Why Do Great Leaders Make Terrible Bosses?

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About 6 months into my first year of business I was offered what I (incorrectly) thought was a sparkling diamond of an opportunity.

One day, an email landed in my inbox asking if I had space to take on a new copywriting client.

Specifically: a client who was a personal hero of mine. I’d read their books, watched their videos, and devoured everything on their email list.

Even more specifically: a client whose work I admired so much, when the phone rang for our kickoff call, I had to take three deep breaths before I answered because my hands were shaking so violently.

“You like me! Right now, you like me!”

(Me??? A 22 year old n00b?!?!?! Working with this client? This could be big for me. HUGE. LIFE CHANGING.

I could be the next writer on this client’s list that they make industry famous because I’m just soooo cool and talented. Oh god please please please, I wanna be cool and talented so bad.)

“Good luck… and don’t f it up,” said the RuPaul angel that lives on my shoulder.

And you know what happened, Patty?

Oh yeah. I f’d it up.

In fact it would go down in my personal career history as one of my biggest client bungles ever.

Okay, maybe not so much now

I was so green I didn’t really understand the flow of the industry, or the strategies behind empires like the one this client was running.

So I wound up missing assignments due to my unfamiliarity with the project management software and asking, according to the client, “too many questions”.

I was fired from the project in a matter of weeks.

I got the email about 2 AM, and I sat on my bed in my tiny apartment in Miami and sobbed until my head ached, humiliated and furious with myself.

That was it. I wasn’t cut out for this. I’d screwed the biggest opportunity of my lifetime, and there would never be another one like it.

Fool me once…

THE GOOD NEWS WAS — as I’m sure you can imagine — that fear was a crock of bullshit.

Eventually I’d get back into the saddle, and while no industry behemoths would ever write long emails and notes about me to their gajillion-person email list, casting me as soooo cool and talented, I managed to make my way anyway.

Along the road, I’d relay this story about my biggest client bungle in “Pls don’t tell anyone, but…” text exchanges between confidant colleagues, and quiet corners of conference hotel bars.

And eventually, whispers got back to me that I wasn’t the only one. Not by a long shot.

This client apparently blew through writers at a record pace, and a lack of information followed by abrupt dismissal was not at all an unusual pattern.

As years went by, I began to think: maybe it wasn’t just me being young and dumb after all…?

(Well, I was still definitely both of those things at 22. But maybe the failure was shared — and it wasn’t ALL tied to the fact I was a waste of space in those early days.)

So imagine my surprise when I heard from this client again, years later about another project.

But fool me twice…

Two thoughts entered my mind:

Thought 1: “Oh man, this is my second chance. This failure has been bugging me my whole career — but if I blow this out of the water, I can restore balance to The Force. I can still be so cool and talented, at last!! REDEMPTION ROUND!”

Followed closely by Thought 2: “Oh man… did this client just chew through allll the other writers in the industry, only to come back to me? That can’t be good news.”

And guess what happened next?

Oohhhh yes friend. It, once again, did not go well.

Only it DEFINITELY wasn’t me this time.

Maybe shoulda seen the writing on the wall

After weeks of work (at least two of those spent arguing about my contract pricing, and that I required a large chunk of my fee up front), research, customer interviews, and carefully designed outlines, I’d heard 0 from the team.

Then, after about half a dozen follow up emails on my end, I was told the project I’d been working on had been unceremoniously shelved.

The end.

At this point I was industry battle-hardened enough to wind down the relationship with a resounding “Harrumph”, and without my sense of self-worth entirely dissolving — but I couldn’t take the feeling that I’d been tricked. Again.

And for a long time, it made me extremely bitter.

But it’s hard to see with stars in your eyes

The most interesting thing about this story, in my opinion, is the fact that almost everyone in the field has one like it.

The industry famous client swoops in with an inquiry. We reply, starry eyed and excited, ready to do anything to please them. And the experience goes south quickly.

For a while the disillusionment was almost physically painful for an optimist like me.

I wondered: maybe everyone ultra successful is just kind of a jackass?

Well actually… no.

As a matter of fact, the further along in my career I got, the clearer the truth about this common problem became…

… And it was MUCH more benign than “everyone who builds an empire becomes a trash person after absorbing too much wealth and power”.

It’s not you, it’s…well…not me either

Realizing this truth helped me be more forgiving of past clients (the ones who deserved my empathy, anyway) and, eventually when I fumbled the ball on the “BEING the client” side a few years later, more forgiving of myself.

So: what’s that truth I’m talking about exactly?

**WELL FRIEND, **you’ll just have to catch today’s episode of #HAMYAW to find out.

Now, don’t get me wrong here: some people just suck, period, and don’t deserve your grace.

BUT! Once you reach a certain point in business where your team and output is growing, you suddenly realize have to straddle an entirely different skillset… and it doesn’t always work out the way you’d hope.

And it often requires consuming at least one giant slice of humble pie.

Leader vs Business Person

So head on over to catch the episode to hear the whole story, and let us know in the comments:

Have you seen this “two entirely different skillsets” problem at play in your business, or with your own clients?

What’s your take on it? When is it forgivable, and when does it slide into “inherent moral failure” territory for you?

And hey, I also want to say: there ARE leaders out there who juggle both these skillsets beautifully. But it takes a ton of work to get there.

So, on your own continued rise to prominence, just remember to be gentle with yourself.

Give yourself space to not be stellar at all these Fancy Business Person Things immediately, and learn as you go.

But just remember to do the work to improve. You’re not above it. No one is.

After all: you’ll be somebody else’s hero someday (if you’re not already).

Make yourself one worth meeting.

Write on H


YES this episode does feature Dolly Purrton yet again at around 12:46 — so YOU’RE WELCOME, WORLD.

Episode Transcript

Yeah, I have therapy. I can just tell my therapist that I’ll be a couple minutes late, worst case

Don’t use me as an excuse to not.

(both laughing)

I will not condone this.

(both laughing)

I promise I’m going to therapy ma’am, okay?

(upbeat hip hop music)

Welcome back marketing nerds of the world.

It’s time for another episode of HAMYAW, and today we wanna talk about something that was a bit of an awakening for me when my business started to grow and I started working with bigger and bigger clients. We wanna talk about the difference between being a good leader and being a good business person because there is often a disconnect between the two and I’m gonna start and open this before I hand the microphone to Margo.

Thanks for your patience, Margo.

I wanna open this by actually just telling a brief story about an experience that I have which I think is fairly universal in the online business space, especially when you’re a subcontractor is you start climbing the ladder of those clients, things start getting better, you start working on bigger and bigger projects.

And then you notice something while you’re working with these huge names who have all this money and are doing all these sales, and serving all these people and their businesses on the back end are disasters in some way. Either it’s disorganized, or the team doesn’t know what they’re doing or you can’t get a hold of them and it’s really reactive.

Yeah, they’re reactive.

It’s a really disillusioning moment to have and I think it really happens across the board but the reality is not everybody who is a good leader, a good creative, even a good producer of content is necessarily good in a managerial role or good in a CEO role.

They make mistakes just like all of us do, just because you’ve hit seven figures doesn’t mean you’re not a human being prone to error let me tell you. But we wanna dig into this a little bit today and just talk about, what is the difference between a good leader and a good manager and business person, and sort of what can we do to start to fill the gaps?

Before we do that Margo, are you a better leader or a better manager?

(Hillary chuckles)

I think everyone who’s worked with me would be like “Leader”

(both laughs)

“We love Margo, she’s a good leader”.

That, very that.

It’s our new backhanded compliment but we should parse out that like we are not Brené Brown like there’s leadership definitions here of being a CEO and being a leader. That’s not what we’re talking about. I think we’re talking more about like thought leadership, content creation, being the leader of a movement and of your audience and being better… 

Inspiring people.

Yeah, inspiring, and like that version of being like really amazing, powerful figure versus the day-to-day mechanics of operation. And they’re not the same skill. And so I like you was disillusioned. I also believed that I had all of the skills…

Oh me too.

And I’m like shocked (laughs) to discover then they weren’t transferable.

I hadn’t tried to use the skills yet but I was certain that I had them and I would do a much better job in there.

Exactly. But how you obviously not see these very obvious blind spots that you have and it’s like, “Well it turns out there’s a reason they’re called blind spots.”

I’m very good at pointing them out in others but…like my superpower.

No, it reminds me of, I think you guys all, if you have friends that were in med school or doctors now one of the complaints I would often get from them, is that if you wanted to move up in your career as a doctor which is a clinician, someone who works with people or even a researcher who’s conducting scientific research the movement upwards on the ladder is management.

And you can see in this case, the obvious disconnect for them, the ability to diagnose and treat someone and work with people needing to manage a system or finances or difficult behaviors like they’re completely separate skill sets. And yet this is considered the linear ladder. And there are so many, it’s ridiculous when we’re talking about it, but when you’re in it, like that is just considered the norm for people. And there’s no one helping you navigate the transition.

And I would say that’s the same in so many of our industries where the thing that got you to where you are is a completely separate skill from what you need to move forward.

Yeah. We see this jump kind of happen at multiple stages in the entrepreneurial journey where it’s like, “Okay, you’re starting your business. You have some clients, they’re doing well. Perfect! ‘time to teach’.” And you’re like, “Oh great.” And then you’re like, “Oh no, this is I don’t have the skills for this at all.”

And that was like my first, I think, slice of humble pie in business is putting together something. It wasn’t that I consciously thought like, “I am going to be a better teacher than all these people,” but then I got up in front of the room and I was like, “I’m not prepared.” Like “I’m not, I don’t know what’s going on here.”

But I think that was so important that it’s like anything else in business is that you have to recognize that it is a journey and that you need to build up these skills. And I think what I don’t want to say is let’s forgive everybody who’s running a seven-figure business, who’s kind of shitty a manager and doesn’t want to work on their blind spots. And it’s true they are. But there are some people who aren’t great in that category. We shall not name names.

But I think what we wanted to talk about and what we really wanted to underline here is the reality that we sometimes forget that these are not the skills that got us started: Is managing these huge teams, is scaling. And you really need so, so much support. And I actually wrote a post on Facebook today, personally. I also tweeted it, but it was basically like everyone thinks the hardest part of hiring a team is hiring the right people but it’s not.

The hardest part of hiring the right team is knowing when to put your hands on your head and just let your team do their goddam jobs instead of tinkering with everything.

And this is a habit I’m trying to break because personally like I made my living writing, right? I made lots and lots of money doing it, I used to market only for myself, I used to be a team of one with a VA, that was it. Now I’m a team of three with an OBM and a CMS and things have grown.

But I think that what I didn’t realize at the time was that having people on and paying them to do the work is not something that you should be hovering over. You can’t be precious if you want to move forward. If you want to outsource things you have to learn how to let people do it, and how to let people make mistakes and how to see what happens if they take the reins.

And that, I also noticed on one of my launches recently where my CMO Hunter (fabulous copywriter she is so great, she repurposes a lot of my stuff). But I was like, “you know what? I’m not going to tinker with the rest of these emails.” Like I think that they’re awesome. I know that they’re good. Just because I didn’t, you know, have my right every single word of them does not mean that I need to go in and tinker.

So I’m gonna put my hands on my head and just let them ride. And it went great, but it’s that discipline. And I think Mike Michalowicz, if I think that’s his name, has this book called “Clockwork” where it talks about letting your team own their section and letting them make mistakes versus doing the “bug the shit out of me” method, where it’s like, “Okay, just if you don’t hear from me just bug the out of me until I give you an answer.”

Like you need to give people that runway. And then it’ll be incredible even though it’s a letting-go skill it’s essentially a skill of passivity. It is so, so hard to build that muscle and have that trust because frankly, I got frustrated with this in the copywriting world, or people were like, “Well I can’t possibly just let anything go. You know, it’s my voice, people are gonna know.” 

I’m sorry, unless you are a Pulitzer prize-winning novelist, chances are, you can have someone mimic your voice and it’s going to be okay.

Not mine, Hillary!

Your work is not gonna take… My voice is very special and I had this problem so I could speak to it where I was like, “They’ll know it’s not me.” And frankly, maybe, but at the same time is it going to tank your results? No, is it going to make it easier for you to show up and focus on your shit? Yeah, so that’s my role.

I want also to argue even if you are a Pulitzer prize-winning person, copy’s a different skill. In the writing world, people often think because they have written a sentence before that they are qualified to then edit and that they need to be doing your job.

Like, I’ve taken classes in accounting and I have never tried to tell my bookkeeper they were wrong or tell my accountant that he was wrong. Never in my life. I’ve just asked for clarification on something. I’m paying them for their expertise but it doesn’t translate to things like marketing and it doesn’t translate to things like writing in part I think, because we feel like we can do it. 


We feel like it’s a part of who we are. My aunt is a teacher she’s retired now, but she said that often you would find administrations, be like, “Oh this person has a PhD in history.” And she would look at them and be like, “Why does that mean that they can teach 17 year olds? Like what does one have to do with the other?’ Everyone thinks that that’s a logical jump and she’d be like, “You know what? In the end I stopped fighting because then they get in that classroom with the 17 year olds and they can’t do it.”

And that’s when you start to realize that teaching is a skill, that curriculum building is a skill. That facilitation is a skill and you go to school for educating and to understand these things and they don’t value it until they get in it. And I think that is the same thing that you’re seeing happen with management is that you think, “Okay, well once I reach this level of proficiency in my subject matter expertise or in my ability to corral an audience, or my ability to dazzle people on stage and perform that that should somehow transfer to something else,” until you try and do it.

I think the more important piece of this is not that there’s a disconnect, but that we recognize it. And then you do your due diligence to get there. 

And then there’s a second step. So first do your due diligence, like right now you and I are in the teaching world like trying to really unlearn everything we’ve ever learned. I’m going to do it a separate aside on that. It has been so taxing, but there also comes a point with certain skills like bookkeeping for example, I tried to learn that one too. And I was like, “I’m outsourcing that”. Like, I don’t touch it. I don’t even care if my bookkeeper makes mistakes, don’t make me look at it. I don’t know what that is. Just figure it out.

But I know enough to know that it’s not a good use of my time because I will spend so many hours trying to understand something that is not my proficiency. But at least I know enough to know who to hire and if that person’s good enough.

When it comes to teaching I don’t want to hire it out. Like, that’s something that I was like, “Oh this is something I could get better at. Let me find out how.” And so knowing the difference between the things you absolutely should not touch and those weaknesses that like aren’t worth getting better at.

Just being proficient enough to be dangerous, but like, you know what’s a bad use of your time. But let the experts handle it, take off the reins, and then enhancing your strengths on things that you might not be familiar with but you can build the muscle.

Yeah, absolutely. And I think that the divide is so important. What’s so interesting is that what classifies someone as like a good inspirational leader and a good like personality, it’s just a totally different skill set to what makes someone a good manager and CEO. Because with the personality and leadership, you are very eloquent. You have really good ideas. You can explain things to people very well. You know how to put some kind of like step-by-step together.



I mean, who am I?

Not me. And then stage presence, which builds all of this trust. One of my favorite YouTube channels, “Philosophy Tube” by the amazing Abigail Thorn. there’s this whole episode that she did called “Who’s afraid of the experts?” And it’s basically about the fact that the actual experts in let’s say immunology, for example, aren’t really media trained people.

They don’t really have a face. They don’t want to be visible. So they’re back there doing the work. Whereas you have someone who’s media trained who has that presence, who knows how to talk to the press, who’s at the forefront. So they’re kind of like the leading voice, but they’re not actually the one doing the things behind the scenes but we equate their presence with the fact that they’re here and they’re also there at the same time.

So we see these people with the stage presence – it’s awesomeness, and then of course it’s disillusioning to realize in the backend that they’re not really comfortable outsourcing, they’re still kind of a bottleneck and obsessive about their work. They don’t track details, or there’s someone on their team who’s supposed to…or there’s so much going on that it’s not working right now.

Like a million things can be going wrong here that you just don’t notice here. But just because here is good, also doesn’t mean that here is bad. It is again, two totally separate skill sets. And I know for me that I’m actually more hands-off on my team now than it was when it was one person.

Like right now, my strengths are creating new content showing up, giving my talks, teaching, serving my clients. Whereas my team helps create that omnipresence, helps create that content helps me put my launches together.

And if I were the old Hillary, it would be almost impossible to get anything done. ‘Cause, that would be like, “Okay, I’m just going to write all the sales emails. Everyone sit over there, I’ll let you know when I’m done.” And then it’s three o’clock in the morning, the night before a launch, and I’m like, “Guys, please help me.” So it’s been a real test for me because I knew I had a gap. Zach knew I had a gap, my husband, he was like, “It’s a [inaudible] thing, stick with it.” 

We’ve talked about this on the show before where we want to be everyone’s friend. And you know, it was hard for us to let go of things sometimes. 

“Oh, hi Dolly! 

It’s hard for us to really kind of bring the pieces together in that way and trust somebody to take care of our businesses for us. But if we want to grow we’ve got to learn how to let that go. And we have to make sure that we’re growing at a pace where we can kind of sustain this build and this skill-building. And that’s sort of what I’m focused on this year. But I think some people just grow too fast or are so into their presence that they forget about the skill.

Oh my God, hello! So it becomes obsessive. Like I’ll speak for myself, like misperceptions of me,


Like branding, was so important. So like part of its control, part of it is like wanting to control what other people think, which like is not possible.Realizing that I was the bottleneck on top of the funnel stuff. It was like such a huge sobering moment. And I’ve chosen like creative ways to outsource that. And at first, I thought of it as like a moral failing. I was like, “Oh, well, if you can’t do (inaudible)”

It is not a moral failing!

I was like, “No, it actually turns out you’re smarter, if you have, you can figure out that you can outsource it. So like one of the ways I’m outsourcing it is partnerships. So I’ve done partnerships where I try to have as much creative control as possible. But there’s one product that I launched where I totally forgot about the artwork because it was all virtual. So I was like, “Oh, it’s an audio file. People will just download it, it’s not a big deal.”

Nope, there was like a cover. And I looked at it and I was like, “Ugh!” It looked like the 1990s, like, nobody even tried! The font doesn’t even make sense.” And I’m looking at it, I was like, “Well, this is a travesty! Everyone’s gonna think that I’m some hack,” and it turns out no one cared.

It did not affect whether they listened or not. It didn’t drive or reduce traffic because there are so many other factors besides that one thing. And like our creative control is important. I don’t mean to discount that because I yeah, definitely not. You do need to pay attention to the details when you are in this position that matters. But as you are building, knowing which fights to pick – this would have been a waste of time at this point in my career to die on that hill.

Now maybe in 10 years when I have really, really clear brand guidelines and they violated them, for example, okay then, but like also, the onus was on me to have like noticed it in the contract, which I did not. So like, if anything, it was a better use of my time to not have to hire a designer or try and do it myself, like an idiot which is totally what I would have done, right?

And then I would have gone back and forth with the designer and all it is is a frickin’ icon and it can be updated at any time. It doesn’t matter but for launch, my ego was so wrapped up in it. I’m like, “Oh my God, people are going to see this. They’re going to see this, what are they going to think?” And it’s like, “Well they’re not gonna think anything. They’re gonna move on with their lives.”

That’s so true.

And I think that when it comes down to, it’s like so we have, we know what the leadership skills are but if we were to talk about the skills over here at the CEO of the business, I think it would be first of all, like learning to prioritize what you own and what you don’t own. And it can’t be everything guys, it just can’t. As much as we want to, it just can’t be everything.

And also like of course, good hiring practices like be willing to pay a little bit more for people who can handle it. And I’ve talked about this on the show before and my team makes fun of me because they heard me on the episode be like, “I am Baby.” And so now (laughs) I’m training and they’re like, “So we know that you are Baby.” But being able to know like what you own, what your team owns, having the systems, like taking the time to put the systems in place and make sure that they work.

‘Cause I feel like a lot of business owners are like, “Yeah we’re in Asana” and it’s a mess, you know? And there’s like all these project management systems that get updated once and are never used again. Like it is just hard to stay on top of that but having really clear systems in your business so that when you bring someone on, you’re comfortable doing that.

And I think most importantly, like learning to put your ego to the side, I think learning to let people own things and make mistakes and be resilient is how you build a much stronger team. And that is the hardest thing to do when you’re a perfectionist and you know, a  micromanager, which I think every creative is in their special way.

Also being wrong. Like I think one of the most humbling thing was realizing that I shouldn’t be doing my own marketing. And like as a marketer, I was just like, “What?  No, this is mine, I will write all the sales pages. I will write all the emails, I will do all the promotion. I will do all the ads, I will do all of this.”

And then it just came into a point where I was like, “No, actually because you are a marketer you are so bad at being objective about yourself. You need to have right of refusal, but after that, you need to like let the experts do their thing and put yourself in content creation mode.”

Yep, no doubt. And own what you own. Like maybe it’s content creation mode, maybe it’s like doing your podcast, maybe it’s like serving your clients, but figuring out sort of someone that you can trust to outsource and then letting them do their damn job so that you don’t become the bottleneck.

‘Cause for me, I think like I have my solid team members, but now we brought someone on for Facebook ads, Debbie Reynolds who’s awesome. We’re going to work with probably Latasha Booth for the upcoming launch of “Hot Seats.”

Like we’re bringing on these other teams to build things and focus on things that none of us own. So I think really getting in that habit of figuring out what do you own? What does your team own? And how can you continue to build these sort of managerial skills as you grow?

This is one of the most important questions you could ask yourself. So you get out of great leader mode and into how do I kind of do both? How do I walk into gum at the same time?

All right, before we wrap up, anything else you want to add?

Yes, this is Dolly Purrton. She’s my new kitten. Thank you all for your patience, and I’m sorry her purring just straight into the microphone, but she’s really excited to be here, and I’m sure it will be a fixture on more HAMYAW episodes.

I think our viewership just went up.

(both laughs)

It definitely did.

Look at that. Subscribe to Dolly Purrton’s channel everybody. 

She really should have a channel.

I know she really should. I’m gonna look in on how to make an Instagram account for her.

Do it, you’re going to be an instant celebrity.

All right, so we talked about the disconnect between subject matter expertise and the ability to teach. We talked about leadership versus management and what why these disconnects exist because they are completely different skills and how acquiring those new skills, one, requires self-awareness.

It requires humility and the ability to work on building up your weaknesses, but also enhancing your strengths and let the other people do what they are good at.

So we want to hear from y’all. Where have you also made this mistake? Where have you reached a certain point in your career where the skills that got you there can no longer take you where you need to go?


Where have you had to eat a slice of humble pie? Tell us how you’re doing on outsourcing. We want to hear all the dirty details down in the comments. And if you like this episode, please like it below, subscribe to our channel and share it with your friends.

I am Margo Aaron 

And I’m Hillary Weiss.

This has been Hillary and Margo Yell at Websites, HAMYAW, and we will see you in two weeks.

(Hillary smooches) 

Bye for now guys.

(upbeat music)

Photo by Juliet Clare Warren

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