#WFU Episode 13:

In this episode we talk about our journeys through the AI revolution:

00:00:00 - Intro

00:03:07 - The farmer’s mentality and AI reliance

00:03:51 - Blind trust in AI and its risks

00:04:52 - AI-generated emails: Overkill or useful?

00:06:17 - Lazy habits and losing the spark in CS

00:08:16 - Correcting AI: A time sink or necessary evil?

00:09:11 - Striking a balance: Creativity vs. automation

00:11:00 - The myth of the perfect CSM

00:14:49 - Personalizing customer interactions with AI

00:17:05 - Handwritten notes and meaningful gestures

00:19:37 - Rethinking customer engagement strategies

00:22:15 - Direct meeting invites: Bold or intrusive?

00:24:23 - Non-responders and alternative approaches

00:27:03 - Bye bye!

And hey, we want to hear from you! What topics do you want us to tackle next? Reach out and let us know. Remember, we’re here to share how We Fucked Up So You Don’t Have To.

Reach out to Melanie: https://www.linkedin.com/in/melanie-faye/

Reach out to Stino: https://www.linkedin.com/in/stijn-smet-%F0%9F%90%B3-330435a9/

Sign up for the Lifetime Value newsletter: https://lifetimevalue.link/subscribe

[Stino] (0:00 - 0:22)

I literally vomit. There is no such thing as a perfect CSM. Listen to me, Annie.

It's a hard knock life being a CSM. It's all about driving value and align your personality into it. So, grab that bucket, build that foundation, and think like there is no tomorrow, Annie.

[Speaker 3] (0:27 - 1:08)

Welcome to another exciting episode of We Fucked Up So You Don't Have To. Get ready to dive into the wild world of customer success with your hosts, Stino and Melanie. Join them as they peel back the curtain on their own mishaps and triumphs, sharing candid insights and practical advice along the way.

Stino, a charismatic head of customer success, brings his unfiltered wisdom to the table, while Melanie, the seasoned customer success manager, offers invaluable career insights. Together, they'll laugh, learn, and navigate the twists and turns of the customer success journey. So, buckle up, and let's dive in.

[Stino] (1:13 - 1:48)

And we're back. It's 2025. B-word.

I'm so happy, and I'm more happy that we're kicking off this year just the two of us, No menagerie a trois. We are back at our normal setting. That doesn't mean, because we have some amazing guests lined up further down the line.

But I wanted to go back to the roots a little bit for the first one of 2025. I just wanted it to be cocooning between you and me.

[Melanie] (1:48 - 1:50)

The original duo.

[Stino] (1:50 - 1:54)

The originals that fucked everything up.

[Melanie] (1:55 - 1:57)

And are still fucking up.

[Stino] (1:57 - 3:07)

And we're not slowing down in 2025. We're not, we're not, we're not. No, so I think it's maybe an interesting topic, because we were going to talk about how we fucked up relying too much on AI.

Although I love, I love AI. I built extensions with it. I use it on a daily basis.

If I have all these ingredients in my fridge that I don't know how to cook, it gives me back a beautiful recipe. But I want to talk about today on how we fuck up on relying too much. Because there is something that we love to call in Belgium, your farmer's mentality.

You know, farmers are like old school, working hard, go on the field very early, go off the field very late. We in Belgium believe that you need to rely on that farmer's mentality, because it's like that healthy, logical thinking. You need to be like, how would you call it?

Down to earth.

[Melanie] (3:07 - 3:10)

Yes, that's what I was looking for. Down to earth.

[Stino] (3:10 - 3:51)

Down to earth. We need to be down to earth. We need to incorporate AI on a healthy way and don't rely to it too much.

Because let's be honest, AI still makes mistakes. Let me start with maybe the first fuck up is that I noticed myself that I blindly almost copy-paste everything from AI. And it's a very dangerous trap, because I've been using it for over a year.

It literally can copy my voice to the nail where I go in. Basically, I don't read it anymore because I rely to it a little bit too much.

[Melanie] (3:51 - 3:53)

But what are you using it for right now?

[Stino] (3:53 - 4:16)

Like everything. Like I said, for recipes, for emails to customers, to do analysis. And it goes that far when I'm now building new projects for Q1, that I was like trying to catch speeds.

And then in hindsight, I look back and I watched my analysis of something and I was like, this is completely off.

[Melanie] (4:17 - 4:17)

Yeah.

[Stino] (4:17 - 4:52)

Didn't really need to receive an email or I flagged some customers that weren't at risk or all of that. And I was like, okay, let me take a step back because AI is great and all, but we still need to, again, be down to earth while we use that. Because AI still makes mistakes, just like we do.

So it's all about not relying too much on AI. Because in all honesty, if I see another post on LinkedIn that says, oh my God, AI is my best friend. I'm going to sucker punch that person.

[Melanie] (4:53 - 6:16)

I think we were all really excited to jump on the AI bandwagon and figure out what it can do and make our lives easier, especially as CSMs. The number of times that I get emailed, and I'm sure this is everyone at every company with the new hottest AI tool. This is why sales should be using it. This is why CS should be using it.

It's everywhere now. You really have to weed through the software and the products to find what's going to work for whether you're a small team or a large team or what that looks like. But also what you said in sending emails, I was using it all the time to send emails to clients and then realized even the language, like, yes, it was picking up on my tone and was getting used to the way that I send emails to clients, but it just got to be so much.

I stopped sending them because it was overkill. It was like overly professional or not really quite my tone yet. And I just can do a better job sending a personalized email based on the goals of the client.

I don't need AI to help me with that necessarily. Maybe down the road it can help me with that, but I'm not using it that way right now because I have access to my client data and I can pull that info out really quickly and send out the email. Not right now, maybe down the road when I need to put together some more in-depth sequences or onboarding sequences, that kind of thing.

I think that's where it can be really helpful. But for a one-off email where you're trying to provide value to the client, I'm not using it for that. I don't see value there.

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

Yeah. Also, it's also all about not getting too lazy. Like, we're getting lazy as fuck.

[Melanie] (6:25 - 6:26)

Yeah.

[Stino] (6:26 - 8:15)

We are. We totally are. Where is the challenge?

Where is the ambition? Because I got also to the point where I'm like, I didn't get any excitement anymore. Like, that's the thing though.

I will run it through AI, it will give me something back and I will send out an email or I will build that automation. Don't get me wrong, I am super excited when I'm using AI to build an automation or an extension, but that's me. But let me tell you this.

How many times are you like replying to your AI? No, that's not what I meant. More my turn of voice.

No, you got it wrong. Do I need to re-explain it? Oh my God, you're stupid.

Let me do it myself. That's the thing. AI can make things faster if it's right from the get-go.

AI slow things down if you give those responses. And anyone that says, I never ever gave such responses, you're treating AI like it was your B-word. Yeah.

Because you're replying with, oh my God, no, that's not what I meant. I meant this. Or no, that's no.

I need more details. I need more best practices. And before you know it, you are in this rabbit hole of 20 to 30 minutes constructing an email in your turn of voice.

And okay, maybe that's good because it remembers this for that further down the line. But in hindsight, you are spending way more time instead of you just sitting your ass, sorry, sitting, I'm super passionate about this, sit your ass down and write that email. Yeah.

It took you 20 minutes to do it before AI. Come on, guys. It's like we all forgot on how to do our job before AI.

Yeah. What happened?

[Melanie] (8:16 - 9:09)

Did you see at the end of the year, there was that trend on LinkedIn where people were asking AI to roast them? So I did that. And it had like half of the thing that it gave back to me was about how I'm constantly correcting it or telling it, no, I don't like that.

Change this, change that. Because like you said, that's all I'm doing. Every time I ask it for something, I'm correcting it over and over and over again.

It happens every time. Every time I ask it for a prompt or help me write an email that doesn't use the word check-in. What comes back to me, I could have just done if I had thought about it for an extra 30 seconds, I can just send it off.

I don't know. I definitely see the value, especially internally with predictors and that kind of thing on the account level. But maybe on the customer facing level, maybe we can do a little bit better job of, I don't know, getting a little creative.

[Stino] (9:11 - 10:33)

Everything? Again, it all drags down of us being too freaking lazy. We are those moody teenagers now.

And again, this is not an episode about breaking down AI. It's more, like you said, Melanie, we first were very curious of what it could do for us. And then we just slept on it or we're sleeping on it.

It makes us brain dead. It works both ways, right? I receive emails from my customer's success managers as well for the tools that we use.

I can tell it if it's something AI generated or not. Like, guys, we need to stop. I'm tired.

If something for 2025, I think my main key is going back to the roots with AI as an amplifier, research material, best practice material. But the foundation needs to come from me. Write a foundation yourself and amplify it with AI.

We need to basically reverse engineer it. Because let's be honest, if anyone listening to this isn't sick and tired of AI, DM me. I want to sit with you.

And explain me your views. Because I don't care anymore.

[Melanie] (10:33 - 10:59)

I don't, yes, I'm kind of stuck too. And every day I'm seeing new posts on LinkedIn and thinking like, maybe I'm behind the times. Everyone's telling us, as CSMs, you need to use AI to save time, right?

To be a better CSM. Like all of these posts that I see every day, I'm like, what am I not using that everybody else is? And they're surpassing me.

And they're a way better CSM now because of these.

[Stino] (11:00 - 11:01)

I...

[Melanie] (11:01 - 11:02)

What am I missing?

[Stino] (11:02 - 11:53)

You're opening up Pandora's box. I literally vomit. There is no such thing as a perfect CSM.

Listen to me, Annie. It's a hard knock life being a CSM. That is a thing though.

It's all about driving value and allowing your personality into it. So grab that bucket, build that foundation and sing like there is no tomorrow, Annie. I want you to listen.

That is... There isn't such a thing as what a great CSM does. If you're driving value on your way, do it.

Do it. I don't want you to hear it. Like that's the thing.

Like if I... Okay, take over. Take over because I'm going on a run.

[Melanie] (11:53 - 12:28)

Okay, so we're saying don't panic. If you're not using AI to do all the things that you're seeing on LinkedIn that you should be using it for. I mean, maybe explore a little bit here and there.

If there's something that you really know can help you in your role and save you time and make you be a little bit more efficient and effective. That's one thing. But if you're just using it because you have a subscription and you're generating emails out of it.

I don't know. It's not making you a better CSM like what we're seeing online. And it almost becomes like you're on like...

What's the word I'm looking for? You're just on your...

[Stino] (12:30 - 12:31)

Way out.

[Melanie] (12:33 - 13:10)

Okay. I wasn't looking for a way out. But you know what I mean?

Like where you're just doing the same thing every single day. You're just using these generated emails and maybe they're saying what they're supposed to say. Maybe they're not because sometimes I find myself copying and pasting and you send it off.

When I was using call recording emails, when you use a call recording software and it generates the transcript for you to email afterwards, I was sending those after calls. And then when I started reading them, I was like, Oh, this is really not even what I wanted to say to the customer as a recap. Like there you go.

No personality. No nothing. Just like a basic...

Here you go. Here's what we talked about. And here's the link to the recording.

[Stino] (13:10 - 13:11)

There you go.

[Melanie] (13:11 - 13:20)

I stopped sending those too. I just spent a tiny little bit more time crafting something, injecting personality because I think they can see right through it. And it's not meaningful.

[Stino] (13:21 - 14:49)

That's the thing though. If you're sitting into a call and where you're like, Let's drive value. Let's drive value.

Sorry, I stopped on the tail of my hat. Sorry. But like, Let's drive value.

And you're sending afterwards an auto-generated dry ass email like during the disconnect. That's what I mean with relying on the AI too much. Ride it out first yourself and be like, Okay, let me structure it more.

Let's make it more clear. Run it through AI and with a prompt saying like, Hey, these are my meeting notes. Can you structure it a little bit more?

This is the message that I want to get across. I'm searching for a clear CTA. Those are the things that you want to use AI for.

That is on how you reverse engineer and amplify it. And again, next time I'm seeing a post that people are saying, This is what a good CSM needs to do because it does this, this and this. Show me the numbers.

Show me the freaking receipts. Show me on how you've done it. And how it resulted.

I want to see numbers. Don't pull it and take it from thin air. I want to see it.

Show me the receipts. It's as simple as that. I'm trying to be as authentic as possible.

And if I use AI like I did with those extensions, which I was super excited about, show the numbers. You have the receipts. If you come up with the numbers that the conversion rate went up 30%, show me the numbers.

[Melanie] (14:49 - 15:40)

Mm-hmm. Yeah. I definitely think that there's value in AI to scale because especially I know I've talked before about how I manage over 220, 230 accounts now.

It's really hard sending 20 or 30 emails a day and still monitoring my book of business and monitoring the health and checking usage and all of that. It's really hard to do that while still crafting these personalized emails that need to go out to clients. So I think there's a balance somewhere in there.

I don't know what it is yet. I don't have access really to any AI tools yet that we've brought on board that will help me do my job better, scaling what I need to do to monitor my accounts. But I know that there are things that exist out there.

Do you use any at Whale, like tools for AI predictors or?

[Stino] (15:41 - 15:42)

I build with myself.

[Melanie] (15:43 - 15:47)

Yeah. Okay. That's right.

You have your ROI calculator that you build.

[Stino] (15:47 - 15:58)

I try to build those automations myself because also I'm a little bit of an anarchist on that part because every AI tool has like seven competitors nowadays.

[Melanie] (15:59 - 15:59)

Yeah.

[Stino] (15:59 - 17:04)

And that got me thinking like if seven companies, AI-driven came like mushrooms out of the ground, why can't I build it myself? Like let me ask AI to build me a tool. That's where I love AI.

But it's totally fair like to find that balance. I'm not saying that you need to write every email from scratch again. It's like it helps like segment your customers.

If you know that you have high-risk customers or just want to schedule a meeting or a follow-up email, you can always use the same prompt. The other thing is then all about prompt refinement. And that's something that I went heavily in on Q4 last year.

Instead of having a new chat for every email that I need to write, it's like really refining that prompt that I can use over and over again without just filling in the details that I want. And that helps. Also, it remembers your tone of voice and it does all of these amazing things.

So instead of doing one-offs, it's best to better your prompts basically.

[Melanie] (17:05 - 17:46)

I totally agree. And I think that you posted on LinkedIn about your handwritten note that a client got, right? Or multiple clients have received now.

So I love that idea. I can see that being like such a nice touch. And especially because a lot of our customers have multiple softwares that they're dealing with.

They're all getting emails. They're being bombarded, right? I think that's a huge, that's such a nice way to go back to the things we used to do.

Yeah, things we used to do and just change it up a little bit. So you stand out, you catch their attention. It's more meaningful that way, rather than just the email that they're going to delete because it looks like you just copied and pasted.

There you go.

[Stino] (17:46 - 17:51)

You have AI tools that auto-generate that literal letter on the mail.

[Melanie] (17:52 - 17:52)

Yeah.

[Stino] (17:52 - 17:58)

You have those tools, you have those automations. So what is it, 90 cents per letter?

[Melanie] (17:58 - 17:58)

Right.

[Stino] (17:58 - 18:42)

But if you incorporate that within your playbooks, which I've done, it's, you're writing that email as well. So why not post it on the mail? You have that same rush.

If you took like 20 years back, we all received letters. There was nothing exciting about that. And then the email came forward.

We're super pumped, like, oh my God, I got an email. I got an email. But every one of us has, if they're, even with an Android or an iPhone, we all have like plus 500 as notification badge because we can't be arsed to open every email.

That's the thing. That is, that's how it is. But nowadays, if you receive a letter, we're like, what is it?

Like Christmas cards. It's super excited to open because you want to know who it's from.

[Melanie] (18:42 - 18:42)

Yep.

[Stino] (18:43 - 19:35)

Everything, every letter that comes in that doesn't have that dreadful paper foil on it that your friend already knows that it's an invoice. Yeah. So if it's just a normal letter that doesn't have that plastic foil, you're like, oh, what is it?

I want to know what's inside, right? Because also everything marketing related is no longer coming any via mail because all those companies switched to email. So you're not afraid anymore that it's marketing material because we, people aren't investing in that anymore, which is totally fair and which is fine.

Like I get companies can't invest in that anymore. As a thing though, there is something cool about traditions, can use AI to amplify, to help you create that letter. It only takes two seconds to mail it via an online tool.

[Melanie] (19:36 - 19:36)

Yeah.

[Stino] (19:37 - 19:39)

Sometimes we need to just go back to the words.

[Melanie] (19:40 - 20:13)

The key there will be that, you know, how like when you send an email, you can see if it's read right away, you expect a response right away. You expect the client to book a meeting with you right away because it's instant, right? So it'll be kind of interesting to see what happens with your letters and how long it takes that to actually turn into the outcome that you're asking for in that letter, right?

Like if you're requesting that they book time with you, how quickly is that going to get done or is it? It'll be interesting to see. I guess, do you have any stats on that so far?

[Stino] (20:14 - 20:31)

So far, yeah. So the thing is that email in all fairness, that letter isn't going to get sent out as a third point of contact. So the thing is the first one is of course email because for now we only like install it in our high-risk customers.

[Melanie] (20:32 - 20:32)

Okay, yeah.

[Stino] (20:32 - 21:34)

So the first one is an email, of course, because that's the easiest trade. The second point of contact would be a phone call because again, that will be quicker. But then the third one, if all else fails, is that letter.

And what we've done is create a separate meeting link. So not my generic meeting link, but really a meeting link that I know that if it scans, even if it's not booked, it also tracks like the view rate. And from the 15 letters that we've sent, I have five meetings booked, five are still on the way.

But if I look at the amount of the meeting page as being opened, it's a little higher than those 15. But I also think it's because like, ooh, this is fun. And the people are showing it around.

So in that sense, the meeting link has been viewed like over 25 times. So in that sense, that's good. One out of five, or I suck at math.

But like, it's a good thing for meetings. Like it's cost me $1, literally $1 to get a meeting on the books.

[Melanie] (21:35 - 21:47)

And you've got five meetings booked now that you did not have before after emailing, after calling. So your third strategy, that's what got those five out of, yeah.

[Stino] (21:47 - 21:53)

It cost me $1 compared to the MRR that the company is generating. It's like nothing.

[Melanie] (21:53 - 21:55)

Yeah. Interesting.

[Stino] (21:55 - 22:10)

And that's what you want to do. And then my fourth, but this is more controversial and I'm still like on the fence of actually doing that when that letter fails. It's like basically getting a meeting scheduled.

Like no questions asked, just invite them to the meeting.

[Melanie] (22:11 - 22:14)

Oh, picking a day and time and doing it. Yeah, I've done that before too.

[Stino] (22:15 - 23:30)

Yeah, I'm a little bit on the fence, but I do think like if you get the messaging straight in the invite, I think they would appreciate it as well. Email can land into spam. The phone call, you can decide to ignore.

Letter as well, if you're not a fan of a letter. But the meeting invite is something that you will always see in your calendar. So in that sense, that will be the fourth that I want to try out.

I've done this in the past, but I really want to make it a thing for like high risk customers with a high MRR. Yeah. Because I just want to know.

I've tried it three times. This is my fourth and last attempt. If you want to churn, just tell me.

Because I'd rather you telling me that you don't get value out of our product, which again is totally fine. That's a conversation for another day, but it's totally fine to let go of a customer if they don't have any value. Again, conversation for another time.

But that being said, with a calendar invite, I would just want to like really make it sure like, okay, we're at the crossroads. Or after this, I completely get off your back and you just pay and I will see when you pop up. Or let's get together and start fresh again.

And that is basically the crossing point for a matter.

[Melanie] (23:30 - 24:23)

I tried that too, and it did work for some clients. But I had a whole segment of clients that just like were the non-responders, right? They don't book calls with you.

They have low, they're at risk. And then what I did was I created a survey and I sent it out to them. And it had several questions on them.

But one of them was, how do you like to communicate with me? Do you want a one-on-one call? Do you want a lunch and learn?

Do you want video? Like what do you want so that you're going to continue to learn and consume the information that you need to be able to use the product? I sent out maybe like 50 surveys and got about 30 something responses back, which is pretty decent for these non-responders, right?

Not one single customer wanted a one-on-one call. Zero percent wanted a one-on-one. Everybody else was like, I'd love to learn from what are other people doing?

Let's have a lunch and learn.

[Speaker 3] (24:23 - 24:24)

Let's have an office hours.

[Melanie] (24:25 - 25:02)

Or I would love this video content. If you have that, give it to me that way because I don't have time to meet with you. I prefer to learn on my own time when I'm not like being bombarded with questions by you or you're trying to figure out why we're not necessarily where we should be.

So sometimes it's just like a thing where they just need to be able to go at their own pace. They still want to learn and you just have to give it to them in a different way. That's not forcing them into a one-on-one call.

But eventually coming back to that, obviously we're not going to let them go forever, but that's what I did and saw an increase in usage.

[Stino] (25:02 - 25:04)

And did you use AI for that?

[Melanie] (25:06 - 25:46)

No. However, I did create... So it was just a video series.

That's what I did. And then we also had like a little webinar time where people could join and ask questions. But that's where I got all of these high-risk accounts looking at these videos, responding back saying, thank you so much for this content.

There's comments all over the videos and they joined the little webinar where they could ask questions. That's what we wanted. They're not showing up to calls.

They're not booking calls, but they're coming in this way, in a way that works for them. And they're not feeling... What's the word?

They're being forced to do something.

[Stino] (25:47 - 26:22)

Yeah. So you used AI to amplify it. Our point, exactly.

I'm not saying that we're right, but it's something that we need to be cautious about because the only thing that we live and breathe is AI, AI, AI, AI, AI. And also if you see those posts, please take that with a grain of salt. Don't be afraid to ask those questions.

Show me developers. Show me the receipts. Can we jump on a call?

You don't need to publish them, but can you give me some high level numbers?

[Melanie] (26:23 - 26:32)

Yeah, because maybe we're wrong. Maybe there's something we're missing here and it's just gone over our heads and everyone knows something we don't know. Please enlighten us.

[Stino] (26:33 - 27:03)

Okay. Maybe there are like two good CSMs on this entire planet. Who made you in charge thing?

Who is a good or bad CSM? Like we're all driving by. That's the thing.

We're all carrying the title of a customer success manager, so we're doing something right. Who made you in charge saying that we're a bad or a good CSM? I love my job.

I drive value for the company and we do some decent numbers. Well, we're doing some great numbers, but we're like getting our targets. Isn't that our job?

[Melanie] (27:03 - 27:03)

That's our job.

[Stino] (27:03 - 27:43)

Yeah, that's our job. If it doesn't line up with what you think would be a good CSM, well, again, Annie, it's a hard knock life. We're all here trying to hustle and make it.

So please refrain. Anyone saying what a good or a bad CSM is, use AI as an advantage. Don't sleep on it.

I'm not saying that you need to sleep on it. Don't do that whatsoever, but use it to amplify it. Don't get lazy.

Yeah. Don't get lazy. There is a reason why you went into this profession.

Keep that reason in front of you. Keep that passion in front of you. I think that's a good note to end this.

[Melanie] (27:43 - 27:44)

I think so too.

[Stino] (27:45 - 28:06)

Episode on Unhinged. I loved it. We're back.

We're back. Did you miss us? Oh, I love doing these.

If there is anything that I really love to do, this is the best thing that came forward out of 2024, literally.

[Melanie] (28:07 - 28:13)

I agree. I'm excited for the rest of 2025. We have some interesting people coming up.

[Stino] (28:13 - 28:29)

We do. We do. We do.

Not only I love you. I love you too. These are the highlights of my day, and I can't wait to see you in real life.

Maybe the next one is going to be real person.

[Melanie] (28:29 - 28:33)

Live in person. And maybe we should have a guest with us.

[Stino] (28:34 - 28:35)

So anyone...

[Melanie] (28:35 - 28:38)

That means we have to find a Toronto. We need a Toronto.

[Stino] (28:38 - 30:10)

Okay, I think this episode will be published before we head up Toronto. Yes. So if you are from Toronto or in Toronto on the 1st of March, because we're both in Mississauga near the Toronto airport.

So if you want to record in a hotel room... Okay, this is going the wrong direction. But if you want to record a podcast episode, although we fucked up so you don't have to, please shoot a message or DM to me or Melanie, and that would be super cool.

Let's do it in the lobby. Let's open up a bottle of wine. Let's set up some cameras.

And just talk about customer success and how we fucked up. That would be maybe the first video podcast special edition. Maybe that kicks off season two.

Because maybe we need to have a season two with some different art, a different intro, a different hairstyle, a different... Okay, let's put a stop on it. So AI, don't sleep on it.

Use it to amplify it. Don't get lazy. If you want to meet us in Toronto, 1st of March, 2025.

We're so happy to be back. This was We Fucked Up So You Don't Have To. Hear you next time.

[Melanie] (30:11 - 30:13)

See you next time. Bye.