to know how well you reach exactly the people that we want to reach, which naturally she should, because that's the reason she's going to spend money with Entrepreneur. All right, there's that. Now, today I was listening to a podcast interview with Chris Voss. Chris Voss is a former FBI hostage negotiator who's now, like, this negotiation guru. Wrote this book called Never Split the Difference. And he said that a thing that he loves asking in negotiations is, or rather not asking but saying is this phrase. It seems like there's a reason you're saying that. It seems like there's a reason you're saying that. So somebody says something and it doesn't exactly make sense, or they're fixated on a thing that doesn't seem to be moving things forward. It seems like there's a reason you're saying that now. That's basically what I did in that meeting without realizing that it's a negotiation strategy. But Chris is really nicely encapsulating what it is. Now, I take this back to Morgan. I think that there's a reason, and I don't exactly know what it is that they're hyper focused on this process. I have this hypothesis that it's like they think that this is the thing that drives a better outcome. But like, what would they say it is? Because I don't think that it's that. I think that maybe it's that this project is, you know, maybe like they're not internally managing this project all that well and so it's becoming too time consuming. Assuming they're trying to figure out how to streamline it or like there's. There's something that they're trying to solve for. And until you know what that is, you will never escape the nonsense of the process obsessions that they have. And so my challenge to you would be, in some way or another, the next time this comes up, to say to them, like, it seems like there's a reason that you're saying that and try to get them to articulate what that is.
C
I love both of those examples because when you gave the first example with the entrepreneur meeting and you were so nicely able to articulate what she was trying to get at, I was thinking, how will I do that with these partners when I feel like what's happening is that they're very stressed out and feel out of control. And so how do I say it? Seems like you guys are feeling stressed out and out of control, but I like putting it back on them to do the work of articulating it themselves. With the Chris Voss, like, seems like there is a reason you're saying that. Like, what are you. What is this really about? And I also just can't wait to use that line next time I'm trying to start a fight with Jack. Seems like there's a reason you're saying.
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That, oh, I want to hear, I want to hear what happens.
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Or essentially, in other words, you're saying, why Is this important to you?
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Yeah.
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And I think reframing that around KPIs, like, we're all KPI focused. We want the best outcomes. We want to reverse engineer from the goals. Why is this important to you and letting them explain that? Because I think Jason's right. We don't exactly know what is underlying this micromanagement of emails and storage methods and other nonsense that are outside the scope of truly what they want. They want money like everybody in business. They want success, they want reach. They want important metrics that we can clearly define. And I think refocusing around that and saying we are all super laser focused on getting there, why is this important? Help me connect the dots.
A
And I have found. Well, so first of all, Morgan, even though you were joking or maybe not about utilizing this with Jack, your husband, for those who don't know, that is actually a pretty astute observation, which is that this problem shows up in every part of our lives where somebody gets fixated on a thing that is not actually the important thing that they care about. Right. Like, yeah, like Jen and I recently. Jen, my wife and I recently had a. It was like she. She got very upset over a broom. And. And so I. It was, whatever. It's a long story. They wanted to throw this broom out because it had been used outside. But it wasn't about the broom. This is the point. Like, eventually that's what I had to do is like, I was like, this is not about the broom. What is this about? And what this was really about was like, she was extremely stressed out and she felt like I wasn't helping. And so anyway, like, we need to get under that. And I think that that will manifest in different ways in work and business than it will at home. But it's the same thing, which is that if somebody is acting in a kind of irrational way in which they're focused on something that doesn't seem that important, it is likely because something else is happening. And the problem, by the way, might be really internal to them. And then it's about understanding, like, what are their internal stressors. I'm reminded now of I was hired to do a couple career coaching sessions for this fast growing tech company. And I'm on the phone with their head of. I can't remember, head of HR or something like that. And usually when I get hired to do some kind of speaking engagement, we have one prep call and that's it. And then the event happens. And in this case, there were like three or four of them. And she kept coming Back for more. And I could tell on these calls, sometimes the CEO was on the call. Everything that I was saying was like, somehow not landing with them, like, they were getting nervous. And she kept emailing me and wanting to refine or return to or like, maybe we can set up some questions ahead. Like. And I just couldn't figure out what was going wrong. Like, why was I unable to connect with her in a way that every other client seems to be easy? And at the start of the next call, that's basically what I told her. I was like, you know, look, I'm happy. I said, I was like, look, I'm happy to have as many calls as you need. My philosophy is my job is to make your job easy and to have a great event. And I will do whatever that takes. But I want to let you know that the process so far has been very unusual for me in that I'm usually having one call with a client and we just settle on the kind of general thing that I'm going to do, and then they trust me to execute it. And I've been doing this a long time, and I appreciate that there is a level of trust involved here, but I, you know, I'd like to think I know what I'm doing, and I think that the reason you should pay me is to make your life easier. So can you explain to me what it is that you're trying to accomplish that we haven't accomplished yet? And her answer was amazing. You want to guess? Just take a guess.
B
Where would that question again? Because it was so good?
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Well, the question was, what are you trying to accomplish that we haven't accomplished yet? Like, what is driving these constant returns to process and to. Let's try to kind of micro schedule this event in a way that nobody else usually does with me. What would the answer be?
C
It was their first time doing it.
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That's close.
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Nicole, what do you think? Peace of mind, assurance.
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It was their first time paying someone to do it.
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All of these answers are wrong.
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Maybe, but they're all.
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But they're like they're on the path to correct. The answer was because she's new at this company. She's very experienced, but she's new at this company. This is the first time she's doing it at this company. And there is a problem at this company. And the problem is that nobody understands what leadership wants and she cannot figure it out. And there's a tension throughout the company where people will do things and then it will get to the higher level and then People will be upset or they'll say that that's wrong. And this woman who I am dealing with is, is feeling extremely unsteady. So what keeps happening is that because she is unsure about her own decisions and what is going to actually pass the bar above her, she has to keep coming back to me and thinking it over and thinking it over and thinking it over. And I think that that shows up in a lot of businesses. I mean, I remember Nicole, did you ever write for like women's magazines? Did you write for like Cosmo and Marie Claire?
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Yeah, yeah. Red Book, Rest in Peace.
A
Did you run into crazy micromanaging processes at these magazines?
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I don't really run up against this type of stuff because I feel like I just don't engage with it at all. So I just don't have any strategy. So I don't really serve myself well. Nitty gritty process. But probably yes.
A
Yeah. If you were willing to come down to earth where the rest of us live, you would have experienced this. So Jen, my wife Jen, used to write for them all the time. A lot of these magazines don't exist anymore, but it was the most maddening process. The first thing you'd have to do is write an outline without having done any research for the story. And then you've got to work with the editor and revise the outline and then make a first call and then revise it again. And it was like over and over and over and over. And it was absolutely crazy the amount of pre work that went into making a basic article in a magazine. Whereas if you write for me in a magazine, then we just decide what you're writing about and then I just say go forth and send me a draft. Right. I couldn't figure this out until I became friendly with some of the editors there. And then I learned the answer. The answer is fear. These magazines have layers and layers of approval. And so the editor you're working with will ultimately have to pass their work on to the person above them who will ultimately have to pass it on. Person above them. And there isn't a lot of communication throughout the process. And so instead you have to get to a certain stage of development with an idea and then pass it along to the person above you, not knowing if they're going to like what you did and if they didn't like what you did, then you're going to feel like you look like a screw up in their eyes. And so over time, because there isn't good communication at these magazines, this process was created that Essentially tries to mitigate risk for everybody at every stage who works at the magazine. Right. So the reason that the lower level editor. Editor. Wants an outline and then wants you to revise the outline is so that she can eventually show the editor above her who can possibly show it to the editor above her, and then they can all trickle down their feedback and then they can pass it along to the writer who then does the whole thing over again. And it's crazy, but I think that this also explains a lot of why people have bad processes, because there ultimately isn't a good internal communication system happening, and that's manifesting in madness. And so another thing that could be happening, Morgan, is that you could just be talking to people who are ultimately unsure how to engage with or bring this project into their larger organization. And so they're stuck trying to figure out some system that will, like, mitigate risk for them. And again, you won't know that until you just say, what is the reason that you're focused on this?
C
Yeah, that is so useful. I feel like I know exactly what I'm gonna say to them in the next meeting. And I came into this conversation being like, am I the asshole? Am I? Do I have these crazy expectations? But also because the three of us have it as a team, don't have these granular processes, I'm now going to infer it's because none of us are scared of each other and we all trust each other to do our job.
B
And you just said trust. And that's actually what I wanted to pick up on. Because, Jason, when you talked about letting your writers go forth and prosper and write, that's because there is a certain amount of trust. And I think what was missing in the, you know, game of telephone within the corporate ladder structure was trust. And so maybe we can improve on some of our processes. But I think that the positive analysis of a lack of granular process is trust. And maybe they're reporting to somebody who doesn't trust them as much as we trust each other. And that's a them problem, not a you problem. And you can also always blame it on me.
A
That's true. That's a good strategy.
C
Okay, now I have two possible responses.
A
Yeah, blame it on Nicole. I blame a lot of things on Nicole just on my day to day life.
C
Yeah, the broom. The broom with Jen.
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The broom that.
B
Yeah, it seems.
A
Yeah, Nicole was really obsessed with that broom. So you got to take it up with her.
B
It's not about the broom. It's not about the Dropbox. What is it about?
A
What you need to solve for. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.
B
Pfeiffer, and me, Nicole Lapin. Our executive producer is Morgan Lavoy. Do you want some help? Email our helpline@helpwantedoneynewsnetwork.com for the chance to have some of your questions answered on the show. And follow us on Instagram @moneynews and TikTok @moneynewsnetwork for exclusive content and to.
C
See our beautiful faces. Maybe a little dance?
A
Oh, I didn't sign up for that.
B
All right, well, talk to you soon.
Money News Network
September 2, 2025
Hosts: Jason Feifer (Entrepreneur Magazine Editor in Chief) & Nicole Lapin (Money Expert)
Producer/Guest/Callee: Morgan Lavoy
In this episode, producer Morgan Lavoy brings a work challenge to hosts Jason Feifer and Nicole Lapin: How should you handle partners or teammates who get lost in micromanaging processes and granular details, often at the expense of big-picture goals? The team dissects why "process-obsessed" behavior happens and offers practical strategies to address it, emphasizing the importance of trust, clarity of purpose, and honest communication.
(12:29–13:26) Morgan notes that granular processes seem to give her partner a sense of control in a fast-changing industry, as well as calm for some team members—though it has the opposite effect for her.
(23:57–26:50) Jason draws on examples from magazine publishing, where layers of unnecessary process exist out of fear, a lack of trust, and poor communication.
(09:39–10:15) Morgan’s initial idea: pre-set hard time limits and clear agendas to avoid the minutiae.
(13:26–17:41) Jason recommends a negotiation-inspired approach:
Try to surface the real concern behind the behavior using open questions:
Ask partners to articulate the reason for their process fixation.
(26:50–28:04)
The episode is conversational, empathetic, and laced with humor ("process assholes," gentle ribbing, relatable analogies). The hosts maintain a supportive, constructive tone, balancing honest critique with actionable wisdom.