240: Fireside with Reagan Helms

Charlotte Ward: 0:13

Hello and welcome to episode 240 of the Customer Support Leaders Podcast. I'm Charlotte Ward. Today, welcome Reagan Helms for a fireside chat. I'd like to welcome to the podcast today, Reagan Helms. Reagan, it is lovely to have you join me for the first time. Thank you so much for coming on the show. And uh for the benefit of our listeners, first of all, would you like to introduce yourself?

Reagan Helms: 0:46

Sure. Yeah, my name's Reagan. I work at a company called Planning Center. I've been there for about 12 years. I started as uh one of their only full-time support agents, and now I've grown it to a team of almost 30 people.

Charlotte Ward: 0:59

So wow. Wow. That's uh that's a a change of circumstance, isn't it? It's uh oh, definitely.

Reagan Helms: 1:05

I'm not doing the job I was hired to do by any means.

Charlotte Ward: 1:08

Yeah, yeah. But that's good. I mean, that's a lot of growth for you, uh, which is which is great. And obviously, like you're able to provide uh a lot of opportunity to to other people as that team grows as well. And and I um know why you're here today. I know what you're here to talk about because we talked about it a couple of weeks ago. Uh, and it was a super fascinating topic because I think it's something that as leaders, we will all, if not already, have experienced. We certainly will at some point if we stick with an organization long enough and have and and a good enough leaders that we retain our people, right? So, so what are we here to talk about?

Reagan Helms: 1:49

Yeah, today we're gonna talk about uh how do you grow people or continue to invest in people that might be at a glass ceiling or uh have grown beyond you know the support department. Um, I think especially for our line of work, it's typically a way in, a stepping stone into the company to do something different or you know, kind of a bit, it's not transient, but you know what I mean. Like it's it's someone that that they're looking for. If we're hiring smart, capable, passionate people, they're not going to want to be answering customer support tickets for the rest of their career, right? They're gonna want to do something else.

Charlotte Ward: 2:25

So speak for yourself, Reagan. I I I built a career in it, but you know, I did I did transition out of the the the queue into into leading it, but I'm still still in good old support and love good old support. Right.

Reagan Helms: 2:40

And those types of roles are limited, right? You're either the person that's on that team or you get promoted, but not every agent that you have can rise to that same exactly.

Charlotte Ward: 2:49

And we kind of bandied around the idea of like this sort of technical glass ceiling, didn't we, before where um which which I think is a really interesting to uh challenge as a leader, and it's one I've encountered before. Um, it's a good problem to have though, right? I mean, it says that you've got great retention, it says you've got people who are, as you said, passionate about their role, passionate about the environment they're working in, and have grown in that environment, which I think is great. But but yeah, what happens when they're they're at the top of their game, that the end of the path, the end of the line, the you know, the the top of the tree. Well, how many more idioms can I squeeze into this?

Reagan Helms: 3:34

End of the road.

Charlotte Ward: 3:35

Yeah. Like because there is, I mean, I had a conversation, I'm I'm going back 15 years now, but I I did have a conversation with someone on my team once where effectively he was the most senior he could be in the environment that I could offer him. And I the discussion went something along the lines of, well, if you stay technical, you can't be the CEO. You know. Uh so I'm yeah, I mean, what do we do?

Reagan Helms: 4:03

Right. There's only so so high up the ladder to go. I think there's a few things to do. The first one is, and I I think that any good leader uh is tasked with this already, but but actually knowing your people and knowing what makes them passionate. So, like what makes that person gifted? Um, and is there a way that that fits into the organization, maybe not on your team? Um, if there's room for that type of organic growth of, you know, hey, you know, what you're doing is so valuable that uh it's worth doing full time, not just part of time. That's more of a startup environment though. And obviously, like there's only so far that that can support everybody's trying something different and nobody's happy in their current job. So um I think there's that option, and I've seen that work out really well. We've had some support agents go on to become product managers at Planning Center or uh some more like technical support or QA roles uh where they were more inclined for that. Um, it's a little bit harder when it's more of a customer service bent, a less technical bent, and more of like a customer success type role. Um, because obviously there's there's uh sometimes that's a completely different department, and sometimes that's just not a value to the organization as much as it is on a support team. Um, and I think that then when you're out of options in your organization to empower these people to grow, or that their growth is healthy and and leads somewhere, I think it does come, you know, if you do care about these people, it becomes kind of your responsibility to start thinking about avenues that they can pursue outside of the company, either in a side gig or helping them and enabling them in whatever way you can for them to transition and even coaching them and like uh and encouraging them, finding finding job posts for them that might fit that type of a role or offering to help them uh by like writing a letter of recommendation. Um, LinkedIn has this concept of a tour of duty, which I find super interesting, especially for the this type of a conversation. Um, they get it from the military, which is like you sign up or sign on to do something of a mutual exchange. So if from the company side, you know, uh, hey, if you're going to take this role or these additional responsibilities, here's what's expected of you in that role. And here's what you as an employee will gain from that exchange and the experience that you'll get or um the opportunities that it offers you in the job market, the the bullet point you can put on your resume. Um, but then at the end of that period of time, it's typically like a two-year, four-year period. Um, you kind of re-up. You could say, okay, do you want to keep doing that? Or do you want to try something different? Now that you have that resume box, now that you have that box checked and you've grown in this particular way, are is there another uh thing that you'd be interested in learning or advancing in? Um, or would you like to get off here? You know, and that's um something that we haven't really done at our company, but it's something that we've looked into in the past because obviously, like I said earlier, you don't I don't think anybody, you know, wants to become just an individual contributor for the rest of their life. They have, they want to be a leader, they want to get leadership experience. And it's really hard when they don't have the uh power or influence, or maybe maybe even like direct report, you know, that they can actually become a manager, but they want to become a manager somewhere else. So I'm looking at those types of challenges on my team of this person is a good leader. I just don't have a leadership position for them to fill or in the foreseeable future. So, how do I give them the necessary experience, or how do I build into them and advise them and mentor them, even to show them how I lead and how, you know, all the how things work under the hood at our company so that I could say, like, hey, you know, there's a management position open at that other company, I would like write you a glowing recommendation. I think you should try it, even to just get the experience. Um, and it's hard because you don't want to, you know, when somebody's at that level, uh, you're it's a big hit to you, right? Um so I think it it requires a little bit of uh self-sacrifice to you don't want to hold on to them uh in an unhealthy way, but you also want to empower them to to make their own decisions.

Charlotte Ward: 8:46

So yeah, yeah. Uh I mean that there were so many good ideas in there. Um I think like just you started that by talking about growth outside of support and and you know, um moving into other business functions. And and you know, for me, and I think you're absolutely right what you said at the start, by the way, that um that uh I think the environment is different in a in a more customer service focused role versus like a technical support role, which tends to be where my experience is.

Reagan Helms: 9:22

Developers and yeah, yeah, yeah, yeah.

Charlotte Ward: 9:24

There are different opportunities, but I think the same principles can be somewhat applied to them, right? I think so. For me, I think that first of all, I do get like you said, as you said at the end there, a lot of people uh want to be leaders and lack the opportunity in the environment they're in. I also know plenty of people who don't want to be leaders, though, in in terms of people management, but I think you don't have to lead people to be a leader. You know, you can lead a project, you can lead an initiative, you can lead a business function or a piece of delivery that isn't managing people. So I think I think it's important for us all to think about leadership as being different things, actually.

Reagan Helms: 10:05

Yeah, that's a good point.

Charlotte Ward: 10:06

And um, and then going back to what you said earlier about, you know, the sort of sideways moves, I that's how I think of growth. Um, and when I'm crafting career matrices in organizations that I've been in or or worked with, and including where I am now. It's uh for me, it's important to kind of codify those opportunities somewhat and say that growth is not just straight up, you know, um, there are opportunities sideways, and that might be all the things you said about actually moving in into different functions, but it can just be somewhat in the LinkedIn uh philosophy, if not model, but that you gain experience and exposure with other business functions actually as part of the support team. So the way I do it is is kind of define growth as as two-dimensional. It's it's it's like applying your skills more deeply with more expertise, but it's also an opportunity to gather breadth skills as well.

Reagan Helms: 11:09

Yes, yeah, yeah. It's on two axes, it's not just vertical.

Charlotte Ward: 11:13

Exactly, exactly. Um I really like the idea of the LinkedIn Tour of Duty, actually. I mean, I've never come across that.

Reagan Helms: 11:20

Um Yeah, they have a book about it. It's super short, it's like a three-hour audio book. Um I don't remember what it's called, but I'm sure if you Google Tours of Duty, you'll find it.

Charlotte Ward: 11:30

It sounds a great way to retain people. Um, but you said you haven't done that at Planning Center, but but do you think do you think that there is a a kind of shrunk down version of that to be had by way of shorter secondments into other business functions, then? Do you think that might work as well?

Reagan Helms: 11:48

Um I missed part of your question. You said, is there another way to do that that what like oh shorten?

Charlotte Ward: 11:54

Like shorter, shorter tenure, like secondments and things like that. So, you know, doing going around your business six months per function or something rather than committing to the big two to four years, which seems quite a commitment.

Reagan Helms: 12:07

Yes, yeah. I think that um one of the reasons or one of the barriers to this is obviously it it you can't have everybody re-upping at the same time. Um so I think another part of it is uh so with an established team like ours, we're kind of experimenting with how do you put that out in little pieces? Uh what parts of the what are the extra tasks or responsibilities that the support team helps with um that that do grow people, right? Um and then how how do we make it so that not everybody is on the same same amount of renewal? Um I think the second part is it really kind of depends on what the business uh or the company is willing to invest in people learning a skill. I've heard this concept is a lot easier at larger organizations, like Adobe, I think has just kind of like a shadowing program. I know Apple has something similar where you can basically be an intern while still retaining your salary. You know, you can shadow a person in a different role than you for a certain amount of time and receive training and decide if that's something that you want to pursue. Um, obviously, with a team of 30, that's a lot harder to do um because you don't without a structured program, you don't have the that oversight to know if the person's being successful in that role or if their current role is suffering because of um them, them trying something different. So I do think it is possible. And I think it especially in a shorter amount of time, it gives people uh the ability to to know, okay, is that something I want to do? They're not having to like lock in themselves for a long, long commitment to something that they don't know if they're gonna like or not. Um so and I I think they do talk about that in the book a little bit too, why they landed on the two to four year period as opposed to something shorter. But I have heard of similar, similar programs.

Charlotte Ward: 14:04

The the shadow, the short, short-term um shadowing exercises put me in mind of and this isn't exactly growth in terms of um, you know, job title changes or transitioning to different functions or or whatnot, but just in terms of a bit of CPD, a bit of uh exposure to other parts of the business, puts me a little bit in mind. I think I want to say it's GitLab. I don't think I'm pulling that completely and like I I think that it's GitLab, but I'll double check after. Um but I think it's GitLab that do something called I think it's called like CEO for a day. It's CEO for a day, although I think actually, or a week or something, where you step out of your normal job and for a week you follow the CEO round. And as far as could as far as you can, you sit in on his meetings, you get exposure to the kind of thing he's doing. Um yeah, yeah, that strikes me as something that could work for other business functions as well, not just the CEO. I I doubt that Apple's CEO or Adobe CEO is going to tolerate every employee shadowing him for a week.

Reagan Helms: 15:16

Yeah, there are some things that you can't shadow anyway. Yeah, and I think that that really kind of touches on another point of this, which is that it requires buy-in from the company and sacrifice from the company. Like obviously, uh, you know, my time is not as valuable as Tim Cook's time is to Apple, but you know, I uh explaining how I do my job or um letting someone do tasks that I would normally do doesn't have a lot of value to me. Maybe it does in that you know, I have to articulate some of the things that I just hold in my head or document the things that so there are there are benefits uh to a leader exposing how they do things to to somebody or teaching somebody how to do what they do, but they're getting a lot more out of this than than me, right? Um and I think that it kind of requires you to weigh in and figure, okay, how valuable is that actually to them, you know, on a resume being like, I was I was CEO for a day. Um, does that actually make them a competitive candidate for a leadership position compared to somebody that has been a leader for a certain amount of time, you know? And so you kind of have to weigh the cost and balance and balance of that um when you're making those decisions, I think.

Charlotte Ward: 16:37

I think you're absolutely right. I think um it has benefit in the moment, something like that, that sort of program, I think, uh, in terms of, you know, just just kind of demystifying the the the senior leadership, particularly.

Reagan Helms: 16:54

Making you more accessible for sure. I think that it's appealing to me from that standpoint. There are agents, even on my team that's relatively small, that are two or three steps removed from me, don't really know me that well. So it would be a good way for them to just to just spend time with them, you know.

Charlotte Ward: 17:09

Yeah, yeah, yeah. And and and I can see how exactly as you said, because I've experienced it, you know, the the benefit to you is uh probably not there, except that it allows you to articulate and explain what you're doing, which sometimes gives you greater clarity, but certainly, as we just said, kind of demystifies. I do have one example where it benefited me no end though, which was when I was beginning to um I I used to do a lot of heavy data lifting just in spreadsheets. You know how it is, right? We've all been there. Like pulling together three different sources, lots of cut and paste, pivot tables, pivot tables, uh like a 12-tab sheet that just my friend Craig Stoss says we all have it, don't we? The spreadsheet that we call the source of truth.

Reagan Helms: 18:02

Yes, your central database.

Charlotte Ward: 18:04

Yes, exactly. Um, and I was doing a lot of manual work in this thing, and um I I currently work for a data company, and I was I just fell into my my old habits of like, well, I know how to pull together kind of time tracking and costing and forecasting and ticket numbers and and you know, 24 by seven and all of that. I just do all of that in a sheet. That's that's easy. Um, until I then attempted one day to explain it to someone on my team who looked at it and said, Well, that's absolutely ridiculous.

Reagan Helms: 18:40

It's the uh the Pepe Silvia meme. Have you seen that with Charlie Day? He's got all the all he's got the spider graph going all the same name. Um it's a very popular internet meme, but yeah, you it's it normally shown as like a crazy person seeing between the lines, and the other person's just looking at them super shocked.

Charlotte Ward: 18:58

So yeah, yeah, and it really was. I was told that that's absolutely ludicrous. Um, let me automate that for you. And it took it took one of my team, uh, you know, a few hours over the course of a week to automate most of this stuff into an actual dashboard, not even a sheet, but an actual dashboard, um, which has saved me hours and hours and hours every month since. Um, so it did benefit me in that sense. But I just thought I'll I'll I'll kind of give like a bit of a peek into what I do and how I do it, just in case I want a holiday at some point, you know.

Reagan Helms: 19:34

Yeah, that's a great case against the it's no value to me because I think getting fresh eyes into any system or process um that you're biased to because you created it, you're the one that uh you know has pieced this together over X number of years. You're not you're you've got blinders on to any new solution or or way to do something. So yeah, I would agree for sure. So having somebody that has the it takes a lot to create. that space, I think, and trust of them, you know, as a the air quotes inferior to the superior, like, hey, you know, why do you do it like that? Uh, because it seems really inefficient to me, you know. But yeah, that opportunity is there for sure.

Charlotte Ward: 20:14

Yeah, yeah, yeah. And and in and in that case, you know, it's a it's a new, you know, it gives gives that person uh, you know, in and more generally speaking, I think it provides opportunity, you know, it comes back a little bit to that shadowing. It it may be something they're super skilled at and can do with their eyes closed as it was in this case occasion. But on the other hand, they might have the fresh pair of eyes, but it's still a learning opportunity for them to find a better way to do something for you. And I think uh Simone Secci at Doodle has some great examples of this where he has had individuals who aren't ready or or don't want to be people leaders, but he's able to hand certain aspects of his role off to because they form sort of near enough small business functions in their own right and certainly serve the team. Yeah. But but this is all this is all kind of in in the model of that sort of sideways growth, isn't it? It's still we still haven't found a solution to the technical glass ceiling.

Reagan Helms: 21:20

Yeah, sorry Charlotte I mean I think that some of these problems can't be solved. I will say one thing though is that or one pitfall is that it is uh in leading the team as long as I have it is typically a natural step where when you do find an avenue or one of those buckets that the person can fit into um that you know you're like, okay, great. Now this is like their full-time job. We used to the support team used to own document the documents until we needed a full-time person to write docs. And so we obviously that person that was more proficient in that and skilled in that, we just gave her that role um I've actually kind of navigated back to making it more of a role that that is a secondary role in addition to being a support agent because you get siloing and you get um if you give out so many of the extra responsibilities to individuals, then the collective has nothing to do but the one task right of answering support tickets or or uh so there's real you kind of I guess the caution I would just say is if you in encouraging that sideways growth, just be sure that when you're taking away one of those uh opportunities for sideways growth that you have something to kind of replace it or else you'll wake up with just a silo of uh one way up and down, you know.

Charlotte Ward: 22:43

Yeah, yeah. It's super insightful. Uh I will definitely be on the lookout for unintentionally creating silos. I think that that's a really interesting point. Um thank you so much for joining me today Reagan. Sure you're welcome. Pleasure to chew over the the glass ceiling card if that's a thing.

Reagan Helms: 23:02

Um it yeah I don't know sometimes glass ceilings can be broken and most of the time they can't you just have to know they're there.

Charlotte Ward: 23:09

That doesn't mean that there is an interesting work to do. I think that's what we've established yeah and that's that's the main thing. Awesome. Thank you so much. Come back and talk about something else another time won't you all right let's do that that's it for today go to customersupportleaders.com forward slash two four zero for the show notes and I'll see you next time