Episode 281

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Published on:

25th Apr 2025

Fifty bosses and one big ego | Ep. 231

Episode 231: Do you treat each of your customers like a boss that holds the leash?

⏱️ Timestamps:

00:00:00 - Intro

00:01:19 - CS is not for me

00:02:58 - Who’s the boss? The customer... kinda

00:05:02 - Meeting overload and the myth of agency

00:05:57 - Power dynamics and setting the agenda

00:07:51 - Misaligned roles and the wrong career fit

00:09:13 - Why teachers turn to customer success

00:10:13 - Seeking creation and completion in CS

00:10:36 - Context matters


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🤝 Connect with the hosts:

Dillon's LinkedIn: https://www.linkedin.com/in/dillonryoung

JP's LinkedIn: https://www.linkedin.com/in/jeanpierrefrost/

Rob's LinkedIn: https://www.linkedin.com/in/rob-zambito/

Transcript

[Rob] (0:00 - 0:25)

What do those all have in common? They're all client-facing roles. I mean, look, it just comes with the territory.

It's like you said, JP, like, you know, could you imagine if a garbage person the first day on the job, garbage engineer, whatever they might be called these days, shows up and is like, do you guys know that we deal with trash? And it's like, of course. Did you read the job description?

[Dillon] (0:34 - 0:45)

What's up, Lifers, and welcome to The Daily Standup with Lifetime Value, where we're giving you fresh new customer success ideas every single day. I got my man, Rob, with us. Rob, you want to say hi?

[Rob] (0:45 - 0:46)

Lifer country, let's ride.

[Dillon] (0:51 - 0:58)

JP's so disappointed. And we have Jean-Pierre with us.

JP, can you say hi, please?

[JP] (0:59 - 0:59)

Playoff.

[Dillon] (1:01 - 1:16)

And I am your host, Mr. Unlimited. My name is Dillon Young. Boys, it's just the three of us, and I'm going back to the well, baby, only because I've got a real spicy meatball for you guys today. Are you ready?

Are you ready for this?

[JP] (1:17 - 1:19)

I need some of that. I forgot. Come on.

[Dillon] (1:19 - 2:58)

Oh, okay. Okay. Take it easy.

Don't swear at me. All right. This is on Reddit.

Of course, that's what I mean by going to the well. If you know, you know. And if you don't, then get educated.

Okay, Dash Masterpiece Dash:

Maybe a little clickbaity, but I think the body of this post actually delivers. Okay, so there's a number of bullets here. I can't read this whole thing.

It's very long. Maybe I'll link to it in the show notes, but I'll read some highlights. Number one, number of, quote unquote, bosses.

I hate having 50 plus bosses. Think about it. Each one of your clients is like another boss, always asking you to do something.

Multiply that by 50 accounts, and you've got 50 bosses. CS is one of the only jobs in tech where you have that many bosses telling you what to do. Do this training.

Fix this implementation problem. Send me a copy of our contract, so on and so forth. Number two is related, and then I'm going to stop, and JP, I saw you.

Maybe you were mad, sad. I don't know, but I'm going to let you get in here. Number two is your bosses can't promote you, but they can complain about you to your actual boss.

I hate how you can drive yourself into the ground helping customers, but all that hard work means nothing, because at the end of the day, they have zero influence over whether you get promoted or not. But don't forget, they can complain to your actual boss, so there's only downside and no upside. JP, hit me.

Yeah, this one- Hey, if you were having a good day, kindly stop it, right?

[JP] (2:58 - 5:01)

Yeah, yeah. The point about the bosses is really interesting, because in one aspect, it makes me think about the involvement of ego. What does that mean?

If you're of a service mindset, do you call all your customers your boss necessarily? But I still get what this person is saying. From the perspective of, if I zoom out, it's like, what am I doing this for, right?

When you have something like, he says, CS is not becoming like sales, but a lot of sales folks, they are driven by the dollar. They're looking for the expansion, the upsell, what have you. We are typically looking for ...

We are attached a lot of times to wanting a certain outcome in terms of revenue, but we deal with a lot of ... We deal with a lot of the collagen in an organization, the connective tissue in an organization. Because of that, it may not go appreciated until something's wrong.

No one is walking around like, damn, I got the best ACLs. It's like, no, until you tear your ACL, then you're like, oh, my ACL is so crucial to my life. It's like, yeah, it does its work in a way that's a little more quiet.

When I hear this, I have a multitude of feelings around it. I think my solution-oriented mind begins to say, okay, is part of this maybe just being able to just suck it up and just do it? Okay, you have 50 bosses, I'm going to do this.

If it hits a limit, it hits a limit and you got to deal with it. Part of me says, as I mentioned before, the garbage men probably hate the smell of garbage. Some people get used to it and they say, well, this money is good.

Some people are like, oh, the smell of the garbage is too much. I got to leave this job.

[Dillon] (5:02 - 5:57)

So let me add in this third piece before you jump in here, Rob. This is number three, a lack of agency. I haven't read this whole thing, but basically they do some crazy math here.

Are you ready? Let's say you have 50 customers. You are expected to meet with each of them monthly, some more, and do QBRs every quarter.

That's 50 monthly meetings plus about 16 QBRs per month. Then add on to that two team meetings per week to, quote unquote, kick off the week together, so hashtag bitter. That's 68 meetings per month.

Now add all the urgent client meetings that come up, let's say two per week to be conservative, and that's eight more meetings. So before your month has even started, you're already locked in for 76 meetings. That's 18 meetings per week.

Now compare that to almost any other role in tech, engineer, designer, marketer, any of them get to start their month with a clean slate and ask, that's not true. How do I want to spend my time this month to be most effective? Rob, how do you feel?

Yeah, Rob, come on.

[Rob] (5:57 - 6:12)

He's in the wrong business. You know what I did? I wrote a random list of just some random jobs off the top of my head.

I wrote down RevOps. I wrote down product. I wrote down an event planner.

I wrote down a waiter. I wrote down my dentist.

[JP] (6:13 - 6:16)

What's that?

[Rob] (6:17 - 6:25)

Your dentist specifically? He's actually my dad. No.

There's the episode title.

[JP] (6:26 - 6:27)

My dentist is my dad.

[Rob] (6:28 - 7:51)

What do those all have in common? They're all client-facing roles. I mean, look, it just comes with the territory.

It's like you said, JP. Could you imagine if a garbage person the first day on the job, garbage engineer, whatever they might be called these days, goes up and is like, do you guys know that we deal with trash? And it's like, of course.

Did you read the job description? And look, I'm sure this person did, and they probably just didn't fully size just how much they just don't like that activity. And that's okay.

But I do think it conveys a fundamental misunderstanding of not only A, the nature of the job, but more importantly, B, the power dynamics of the job. I think this person has a fundamental misunderstanding of the power dynamics of the job when they're calling everyone their bosses. If we really want to do our job well, then a lot of the time, that means having an equal playing field with our customers, or potentially even being in the driver's seat more of the time.

I'm working on a sales playbook right now, and that's one of the key things that comes up in that playbook, is how do you make sure that you maintain the agenda for the call and stay in control and manage time appropriately and set expectations correctly and all the stuff we want our counterparts in sales to do. I'm working on that as well. But yeah, to call the customer my boss, it just feels wrong.

[Dillon] (7:51 - 9:13)

A little strong worded. So it's funny. I mean, they're kind of your boss, but I think a lack of agency is not comparable to the first two, because I think it's a lack of agency that has them feeling the first two.

If they don't have control over the way they're running their meetings, like you said, Rob, the way they're controlling these relationships with their customers, or if they don't feel like they've got the back, their company doesn't have their back when they go and have these customer interactions, then yeah, I mean, the job's going to suck in a lot of ways. But I want to read this. This is a long post, but I want to read this one last passage.

I'm tired of meeting other people's needs all the time. I want to start meeting my own needs. I want to reclaim my time and my energy, and I don't want to be client facing anymore.

I don't even know where to begin. CS Ops, where would I even start in terms of building up the qualifications for that kind of role? What course would I take?

Would a course even matter? This person just is in the wrong job. They don't, their personality type, or the way they communicate, or the pressures of a job where you have to talk to this many people and juggle this many priorities.

I'm not saying it's virtuous or not. Some people just don't like that work. In the same way salespeople don't think what they do is in any way abhorrent to this huge swath of the population.

And I'm not saying I agree with that or not. I just think they're in the wrong job.

-:

I agree. I agree. And I think that there's, you have to, we always are asking customers to go back to the value proposition of why they bought a product.

So I think it stands to reason you can go back to the value proposition of why you're in customer success. What was it that attracted you? There could have been something that attracted you when you initially got there that no longer works.

People grow, people change. There's a lot of folks that, we have a lot of transitioning teachers. Why do we have that?

I don't think it's necessarily because teachers automatically make great CSMs. I do think that there is maybe some crisis around education and around people not feeling like they got into that situation and weren't valued, but maybe through tech they can put some of those same sort of intrinsic skills that they had to use. So they're making the best of their situation. But maybe that outgrows itself once you've been there for a while.

[Rob] (:

I do want to give this person credit. I think they're unpacking their situation pretty well and processing in some meaningful ways. There's a part of the post is about being able to create something concrete with a finite finished product.

I can totally relate to that. That's part of the reason why I fixate on these playbooks all the time is because they give me some semblance of having a finish line, a point of completion.

[Dillon] (:

But it's not easy in this space. I don't think that's in customer success. I don't think that's a customer success value or itch that you're scratching, Rob.

I think that's like a process. And in your role as a consultant, you can do that. In customer success, it's all temporary.

This is just the way it is. Anyway, that's our time. I think the last thing I wanted to say, actually, is call this out, is this is not a universal experience based on the company.

This changes based on your product, your client set, maturity of the company. And so anybody who might be feeling this, also explore that. You want to do customer success at a huge company, maybe, because they'll have a lot more of this figured out.

Your company's going to have your back a lot more, so on and so forth. It changes from scenario to scenario. But that is our time, boys.

Hey, come back soon.

[VO] (:

You've been listening to The Daily Standup by Lifetime Value. Please note that the views expressed in these conversations are attributed only to those individuals on this recording and do not necessarily reflect the views and opinions of their respective employers. For all general inquiries, please reach out via email to hello at LifetimeValueMedia.com.

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About the Podcast

The Daily Standup
Delivering fresh new customer success ideas every single day.
Do you want to know what other customer success and post-sale professionals are thinking about, struggling with, or succeeding with?

The Daily Standup is the flagship podcast on the Lifetime Value Media network, cohosted by Dillon Young, Jean-Pierre "JP" Frost, and Rob Zambito. We're publishing daily and sharing the most diverse and unfiltered array of guests. Tune in to hear industry titans and newbies alike chopping it up, sharing their hot takes, workshopping their current challenges, or just giving Rob another new nickname.

The Lifetime Value Media network is your destination for customer success and go-to-market content.

About your host

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Dillon Young

Dillon is a career Customer Success professional, having done tours of duty in Technical Support, Training, and Implementations as well. He did Sales that one time, but doesn't like to talk about it. Since 2019, he has been a people leader in CS orgs for early stage technology companies, primarily in the financial and human resources spaces.

Dillon founded Lifetime Value in 2023 with the vision of delivering entertaining, educational, and non-biased content to this exciting profession *without* selling (gasp) an ebook.

So far, so good.