Conor Pendergrast I think in general, it's when the language diverts away from process or product and diverts to person. That's a very clear boundary for me. It's less about "this product is kind of crap" and more about "you, as a person working here, you are crap."
Jen Weaver Welcome to Live Chat with Jen Weaver. Today's guest is Conor Pendergrast, founder of CustomerSuccess.cx. He shared the innovative approach that he created at Expensify for managing spicy customer conversations — you know, those escalations that make your blood pressure go up and feel a little scary. From setting clear boundaries to creating leadership accountability, Conor's strategy prioritizes team well-being while tackling the toughest interactions.
Welcome to the podcast. This is Live Chat with Jen Weaver, I'm here with Conor Pendergrast. Would you tell me a little bit more about yourself, what you do, what your customer support journey is?
Conor It would be my pleasure. My name is Conor Pendergrast, I run CustomerSuccess.cx, where I help CX professionals — mostly customer support, and in particular leaders — to stabilize and grow their careers. I do that through coaching, newsletters, free products, and consulting as well.
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. When you play music, you buy sheet music. Back in the day, Jen, you used to go to a shop and buy sheet music to play. So if you're a violinist you would have gone and done that.
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, that was my first customer-facing job and I was just a terrible employee. So, to Liz, I apologize. And I promise I'm better now — 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 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 left in February 2024, and I've been doing my own things since then.
Jen That's fantastic. That sounds like an exciting year for you this year.
Conor It has been a real exciting year, yes. As well as having two children, and my wife also just finished her PhD. So we're all quite tired and busy, but things are good.
Jen That's great, I love it. Well, thanks for joining us, I really appreciate it. Can't wait to hear about the process that you're going to share with us. But first, do you have a joke for me?
Conor Oh boy, do I have a joke. Why did the customer support agent bring a ladder to work?
Jen I don't know, why?
Conor Because they heard that CSAT scores were through the roof.
Jen Could barely keep a straight face at that terrible joke. That's great. Well, it's a good problem to have.
Conor Absolutely, yes. If you've got a roof rack on your car, throw a ladder on it, sure. Why not?
Jen Obviously. Bring a ladder to work. I would love to hear about this process that I don't know much about yet, so I'll be learning along with everybody else.
Conor Segueing into something totally different, really bringing the mood down. So while I worked at Expensify, I was on the senior leadership team, as I mentioned, and I also had a heavy focus on customer support and customer success, because that was one of my main interests and how I found a lot of joy and value and excitement at work.
For some background context: one of the things that Expensify did, and became quite renowned for sometimes, was taking big swings at addressing difficult social topics, we'll say. In particular I'm thinking about a time that we advocated for a particular political candidate in a contentious election, about — oh, let's say maybe eight years ago or so.
How we did that was by sending newsletters about it to our customers, and that was like millions of people. So that was one example. We would also do things like, in product, on our sign-in page, we would put social causes we cared about and try and promote those.
Both of those approaches that we took brought on some heated and interesting replies. Our 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. Whenever we launched one of those campaigns, it would cause quite a bit of stress for our support team. Obviously — suddenly they're being engaged with on topics that they're like, "Why? I don't understand about democracy in the United States. What's this got to do with me? This person is making a point about the United States of America being not a republic or a democracy — what are they talking about?"
Jen Were they out of the country?
Conor We actually had a mix. We had an outsourced support team and an internal support team as well. We did have it tiered, but our outsourced support teams would very quickly be like, "I don't know, what are we supposed to do here? We don't have a process for this."
So some of the conversations would sometimes devolve into less friendly language, and more abusive language, and sometimes threats and that sort of thing. And alongside that — 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.
Based on that context, what we did was introduce automatic and manual processes for bringing those conversations specifically to our company's senior leadership team, and having them be responsible for managing those interactions.
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. It was quite novel in a lot of ways, because you would end up talking to sometimes David, the CEO. Which I found to be quite a good thing, because he was at the forefront of advocating for a lot of the messaging that we were sending. It was nice to see him take on responsibility for engaging with people as well, after the fact.
So what we did was, as I said, manual and automatic processes. This is a project that I led. 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 those words.
Most of the time, I'd say probably after our initial surge of conversations, a lot of the time that would be someone accidentally typo-ing a word and then it gets sent the wrong way.
Jen So there were definitely periods of time where this was more crucial, right after an announcement or a newsletter.
Conor Absolutely, yes. And part of it was, once you've sent that first initial big newsletter, it doesn't matter what you're saying in subsequent newsletters. It could be 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.
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 team, felt like a conversation was devolving to a certain point — where the customer was, you know, we've all seen this sort of behavior sometimes, unfortunately, 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 engage with the conversation.
For us as senior leaders, our aims were de-escalation and learning as well. If it's a topic that we don't know much about, or a topic that we do know something about but there are some novel arguments against it, then we try to actually learn from it and see, what is it that we can adjust in what we're saying? Where can we change our minds? Or how can we change their mind, some of the time as well?
In the de-escalation sense — if we're not able to de-escalate it, a lot of the time it's just like, "Hey, no, that's not how we expect you to treat our teams. That's not how we expect to treat you." Setting boundaries. Setting clear, unequivocal boundaries.
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." And then our CEO would be like, "I am the CEO. You are talking to me."
Jen The buck stops here.
Conor Exactly. And it's like, no, we've said no 16 times, and actually I am just very clearly saying no. It's not someone who doesn't know what they're doing — we have clear processes around this.
In the event that we weren't able to de-escalate the situation, then we also had the option to either temporarily or permanently block conversations as well. Because we considered that to be non-negotiable. You can't just abuse our support team. It's just not part of the deal.
Jen So those were some features of the help desk you were using — the ability to block?
Conor This is why it was actually quite a significant project. At the time Expensify, and still now, had rolled out our own custom-built customer interaction system, basically, where everything was run on top of Expensify's own systems. 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 describing the problem and the solutions and how it should work, I was the one saying, "Okay, we should block for this period of time, and then allow for unblocking automatically" — those kinds of ideas. So part of it was being able to design it exactly to our needs.
Jen That makes sense. How did this land on your desk in the first place? Did you have support specialists who were saying, "Hey, you're my boss, this is not going well, what should I do here?" Or did you just sort of organically know it was happening?
Conor There were two paths to it. For our outsourced support teams, it was hearing the feedback from their leaders and saying, "Hey, it's not clear what they should be doing." So we tried a little bit to educate them on how to engage in the conversations, and how to try and de-escalate the situation for those more abusive behaviors.
But it always felt like it was creating a psychological stress that was not theirs to bear. It's not really their responsibility and it's not really their job to have this. Whereas me — I'm in a very comfortable situation, I'm very lucky, very privileged, and I'm not nervous about the next interaction. I'm not jumping from a QuickBooks Desktop question, to a QuickBooks Online question, to someone telling me that they want me to die, to the next question. I don't have quite as much stress around it.
And I also don't have the same expectations from a KPI perspective, or any concerns around that.
Jen Was it affecting their KPIs, their CSAT ratings?
Conor Not CSAT ratings, because that wasn't something that we actually measured, or looked at on a per-agent basis — because of these sorts of things. Because they just, a lot of the time, got affected, and so it wasn't really fair to look at it from that lens.
Jen It's a little bit of an aside, but what did you measure instead of CSAT for agents?
Conor We were looking at quality scores instead. So we were looking from the other perspective, basically saying: do we think that this person did the right thing, from our knowledge of the product, and from our knowledge of the processes, and from our understanding of what the customer wanted? So we were looking from that internal perspective rather than the external perspective.
Jen All right. So you've got your leadership who is creating some political situations —
Conor Creating the political situations, to be clear. Responding to the political situations.
Jen — in ways that some of your customers were not delighted with, and they wrote in and had some spicy conversations. And then support specialists were coming up to their managers saying, "We don't know what to do." Managers saying, "I don't know how to handle this." And then you responded by saying, you know what, we should take these conversations to the source, to the leadership team who's making these decisions.
Conor Exactly.
Jen And then how did that go?
Conor It went okay. It was nice to be able to — because it was a much smaller group of people. We weren't talking about a hundred or so people who were trying to very rapidly learn about all of these issues. We were talking about, I think, about 12 or 13 of us at the time engaging in these conversations. The senior leadership team, which includes all the senior leaders, the directors, and the C-suite as well.
It was difficult. Sometimes it was simple — you know, someone who's just sending us repeated abusive messages, that's a very clear-cut one. Not easy, but very clear-cut. 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 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."
Jen You know what's funny, you said that — I've often felt that with spicier conversations, actually letting them stew for a little while. 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.
Conor Exactly. That would be a tactic that I would employ as well. Sometimes where someone's just going, going, going, I would literally send a message just like, "Cool, you let me know when you're done and I'll address your points."
Sometimes that would be a bit of an enragement point for them, and sometimes it would just be like, "Okay, cool, fine — there's a person who's actually reading these messages and they're taking me seriously."
Jen So did you answer a good portion of those?
Conor Yeah. Certainly at the beginning, I think I was the only person in the UK on the team, only person outside of the US maybe on the team at the time. So it was like I'd start my day and be like, okay, here's a nice big backlog.
A lot of it depended on when we were sending newsletters, so thankfully a lot of that was during US hours and we'd have the bulk of our team there to engage in those conversations. But without a doubt it was large numbers of conversations at times.
Sometimes, like I said, it was very simple. Sometimes it got a lot more complicated — like when you're, I don't know, if you think about the topic of Black Lives Matter coming up. I can't view it through an American lens, really. I'm not in the United States, and so it's a little bit more difficult for me, because I'm looking at it from my British lens, which has different connotations behind it, both in terms of language but in terms of how race is manifested here and how we think about it. Or how I think about it, I guess.
So trying to balance my own perspective and the company perspective — or whatever you would say the company perspective is — and listen to people and think, okay, are they making sensible points, are they making reasonable points? Or is it just, let's be honest, is it just racism with a little veneer over it, or no veneer at times?
It was, without a doubt, worth it, because it was creating that psychological safety for a huge number of people who worked for Expensify. And if we're advocating for taking these stances, we should also be the ones who are taking responsibility for engaging with the follow-up about it as well. It should be your job to do that. You can't just shy away.
Jen As a leadership team.
Conor Exactly that.
Jen That makes sense. So at its height, how much of your day was this taking up?
Conor Not a huge amount. I'd say at its peak it was probably like 30 minutes to an hour at most a day. But that was really the peaky peak. And totally worth it, like I said, to create that safety for our colleagues.
Jen At what point did you bring your CEO in to answer some of those?
Conor He was into it from the very beginning. He was a supporter of the project. He was also seeing the same problems and trying to work out how to address it. He was involved in the problem statements, in the design, in all of it really. He was very keen on doing it. It wasn't me just surprising him being like, "Hey David, I've got this thing, so just start now." No, it was him from the beginning as well.
Jen 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, and then you also had this manual process where specialists could say, "Well, I'm basically tapping out of the conversation." Was that all you needed to do, or were there other tweaks you needed to make?
Conor There were definitely tweaks. I would go through and review which keywords got conversations escalated automatically, and then I would edit that list to make sure that those false positives weren't coming up so much. There were obviously bugs that we found with the system as well — funny things where if something happened to be on the next line and it looked like it was part of the thing, then it would still automatically escalate.
One of the interesting things we found, like years later — maybe two years later after we'd implemented this, or maybe even three years later — was that there were people who just didn't know that this was an option. We found that once again there were some of our outsourced support agents who were ending up in really awful conversations and who thought that they had to see them through.
So we had to retrain and reinforce the process, re-document the process, and just very clearly state: no, this is not your job, to be the punching bags here. When you see this situation — either one that you're engaging in, or one that you see with a colleague — you should always feel empowered, and feel like your default is to send it to the senior leaders so that they can engage.
Jen What do you think the line is between "I'm a support specialist, I should keep this conversation" and "actually, I'm going to wash my hands of it"?
Conor I think in general it's when the language diverts away from process or product and diverts to person. That's a very clear boundary for me. It's less about "this product is kind of crap" and more about "you, as a person working here, you are crap."
I think there are other cases where you can talk about product or process in a way that is not great. But for me it's really when you're targeting an individual person — the person you're having the conversation with, or someone else. Like, "How can your engineers work here? They must be absolute garbage. How dare they. They can't do a job," blah blah blah. This kind of stuff that sometimes you see coming through our support channels.
That kind of stuff is like — nah. This is still work. You're not just spouting off on Twitter. I don't fully understand — I understand people getting really annoyed, I get really annoyed in some support interactions, but it's still work. And it's work for me, and it's work for the person I'm talking to most of the time. So just treat it as if it's work and act accordingly.
Jen I like that rubric of when it changes from being about the product or the service to being about the person that they're talking to — or a person they're talking about as well.
Conor Yeah, exactly.
Jen He has his flaws, but he's still a human being. And at some point it's just not productive. Like you said, a no is a no. Your CEO had made the decision. A person writing in and saying "well, you've lost my business" is not necessarily going to make that change.
Conor "That sucks, I'm sorry to hear that. If you change your mind, we are here."
Jen It's a bold stand to take, and unusual, I think, in the software world.
Conor Yes. I mean, like I said, I'm not at Expensify any more so I can't speak to how — 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, as of recording. So it's possible that that policy changed.
Jen Maybe so. The process that you used to drive those escalations manually and automatically — did you have any measurements of success? I can think of a few, like agent wellness or feedback about it. But did you have anything where you said, if we meet these numbers then we've succeeded with this process?
Conor No, not really at all. It was about creating conditions for that psychological safety that we were looking for.
I guess you could look at — certainly some of our vendors were measuring employee satisfaction scores, and there may have been trends in there that we could have picked out. But 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 grateful for taking the approach that we did, and making it clear it wasn't their responsibility.
Jen 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?
Conor Yeah, there was one person who wasn't part of our senior leadership team who opted into the responsibility as well. It was exactly that — "I kind of like these spicy conversations." Literally while we were designing it, we were talking and they were like, "Can I just join?" And I was like, "Yeah, I mean, you can, sure. Go for it, you have fun."
Jen It sounds like overall it was a really great experience and 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?
Conor At Expensify we had a defined project documentation document, which was basically the embodiment of our product and process design into a single document. So I'd say Google Docs is the top one for that. Obviously Slack for any kind of design conversations.
We were primarily very widely distributed around the world and relied heavily on asynchronous communication, including for meetings effectively, to discuss product changes or anything like that. So we used Slack very heavily to have all kinds of discussions around it.
There was also a GitHub repository that I found which had a text file in it which was basically "here's all the naughty words." So I took that as the source of the list, and then trimmed out a couple of them that were creating strange false positives, and went with that.
Apart from that, as I said, because we home-grew our own help desk, our own conversation solution, it was just working with our engineers to get it built into there.
Jen So if I'm 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?
Conor Absolutely. If you're using Help Scout, if you're using Zendesk, if you're using Intercom, the simplest way to do it is just first set up a separate inbox, a separate grouping of conversations, and have your senior leaders get into there. 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.
And then, 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. So just have clear expectations around when to send the conversations over. For example, if it's a particular topic, or if the conversation devolves, as we were talking about earlier, so it's no longer talking about process or product and it's now talking about a person or people instead — then you can move them over to that separate inbox.
I honestly think that you don't need — we had quite a bit of scale on our side. We wanted it to happen from a support team perspective, we didn't want to have to train everyone on exactly what to look for, but we also wanted it to be able to handle getting dozens if not hundreds of conversations a day 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 that sort of awkward conversation of, "Hey, this might not be our support team's job to engage with these conversations. Our speciality is in our product and our customer base and how they solve their problems at work. So maybe someone else should engage in these."
Think of it as a bit of on-call support, but for your senior teams.
Jen Was it your first thought to send those to the senior team, or did you consider having managers handle those?
Conor I certainly considered — not managers, but I considered whether it would just be our internal support team or not, or if it would be an opt-in group of people, before we landed eventually on "no, this is an explicit responsibility of the senior leaders."
Jen I just think that's beautiful. I think managers often get saddled with a lot of that, and so just skipping them, letting them do their job, and then having the senior leadership handle it is really — exactly.
I'm super excited to share this 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 really excited. I can see how we can make it into a really clear step-by-step for folks. Really, really cool. So thank you for sharing, I appreciate it.
Conor That's my pleasure. Do you have a joke for me?
Jen I do have a joke for you. It's one of my favorites. All of my jokes come from my dad, so there's some pressure to tell them well.
Okay, so this one is The Lone Ranger and Tonto — which is a throwback to a previous generation. The Lone Ranger and Tonto are out camping and they're asleep, and The Lone Ranger wakes up and sees the sky up above with all the stars, and the beautiful 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?" And Tonto says, "It means somebody stole our tent."
That's it for today's episode. Big thanks to Conor Pendergrast for sharing how leaders can step up and protect their teams during challenging interactions.
The big takeaway here for customer escalations is to start small and focus on creating psychological safety — but you can get Conor's whole process in the show notes. Also, check out Conor's email list for encouragement and more tips on how to thrive as a customer support leader.
When you subscribe to Live Chat with Jen Weaver, you'll also get access to all the playbooks from all of our episodes, including templates and other features you can use now. See you next time.