Blog Webinars and Podcasts

Escalated: How CS leaders tackle real customer crises | Webinar

June 30, 2025 31 minutes read

Summary points:

In this webinar, Irina Cismas, Head of Marketing at Custify, sat down with Matt Woodward, VP of Client Success at Link Investment Management, and Miles Goldstein, Executive Member at the International LEAP Network, to explore a critical topic: tackling real customer escalations and crises head-on.

Together, they discuss practical strategies for managing urgent customer issues, balancing transparent communication with internal alignment, and effectively navigating challenging situations to maintain strong, trust-based relationships even in times of stress.

Summary points

In this session, we explored how Customer Success leaders effectively manage and navigate customer escalations, maintain clear and honest communication, and build trust even during high-stress crises.

Key takeaways include:

  • Navigating Customer Escalations: Escalations are inevitable and healthy. Swift, clear communication and thorough preparation are crucial for managing expectations and preserving relationships.
  • Transparent and Honest Communication: Transparency builds trust. CS leaders must maintain open, truthful communication even when delivering unfavorable news.
  • Effective Internal Alignment: Clearly defined internal escalation processes, supported by structured communication tools like Slack, enhance team responsiveness and efficiency.
  • Prioritizing Customer Issues Strategically: Escalation procedures should be proactive, with well-defined protocols and documentation to ensure efficient resolution.
  • Identifying and Addressing Recurring Issues: Deep-dive analyses of repeat problems are necessary to uncover root causes and establish effective, long-term solutions.
  • Proactively Managing Quiet Customers: Silence from customers often signals hidden dissatisfaction. Proactive engagement helps identify risks before they escalate.
  • Balancing Customer Requests and Product Roadmaps: When facing demands that conflict with product plans, assess requests strategically using frameworks like RICE (Reach, Impact, Confidence, Effort) to prioritize effectively.

Transcript

Irina 0:02
Hello everyone, welcome. I’m super excited to have you all here today. I’m Irina Cismas, Head of Marketing at Custify, and I’ll be your host for this session.

Today, we are talking about something every CS team has faced, but not everyone likes it to admit, and this is customer escalations. They aren’t rare. They are actually part of the job and sooner or later, we all end up in the middle of one.

So in the next hour, we’ll walk through six real escalation scenarios. The kind where you need to act fast, get the right people involved, say the right thing, and still walk away with the relationship intact. I’m not going to tell you how to do that.

Matt Woodward and Miles Goldstein will. They’ve been through it, they will break it down. They’ll let us know what they did, why they did it, and what they would do differently.

Matt, Miles, thank you for accepting my invitation and for joining us today!

Matt 1:08
Thank you. Pleasure to be here.

Irina 1:12
Before we dive into the topic of today, I want to address a quick word on Custify and then we’ll continue. Well, Custify will help CS teams stay on top of their accounts before they hit red. That means better visibility, early signals, and fewer surprises.

Yeah, escalations still happen, but you catch them earlier. You come in more prepared and you are not scrambling last minute. That’s also why we are hosting this session because even with all the right tools, the hard part is still knowing how to react when things go sideways.

A few housekeeping rules. This session is being recorded, so you’ll get the replay. And if you have questions, drop them in the chat or in the dedicated Q&A tab.

When the clock is ticking: How to manage delayed resolution

We’ll try to take them as we go, if they make sense in the context of the conversation. If not, we will have a dedicated Q&A session at the end. And now I suggest let’s jump in and we start with the first situation, a situation that I’m sure most of you have seen it.

We have an open ticket. The customer is waiting. Time keeps passing and nothing’s moving.

You are chasing updates on your side while trying to keep the customer calm and the pressure is building. Miles, how do you usually go about this?

Miles 2:51
Well, for me, communication is the key. You’ve got to get frequent updates to the customer. You’ve got to make sure they understand what you’re doing on their behalf.

And you’ve got to be pulling updates from everyone else. I’ve been fortunate in that several of my companies I’ve had very good relationships with engineering with customer success. Everyone has to be talking.

The customer has to be getting real time information. You’ve got to set realistic expectations and then meet your status frequency commitments. So if I tell you, I’m going to tell you in an hour whether engineering’s got to fix, you’ve got to meet that commitment.

And from the engineering side, I don’t like just escalating. You’re not just, you know, call VP or director and toss the ball. No, you’ve got to work closely with whoever’s assigned.

So support, success, engineering, they all have to be together and keep that communication loop going with the customer.

Irina 3:43
So you mentioned that you aren’t basically jumping in directly, but do you have a structure to push things forward?

Miles 3:52
Yeah, with the engineering teams, I usually set up escalation procedures, which depending on whether you’re frontline, backline, there’s steps you have to do. So with one of my frontline organizations, we had 800 wiki documents saying for this situation, here’s what to collect, here’s what to ask for so that we don’t just send it’s broken to engineering. You send it’s broken to engineering, it sits there for three weeks, it comes back with what’s broken.

And you don’t have logs, you don’t have reproducible test cases. So you’ve got to prepare your frontline with that. With these organizations, typically my backline, my level two or level three, know to collect that.

So if I’ve got a level three person escalating to engineering, they’ve got that working relationship, that credibility, and they’ve done their homework. But you don’t want to waste engineering’s time because that wastes the customer’s time.

Irina 4:42
And on the customer side of things, how do you balance being transparent without making things worse?

Miles 4:55
I missed the first part of that.

Irina 4:57
How do you balance on the customer side? Because, okay, there’s a lot of work internally to solve the things, but on the other thing, you also have to, okay, be transparent with the customer. How do you balance this?

Miles 5:14
It comes down to just, for me, it’s being truthful. Long, long ago, I had an altercation with the sales league because he wanted me to give misinformation to the customer. I feel credibility is my coin.

If I don’t have credibility, I should take a walk. So I’d rather tell a customer honest, bad news with expectations. This is what’s happening, but here’s where we’re going, rather than lying.

I’m saying the fix is an hour away, the fix is an hour away, the fix is an hour away. If the fix isn’t coming until Tuesday, tell the customer that, and then each day getting the status, we’re still on track for Tuesday. Here’s what’s happening.

Here’s what we’re testing. Here’s the theory. And sometimes the theory you’re testing today proves wrong, and you do a different theory for tomorrow.

And that’s not not knowing where you’re going. That’s a scientific approach. And if you tell the customer this, most of my customers have been mature enough to accept that kind of information.

Irina 6:09
Do you think in some cases, we are afraid to tell the customer the resolution, to communicate the right resolution to them, because we don’t know how to manage their expectations?

Miles 6:26
Exactly. Some people, again, would rather keep the customer, quote, happy by saying, you know, it’s coming, it’s coming, it’s coming. Which by the third time you say that, the customer’s not happy.

They’re escalating. They’re calling everyone whose number they’ve got with a title, right? I’d rather head that off.

I’d rather, again, tell them what’s going on. And even, you know, if you feel the need to escalate, here’s the three VPs that can make this thing happen faster, but it takes nine months to have a baby. They’ve got to eliminate possibilities.

They’ve got to design the fix. They’ve got to test the fix. I’m not sending you something that’s going to make matters worse.

And as long as we have that communication, that’s also where the trust between support, success, engineering comes into play, is that they know that you’re managing the situation, not setting them up for failure, right? If they’re telling me next week and I’m telling the customer tomorrow, nobody’s happy.

Irina 7:24
I like it. Thanks, Corey. He sent us a message on chat, and he said that in their case, they use three different Slack channels. One is for low escalations, reviewed once a week.

One for medium, should be reviewed within a day. And one for urgent matters to be looked ASAP. What do you think about this flow, about this procedure?

Handling, we’re sorting down the type of escalations into three different slack channels. Yes.

Miles 7:58
So my last team was very, actually my last couple of teams have been very slack. It’s a wonderful tool. And that way, you can document the conversations.

You can go back and read it. You can identify people, and that will send them notifications to their screens. I’ve had Slack channels directly with the customer where we can share information.

And I’ve had internal Slack channels of use as you’ve suggested, with engineering and with success. Those are great places to have open conversations. You don’t need to have a bridge line like we did back in the dark ages.

Or if you’re not on the phone, you don’t get the statuses. They have to be used appropriately. I mean, everyone knows the boy who cried wolf.

You don’t want to just keep throwing stuff into the hot channel if it’s not hot. If you’ve got a question for what does this mean? What do I need to do?

You do that in your team channel. You don’t bring in the VP engineering or whatever. But those work really well if people have the maturity to use them correctly.

Don’t just throw stuff in there, throw the right stuff in there.

“Can I speak to your manager?”: Handling escalation requests

Irina 9:00
All right. Speaking of that VP of the engineering, that basically brings me to the second scenario that I want to tackle. And the second one is you’ve been working with a customer for a while.

There’s been some friction. Maybe something didn’t get fixed fast enough. Maybe expectations weren’t aligned.

And at some point you get that message. Can I speak to your manager? Matt, what’s your move when a customer asks to go above your head?

Matt 9:35
Yeah, absolutely. And I mean, I think naturally CSMs or anyone that gets that, their first reaction can be, oh no, right? So we’ll get to, I’ll talk a bit later about removing the oh no from that moment, because that’s the first unhelpful thing that happens, but it’s so ubiquitous.

These cases I think are, as you mentioned, Irina, you may have just had to tell them no on something that they wanted. Maybe you found some unclear expectations or there were some expectations set before you got them. For implementations, we’ve all been there.

I think this, it’s like a misdeliverable. These are often sort of the types of cases where this comes up. The first thing to do is to accept immediately.

Absolutely, yes. If you do anything other than that, everything else becomes adversarial. And that’s the last thing that you want.

So it’s an immediate, full-throated, absolutely. But not a hot potato. You gotta swallow your pride.

Escalations are healthy. I bug my team when I don’t get escalations as much as I do when we do get those, when everything’s perfect. So it’s a healthy, natural, important part of what that job is, what our role is, and why there’s a leadership structure in the first place.

So no problem, swallow that pride. But instead of absolutely doing that quickly, which is easy to do and very simple to do, especially if the emotional state of the conversation is a heated one, best case scenario, a CSM then interrogates what’s going on very deeply because the quality of the engagement with leadership, with the manager, depends very, very much on the research and your understanding about what exactly the nature of the challenge and problem is. So yes, immediately, do you have five minutes for me to ask you a bunch of questions about exactly where we’re at so that I can make sure to hand this over really well before we engage? Yes, it’ll always be a yes, 99.9% of the time. I think when this happens, in my personal experience, 90% of the time, they just need to hear the same thing you told them from somebody else. Usually, it’s about that simple. This is not how our product works.

This is not a use case we currently support. This is the use case we’re designed, for example. Here’s how we’ve seen this circumstance be managed with other successful clients.

If all of that happens and then it’s a no, oftentimes 90% or so, they just need someone with a higher level of authority to say the same things to them and accept it. The other 20% of the times, it’s a part of feeling heard or possibly just expressing. But of course, there is that group that might need a concession or some type of leadership involvement.

So whatever happens, just to talk briefly about what happens right after and maybe what could have happened before. Right after, I’ll double down on Miles saying, clarity and consistency of communication. Even if there’s nothing to communicate, if you said, I’m gonna get back to you tomorrow with an update and there’s no update, get back to them tomorrow with the fact that you don’t have an update and don’t mince words.

Clarity is kindness. I think that’s Brené Brown. But it does, happiness and go-luckiness, filling it with things that they might wanna hear is not kind to your relationship or to that person or to yourself, even though it might sort of smooth out the initial jagged edges.

Often leaders are concerned with getting involved because it’s hard to disengage. So in the aftermath of this, often what’s very useful is if they’re asking your leader a question and you’re on the CC, you reply, you reply, get them back used to hearing things back from you. And this over time will help a leader who needs to engage to then be able to disengage properly.

What could have happened before? Ideally, you can feel that coming. Very often you can feel this event coming.

And a heads up saying, hey, I think this might escalate soon. And this puts you on the balls of your feet instead of the back of them. You can strategize, you can figure out exactly what will happen in that case.

Offering it also before you get there, depending on the size of the relationship. If this is an enterprise client, obviously it’s something you might be able to say, look, I think that we might need some assistance here to get things cleared up. The only thing I would add to that before I stop talking is management layers.

This is a great spot if you’re a big enough having management layers, right? CSMs, senior CSMs, team leads. Every layer you can put in there is very helpful in managing this type of escalation because you can handle it in more than one way.

One of the biggest traps and things I would caution leadership to avoid under these circumstances is to be engaged and then reverse what the CSM has been asked to toe the line on that got us to the no or can I talk to your manager? Sometimes it happens, sometimes a concession is made but I often find sometimes that when it gets to this level, a leader will too often make that concession that the CSM was told not to or said, this is not how we do it anymore. What this does is undermines things in a couple of circumstances.

It undermines the CSM’s authority and ability and trustability with the client. And then of course morale, morale, it happens sometimes but too much, it’s a real morale killer to be asked to have these really hard conversations with clients, they escalate and then it’s reversed. So those are my thoughts generally on this type of topic.

Irina 16:28
Matt, I wanna ask you something because it’s an escalation scenario that based on your answer made me realize that we may have another type of escalation. How should the CSM when the manager is having the conversation with the customer and he is basically going or approving or saying things that the CSM said no to or so basically exactly the scenario that you advised against. I’m not a CSM but I’ve heard a lot of this type of scenario when the CEO goes into a room, he’s promising everything he said no previously.

How can we handle it internally if those things are happening?

Matt 17:24
Yeah, I would say it’s just two points of awareness. One from both sides of that circle. I mean, a CSM really does need to understand that that’s a part of the role.

This is gonna happen, right? It happens once in a while, right? So like especially when a company is moving into a scale up from a startup, certain things are frowned upon or work around stop being a positive thing and start being debt that you’re adding, no more of this, no more of that.

And so I think it’s just awareness that sometimes this happens and you have to grow as a CSM when it does, that’s the role, that’s why this exists. But also just to keep in mind that when you ask a CS team or a team of CSMs to toe line that you know there may be challenging conversations about see it through. You know, walk the walk as well, whenever you can because otherwise it’s a very damaging thing to morale.

You know, live through that both as a CSM and as a leader.

Irina 18:33
Thank you. Let’s move to a different kind of escalation. This time it’s not on the customer side, actually on us.

We are the one dropping the ball. Maybe it was a bad config, a delay, a mispromise. Whatever it was, it hits the customer hard and now we’ve got to clean it up.

Matt, this is again for you. How do you handle it when the mistake is clearly on your side and trust is already shaken?

Owning your mistakes: Managing trust after internal failures

Matt 19:09
Yeah, yeah, again, a big oh no moment except it usually happens in the middle of an update or a team meeting. Oh no, that sort of five or 10 second realization about the number of clients. Me as a CSM, I’m gonna have to break this news too and it can be from any source.

You know, like whether it’s a functionality or a release or, you know, a setup was wrong or CSM had the wrong impression and said, yes, do this. And then it turns out that that was an error. You can get there in a lot of different ways.

You have to sort of take a moment to center and then get prepared for full ownership. Part of what a CSM role is, is to take ownership for the company. Not be too transparent about, oh, well, it was this person’s fault or it was this group’s fault or this process failed.

You know, I work for Link Investments Management. Link screwed up. We did, right?

We, not I, not them, not this part, you know, full ownership as the company because you’re the face. It’s important to predetermine and get your sweater thread pulling going on. It’s like, okay, here’s the problem.

Through the lens of my administrator at this company, what does this mean for them? What’s that attached to? Where is this going to impact them specifically?

Really understand that depth. You know, think about the questions that you would have if you were them about what you’re about to tell them. Take 10 minutes, take a half an hour to do that.

You know, it might seem like the clock is ticking but if you do that, you’re going to have a much more effective conversation. When it comes time to that conversation, I always tell teams of mine that of all the kinds of news that you can give someone, bad news is not the worst. It’s no news or it’s incorrect news, right?

Everyone loves good news. Bad news, if it’s true and well-delivered, can be trust-forming because they trust you. What comes out of your mouth is the truth.

They might not like what they’re hearing but if you can show them that it’s never opaque and it’s not gussied up to Miles’ earlier points too, truth is trust-forming and it can be. So get in there, tell them exactly what’s going on. Don’t be hopeful to yourself about, oh yeah, I think we can get this solved in a couple of days.

Base it on fact, base it on what’s going on. You don’t know, you don’t know. Post, after the band-aid is ripped, it’s an opportunity to have a bad news conversation.

So don’t phased disclosure it. If you’ve got bad news to talk about, talk about it all. If they don’t raise some things that you know they should be raising, offer it.

Show them that you know their program. Oh, and by the way, this is also going to affect X, Y, and Z of your program with us because ABC. Again, get it all in there.

Show them you know the program and get it all done. Rip the band-aid so that you can start fresh with it. Diarize, prioritize, all the communication stuff that both myself and Miles had mentioned earlier apply.

Yeah, I mean, I guess the only other thing I would say is these are the conversations that CSMs need to save for a rainy day for. It’s why we need to make good conversations great every time. Banking, this relationship currency that we all hold as CSMs because you are going to need to spend it and it’s often not going to be your fault.

You are the face of the company and you need to spend it and you’re gonna be broke for a while in that relationship. So whenever you can turn good into great, that’s how you bank this so that these aren’t circumstances that break the relationship irreparably.

Irina 23:41
And after the fire is out, how do you handle the internal side? How do you, what happens internally? Let’s say that you managed to mitigate the external side of things.

What happens internally?

Matt 23:55
Yeah, so it’s one of the easiest things to say and the hardest things to do is solve for the client first, solve for us second.

Irina 24:04
Okay.

Matt 24:05
That’s easy to say and very often under high pressure, large workloads, a few fires always burning, solve for the client happens and then we don’t solve for us second. They’re both just as important as each other. They’re halves of a whole.

So making sure that there’s that retro, making sure that everyone does sit down and the risk is talked about in numbers, where it broke down is identified, written up, what’s gonna happen next. It’s an expensive meeting usually because there’s a few leaders from different groups and departments and the schedules are hard to line up, especially in really busy sort of scale up kind of circumstances. But without that meeting, you’re missing half of what the whole needs to be.

So solve for yourself, second isn’t second place. It’s just the second half, I guess I would say.

Irina 25:04
Do you usually, how do you… Because it happens to screw up things in front of the customer and that’s a reality, but it all depends on the type of impact, I would say. There are minor things and there are major things.

My question is, you mentioned the retrospective and basically a post-mortem after it happened. Do you do it for all the types of mistakes, let’s call them mistakes that you did or do you prioritize depending on? Some of them with lower impact, it’s just an apology and admission.

Some of them, how do you prioritize?

Matt 25:52
Yeah, and you’re right. There’s certain levels you can prioritize by impact or also about if it was just a mistake that was made by someone or a group to a note, like within a known process and something shouldn’t have happened the way it did, then there’s less to interrogate in a retrospective or a post-mortem. Like a lot of it is just, yep, that fell through the crack.

The crack shouldn’t be there. We’re gonna make sure that doesn’t happen as much. But when something is either extremely business impactful or is a part of a trend of similar things or is not necessarily a failure in a documented understanding about how things should have gone, but is a failure that’s not a part of things, I think that’s where the important retrospectives should happen.

Repeat issues: How to stop the cycle

Irina 26:44
Okay, now let’s talk about the kind of escalations that feels less like a fire and more like a slow leak. Let’s imagine that the issue was fixed and everyone moved on, but then it comes back. And maybe it’s not even the second time, it’s the third or the fourth.

And you know what? The customer is tired, you are tired, and now it’s not just about the issue, it’s about the fact that it keeps coming back. Miles, how do you deal with repeat issues like this?

Miles 27:29
Well, first of all, too often we stop when we’ve stopped the bleeding without, you know, we provide a workaround, but we don’t solve the root cause problem. So just because the customer’s not bleeding anymore doesn’t mean it’s any less urgent. It means they’re gonna live through it.

You can’t stop. And sometimes it was because we just didn’t fully understand the problem. We need to dig deeper.

We need to see it, reproduce it, and think it through. Too often, especially longer than my past, I’ve had people look at a problem and say, well, you know, I don’t get it. Well, if you’re an engineer, look in the code, try and think through what could be causing this.

You know, the customer keeps having this problem. Well, they shouldn’t. Yeah, they shouldn’t.

We all agree they shouldn’t. But, you know, I have a science analogy where, you know, science keeps evolving. You’ve got a theory and it works for a while, but then new information comes up and you adapt your theory.

It’s the same. It’s like during that crisis we were talking about earlier where you keep giving updates that this approach proved to be a dead end. We’ve got this other approach.

If the customer keeps having the same problem, you’ve got to dig deeper. You can’t just solve what’s on the surface. You have to understand what’s happening behind the scenes there.

Irina 28:42
How do you usually dig deeper? Because you mentioned that. What do you do exactly when you dig?

What’s the process?

Miles 28:51
Well, there’s the support one-to-one, the reproduction, the logs and all that. But you’ve got to be able to think if it’s not A, it must be B, right? Long, long ago, I was supporting a product that was a full screen thing long before Windows.

And one of my customers was a university and they kept getting weird data in their full screen application. And we couldn’t figure it out. I said to my, my TSC was working for me, I said, take a book and drop it on your keyboard, right?

You’re a student, you’re in a library, think it through. They dropped the book on the keyboard and they reproduced the problem. Now we understand it.

As Matt was alluding to earlier, you’ve got to have that customer empathy. Think through the lens of the user, not through the lens of the people who developed the product. You keep hearing, well, it’s working as designed.

Well, maybe it wasn’t designed for this use case, right? So think like the customer. And Matt went there several times.

That’s absolutely true.

Irina 29:48
How do you keep the customers calm when they feel like it’s the HR queue?

Miles 29:56
I hate sounding redundant here, but it’s still the communication. It’s telling them the plan. This is the theory we’re working on.

This is what we’re doing. It’s not enough to say, yeah, whatever. I mean, they get that.

You can, Matt said this too, you can’t lie to them. You lose trust and then you get nothing left. But, excuse me.

It’s telling them the reproduction. It’s digging deeper. In some cases, I had a customer recently who had this really weird data synchronization problem.

And I was saying earlier, I had a high level team that had the trust with engineering. We actually got engineering on a series of calls with the customer. And through the investigation, what we learned is the data wasn’t syncing because of this really interesting bug in our product.

We were selecting a whole bunch of data, taking the first thousand records and syncing them, going back, taking a whole bunch of data, taking the second thousand records and syncing them. That sounds really good until you realize the data wasn’t coming in the same order. We weren’t sorting it.

And that’s how we were losing records on the sync. But you’ve got to look at it deeper. It’s not, well, we took a thousand, we took a thousand.

Can’t understand why it’s not working. Think it through. Which thousand are we getting?

We’re not getting that same thousand. And it took several days of my having engineers on the call for them to realize this, that it is our problem. It is a bug.

And you have to think through what is really happening behind the scenes. And when the customer saw this thing happening, they loved us. We got them through this really weird problem that only they were having because of just the massive amount of data they were trying to sync on a daily basis.

Irina 31:31
I think I really liked the comments and the interaction on the chat. And I’m gonna mention it. Thank you, Corey, for your contribution.

He is mentioning some problems are unsolvable though. If it stems from somewhere outside internal control. In that case, you must have a workaround documented and shared as best as you can.

Additionally, some problems are technically solvable by the engineering team, but they may be highly time-consuming and low impact that it’s not worth steering away from the more impactful roadmap vision. What’s your take on this, Miles? Do you agree, disagree?

Miles 32:17
A little of both, I have to admit. Very good question. Thank you for asking it.

So a while ago, I wrote an article on escalations and I have this priority severity frequency age algorithm that you can apply. So yes, this may be a huge problem. It’s gonna take a lot of time.

You’ve got to think through how many customers is it impacting and what’s the true net impact doing to this customer. It may be that they’re trying to do something which is unique to their environment. And maybe there’s another way of doing it.

Doing it this way is never gonna work and we can’t invest the resources, but you can get the same results by doing it this other way. Or again, if it’s something which you’re not really intended to do, it goes back to, you were talking earlier about the feature that’s never gonna happen. The hard truth at least gets the customer past it.

This isn’t gonna happen. You can’t tow a 10,000 pound trailer with a Volkswagen, not gonna happen, right? So what are your options?

Get a smaller trailer, get a bigger car, do something else, load the car instead of the trailer. You’ve got to give them other ways of solving the business problem. Sometimes solving the technical problem doesn’t solve the business problem.

I’ve got a silly story. I like to tell someone says to you, does this road go to San Jose? And the answer is no, but that’s not solving their problem.

This road goes to San Francisco. This other road goes to San Jose. What are you trying to do?

Find out what the business problem is and solve that. Because sometimes again, if this problem can’t be solved the way everyone or the way the customer thinks it should, there’s another way to solve the business problem. People don’t care about the bug.

They care about whatever they’re trying to solve in their business operation.

Irina 34:06
Matt, you raised your question. I wanna mention Kenneth and Corey wanted the link to the article you mentioned, Miles. You can drop them in the chat or send it later on.

Matt, you wanted to say something?

Matt 34:33
Yeah.

Irina 34:33
Miles was saying.

Matt 34:35
Yeah, to your point, Miles, another way that I’ve always thought of that, which is the same thing you’re talking about, I think. It’s a quote, certainly not mine. I should know the gents name, but famous marker, the whole people don’t want a quarter inch drill.

They want a quarter-inch hole.

Miles 34:54
Exactly.

Matt 34:55
Right, and so that kind of thinking like you’re describing can be a very effective sort of pair of lenses to put on as a CSM around what’s the problem they’re trying to solve, right? Well, they want a green button here, okay? Where they’re trying to get to.

Why do they want to be there? Is there another way sort of around it? So just, yeah, two hands raised to that point.

It’s a great pair of glasses to have in your back pocket as a CSM to kind of look at a problem through in a new way when it feels stuck in that sense.

Irina 35:36
We also have it on the marketing side. We call it, try to find out the job that the customer is trying to solve. And usually this applies to many different areas.

You try to understand that to make sure, okay, how can you pitch the product? And I think on the CS and on the CSM side, you are trying, on the support side, you are trying to understand what’s the job they are trying to solve in order to see how you can help them move forward. In the end, it’s just, okay, a matter of trying to understand why are they there in that particular situation?

What was the driver? Let’s move forward with the fifth scenario that we have prepared. Some escalations are crystal clear.

Something is broken and the customer just want the fix. They want the resolution. But in other cases, it’s not so clear.

What’s clear is that the customer is upset, but their messages are all over the place. They’re frustrated. Maybe it was a bad day.

But they can’t tell you exactly what they want. So now you are trying to solve a problem you don’t fully understand while also keeping things calm. And I think this relates very well to what we just discussed, trying to understand what are they trying to solve.

Matt, how do you handle this kind of situation?

Decoding unclear customer frustrations

Matt 37:13
Sure, yeah. And so, I mean, I was recently through this, something like this a couple of times. I’ve been with Link Investment Management now for just about four months.

And so, you know, a big part of ramping up in any company, especially heading up a fledgling CS musculature is getting to know people that are happy with us, getting to know people that aren’t, you know, just understanding that whole thing. And so, I did spend a few conversations, very much of this nature, where there was a general sense of frustration. And the challenge was, is that there were so many threads to that frustration that, you know, it was hard to pick apart or understand exactly what were the big contributors.

So absolutely, this is fresh in my mind. Often, sort of outside my particular experience that I mentioned, often these things I find tend to happen after periods of, quote, calm, unquote. You know, it’s a middle-sized client, you know, obviously if they were enterprise or something like that, you know, there would be executive relationships and it’d be very unusual to have a whole bunch of things come out at once that are frustrating, that are a challenge to determine exactly the nature of it.

So most often I find this is sort of like the middle of the client group, they’ve been chugging along, other parts have needed focus for a little while. After a period of calm, then something like this often occurs. Also, this can happen a few months after like an admin change or a change in your main contact that maybe wasn’t held in hand well enough, but we’ll get to that in a sec.

Let go of the rope is probably sort of what you need to do with this. Take a moment for yourself, which I’ve said a few times before, understand that this is now going to be a process. It’s not to be rushed.

This is like book some time in your calendar for this because the first thing to do is to question them relentlessly. When they stop talking and what else? And what else?

Michael Bumgay-Stanier, one of the seven questions in his amazing coaching book. And what else? If they bring something else new, interrogate that, understand exactly what they mean.

They stopped talking and what else? Not, is there anything else? Not, did you have anything else you wanted to bring up?

Not hopeful closures. Not, oh God, please let this be the end phrasing. And what else?

More, more, more, more, more, more, until you hear the words, that’s it. Your job’s not done until you hear the word, that’s it. Next job, here’s what I heard from you.

It’s really useful to have like a note taker, like an AI note taker for these kinds of calls, especially like a Fathom or an Otter, someone who’s doing this for you for afterwards, here’s what I heard from you. Is that correct? Yes, that’s correct.

Or no, that’s not correct. Okay, what about that wasn’t correct? Like ruthless top to bottom understanding.

Prioritization, what are the three things on this list that are the most important to you that we address right away? What’s the business impact of these? Why are they the most important?

Great, we’re gonna have touch bases regularly and we’re gonna use this prioritization as a sheet. We’re gonna start right here, one, two, and three. Every time we get together, I will update you on where we at with these three, which ones we cannot do, which ones are outside of what we’re able to do, I’ll tell you why.

And we’re gonna reprioritize as new things come up, where does it fit? One to 10, one to 20 kind of thing. It’s a process that will save you and provide clarity through the wrestling of cats.

That’s probably enough yammer. I do have something, I want a concept that I’d like to bring up that I think is related to this, but it’s probably a good spot to start for questions or other thoughts.

Irina 41:50
There are no questions on this topic. So you can continue.

Matt 41:59
So I’m about to amaze everyone with a well-thought through, highly designed visual presentation. Excuse me. We are going to talk about, and this is all related, I promise, right?

Before I share, I will say this is related to, where is all this coming from? How has this happened? Because they don’t even know under this circumstance how to be clear about their frustration.

It’s usually jumbled up within a bunch of different things, a bunch of different threads, and it tends to come out of left field when it does. So this is what I think about and what I talk to my teams about when we’re doing this. Can everyone see my screen?

Yeah.

Matt 42:50
Laser pointer. So steady state, let me talk a little bit about this. So there we have our happy CS team, right?

This isn’t meant to be a person, this isn’t meant to be a team. They’re holding a ball, and the ball is a client customer. And please give me a little bit of bandwidth on this.

I will get to my point. We have, on this side, the best relationship ever. On this side, crisis or churn.

And the teeter-totter here, or the seesaw, is a relationship dynamic. What I’m trying to show with this image is that when you are over here, like this guy is, when you drop balls, what happens, right? You drop a ball, but the relationship dynamic is such that they’re easy to pick up, they kind of roll back to you, no problem, right?

Like, this is a good thing. Every time you drop one of these balls, though, you get closer to the center, right? So this CS team is kind of like in that middle.

What people think, excuse me, sorry, just navigating my technology. The perceived crisis point, generally, which I’ll argue is incorrect, the perceived crisis point is over here, right? Crisis or churn.

We’ve got, we’ve dropped it. Everything’s over. They’ve asked to flip.

They’re gonna leave us. And I had to put in this sad face myself. AI didn’t wanna put a face in, so apologies.

This is, in my mind, and something I try to instill in the teams, the crisis point is not the churn point. The crisis point is a little spot right here where tiny little things that have always been easy to solve, that always kind of roll back, something very minor, something very small can happen, and the nature of the relationship will change. The weight shifts, and all of a sudden, balls roll away from you.

Things are harder to manage. And so what I’m showing up all this for is because this is where these kinds of conversations can happen right here, when the nature of the relationship changes. Well, and this, and this is a problem.

And that, and I’m frustrated with this. Maybe you thought that they were done, or you thought that they were addressed, or they’re bringing things up from two months ago. I thought it was solved.

This is the crisis because the nature changes, and it’s very hard to manage the challenges that happen between here and here. Churn is still, of course, at the end. The other thing I wanna illustrate or point out here is that by the time you are here, right, look at the whole length that you would need to do in order to flip this relationship back.

It’s almost impossible. This effort, this effort is usually way too late. And it’s, after someone says we’re done, I’ve been only very rarely in my experience been involved in conversations that actually come out saving that.

If we think about crisis point here, small things can change things back. Efforts, concerted efforts by the company to do it, we can get back there. So I just like to think of all of this sort of in my head in this way, in relation to this topic, because when someone calls up, and they don’t know what they’re talking about, but there’s general frustration, and it’s hard to determine.

This is almost always what has happened. And it should be treated like a five alarm fire for the reasons I’ve been through. So I hope that wasn’t too cheesy, but.

Irina 47:11
No, it wasn’t, and actually you have a question, Matt. Corey is asking, how do you know when you are at this critical stage?

Matt 47:22
It’s, yeah, it’s a good question. And I would certainly love to hear from the group or Miles or anyone like on thoughts about how they’ve seen, I don’t have a magic bullet for that. It is these changes, right?

So like in this circumstance, everything’s been going well, no problem. Yeah, we’ve dropped a few balls, but things are fine. And now we haven’t talked in a while, and they’re here, what I can tell is they’re agitated, but there’s no clarity around what it’s about.

Something’s changed for this administrator about you, about their goals in their company, and their idea about how you fit into them achieving it. And so that is the critical thing for me about how you can tell if it’s here. What else?

Irina 48:17
Like, does anyone else have- Miles, do you have a different view?

Miles 48:25
Well, yeah, this kind of segues into what your next planned question is about, and that’s identifying the issue. So I’ll wait for that discussion rather than interrupting this.

Irina 48:35
Okay, then I’ll introduce the last scenario that we had prepared.

Matt 48:42
Sure.

Irina 48:42
When the customer hasn’t said anything, and there’s no big complaint, or no angry emails, no open tickets, but somehow something feels off. And they’ve gone quiet, and the usage dropped, engagement isn’t what it used to be. And your guide says, if we don’t step in now, this is going to blow up later.

So how do we handle this type of conversation?

When silence speaks volumes: Engaging quiet customers

Miles 49:15
So, again, I’m on the support side, not the success side. So I don’t necessarily see a decrease in usage upfront, but as all of us have said so far today, that relationship between success, support, engineering, and others is critical. I saw a clip of a Custify webinar, Grant Dutton talking about a unified customer experience there.

And we all have different pieces of knowledge. So I might notice that a formerly active support customer their case frequency or behavior on those cases has changed. There’s aging, there’s non-responsiveness, there’s repeat tickets, or I’m getting pings from the field team, whether it’s success or accounts or whatever.

And we all have these different pieces. The CSM is sensing that he’s not getting the warm welcome when he walks in. I’m sensing that when they call support, they’re no longer collaborative.

There’s hints along the way. And you’re absolutely right, Matt, that once you pass that fulcrum, it becomes a very difficult recovery. You still have that moment at the top there if you should ever get there.

But once you’re at the far end, it’s a long climb back if you can do it at all. But if I’m aware of something, I’ll proactively reach out by phone if possible, otherwise by email, introduce myself if we don’t already have a relationship, explain what I’m observing. And as Matt said to the other thing, own it.

It’s not, well, engineering this, well, support that, well, if sales, this other thing. It’s, hey, I’m the face of the company right now. I’m sensing you guys have an issue.

Let’s get in front of it. Let’s fix it. And it’s hard in support to have that opportunity to be that proactive, but those indicators are there.

I’ve got data which shows the reduced cases or the increased lag times or whatever. And that’s just data, but you have to use your intuition to understand and interpret that data. Now, what is this report telling me?

And it’s not just telling me XYZ company isn’t opening as many cases anymore. Oh, isn’t that great? They must be happy.

No, silence, as Matt said, silence is not necessarily a good thing, right? I’d rather reach out and say, you guys have this big project going on and all these little incidents, well, not incidents, but little problems that we’ve been resolving. Did you roll out successfully?

How are things going? Or if I don’t wanna risk that with the customer directly, talk to your success if they’ve got a CSM assigned.

Matt 51:47
Yeah, absolutely. And like in all my time doing this, I’ve hardly ever seen a customer or a client get really angry and then flip the table and quit as a part of that anger. Where, almost all the time where I see this happen is we think we’ve solved it.

They say, okay, yep, to the solution, but what they are is just tired of this happening and they’re not content. And then they’re quiet for three or four months while they put out an RFP. And four to six months after this has happened, the company thinks, great, yeah, we had this big escalation with them and we totally managed to douse the fire.

And they’re just chilling out over there now. And then it’s just like a left hook. We’re leaving you.

It’s quiet clients scare me 10 times more than even the ones who are willing to call me up and yell. I’d much prefer that because we’re speaking.

Miles 52:52
Anger is because they care, right?

Matt 52:54
Yeah, they’re engaged. You are risking their success. I have goals here in my company and you are screwing it up.

This is a, how can we get to the other side and fix the conversation exactly? Quite enough for that is I need a new solution.

Miles 53:13
A lot of companies I’ve been through have a red account process or however you want to escalate a critical account. And that’s great because that gets executive sponsors involved. It gets VPs from across organizations involved.

It’s a great communication tool, again, between support and success and the others. And that’s how you track this. And now you’ve got your C levels watching this customer too.

And rather than the customer saying, I want to talk to your CEO, your CEO is saying, I want to talk to this customer and flipping the table that way. Again, the fact that you’re reaching to the customer, you care, right? If you’re oblivious to the customer and the customer is apathetic about you, you’re already way past the fulcrum on that little pivot there.

Matt 53:54
Yeah, I was going to add something similar to that to this circumstance too. So something’s fishy, but we’re not sure what it is. Like that’s part of what, Irina, you sort of, you laid out.

There’s a sense that there’s something not quite right going on. At an enterprise or a higher touch kind of CSM level, you should always have a few threads going on, right? You should know a few other people.

If myself as a CSM isn’t comfortable just like flat out saying, I’m itchy. Client administrator, I’m itchy. Why am I itchy?

What’s going on? If it’s not that kind of relationship, then this is the right time to say, hey Matt, you know so-and-so, this person’s boss from X company. I think it might be a good time to just check in on the general side.

Like, are they getting acquired? You know, are they like, how’s the business doing? Like, can you please have a check-in because my Spidey sense is tingling.

As we march more into the one-to-many side of things or the more sort of tech touch thing. I mean, like, as you mentioned, if we’re lucky enough to have software to automate some of this stuff, that product usage should be flagging things. You know, in the very tech touch, it should be automating outreaches.

It should be doing check-ins in that way. You know, so like across the size spectrum, you’ve got different ways of getting this done. But otherwise, as in this case, if it was too late and you didn’t do any of that, the only thing left to do is to learn.

If this was a really key client, I think money spent on third-party exit interview outputs is just gold dust. They will tell someone else what they would never tell you, even your CEO. So if it was a key partner or a big, like a whale of a client or some important client, spend that money if you have it to do it.

Otherwise, figure out what happened. It’s the only thing that you can benefit from at the end.

Miles 56:08
And some of these new AI tools, I’ve not used them, but they tell you customer sentiment in their communications, in the emails, on the cases and whatnot. So if you can get that kind of automated eyes telling you customer sentiment, you might get some of this early warning as well.

Irina 56:26
I really like the fact that we transformed the escalation, which I think they have a negative connotation into a positive thing. And I really liked the way you explained that we can also see the full size of the glass of water. And not necessarily a fun fact, a thing that I wanna share.

In a previous company that I used to work, I was super concerned about escalation support tickets. And I always saw the negative part of things until I ran an analysis. And I realized that there was no direct correlation between the number of support tickets and churn.

And that was the moment when I actually realized that churn and support tickets are not necessarily a bad thing.

Miles 57:32
And with that- They’ve gone silent from apathy, yeah.

Irina 57:37
Can you please repeat that again?

Miles 57:40
When they’ve stopped logging the cases, they’ve gone silent, they’ve become apathetic. And like Matt said, they’ve got RFPs out at that point.

Irina 57:50
Yeah, watching the time, I think we are going to wrap up things here. And but not before saying thank you both Matt and Miles for being so open and honest today. You didn’t just talk theory, you gave real examples and real lessons.

And I know that’s exactly what people came here for. And for everyone watching, if you wanna pitch escalation like this early, take a look at Custify. We help CS teams stay ahead of risk, spot early signals and act before things turn into fire drills.

If that’s something you are struggling with, we’d love to help. We’ll send the recording shortly and we hope to see you at the next Custify webinar in September. More on that soon.

Until then, take care and enjoy your summer.

Miles 58:47
Thanks everyone. Thank you for hosting. Thank you for attending.

Have a great day.

Irina 58:51
Have an awesome day. Thank you. Bye all.

Nicoleta Niculescu

Written by Nicoleta Niculescu

Nicoleta Niculescu is the Content Marketing Specialist at Custify. With over 6 years of experience, she likes to write about innovative tech products and B2B marketing. Besides writing, Nicoleta enjoys painting and reading thrillers.

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