Navigating Leadership with Humility and Accountability: A Conversation with Reagan Helms
Meet Reagan Helms, Director of Customer Experience at the Planning Center who has spent 13 years at the company, transitioning seamlessly from customer support agent to manager, and now thriving as a director leading a dynamic team. He excels at harnessing his team members' diverse skills and passions to deliver exceptional customer support while fostering a culture of growth and collaboration. Reagan's passion for hiring, team development, and maintaining a harmonious support-product relationship underscores his commitment to excellence in leadership.
Check out this video featuring Reagan Helms our upcoming speaker for November's Leadership Summit, where he discusses the importance of leading with humility and accountability in leadership roles, emphasizing the need for leaders to be open, honest, and human in their interactions with team members. This video offers a sneak peek into the compelling insights Reagan will be sharing on stage in Oakland.
Charles: Hello, Support Driven Community. My name is Charles Sustaita. I'm Director of Customer Support at a company called Coastline Academy, and I am part of the Support Driven Community, have been since 2015, and today I'm talking with Reagan Helms. Reagan, you are currently the Director of Customer Experience at Planning Center. And you've worked there for 13 years and lots of different roles from customer support agent, manager, now your director leading the team. You love building teams and utilizing each member skills, passions and experience to the best of your abilities, their abilities. And then making sure that you're also providing an exceptional customer support out of that process, Reagan is passionate about hiring practices, growing teams, maintaining a healthy relationship between support and product coaching and leadership.
Reagan: I moved into this director role probably about a year and a half ago, two years ago. So it's really more about learning how to manage managers and then also growing a team responsibly. We had a fourth support team that we created at Planning Center just recently out of some existing agents then some new hires, and then a promotion from a senior agent to a manager role. So that's been a lot over the last four or five months.
And now we're moving more towards a season of focusing more on our community impact in our Slack community and our Facebook community where we have thousands of customers in there. Rearranging some resources that we have among agents and extracurriculars to those areas.
Charles: And you will be speaking at the Support Driven Leadership Summit. And the title of your talk is, "It's Okay to be Human: How to Lead with Humility and Accountability," which I love by the way. You and I had a chance to catch up not too long ago to talk about this. I'd love for you to tell the community a little bit more about why is this important to people leaders?
Reagan: I think that any leader will learn this lesson over time, whether through positive or negative reinforcement of the need for this, which is you are a human and you're managing humans and humans need relationship and interaction with each other. And I think anyone who's been a leader for any amount of time knows that you don't have it all figured out and you're never going to have it all figured out.
But one of the things that makes people willing to follow you as a leader is how willing or reticent you are to admit that fact that is a universal standard of all humans, right? We're not perfect and we don't need to be perfect, but we need to be willing to admit when we make mistakes and we need to be willing to admit when we have no good options, but we're choosing the less of a few different evils. And I think that people are more willing to follow you when you're open and honest about that, instead of trying to pretend or hide like you don't know what you're doing.
Charles: Yeah, and you talked about managing managers and moving one of your teammates from more like a day-to-day agent role into a manager role. How do you approach this conversation with somebody who's never managed people before?
Reagan: I think I have a lot of experience in that because it's the same story for me. And I think it's the same for a lot of people in our industry and also in our space of, you start as an at an individual contributor level, or maybe even a little bit above that.
And then you perform well enough to the point where people say, Hey, you should be in charge of people that are also doing that task and teach them how to perform like you. Which is not always the same thing. Very rarely is it actually the same thing. So it requires a whole new set of skills to learn how to instruct and coach people to perform to their best ability and also give them the freedom to reach that same result that you did, but maybe in a different way.
Or, not. And give a good reason why they need to do it the way that you did it. I think that some people are quick to adapt to that, and some people, it takes a long time to adapt to that. I feel like I fall somewhere in the middle of that, where there's lessons that I learned very quickly, never did them again. And then there's lessons that I'm still learning of, Hey there's ways to accomplish and build a team. Accomplished results, build a team without having to strong arm people into your way or the highway.
Charles: And when people are moving into roles like this or navigating, just management in general, they typically will learn from people that have managed them in the past.
And it's very easy to take on some of those traits from lots of different people when you've moved between roles and I've had very similar, you have had the unique opportunity of working with people who encourage us to be human and engage with our themes on a human level. Which is wonderful because part of being in like this leadership role is demystifying what we do, where we don't want to be seen as this, authoritative awesome, great and powerful.
We don't want to be this unapproachable figure within the team. We want to be approachable. We want people to come to us with their ideas. And part of that is just showing people that we are humans.
Reagan: I think it's not a thing that's very hard to do, but I think everybody has examples of leaders that have done it both ways where like you said, you're blessed to have had good examples of servant leadership in the past people that are accessible that are showing their humanity that are approachable. And I think the first step is a willingness to do that. Some people are not willing to invest the time in people. They choose to do that in a different way. And I think you can have that, it just leads to totalitarianism or dictatorships or poor examples of leaders. They still get the results they want. Just the people on the way don't matter. And I think that then you get high turnover rate, you get people that are very dissatisfied with their job and ultimately our job is helping people. I think that it can be an enjoyable and fulfilling thing. I think that the things that make it soul crushing are when you have somebody at the top that doesn't understand, doesn't empathize because you can't conjure up empathy when no one is empathizing for you or when nobody's understanding you.
You can't instruct customers when the person at the top isn't taking time to instruct you and to coach you and to help you succeed. So I think it all pays forward down the line all the way to your customers who arguably are the most important and who should matter the most. You really do need to invert the pyramid, and start with yourself. If you want to see the results on your front line that every one of us, I would hope, hopes for.
Charles: Doing that both from a people manager, but then also just a human who's connecting with another human and holding somebody accountable, right? How do you navigate situations where you're having to hold people more accountable. Let's say somebody who's maybe not hitting their targets, not achieving their goals. How do you balance that level of humility and also accountability?
Reagan: Yeah, that is where I think it can be tricky. It becomes easier when humanity's involved, even though I think the tendency is to turn that part off. You can just become closed off and matter of fact about something. In my experience, those conversations go so much easier when you take the time to hear it from the other person's perspective first and I think accountability and approachability are not mutually exclusive. I would even argue that like Patrick Lencioni as an example gives in his five dysfunctions of a team, a lack of accountability is one of those dysfunctions. It starts with trust. If you don't have mutual trust, which is what we're talking about in becoming human to people, then you don't have the ability to call accountability into the discussion and hold people accountable to not achieving the goal. Because it's not then about you and me, as much as it is about how are we both contributing to the team that we're a part of and accomplishing the team's goals. And what does it look like for you in your capacity to do that? And are you doing everything that you can to do that? And same thing for me. Am I doing everything that I can as the leader to enable you and empower you in doing that? Everybody's got a personal life, everybody has things that they're dealing with outside of work. And sometimes those things bleed into work. And if you don't have the trust and the approachability to communicate with, Hey, I've just been having a really rough week. Here's what I'm going through. This is why my performance isn't good. And then as the leader being able to say, okay I understand why that would be playing into this. How can, what can I do to help you so that this doesn't continue. And how do we continue to move together as a team with this in play. As opposed to pretending like those things don't exist?
Charles: Absolutely. That's a wonderful book. I'm glad you mentioned that because I just read through it maybe six months ago with the leaders who were on my team when we were talking about, all right, how do we take what we do for our team members, how do we take what we do to the next level, right? We need to build trust with each other. We need to not fear conflict. We need to lean into commitment, we need to be accountable and that's ultimately going to help us achieve those results. And that's such a wonderful practice as well, not only using those tools that we have, Patrick Lencioni does the same thing.
Utilizing those tools, but then also showing people how to do it themselves. Because if you can show someone how to do that, if you can show someone how to build that trust, what good conflict, and Patrick Lencioni calls it conflict, right? How to have healthy conflict. Not all environments are going to be conflict necessarily, but it could just be collaboration or a willingness to engage in the discussion.
Reagan: Trust is the bottom of that pyramid for a reason, because it's the hardest one. And if you don't have it, then nothing else can be built on top of it, right? And I think that's what this topic is really about. Is that if people don't see you as a person that is trustworthy, or see you as a person that they can understand, then that layer doesn't exist. You don't have anywhere to go from there.
Charles: Absolutely. So leaning into this a little bit more, when it comes to the people that you report to directly, how does this play into it? So we talked a little bit about, all right, how can we interact with the agents on our team.
Maybe the individual contributors and then how do they interact with managers? How are you coaching managers as well? Then how does that go the other way, your relationship with your boss?
Reagan: I don't have a ton of experience not having this exampled for me, but it's something that you have to work at both ways. So If you have direct reports, it's very easy to model this for people below you. But I think if people that are above you, it takes a lot of work to go the other way, where you have to be very intentional about how you show up and how you engage with your boss.
And it really does depend on a healthy relationship and a willingness to on that side to engage. So honestly, I've not had [00:12:00] a time where I can't relate to or talk openly about how my life's going and, or the things I'm struggling with at work with my boss. I think that it takes a lot of humility to do it the other way where you can say, "Hey, here are the things that I'm struggling with."
Maybe they didn't solicit it, maybe they haven't asked, "what are you struggling with?" Taking the time to say, "Hey, here's all the things I think I'm doing. But here are the things I'm doing wrong. And I need help to understand how do I solve this type of a problem?" I think that obviously it takes a lot of trust, that what you're bubbling up is not going to be looked down upon or judged heavily, but it also shows humility in a different way where you're saying, "I need help. And you're the person in the organization that arguably is the best equipped to help me do my job. How would you recommend I move forward with this thing that I don't understand or know how to do?"
Charles: And from my experience as well, it's a discovery with each person that you report to, or if that changes over time or new company that you work with, learning how to interact with and communicate directly with those individuals where some people may place a greater deal of relationship building on more trust that way. Some may establish trust and build that rapport, talking all about data and how we're moving towards our targets in our metrics. There's humanity in there to some extent, because we're all human, but then being able to do it and then be aware of the way that we're interacting with those people that we work with.
And you can do the same with colleagues as well. Leading, at least from what I've learned in my experience, there's not just a hierarchy between you down. It can be across and it can be up as well and modeling that for the people that work around you.
The book that I read, "Five Dysfunctions of a Team", and I read it with my leadership team, they each were interacting with each other within the same regard. And so we're going through the exercise that Patrick creates of, ranking your team based on all of these different questions, and that just opened up so many more conversation, not just from, me as a director down to leadership team, but amongst each of those leaders. They were able to have these more in depth conversations. And so as an approach to how do we build this trust, how do I build this trust with my team? They were interconnectedly building trust with each other and then interacting with their sphere of influence next.
Reagan: Totally. You touched on something that I think will be another part of this conversation, which is the appropriation of the term leader to mean a position of authority. I think a lot of times people see a leader as a CEO or an executive or a manager or a director and not, how are you leading where you're at?
The stance often begets a title, but the title is not synonymous with the attitude. And so I think it's a double edged sword of people that are managers are not always leaders. And more importantly, people don't need to be a manager before they can be a leader.
I think that leaders tend to have all these best traits of being humble, being human, having the trust of the people on their team, whether it's a lateral team or a vertical team, and engaging with good questions and helping achieve goals.
Charles: Absolutely. That part of it doesn't have to be, or you don't have to be a people manager to be a leader within your team.
I love that. And it's evidenced a lot in the work that we do within the customer support or customer experience realm. For example, in Coastline, we use Slack. And when people ask questions in the support help channel, it's not just somebody above them helping to unblock them.
It's a group, the team, it's a collaborative effort in terms of, "Hey, I'm dealing with this situation with a customer. How do I navigate this?" Where people can chime in and help them approach the conversation that they're having. That's a moment of leadership with from that person here.
And it's that potential of I'm sharing something and I was human and putting this out there. I could be wrong. And we have to show our teams that there's possibility that we're not always going to get it right. Not always going to have the right answer.
Reagan: I feel like there's a quote out there that I'm not remembering fully, but it's along the lines of bad leaders say, I have the answer. Good leaders say, I don't know the answer, but. They're willing to admit when they don't understand something, but find a solution to the problem.
Cause that's what it's really about. And a bad leader just takes everything and doesn't ever lean on the strengths that their team has. Like what you're talking about, that team collaboration, the ability to recognize when you're not an expert at something, but there's someone else in the group who is, what does that person say we should do here? I think that's a great example. That's how I build a lot of my teams at Planning Center, is having that type of open collaboration, that type of honesty and communication with each other and acknowledging when you're not the right person to be answering something or in that space.
Charles: And creating also an environment where you're encouraging that rhetoric, that conversation, where if you as a leader are showing people that it's okay to be vulnerable, it's okay to talk about these types of things, then you create that culture within that person, that relationship, showing people that you can be human. They take that and they can replicate that with the people that they work with and then new people join the company or the team. And they see, this is the culture that is encouraged here.
Reagan: If they see you asking those types of questions in support channels, then they realize that they're allowed to ask those questions too. Because if you're the guy that's "in charge" then why would they get singled out as being dumb, if you're the one that's asking questions along those same lines. I do that all the time. We have nine different products. So there was a time way back in the day when I knew everything or thought I did probably is a better way to say that. But now I can't know everything.
And so I get into things all the time on customer phone calls or research calls or even social media DMs where I'm like, Hey" I don't know the answer to that question." Copy and paste into this Slack channel. And I just say, Hey, somebody on YouTube stuck with this. What would you guys recommend I have them do? And so I like to think that makes me more accessible because people realize that I'm not going to just Slack a person directly that I think knows the answer and keep that answer to myself. I'm willing to let the whole team learn from that.
Charles: That is such a good point of doing that in public channel and public forum. Similar regard of being on site or in an office building is going and asking a group of people, Hey, how do I solve this thing? It takes a lot of self confidence to be able to put that question out there, but then also to show people, hey, we're doing this together. This is a collaborative effort. At the end of the day, we're supporting our customers. We're here for what they need.
Reagan: And just on the flip side of that double edged sword too is that, I think it takes a lot as a leader to hit the pause button and not have to be the one with all the answers all the time. So in that same forum, in that same example, right?
If I know the answer, sometimes I will wait a beat or two longer than I might even be comfortable, doing to see if anyone else on the team can answer that better than me. Because again, I need to be a good steward of how my attitude is perceived. And I don't have to be the one with all the right answers all the time.
Charles: We create specializations or certain teams within our organizations that focus on those, where we're able to rely on these specialists who can then help. And we are regarding them as the experts, the subject matter expert of that thing. But that doesn't mean they know everything about everything. They know that thing, and they possibly know other things around them. And they also will have to ask questions to unblock themselves for certain things. You're talking about this at the Leadership Summit, and you went out of your way to choose this topic. I would love to know why you're passionate about this.
Reagan: Well, hopefully some of the conversation has helped to see why I'm passionate about it, probably because I'm still learning it and still learning the best way to do it. But I also know that there are so many leaders out there that are In the same position I was or a similar position to me five years ago, six years ago.
If I could save them some of the heartache of learning these lessons, because sometimes there are consequences to learning and failing, as opposed to learning through example from somebody else. That was why I've been thinking about this topic, especially in coaching new managers and helping people who've never managed before see both sides of this topic. Of, hey it's your job to be approachable and accessible, but it's also your job to empower other people to be approachable and accessible.
I hope to unpack it a little bit more at the Summit.
Charles: Reagan, how can people get in touch with you?
Reagan: Oh, through any means that they want. I'm on LinkedIn, reagan Helms pretty uncommon name so you can probably find me there. You can email me at reagan@planningcenter.Com or you can reach out to me on any social media channel, Reagan Helms on all those places. Support Driven at Reagan, there you go.
Charles: I think we joined at the same time back in 2015.
Reagan: Back in the first San Francisco conference.
Charles: Yeah it's wonderful to see how things have evolved. And now we're doing this speaker feature series to put a lot of these topics and titles of conversations out there so the community can hear and get a glimpse of what we're talking about when they go to attend these summits, expos, events, things like that. But it's good to catch up with you. I'm glad we had a chance to connect.
Reagan: Yeah, we'll see you soon, Charles. Thanks.
Check out this video now featuring Reagan Helms our upcoming speaker for November's Leadership Summit. Be sure to watch and get a taste of what's to come!
