What makes people stay

Alex Plasket There are questions I never want anyone to ever have to answer again, and I think that's where AI can step in. But as soon as something is complex, it doesn't help the situation for someone to then be greeted by another stonewalling robot, if you will.

You've got Alex the person here. I get that you've been trying to get this resolved for a few days. I'm here to help you. Let's get this taken care of together.

Jen Weaver Welcome to Live Chat with Jen Weaver, the tactical support ops podcast, where experts share exactly how they do it on their support teams.

Today's guest is Alex Plasket. If you've ever wondered how to build a team culture so strong that people don't want to leave, it starts right here. Alex walks us through his approach to onboarding, coaching, and culture — from the first day going over the syllabus, to having a team of support specialists who just don't want to leave.

You'll learn how he uses real conversations to teach team voice, builds trust with his problem versus concern theory, and turns CSAT feedback into learning experiences that really build the team.

Before we get started, as always, this podcast is brought to you by supportman.io, your QA tool for sending actionable feedback from Intercom straight over to Slack. All right, let's dive in.

Alex Jen, first and foremost, I'm so excited to be with you today and talk about what I enjoy most, which is leading people and helping them grow and understand the potential that they have to offer.

Especially in a customer support world where sometimes it is seen as a stepping stone — but in my mind I'm like, let's make it a stepping stone and a landing pad. Let's do both and figure out that perfect blend.

Jen I love that. So what does that mean to you, a landing pad?

Alex One, it could be a soft place to land. I've had a few people on my team that had come from troublesome job situations, if you will. So it could mean literally a soft place to land and be welcomed and celebrated for however long you're with us for.

And then it could also mean, let's grow from that. Your landing pad is your foundation to grow. I've had the opportunity to have folks stay with me for at least a few years and then, if you will, graduate to another department — and everything that they've learned with us is something that they can apply along the way.

Jen I know that you are an amazing manager and have moved team members through, and they found that their time with you was some of the best team time that they had. I've definitely seen that myself.

Some people just have a knack for creating kind of a cult following on their team. Can you teach us all to be that cult-following manager the way that you have?

Alex Yes. That is actually my low-key goal — if people think, wait, is this support team, Alex's team, is that like a cult? Like, what's going on over there? If that's the question that's going on, I know I've done my job.

I know it almost sounds funny. There's no secret handshakes. Maybe there is. We don't have any tattoos. Maybe.

But there's that mystery of it. Because one, you have to have fun. If you don't have that, then — in true honesty, customer support is not always a glamorous job. There are tough days, we can't gloss over that. So you have to have something in the roots and your foundation to go, well, we still have each other, we still have this fun inside joke, we still have our language.

Part of that is really important in the beginning when I first get someone to join the team. When we're talking to folks before we hire them, what I'm thinking is, does this person make sense to join the team? I want so many different minds, so many different perspectives, but overall, do they align? Will they help the team? Will they come to the rescue? Because that's super important in my opinion in the support world — I need folks that will come to the rescue and be able to support each other.

So that's where it starts. And then from there — it's not buzzword-scalable, but I want to spend as much time as possible with this new person.

Jen This is really interesting to me. I'm sorry to interrupt you, but this seems key to your process, because a lot of times we're trying to automate and scale and spend less time one-on-one. It sounds like you're saying this actually saves you time and energy in the future by spending more time with your new team members.

Alex Yes. And there are a few things that I think are beneficial there, Jen.

One, you're building a foundation of trust right off the beginning. They know that you are there for them. Of course over time I want to build that autonomy, and I don't think that can just be done right off the bat. Because especially in support, you're getting folks from a myriad of career paths. I have folks that have been in the corporate space for many years that are just career-changing, or folks that have worked in healthcare and are wanting to try something new, or folks that are brand new into the corporate world not long after college.

So that's one reason why I would want to spend so much time — to establish where are you at in your life and your career path here, and then how can I help you?

Jen What does that look like, spending time with them? Obviously we're talking about remote work.

Alex So, hands-on with everything. The first day I call it syllabus day. We are just going through every item, making sure everybody has the login that they need. I never want it to be two months down the road and they're like, wait, I don't have this. No, we're never going to have that happen. You're going to have everything you need.

It's a little droll, I'll admit, but it's important to just know that I'm with you in the little things too. I'm not just going to give you everything. Plus it's just kind of nice to see all the boxes being checked along the way so I don't have to worry about it later.

And then a few days into it I'll show — chats are a really big part of what we do at our company, it's a majority of our communication. So that's very easy to observe and show, so I can start leading by example.

And that's another thing that's important with this: the voice. I want everyone to build their own voice — because you want consistency, but not so consistent that you think you're talking to either a robot or the same bland thing. So you want the spirit of our company and what our brand should represent and how you communicate with us, and then from there you can give it your personality.

For example, I typically take on a more folksy southern charm, if you will, when I'm talking to folks. That's just my persona. But at the root of it, we are empathetic, we will resolve everything, and we will make you feel like we care along the way. I want that to be established first and foremost.

The nice thing is that comes built in. You can't truly teach that, but you can show people the way in that regard. In addition, you can give them your style. You can show them examples and how my mind is working, so then they can draw from that and come to their own conclusions and make the decisions when challenging cases arise.

Jen What tools do you use to do that? Do you have an internal knowledge base where you're keeping those checklists for onboarding?

Alex In my opinion the first week for sure needs to be as scheduled as anything. They need to know what time they need to show up, what time the first meeting with me is, after they meet with the security team to get their computer set up. And then everything is scheduled — you know when you're with me, you know when you're shadowing another teammate. Because I've still got other meetings I've got to go to as well.

And yes, everything's in our internal knowledge base. Everyone has their own — this is Alex's new hire guide. Week one is highly scheduled, and then week two is kind of, what do you need?

That's the thing where it's tailored. I'm not going to know — some people need one week, some people need two weeks, some people need three weeks, and I can't know that unless I start working with them. And in my mind, sure, let's go to three weeks even though I've written it as two, because I want you to be set up for success.

Like we said earlier, it ultimately does save time in the long term. By committing all of that, there are fewer questions, they have more confidence to look things up for themselves for those more challenging questions.

And then I can even link everything. We've noticed for our particular service model — somebody that used to be on our team that's moved on internally created the "help I can't" series. It's approachable for a new team member, for anybody. So basically, "help, I can't log in." "Help, I missed my payment." "Help, my card is declining."

So whoever calls you, that tells you what doc you need to look at real quick. And instead of it being a two-page textbook, it's just a quick "what's going on," it's bulleted, really easy to read, which is very approachable for new hires. And then even folks that are like, wait, what do I need to do for this? Oh yes, just look up the guide. Okay, yes, they are XYZ, great — now I can solve this problem for them.

Jen We just talked about maybe resisting scalability, but it sounds like that's also a way that getting to know your team can help you scale. With that "help I can't" series, somebody started it, and it was such a great idea that when that person moved on, folks were able to continue it.

So it sounds like during this initial onboarding period, you're really getting to know what their strengths are. What else are you discovering about your new hires in that intensive first week?

Alex One, how they learn. Two, how they receive feedback.

We have an opportunity where I go, hey, do you want to drive? Which means you want to share your screen and you want me to sit in the seat next to you and tell you what to do — the navigator. So typically a lot of people choose that option. Or they're like, I want you to drive and me to sit in the front seat and watch, and you tell me what's going on.

Jen And this is while you're in the queue, screen sharing and working in the queue together. It's either you answering the questions and they're watching, or they're answering the questions and you're saying, well, type this, and let's talk about this.

Alex Depending on what they're comfortable with. Both of those options.

So that's my opinion — you can't just start everyone the same. You can't just throw them in and expect success. Maybe that works for some folks. I had someone who was done in a week. I was like, are you sure you don't need anything else? And they're like, yeah, I'm good. I'm like, okay.

So you just go to what they need. And that helps them feel like they're being listened to, that they can trust me, and that we will figure this out together along the way.

Even though they don't necessarily know what it means or what's going on, it's the kinesthetic approach of, I want their fingers literally typing on the keyboard if that is what they need, and then I'll tell you what it means. Like, for now tell them that their card won't work at this location — without having to give you too much context, just tell them this and I'll tell you why.

And then that's a really good opportunity, tying into how I can give them all of my philosophies along the way. One of my biggest philosophies is the problem versus concern theory.

Jen Problem versus concern. Okay.

Alex To give you and our listeners context: we send a Visa credit card to our members so they can use it for out-of-pocket healthcare costs. Visa is well established, we know what that means. They get a plastic card and they also have a digital version, they can use either.

So — and I always hope this example comes up right away, if not I'll force it anyway — someone has just lost their card. This could be either a new member who hasn't got it yet, or someone who has been with us for a little bit and lost their plastic card. And now they're nervous, because they were really hoping that they could use our card to pay for their copay this week and then pay it back over time. They were really banking on that.

So they call, they're a little nervous, they're concerned. They're worried that, hey, I lost my card, I don't know what to do.

"Hey, I completely understand. First and foremost, we can definitely get you a new card. However, it will take about 10 to 12 business days to get to you." And they're like, well, that's not enough time.

But before they even continue to be nervous, you meet them before that. And what's their real worry, Jen? They're worried they can't use our product to take care of their copay this week.

So the literal problem: they lost their card. But why are they worried about it — the concern — is now they can't go to the doctor. So they think.

So if you can catch them before they continue their spiral, you can say, but wait, have you heard about the virtual card? And they're like, oh my gosh, yeah, I know about that. Or, wait, no, tell me more.

The virtual card, you can add it to your mobile wallet, or literally just tell them what the numbers are and they can type it in. They want their money, they're going to type it in. And you kind of meet and predict — or in the buzzword for the customer support world, proactive solutions. Now they feel like you've been truly listening to them, and they feel taken care of.

That's another important reason why I want to spend this time, so you can read that.

I will one day write a book on the problem-concern theory, but you've got to see it and experience it, in my opinion, to truly be like, oh, that.

And then that makes a wonderful coaching analogy for later. Hey, you did a really great job knowing what they meant, because sometimes people say things differently — and that's one of the skills of support, you're teasing out the important pieces. You did great at solving their problem. I do want to mention that you did not exactly address their concern. Why do you think that is?

So then they can look back at that conversation or listen to the call and go, well, they mentioned that they were worried about this, and I don't think I acknowledged that enough. And I'd say, yeah, I agree. What do you think you could have done to acknowledge that better? Is there a certain word or a certain sentiment? And they're like, yeah, I could have just encouraged them more.

That's a wonderful way that we can establish the building blocks from there. Any time we have to have a more challenging conversation, or good feedback, we have that as our way to do it.

And additionally I can know how people best receive feedback. Do they want the classic compliment sandwich, or do they just want it no holds barred — just tell me like it is? And that gives me, in my mind, the permission. Because personally I'm not a no-holds-barred person, I'm not going to be so dang direct all the time. Unless you tell me to, and then I will definitely do that for you.

Jen You've been doing these one-on-one ride-alongs in the queue as you get started, and then you transition to letting them be independent. Do you go in and randomly sample conversations to see how they're doing, or do you have them come to you? What's your process to wean them off those one-on-ones?

Alex A little bit of both. I'll admit I need to always look at more, for QA's sake.

What I've noticed is helpful is putting it on a little bit of both of us. Either a live check-in — just watch the chats, because we can do that, and write a little note. Or the perfect world solution is, hey, I want you to give me a "toot your own horn" conversation, and an "I need some help" conversation.

Where you think you kicked some butt — show me that, let's show off. And then one where you're like, I don't know how that went, or I know I could have maybe done something better to address their problem and concern, or it was just a difficult conversation and what would you recommend to de-escalate?

So putting it on them, and then they can think about it — because I want them to know what success looks like and what a good conversation looks like internally, so they can make that connection. And then you do a little bit of random, because you find some good stuff with random.

Jen What's your method for finding those? I know it depends on the help desk that people use, but I always found that challenging — to find random conversations without a tool that would do it for me.

Alex The way that I've done it — we use Intercom for chats, again that's our biggest majority of conversations, and they have the happy faces. So I'll sometimes just pick a random happy face.

It is more ideal if it's someone who gives you the starry eyes and has at least two lines of text in their review. Because what did you do to incite someone to feel so compelled to write a glowing review of a customer support agent? That's great.

Honestly, even myself, I have a hard time — I don't write as many reviews as I should. I always feel guilty, because I know how the sausage is made and I know it's important.

Jen I could have increased their CSAT by 1% if I actually did.

Alex Maybe not everyone thinks like that. But regardless, they were blown away by something. What did you do in order for them to feel however they expressed themselves in that moment? Let's analyze that.

And the funny thing, Jen, is it could be the shortest conversation or a really in-depth one. And it's funny, because regardless there's something you can talk about. Hey, why do you think — this was five messages — why do you think they were so happy? They're like, it was fast, they were able to be taken care of, and I did it quickly. And I'm like, great.

It sometimes doesn't come down to just what you say. It's what you do for folks, and how they feel in this busy world where they can hardly talk to a person. They got to talk to you fast.

And then the opposite is, I look at the angry faces in Intercom, especially the ones with comments. And of course this ties into CSAT in general, which is another fascinating topic. But I'm like, why were they mad? Was it at you? Was there something that you could have done differently? Or no matter what, even if you did the best job in the whole world, they still were going to feel that same way — and how can we address it?

So to answer that question fully: it's just parsing through it myself, filtering it by the agent, and looking for the angry faces and the happy faces.

Jen When they surface conversations themselves — do you find that they're often choosing conversations where they actually could have done something better? Or are your specialists finding conversations where it was the product that the customer was angry at, or just the situation?

Alex It's kind of a blend. But typically — I don't have the perfect stats on it — it does seem to be more product-based.

I even remember one review once saying, the agent was fine, I'm just mad about this. And I was like, I really wish I had more people writing that. Because then you could know, okay, well, it's not us. If you look through all the qualitative reviews from folks, I've maybe only seen one or two where they were actually mad at the agent themselves.

But typically when folks want me to review, it's a call — and we haven't gotten all the CSAT figured out for that quite yet. But it's something where they're like, hey, they gave me the runaround, how do I get someone off the phone who we can't do anything for any more? Or — I call it being held phone hostage. I'm pretty adamant on teaching the team to be able to not be held phone hostage.

So that's always a good learning opportunity too. One, they're kind of mad at the product itself, to your point. And two, it ultimately doesn't help, and it hurts the member, to continuously be riled up on the call, in my opinion. So we just want to be succinct to end it. That's always a good call to have someone be like, what do I do? Let's talk about it.

Jen I'm getting this picture of you creating moments where the learning is ripe for your direct report. Instead of "here's an LMS, here's a whole system that you need to run through," you're finding moments where they're going, oh, why did I get a bad rating? Or, this conversation came up right now and I'm thinking about it right now. And you position yourself right there to help coach them when they're ready.

I think that's an organizing theme of what I'm hearing you do.

Alex That's where it's most impactful, in my opinion. You're trying something — you're not just reading about how to ride a bike. Sure, if that's how you learn, great, you should do that. But literally riding the bike is how you're going to get less wobbly over time, and know how to balance yourself and be able to do so independently without someone holding your shoulders, or the training wheels.

To be honest, I don't know what that looks like at other companies with their product offering, or if that's normal. But for us, that's just what I believe works.

Jen I think that nuance is the new normal. Because as AI agents are being implemented, they're taking away the simpler conversations — those that basically could have been answered by the help desk. It's essentially ticket deflection. And so what I'm hearing is specialists are answering more and more complex conversations more often. So I think you're spot on there.

Alex And if they don't see it and they don't hear it from someone who's done this for a while and is able to pass it on — part of that is oral tradition. That's society and how we've grown, that's how we started, and that's still passed on.

Maybe I'm realizing I haven't thought of it like that, but to me that's why I think it's ultimately impactful, because it's personal. And especially to your point with AI, I wouldn't want that to get lost.

Don't get me wrong, there are questions I never want anyone to ever have to answer again, and I think that's where AI can step in. But as soon as something is complex, it doesn't help the situation for someone to then be greeted by another stonewalling robot, if you will, and go, "I will solve this for you." No — it's, hey, you've got Alex the person here. I get that you've been trying to get this resolved for a few days. I'm here to help you. Let's get this taken care of together.

Jen It sounds like for your customer base, emotion is a big part of it. Like you said in your example, they might have a doctor's appointment on Friday, they don't know how they're going to pay for it, and it's stressful. So even if it's a simple question, the emotions are what are human about it.

Alex Yes. We had a fantastic example of that the other day. Someone was having issues getting into their account, and I was like, hey, why haven't we asked what they need to get logged in for yet?

To me — one, could we take something off their mental plate here? Why do they need to get in? And if the reason is just, oh, because I want to log in, great, now we know the severity, or the priority, that we need to put on this.

And they're like, no, I just need to make this one change. And I'm like, great, I can make that change for you.

In their mind — I guess it even applies to Maslow's hierarchy of needs — we've just taken care of a pyramid need here, and now it's off your mind. Because that's how I work: if I can't resolve this one thing, I'm not going to be able to focus on something else.

Once we did that and asked this person what they needed to get into their account for, and we were able to do that for them — in the chat you could just sense a shift, that they were now not worried about it as much. It wasn't as urgent in their mind, because we got something taken care of. And we gave them a workaround: hey, if we're still having issues getting you logged in, this is what we can do to help you as our secondary solution for the time being.

That can help people feel helped and heard and understood, and also just be able to focus better. Because with login issues you've got to do a whole bunch of different hoops, and people don't want to jump through the hoops unless you take care of that.

Jen It's your problem-concern theory. Their problem is not being able to log in, but their concern is whatever that thing is that they need to do. So if you're like, well, I can make this change for you, and then help you log in — their concern has evaporated, and they have more of their brain available to handle those steps.

I get frustrated with login myself, just with the emails and the repeated steps. I've often thought about my customers when I'm helping them — when people are stressed, they lose IQ points. They lose the ability to think critically and achieve things. So if you can relieve that stress for them, I think that's a crucial part of your problem-concern theory, which I love.

Alex Absolutely. And tying it back, that's something that you can teach right away. That's their foundation of approaching every situation. Every situation has a problem and a concern, and they can overlap — as far as the Venn diagram, it could look like two circles completely overlapped, or it could be separate.

And another situation that was helpful for a few of my teammates — this was not necessarily onboarding but over time — is: everything is important. Every time a member reaches out it is important. Is it always urgent?

So the flip side of what we're saying. For my team, how do I help their needs? If everything seems urgent to them, that's them losing their own IQ, so to speak. They're stressed and they're not able to understand and be able to help, and then that might make the member's situation more frustrating because they're not feeling understood.

That's a very nuanced thing. And that's why I like to ask, especially for that example, what's the urgency level here? Because then that tells you what kind of energy.

Of course we're not going to skirt over it, like, oh, you just want to log in because you like logging in, okay, we're not going to care about you. No no no, we're not saying that. It's just, how much mental energy do you need to put forth? If they're just curious, great, let's devote the proper amount of energy to that. That still helps them, and it also helps you — because if everything feels urgent, then what do you start with? So it helps you prioritize and organize.

I definitely have two clear examples of teammates where they still think about it. They're like, once that shifted for me, that helped so much. So now that I know that myself, I can start trying to teach that to folks earlier along the way.

Tying back to onboarding — during onboarding you get to know them, they get to know me, and I've been doing better at opening up a little bit to increase that. Yes, this is my leader, my boss, but they are also a human being who is learning along the way themselves.

But then I know what's interesting and fascinating to them, which might not always develop in the first few weeks, but you at least have that rapport. So you can say, great, you've hit your 30, 60, 90-day mark — that's traditionally our rite of passage, our secret ceremony — and we say, okay, you can now leave the queue occasionally. What other things are fascinating to you?

You've already been building on that. So I have someone who's like, well, I like data stuff, that's kind of fun. Great — well, that's a business need. Align interest with the business needs, because that's two birds, one stone. We've got to get stuff done, but you might as well have someone who likes it and is interested by it, because then that could eventually lead to them launching to something else.

Jen As they do from your team, it sounds like — which is a huge benefit.

So you have launched them from onboarding into this stage where they're mostly in the queue, but they're doing something they're interested in that's also a business need. What are some ways that you're continuing to build trust and that cult-like quality that your team has?

Alex Language, of course, is crucial. Even as silly as Slack emojis. And then just having a business meeting, and then just a meeting where it's just time to hang out — we can talk business if we want, we can talk about that situation, we can laugh about X, Y, and Z.

I'll start with language. I like to call our members friends, because you would do a decent bit of heavy lifting for a friend. And even interdepartmentally, a few people from other departments will say, hey, this friend reached out. And I'm like, yes, it spreads, wonderful.

So I'll post that — you know, "this friend," hyperlink their customer portal, make it look nice and clean, "reached out about X, Y, and Z." That language is important.

And then the team itself — to be honest I sometimes forget what our actual title is, because I just call the team the champions. It almost feels goofy to say aloud, but written it just feels a lot better. The support champs, the champions. I think it's just more fun in that regard. And that's our Slack user tag group, so you don't have to know all the people on the team, you just do @support-champions and that gets all our attention.

Little small things like that. And almost everyone has nicknames too. It just kind of happens.

Jen I know we talked briefly about CSAT and looking through for those super happy emojis and super sad emojis. You mentioned not really including the negative CSAT that's just related to the product. Do you pull those out when you report metrics? Or do you just say, hey, CSAT is whatever it is, but a large proportion of these were not related to the specialist at all?

Alex I haven't parsed out the — what do you call it, the adjusted percentage.

But I do always make sure, when someone asks me, especially from another department who I know is talking to a potential client — I say, hey, disclaimer here, I'm going to show you a number that on paper might not look good. It's going to be about between 80 to 90%, when you would think that we'd have like 100%.

But I just want them to know, I'm going to go ahead and send you the good things that people are also saying. I want them to know the qualitative analysis here. I'd send them a screenshot of the happiest written reviews, and the theme is always like, they were fast, they were helpful and kind, and they actually cared. I make sure that's going through as well, to say, by the way, kind of ignore the number.

Jen Ignore the number, but look behind the curtain and see what's really happening here.

Alex But no, I haven't taken the time to parse it out. I imagine we would be a lot closer to 100% otherwise.

Jen We talked about the cost of acquisition of new hires. It seems like an undervalued function of support is delivering these dedicated individuals with deep product knowledge to other teams, who can do a really good job there. And I think you have achieved that really well.

Do you have any other thoughts about building really good rapport with your reports, and figuring out what they're good at and interested in? And then what does that look like at the end of their life cycle with you? How do you encourage them to move on internally?

Alex I typically leave it up to them. Maybe that's a place where I will grow.

Our alumni group I believe has six people, not including myself, at the moment. And when it first started happening I was a little saddened, going, why are people leaving me? And then I was listening to somebody's podcast talking about it and they're like, no, this is good, this means things are going well. That's my next stage — realizing, no, this is good.

One of my team members felt like they could tell me, at least a few months ago, saying, hey, long term I don't see myself here forever. And I'm like, I get that. Okay, well, what are we going to do? Let's work on this together. I was very honored that they would want to tell me that.

So in that moment, as soon as I know, I'm not going to force them to stay. I'm just going to see what other options are and we can talk about it. So why is this fascinating to you, or what is fascinating about it, and how can I help you? I've been able to talk people through that transition too. I want them to spend the time they want to spend — as soon as they start the conversation, I'm all about, yeah, let's make it happen.

Jen It sounds like it's like everything else you've described. It's very much led by your direct report, by your specialist, in terms of what they need and what their journey is, and then you're there to assist them. It's really truly servant leadership.

Alex Thank you.

Jen I think that's a term that describes you well. And I'm really grateful that you spent some time with us walking us through what that looks like. I can't wait to share this podcast with the world.

Alex Absolutely, Jen. Again, thank you so much, I'm so happy to have this opportunity to speak with you.

Jen Thanks for listening, and thanks again to Alex for giving us a little window into his world.

If you got something useful out of today's episode, make sure to subscribe wherever you get your podcasts or on YouTube. And we also have an email newsletter that sends out this podcast and more — all those links are in the show notes.

Let's go over those steps that Alex uses to create his culture framework.

Step one, start with trust, not scale.

Two, teach the problem versus concern theory.

Step three, coach with real conversations, one-on-one.

Step four, build culture with language and ritual.

Step five, align interests of your support specialists with business needs to help them grow.

Please do reach out to me on LinkedIn, that is in the show notes too, and let me know what you'd like to see in future episodes. And if you lead a support team and want to share your process, I would love to hear from you and potentially have you as a guest on the podcast. See you next time.