When Customers Get Personal: Conor's Escalation Processes for Expensify

I'm delighted to share episode 3 with Conor Pendergrast of CustomerSuccess.cx! In this episode, Conor shares how as the Senior Leader of Customer Success at Expensify, he handled the customer backlash after some contentious executive decisions. We talk about:

• The Turning Point: How Conor identified the need for an escalation process and brought senior leadership into the fold.
• Automation in Action: How keyword flags streamlined the transfer of heated conversations to leadership.
• Psychological Safety First: Why protecting frontline agents from abusive interactions is essential for team well-being.
• Manual Escalation Done Right: When and how support agents should escalate challenging conversations.
• Leadership Accountability: The surprising benefits of having senior leaders engage directly with customers.
• Practical Tips: How you can implement a similar escalation process, whether you’re using Help Scout, Zendesk, or Intercom.

Of course we want you to listen to this insightful episode packed with strategies you can implement today, but also you can get Conor's playbook here.

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If that's not enough goodness for you, subscribe to Conor's newsletter for tons of useful CX content! ➡️ www.customersuccess.cx/newsletter

Transcript

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 I think in general, it's when the language diverts away from process or product and diverts to person is a very clear boundary for me, where it's like, yeah, it's exactly that, where it's like, it's less about this product is kind of crap and more about you as a person working. Here you are crap. Welcome to the podcast. This is live chat with Jen Weaver. I'm here with Connor Pendergrast. Would you tell me a little bit more about yourself? What you do and what your customer support journey is. It would be my pleasure. So my name is Connor Pendergrast. I run customer success dot CX, where I help CX professionals, mostly customer support and customer success. Well, mostly customer support, I'd say. And in particular leader leaders to stabilize and grow their careers. And I do that. through coaching, uh, newsletters, free products and, and consulting as well. And my journey in customer support, I guess, started, Oh, wow. If you really think about it, it started when I worked in a sheet music shop. So when you, when you. Play music you buy sheet. Well back in the day Jen, you used to go to a shop and buy music sheet sheets of music to play music So if you're a violinist, you would have gone and done that and I that was probably my first customer facing job and I was Awful at it. I was reflecting on this a couple of days ago where I was like, wow, I, that, that was my first customer facing job and I was just a terrible employee. And so, um, uh, to Liz, I apologize. And, uh, I promise I'm better now. And to any future clients or employers, good news. I'm considerably better at everything I do now than I was 20 years ago when I was a student and just working in that shop on a Friday to get beer to drink on that Friday. And then I would also come in on a Saturday and make slightly more money and eventually break even. After that, I worked. In a social care company doing the computers, generally speaking, and then went to Expensify and worked there for about a decade on the senior leadership side, eventually within customer support. And then, uh, yeah, left in February 2024, and I've been doing my own thing since then. That's fantastic. That sounds like an exciting year for you this year. It's been a real exciting year, yes, as well as having two children as well. And my wife also just finished her PhD. So it's been, uh, we're all quite, quite tired and busy, but you know, things are good. That's great. I love it. Oh, um, well, thanks for joining us. I really appreciate it. Can't wait to hear About the process that you are going to share with us. But first do you have a joke for me? Oh boy, do I have a joke? Yes, so Um, why did the customer support agent bring a ladder to work? Don't know why Because they heard that CSAT scores were through the roof. Nice. I could barely keep a straight face in that terrible joke. That's great. Well, it's a good problem to have. Absolutely. Yes. If you've got a roof rack on your car, throw a ladder on it. Sure. Why not? Obviously. Yeah. Bring a ladder to work. Yeah, I would love to hear about this. Um, this process that I don't know much about yet. So I'll be learning along with everybody else. How exciting. Yeah. Segwaying into something totally, totally different, bringing really bringing the mood down. So while I worked at Expensify, I was on the senior leadership team, as I mentioned, and also the With a, I had a heavy focus on customer support and customer success because that was my, I would say one of my, my main or my main interests and how I, how I found a lot of joy and value and an excitement to work one of the, so for some background context, one of the, uh, one of the things that expense if I did, uh, and became quite renowned for sometimes was taking big swings at addressing difficult social topics, we'll say, um, and, and, In particular, I'm thinking about a time that we advocated for a particular political candidate in a, in a contentious election, we'll say about, uh, Oh, let's say maybe like eight years ago or so. And, um, uh, and how we did that was by, by. Well, by sending newsletters about us to our to our customers, and that was like millions of people. And so that was one example. We would we would also do things like like in product on our on our sign in page, we would put things social causes we cared about and try and try and promote those. And that also, I would say both of those approaches that we took brought on some some heated and and and interesting replies. And so we are support team. Would be the people who would get a lot of those replies and they found them quite challenging to engage with a lot of the Time and whenever we launched one of those campaigns, it would cause quite a bit of stress for our support team Obviously, you know suddenly they're being engaged with on topics that they're like, well, I don't understand about democracy in the united states What's what's this got to do with me? I don't I don't understand This person's making a point about the united states of america being Like not a Republic or a democracy or like, what are they talking about? And so, um, So were they out of the country? Actually had a mix. So we had, um, outsourced support team and internal support team as well. Um, we did have it tiered, um, but those, those would tend to like. Our outsourced support teams will very quickly be like, uh, well, I don't know. What are we supposed to do here? We don't have a process for this. Um, so it would also sometimes bring in, uh, some of the conversations would sometimes devolve into, uh, into less, less friendly language and more abusive language and sometimes threats and that sort of thing. And alongside that, I guess. You know, occasionally, once you hit a certain scale, some customer support interactions even devolve into those as well, where people reach that typical point of frustration, where they start to take it out on whoever's in front of them. So, based on that, based on that context, um, what we did was introduced Automatic and manual processes for bringing those interactions for bringing those conversations specifically to our, um, to our company's senior leadership team, uh, and and having them be responsible for for managing those interactions. So at Expensify, the senior leadership team was the senior leaders, which is the team that I was on directors and the C suite as well. And so it was, it was quite novel in a lot of ways because you would end up talking to sometimes the David, the CEO, um, which I found. To be quite a good thing because he was, I would say he was at the forefront of advocating for a lot of the messaging that we were sending, and so it was nice to see him sort of take on responsibility for engaging with people as well after the fact. Um, so what we did was we set up, as I said, manual and automatic. processes there. So this is a project that I led and one of the ways that we did it automatically was we'd look through a list of words and you could imagine what some of those words were and we would automatically move the conversation if it hit sort of those words. Most of the time that's actually I'd say probably after our initial surge of conversations, a lot of time that would be someone like accidentally typos a word. And, uh, and then it gets, uh, gets sent the wrong way. So there were definitely periods of time where this was more crucial, right? After an announcement or a newsletter. And so that would be Yes. Yeah, yeah. Yeah. And, uh, and part of it was just like, once you've sent that first initial big Newsletter doesn't matter what you're saying in subsequent newsletters. It could be like product announcements that have nothing to do with political candidates, but people will still reply to it and Reinforce what they were saying in a previous message and that kind of thing and so that was the automatic side of it, but the manual side of it as well was Even in the absence of particular swear words, even in the absence of particular language, if one of our colleagues, if one of our support teams felt like a conversation was devolving to a certain point where the customer was just, you know, we've, we've all seen this sort of behavior sometimes, unfortunately, um, where they get more abusive, where they get sexist, where they get racist, anything like that, then they can send it over to our senior leadership team to, to engage with the conversation. Um, The aim for us as senior leaders, what our aims were de escalation and learning as well. Like if we're, if it's a topic that we don't know much about or if it's a topic that we do know something about, but there's some novel arguments against it, um, then, then, We try to actually learn from it and see like what is it that we can adjust in in what we're saying Where can we change our minds and that kind of thing or how can we change their minds some of the time as well? Uh in the de escalation sense, uh, if we're not able to De escalate it a lot of the time. It's just like hey, no, that's not that's not how we expect You to to to treat our our teams. That's not how we expect to treat you. Um setting boundaries Set sets clear unequivocal boundaries um, and sometimes it would end up being quite funny as well because at that point they'd be like Oh, i'm going to go to your ceo ceo would be like that thing being like I am the ceo I like you are talking to me Um, what stops there? Yeah, exactly. Yeah. And it's like, no, no, we've said no 16 times. And actually I am just very clearly saying no, it's not like someone who doesn't know what they're doing. We have clear processes around this. And so, um, in the, in the event that we weren't able to deescalate the situation, then we also had the option to either temporarily or block conversations as well. That's because we, we considered that to be like, Okay. Not not negotiable like we you you can't just abuse our support team. It's just not part of the not part of the deal So those were some features of the help desk you were using the ability to block well, this is this is this is why it was it was actually quite a bit of a um, It was quite a significant project. Um because we well at the time at expenseify and still Still now, uh, had rolled out her own custom built, um, customer interaction system basically, where everything was run on top of Expensify's own systems. So the, the nice part of that is that you can kind of do whatever you want with it. So when I was designing the project and designing the, I was describing the problem and the solutions and, um, how, how it should work, I was the one saying like, okay, we should block for this period of time, uh, and then allow for, uh, unblocking automatically those kinds of ideas. And so that was, um, That was part of it, was, was being able to design it exactly to our needs. Yeah, that makes sense. Um, how did this land on your desk in the first place? Did you have support specialists who were saying, Hey, you're, you're my boss. Uh, this is not going well. What should I do here? Or did you just sort of organically know it was happening? Yes, it was definitely a case of I would say there were two parts to it for our outdoor support teams. It was hearing the feedback from their leaders and saying, like, Hey, it's not clear what they should be doing. And so we tried a little bit to, like, educate them on how to engage in the conversations and how to try and de escalate the situation for those sort of more more abusive behaviors. But it just wasn't it. It always felt like it was creating a psychological stress that was not theirs to bear, like it's, it's, it's not really their responsibility and it's not really their job to, to, to have this, whereas me, I'm, I'm in a very comfortable situation, I'm very lucky, very privileged, and I know that I don't have to like, what is it, it's, it's that I, I'm not like, Okay. Nervous about the next interaction. You know, I'm not nervous that it's like QuickBooks desktop question. QuickBooks online question. Someone telling me that they want me to die. That's the question. It's not like, I'm not jumping from from one to the other. So, um, I can be more I can be more, I don't have quite as much stress around it. And I also don't have the same expectations from a KPI perspective or anything like that, or any concerns around that, like, Was it affecting their, their KPIs, their CSAT ratings? Not CSAT ratings, because that wasn't something that we, we actually didn't, didn't measure that or look at it on a per agent basis, um, because of these sorts of things, because they just sort of, a lot of the time got, uh, affected it. And so it wasn't. Wasn't really fair to look at it from that, from that lens. I mean, it's a little bit of an aside, but what did you measure instead of CSAT for, for agents? We were looking at quality scores instead. So we were looking from the other perspective, um, us basically saying, uh, do we think that this person did the right thing from our Knowledge of the of the product and and from our knowledge of the processes and from our understanding of what the customer wanted Yeah, so we were looking from that internal perspective rather than the external perspective. All right, so you've got Uh your leadership who is creating some political situations That it's not creating the political situations to be clear. That's true. Responding to the political situations in ways that some of your customers were not delighted with. And they went in and had some strong feelings, some spicy conversations, and then support specialists were coming up to their managers saying, we don't know what to do. Managers, what do I have this saying? I don't know how to handle this. And uh, and then you responded by saying, you know what, we should, we should take these conversations to the source. To the leadership team who's making these decisions. Exactly. And then, uh, yeah, so then, then, then what? How did that go? It went okay, I would say. Um, it, it was nice to be able to like, because it was a much smaller group of people, like we weren't talking about a hundred or so people who were trying to learn, very rapidly learn about all of these issues. We were talking about, I think probably were about 12 or 13 of us at the time engaging in this conversation. Yeah, yeah. Um, the senior leadership team, which, which basically includes, um, all the senior leaders, the directors and the, which also includes the C suite as well. And so, um, it was difficult. Um, there were some, some, sometimes it was simple, you know, it's someone who has just sort of sending us repeated abusive messages. That's a, that's a very clear cut, easy one. Uh, not, not easy, very clear cut, simple one where it's like, Hey, this isn't how we do it. You did it again. Okay. Well. We're just going to put a pause on this for, for 24 hours. We'll come back to it in 24 hours. Very happy to help you with any support problems you have after that point. You know, what's funny, you said that I've often felt that with spicier conversations, actually letting them stew for a little while, rather than it would be my response as a support specialist to just want to get back to everybody as quickly as possible, but I learned over time. They need to sit for a minute. They need to stop having the expectation of immediate replies. Yeah, exactly. Like that would be a tactic that I would employ as well. Um, sometimes where it's like someone's just going, going, going, like I would literally send a message just like, cool, you let me know when you're done and I'll, um, I'll get, I'll, I'll address your points. Sometimes it was like, sometimes that would be a bit of a, an array, an enragement point for them. Or sometimes it would just be like, okay, cool. Fine. Yeah. Like there's a person who's actually reading those messages and they're taking me seriously. So did you answer a good portion of those or was it, yeah, yeah, yeah. Yeah. So I was, um, certainly at the beginning, I think I was the only person in the UK. On the team only person outside of the u. s. Maybe on the team at the time And so it was like i'd start my day i'd be like, okay. Here's a nice big backlog and so, uh That was fine a lot of it depended on like when we were sending newsletters So thankfully a lot of that was during us hours. And so we have our the bulk of our team there to, uh, to engage in those conversations, but, but without a doubt, it was, it was large, large, large numbers of conversations at times. Sometimes, like I said, it was very simple. Sometimes it gets a lot more complicated. It's like when you're, I don't know, uh, if you think about the topic of black lives matter, uh, coming up and, and just, uh, I can't view it through an American lens, really. I'm not, I'm not in the United States. And so I. It's a little bit more difficult for me because I'm, I'm looking at it from my sort of British lens, which has different connotations behind it, both in terms of language, but in terms of how race is manifested here and how, how we think about it, um, or how, how I think about it, I guess, and, and Thank you So trying to like trying to balance the like my own perspective and the the company perspective or Whatever you would say the company perspective is um and and listen to people and think like okay Are they making sensible points? Are they making reasonable points or is it just like? uh Well, let's be honest. Is it just like racism with a with a little veneer over it or no veneer at times so it was yeah, it was I would say it was without a doubt worth it, because it was creating that psychological safety for, for a huge number of, of, of people who, who worked for Expensify. Um, and, and yeah, like a, a really, you know, if we're advocating for the, for taking these stances, we should also be the ones who are taking responsibility for, for engaging with the follow up about it as well. Like it's, it should be your job to do that. You can't just sort of shy away from it. Yeah, exactly. Yeah. Yeah. And so at its height, how much of your day was, was this taking up? Not a huge amount. I'd say at its peak, it was probably like 30 minutes to an hour at most a day. Um, but that was really the peaky peak. Um, yeah, exactly. And totally worth it. Like to, like I said, to, um, to create that safety for our colleagues. Yeah. Yeah, and so at what point did you bring your ceo in to answer some of that? Oh, he was he was into it in it from the beginning from the very beginning. Yeah Yeah, he was a supporter of the project like he was also seeing the same problems and and trying to work out how to address it um, and so he was he was involved in the Problem statements in in the design in in all of it. Really Um, he wanted like he was Very keen on doing it. It wasn't me just surprised being like, Hey, David, I've got this thing. So just start now. No, it wasn't that it was, uh, it was him from the beginning as well. So was there a point at which you felt like you needed to iterate? You'd created this process where these conversations were coming to you. You were using keywords. Um, and then you also had this manual process where, um, specialists could say, well, I'm just basically tapping out of the conversation. Um, and then was that kind of all you needed to do or were there other tweaks you need to make to that process? There were definitely tweaks. So I would go through and I'd review which keywords got conversations. Escalated automatically and then I would edit the that list to make sure that that that like those false positives weren't coming up so much um, and there were obviously bugs that we found with the the system as well where it was like It was funny things where it's like if something happened to be on the next line And it looks like it was part of the thing, then it would still automatically escalate it. Um, one of the interesting things we found, like years later, like maybe two years later after we'd implemented this, was, or maybe even longer, maybe two, two or maybe even three years later, was that we found that there were, there were people who just didn't know that this was an option. And so we, we found that once again, there were, there were some of our, um, some of our outsource support agents who were ending up in like really Awful conversations and who thought that they had to see them through and so we had to sort of retrain and reinforce the process and redocument the process and just very clearly state like, no, this is not your job to be to be like the punching bags here when you see this situation, either you. One that you're engaging in or one that you see with a colleague, there is, you, you should always feel empowered and feel like your default is send it to the senior leaders so that they can engage with us. What do you think the line is? What do you think the line is between Um, I'm a support specialist. I should keep this conversation and actually, I'm going to wash my hands of it. Yeah, I think in general, it's when the language diverts away from process or product and diverts to person is a very clear boundary for me. Yeah, it's exactly that where it's like, it's less about this product is kind of crap and more about you as a person working. Here you are crap. Um, I think there are other, there are other cases where like, you can talk about product or process in a way that, that, that is not great. Um, but, but for me, it's really like when you're targeting an individual person, uh, the person you're having the conversation with or someone else, like how can your, you know, how, how can your engineers work here? They must be absolute garbage. How dare they, they, how do they can't do a job, blah, blah, blah, blah, blah. You know, that's the kind of stuff that, that, um, That sometimes you see, uh, coming through our support channels. Um, that, that kind of stuff is like, wow, that's, that's just like, this is still work. You know, like this is still work, you know, that you're not just like spouting off on Twitter, right? I don't understand. I actually, I don't fully understand. I understand people getting really annoyed. Like I get really annoyed at, um, in, in some support interactions, but like it's still work. And it's worked for me and it's worked for the person I'm talking to most of the time. So just like treat it as if it's work and, and act accordingly. Uh, that was total tension, but, you know, yeah. Uh, yeah. Well, and, um, so it's, it's, I like that, that rubric of, um, When it changes from being about the product or the service to being about the person that they're, they're talking to, um, or a person that talking about as well, like, yeah, yeah, yeah, yeah, yeah, yeah, exactly. He has his flaws, but he's still a human being. Yeah, yeah. Well, and at some point it's just not productive, like you said, and no is a no, your, your CEO had made the decision. A person writing in saying, well, you've lost my business is not necessarily going to make that change. Yeah, that sucks. I'm sorry to hear that. If you change your mind, we are here. It's a bold stand to take and unusual, I think, in the software world. Yes. Yeah. Yeah. Um, I mean, like I said, I'm not an expense buyer anymore, so I can't speak to what. Like, I merely have 70 Expensify accounts that are associated with my personal email address and I can tell you that there wasn't a similar newsletter sent in the last couple of months of recording, as of recording, so it's possible that that, that, that, uh, that that's policy changed. Yeah, maybe. So the process that you used to kind of drive those escalations manually and automatically, did you have any measurements of success? Um, or like, I mean, I can think of a few like agent, uh, wellness or feedback about it, you know, but did you have anything that you said? If we do, if we meet these numbers, then we've succeeded with this process. Not no, not really at all. No, it was it was about creating conditions for that psychological safety that we were looking for Um, we did Yeah, I know. Yeah, I mean I guess you could look at um, certainly our uh, some of our vendors were measuring Uh, like satisfaction, employee satisfaction scores. Um, and there may have been trends in there that we could have picked out. But there was, it was purely anecdotal, both in terms of problem identification and then later on in terms of actually hearing back afterwards that people were really relieved and, um, grateful for, for taking the approach that we did and making it clear that it wasn't their responsibility. In that process, did you find you had any specialists who kind of rose to the top and found, Oh, I actually like handling spicy conversations. Yeah, there was, there was one person who wasn't part of our senior leadership team who, who opted in to the responsibility as well. Um, they did, they, uh, and it was exactly that. It was like, I, I kind of like these spicy conversations and literally like during, while we were designing it was sort of, we were, we were talking, they were like, but I, can I, Can I just join? And I was like, yeah, I mean, yeah, you, you can sure go for it. You have fun. It sounds like overall, it was a really great experience and you, um, you're happy with the process you created. Couple more questions. Were there any tools that helped you with that from internal knowledge bases to just using Slack? How did you implement that? Yeah. So, um, at Expensify, we had a, we had a, like a defined project documentation document, which was basically the embodiment of our, of our product, of our product and process design, uh, into a single document. So I'd say Google Docs is the top one for that, obviously Slack for any kind of design, design conversations. Uh, we are, we were primarily like. Very very widely distributed around the world and relied heavily on asynchronous communication including for meetings effectively, uh to discuss product changes or anything like that and so We used slack very heavily to to have all kinds of discussions around it Um, there was also like there was a github repository that I found Which had a a text file in it, which was basically like here's all the naughty words and um yeah, and so I I Took that as the source of the list and then like trimmed out a couple of them that were creating strange sort of false positives and, um, and went with that. Apart from that, as I said, because we home grew our own, our own help, help desk, our own, our own conversation solution. Um, it was like just work with our engineers to get it, to get it built into there. So if, um, if I'm a. A customer support leader. And I'm in that same position you were in for whatever reason, political or not. And we're getting the influx of these really angry conversations that are not related to the product necessarily. Do you have advice for me on how? I could go about getting started with what you did. Absolutely. So if you're using like Help Scout, if you're using Zendesk, if you're using Intercom, um, the simplest way to do it is just first set up a separate inbox, set up a separate, separate grouping of conversations and have the, have your senior leaders get into there. Um, that could be more or less popular depending on where you work and how they view their own responsibilities as creating the chaos rather than just responding to the chaos or both. Um, And and then I think that's like, honestly, even if you don't have any automatic escalations, the manual step is very simple for most people and is a very quick process for most people. So just have people have clear expectations around when to send the conversations over. For example, if it's a particular topic or if it devolves, the conversation devolves as we were talking about earlier, so it's no longer talking about Process or product, and it's not talking about a person or people instead, um, then you can, you can move them over to that separate inbox. Um, I, I honestly think that you don't need to, like, we, we had quite a bit of scale on our side that we wanted to, uh, to have, have it happen both from a, from an. support team perspective. We didn't want to have to train everyone on exactly what to look for. But we also wanted it to just be able to handle getting dozens, if not hundreds of conversations a day and and putting them in the right place. But most people will not have that same scale. So you can do it pretty quickly and pretty easily just by having having that sort of awkward conversation of Hey, this might not be our support team's job to engage with these conversations. Uh, Our speciality is in our product and our customer base and how they solve their problems at work. Um, and so maybe someone else should engage in these. Um, it's, think of it as a bit of all hand support, but for your senior teams. And you, your, was it your first thought to send those to the senior team? Um, or did you consider having managers handle those? I certainly, I certainly considered having not managers, but I certainly considered, um, whether it would just be our internal support team or not, um, or if it would be like an opt in group of people, uh, before we landed eventually on the, no, this is, this is an explicit responsibility of the senior leaders. I just think that's beautiful. I think managers often get saddled with a lot of that. And so just, just skipping them, letting them do their job and then having the senior leadership handle it. It's really exactly. Yeah. Yeah. Not always possible. I'm sure for every team, but, um, but in this case, it seems like it made sense. Yeah, it did. Um, and a lot of it will be the peculiarities of Expensify. But you know, every company has its own peculiarities. Yeah. Yeah. I'm super excited to share this, um, process. I had no idea walking into this. We were going to talk about one of my favorite topics, which is escalations and spicy conversations. So I can see how we can make it into a really clear step by step. For folks, it just really, really cool. Um, so thank you for sharing. I appreciate it. That's my pleasure. Do you, do you have a joke for me? I do. I do have a joke for you. It's one of, one of my favorites. All of my jokes come from my dad. So there's some pressure to, to tell them well, right. Um, okay. So. This one is the Lone Ranger and Tonto, um, which is a throwback to previous generation. Uh, the Lone Ranger and Tonto are out camping, and they're asleep. And, um, the Lone Ranger wakes up and, and sees the sky up above with all the stars and tells this to Tonto. And the beautiful, like, Milky Way going over, and, you know, they're out in the middle of nowhere, and he's telling this to Tonto, and he says, Tonto, do you know what this means? Uh, and Tonto says, uh, it means somebody stole our tent. Ha ha ha ha ha!