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Building a Leadership Legacy: Evolving from Individual Contributor to Leader with Adam Weber

When you become a leader of a small company, the team becomes a witness to your growth. That might also mean being with you on days when you aren’t your best. But how you handle moments of frustration at the team goes a long way towards forging the leader you aim to be.

In this episode, Adam Weber, SVP of Community at 15Five and host of the HR Superstars podcast, shares how he overcame the struggles of falling into the leadership role unexpectedly. Listen to learn why landing a leadership position might not actually mean the end of your growth journey, but the beginning of one.

After You Listen:

Key Takeaways:

  • As your business grows, your leadership has to grow along with it.
  • Leading in areas you’re unfamiliar with will accelerate your ability to lead.
  • You’re bound to make mistakes with your team as you learn your role. Learning to overcome those moments is vital to your growth as a leader.

Things to listen for:

  • [02:26] Lightning round with Adam
  • [07:50] Shifting from direct to indirect contact with the team
  • [10:39] Stepping into a leadership role
  • [13:40] Overcoming a mistake in public
  • [18:09] Adam’s advice for his younger self
  • [19:52] Craig’s takeaways

Adam’s Transcript:

[00:00:00] Craig: the team doesn’t believe I can lead them because I didn’t come up through their department and I don’t understand their world. to Executive Evolution. I’m Craig Anderson. After spending 25 plus years in corporate America, I learned a lot of leadership lessons the hard way. I created this podcast so you don’t have to. .
Is it true that we have to know everything about what everyone at our organization does before we can lead the team? I’d submit that it’s not, leadership is about people a vision, helping people come together, keeping people aligned and giving, things out of people’s ways so they can accomplish their role.
That is the core skill we look for from leaders. Subject matter expertise can be learned. Certainly there may be some things you need to pick up early on. But it’s not a reason for you to not lead the team. And so I coach that individual through concepts of where he does bring support, things he can share with that team so they understand and can build confidence in him as a leader. My guest today is Adam Weber. He’s the Senior Vice President of Community at 15Five and the host of the HR Superstars Podcast, and he’s also a keynote speaker and a person with a lot of leadership experience. let’s jump in and listen to the story of Adam’s Executive Evolution,
[00:01:26] Craig: Adam, welcome to the Executive Evolution podcast.
[00:01:31] Adam: Craig. I’m, happy to be here. Happy to spend some time with you.
[00:01:34] Craig: Before we dive into the lightning round, Adam, maybe you could share with everybody a bit about what it is you’re doing today.
[00:01:40] Adam: for those who don’t know, I’m a two-time founder. I had a company called Amplify, which was an engagement measurement company, was acquired two years ago and then by a company called 15 five, is where I work now. I a podcast called the HR Superstars Podcast, and I lead a community called the HR Superstars Community, which is about 7,000 HR leaders who are trying to do the new side of hr.
I would say like the strategic aspects, Culture management, enablement, driving performance, that sort of thing. And so I, take some of the lessons I’ve learned in leadership and I share it with them and create resources and content for them
[00:02:13] Craig: Perfect. And that’s exactly what we’re gonna do here today too. So thank you for sharing your wisdom with the listeners on the podcast. So Adam, are you ready to jump into the lightning round?
[00:02:23] Adam: Let’s go, let’s dive into it.
[00:02:25] Craig: Alright, So what is the best leadership book you’ve ever read?
[00:02:30] Adam: Wow. Okay. So the very best leadership book I’ve ever read for sure is Reboot by Jerry Colonna. and now it’s a bit of an off the beaten path book and the sense that it’s not like a traditional, this is how you do business, but it’s an amazing book about what happens to you when you’re a leader.
And helping you work through some of the innate things that happen inside of you, the insecurities that start to manifest from your childhood, that you’re, like, when you’re in the pressure cooker, you’re like, where did this come from? And it helps you ask some of the deeper questions about like,what it is you want in your life, what kind of brings you alive, what stories do you tell yourself that holds you back, things like that.
It just had, dramatically profound impact on my life. Uh,it’s actually a book that I, anytime somebody like is struggling with leadership? I send them the book as a default. I believe in it that much.
[00:03:21] Craig: that’s fantastic. I think until you sit in the chair, you have no idea what it feels like, what the responsibility feels like, how isolating it could be. And,you’re right. I love what you said. It’s likeevery insecurity you’ve had since you were a teenager comes flowing back into your brain. a lot of times when I’m coaching people, it’s like exploring back to say, okay, let’s go back to what the root of this is and let’s figure out how we’ve dealt with it before.
’cause it’s, a lot of that stuff pulls forward. it’s not for the faint of heart leadership.
[00:03:48] Adam: It’s not for the faint of heart. know, one of the things about business books, by the way, I always admire people that are doing the hard work of business, and then on top of that, they’re like, but when I’m done doing that, I’d like to read a leadership book. What I really like for the vast majority of building companies would be like, I love fiction books.
and just getting lost in a different story was actually more valuable to me instead of letting my current . World feel all consuming. I read every single day I read fiction, and just kind of let my brain explore in that creative aspect.
[00:04:21] Craig: Excellent. Okay, question number two, Adam, for the lightning round, who is your leadership crush?
[00:04:28] Adam: I think it’s actually people I know. when we were building, amplify side by side were Max Yoder and Connor Burt over at Lessonly, and who are friends of mine, but also people who, as grew the company, I felt like they did it in a way that was very aligned to their values, there candidly are lots of people that have done that.
But what’s hard is when you raise venture money and then you also still stay deeply true to who you are through the leadership journey. I think it’s just something that’s super admirable and I always, the whole time through that process, I just watch them and go along that journey with them,as they were growing and,becoming leaders.
And I just think they did it exceptionally well. I think they built a really special culture too. was really impressive what they did.
[00:05:13] Craig: And I think that culture even at, because I believe they’ve sold that company, the culture still lives on. Does it not?
[00:05:19] Adam: they did sell the company. their journey was a super successful journey. You know, theybuilt a very sizable company and then were able to have a successful exit. And I think we’re able to,that exceptional level of growth and stay true to who they were as leaders and as people through the whole process.
[00:05:35] Craig: Yeah. You see so much these strong cultures and,I always wonder how do leaders adapt that when you’re molding two cultures together? The last business I had, we sold that business. I don’t really know, as you say, you know, I’m not there anymore, but I often wonder, we work so hard on building a culture and be an interesting study to see those cultural artifacts, how they pass through over time and kind of meld together.
Okay. Last question. In 10 words or less, how do you define leadership?
[00:06:02] Adam: Create clarity, cast vision, align the team.
[00:06:06] Craig: That’s perfect. You’re under 10.
We talk about leadership being important, but I don’t know if we always get into the roots of it around, how it actually needs to be implemented and how you build that culture into your organization around helping those young leaders understand it.
[00:06:20] Craig: So I love getting these definitions. Adam, tell me about your first leadership role. What was your first real leadership role that you had?
[00:06:29] Adam: well, much like you as this accidental leader, I know is a phrase that’s near and dear to you. It’s what happened to me. I started my first business now as probably 12 years ago with my business partner. He was right outta college at the time. I was 10 years into my career. and we had a startup and it grew quite quickly, likelike went from just three people to maybe 15 people in the first four months, 30 people by the end of the first year, and just kept, Growing and . I went from being kindkind of an individual contributor, like I was like a salesperson originally, the company prior to starting to have to manage people. And so that was really what happened was I started to replace myself. As the company started to grow, I got into management because I just kept replacing myself and then hiring people, and then I started managing a team and leading a team.
[00:07:17] Craig: and that’s so interesting. I talk with that with, especially business owners and entrepreneurs who are growing. They start out with that great vision and there’s so much clarity to your definition of leadership for everybody. ’cause you’re talking to everybody in the business every day, but then you grow and you can’t really effectively lead 12 people and keep ’em on track.
So you have to hire that next person under you and before you know it, now you’re trying to get things done through other people. What were you finding in that timeline? The big challenges for you in making that transition from direct contact to indirect contact?
[00:07:49] Adam: one thing that was challenging for me is that as an individual contributor, I was good at it. in the functional area that I led and managed. And I actually think that since my first leadership was under a function that I’ve hadmastery of, it made me a worse leader at times because I would rescue instead of coach and guide.
it’s a trait that I think I’m prone toward that that I have to observe about myself. later in my career, as I’ve been able to manage areas that I don’t have functional expertise over, and I get to manage someone who does, it’s almost easier to stay true to the principles of like,what are you helping them prioritize, helping them unblock things A As opposed to going, oh, if this isn’t working, I’m gonna come in and rescue.
[00:08:34] Adam: Which it could create an unhealthy safety net, I think, for people. or it doesn’t help them gain true confidence and true muscle, around like what they’re learning themselves.
[00:08:44] Craig: Yeah, it’s so interesting with that distinction, because you do run the risk, right? As you move up into the leadership roles, your job is really to start being thinking more forward and thinking six months out, 12 months out, not the day-to-day sales, but if you know the area, it’s so easy for you to say, oh, just step aside.
Let me show you how to do it. And getting sucked back into the day to day. But if you don’t know the area you’re managing that does force you to learn how to lead
[00:09:10] Adam: Exactly. That feels so true of my experience at,15 five, where, I came over, I,took customer marketing, which is a functional area. We our company wasn’t even large enough to have customer marketing . And so to bring in this person who was like a functional expert, you director level,I’m good at
Learning new things, but I don’t know this actual area. and. I genuinely felt, I was like, all the leadership principles that I talk about, I actually get to put in place and I’m doing this in a very traditional way and it’s actually helping, youit was neat to see that help to go, oh, my brute force skill isn’t as needed as my ability to
Triage issues and collaborate and help prioritize, like things like that that really help someone else grow and or, I would just help them think through problems themselves and, make progress.
[00:10:03] Craig: Yeah, that’s such an interesting thing and, and there’s one big client I work with as they’re moving people up, they like to move them around into areas they don’t know anything about. And I think that’s the reason why it forces you to build leadership chops. You also learn a lot more about the business, does kind of you up and say, well, I guess I better learn to lead ’cause I can’t do anymore
so for you in that early leadership roles, It’s interesting ’cause you were 10 years into your career, you said, as that piece started to take off. But what were your lessons learned? I sounds like one was you did learn, you can’t always be in the business like that, but what are some of the other key lessons you picked up through that?
[00:10:38] Adam: I fell in love with leadership in the process too. That’s why it’s the work that I do today and, I’ve started a company that, helps other leaders and, part of that journey was what I call it centeredness. But like, was this that I noticed?
I actually had a moment really early in leadership where my team, we are super intense. know, we’re trying to do a startup My business partner, I had never had success before and we were like, we were gonna be successful or die trying, you know, it was like an all in effort, started every week with a standup on Monday and ended every Friday where every single employee had to show their work.
And, a moment where, I was just like disappointed in my team. And I just wasn’t my best self, right? I kind of lost it.this is embarrassing to say now. I sort of like stormed outwe had concrete floors by the way, so it just echoed forever, . It was like a very long walk to the door and just boom, boom, boom.
You could hear my feet on the ground. And that next day and,quiet reflection. I think I realized like . This is not a sustainable way to lead, and the reason that I reacted that way was not actually because of my team. it was because of me.
And it was like my own lack of being grounded and centered and rooted and confident. Was inhibiting my ability to show any resiliency at all and to help instill confidence in other people. and so that of started and set in motion things like the reboot book, actually, just to bring it full circle of my own personal development and realizing that as this business grows, my leadership has to grow as well, and I have to do the work to make that happen.
so just getting to know myself. Working through some of those tendencies. finding a coach who would both help me when I was running into issues, but also help me source truth from my team to go, how are you showing up? Where are your gaps? What is your growth area?
And just kind it all on the table and actually diving into some of those areas I think was, transformative to my own leadership.
[00:12:34] Craig: that’s interesting. you feel that frustration when you’re, and part of that’s trying to get things done through other people. Right? And then when they don’t do it, you’re beating yourself up, but you end up beating them up unintentionally. Right? Becausethat’s easier than in the moment.
Blaming yourself. , so it is a big lesson to learn going through. And it was a pretty small group. I’m sure you storming out was pretty impressive if disappointed in yourself, but certainly momentous.
[00:12:57] Adam: at minimum, very embarrassing. And, it was probably a team of six at the time. in some ways we’re like professional friends now that was 10 years ago. And so,They certainly all enjoy bringing it up.
Um,they haven’t forgotten it either at that moment And but you know, what’s cool is that, I think that they also got to watch that evolution of growth. the vast majority of that team stayed with me for like almost eight years. really substantial period of time.
And so they also got to watch that growth journey. And I think one of the reasons they were able to stay was because I did actually get better at becoming a leader.
[00:13:28] Craig: and I have to ask this because of how you just talked about that is so it happened, you went home, had the realization, wow, that was Not my best moment. How did you handle the next day?
[00:13:39] Adam: thankfully it was on a Friday, so I had like 72 hours to cool down. and don’t think I was . Fully arrived on this journey or anything, and I’m still not, but, I think it was just an acknowledgement like, hey, I was disappointed.
But that was not the appropriate way for me to react. And there’s a better me that I, trying to get better myself. Just I want you all to get better. Likethere’s a better version of me Too and how I’m gonna show up to these.
[00:14:02] Craig: that moment of vulnerability, right? As a leader, when you do say, Hey, I was wrong. the idea wasn’t wrong. We didn’t perform, but the way I handled it was, and that I think is that vulnerability that builds the connections that are real 10 years later for you as a leader.
[00:14:16] Adam: Exactly. I’ve seen that with other leaders too. Like on our executive team, you know, years ago I hada leader who just had a dynamic issue on their team. Like the, team dynamic. The culture wasn’t working. team was frustrated. leader was, the executive was frustrated. And, I did this, what I’d call like these deep listening tours where I’d go into the team.
And sit with them and work through everything. Talk about all the hard stuff, like everything’s safe. Put everything on the table, work through it. Sat with the leader, did the same thing. found like a real issue, right? and the leader, had done the hard work to go, well, I wanna make things better.
I and sat down with the team and just like named the exact thing that was causing the issues on the team, like this negativity component. it was like this. pressure cooker that was created just immediately was diffused, like, oh, you know now too. was so mature about it was he was like, not only is this a trait that I acknowledge I’ve been doing, it’s also a trait I don’t want to have.
And so I’m giving you permission to like, call me out on it. and I just thought that it was a really cool step in his own growth journey and also healing for the team too.
[00:15:20] Craig: let’s now bring us more current and, youknow, as you look at leadership today for yourself, what is your leadership style today? How, what have you evolved into over this timeframe? I.
[00:15:30] Adam: I think one thing that has probably changed the most from the beginning, other than likethat centeredness concept I talked about is I think I do work with a little bit less desperation and a little bit more confidence that my life’s gonna be okay. will work out. Like just a little bit more perspective.
really did have some . Childhood stuff. I was working through myself that when things didn’t go well, I would just go into these narratives of I’m not gonna have a job, I’m not gonna be able to provide for my family. with some time you go, well, hold on. is that actually true? Like you’ve somehow functionally been able to provide and support your family with, my wife does too.
[00:16:05] Adam: We both support the family, but for decades, this isn’t actually a true story. And I’ve made progress on that. But I would say also as a leader today, I think that it’s interesting having experience. I used to have a really large learning task to every single situation I faced.
because I was facing it for the first time. Whereas now I’m almost surprised when a new scenario comes up and there’s pros and cons to both of those, There’s an energy and vitality to solving things, but there’s also some wisdom and some time saving. that comes that comes from going, okay, I’ve seen this scenario.
This one is little bit different, but here’s the right way to approach this. And so I think I’m a little bit more measured and a little bit more, just steady than I was then. And candidly too, I don’t have the same level of responsibility, right? Like right now, I really feel like my job my current role, is to just, is other people on this journey, right?
What I call my like mission right now is to help leaders who are stuck in the ticky tack and they’re stuck in the minutia. Maybe like me jumping in and doing somebody else’s job and helping them learn how to elevate to become more strategic coaching them on that journey and giving them tools and resources and how to make progress there.
[00:17:17] Craig: And that’s huge. One of the things I think happens so much in companies because we don’t train leaders well, so they grow and they become senior leaders, but no one ever trained them. So they don’t really know how to train other people or coach other people. And you start getting this generational crisis of leadership in business because nobody knows how to lead and develop anymore.
[00:17:36] Craig P: So taking all this knowledge you’ve had and you’ve built up over the years, and you were already alluding to new perspective you gain once you’ve been through so many things as a leader. I’m almost wondering if that’s where we end up here, but I’m gonna give you the chance to jump into a time machine.
You said you like to read a lot of fiction books. You can pick your time machine, a Star Trek, one HG Wells, whatever you want. Jump in there. Go back to yourself in that leadership role that you started, and what’s the one piece of advice you would give yourself would’ve made your life easier as a leader at that time?
[00:18:08] Adam: I think I would’ve to tell myself that my employees really very hard. And that they really want to be great, trust them and really empower them. I think , that’d be something I’d go back and tell myself.
[00:18:21] Craig P: And that’s great advice, and nothing close to what we’ve had before, but so crucial to realize that most people are actually trying hard and are working at their best level and where we can shape and guide them as leaders to really optimize from there. It’s such a great place to build from rather than just saying, looking at what everybody doesn’t do every day.
So that’s great advice. Adam, thanks for sharing your executive evolution for us. You already mentioned your podcast, but how else can people find you if they want to connect with you or follow some of your, your insights?
[00:18:49] Adam: Yeah, I think the podcast, it’s called HR Superstars. You can find it on any of the channels. And I talk about all things leadership too. So, obviously it has a slant towards strategic hr, but there’s all sorts of other topics that we cover too. And then LinkedIn, if you just go to LinkedIn, uh, slash meet Adam, you can follow.
I do post stuff all the time. about leadership, management and culture.
[00:19:10] Craig P: Great. And we’ll get links to all those in the show notes. Adam, thank you so much for being on. Uh, I know a lot of our listeners are going to really benefit from your insights and advice. Thanks so much.
[00:19:20] Adam: Thank you, Craig. Thanks for having me.
[00:19:24] Craig: I really appreciated Adam’s insights into his leadership journey. Someone who was 10 years into his career and thrust into leadership in the crucible of an entrepreneurial fast-growing company. There are so many lessons that he learned, and I was glad that he was able to share those with us today.
And as always, I like to bring them down to three key areas for us to consider in leadership, those areas of competence, confidence, and calm. When we think about Adam’s discussion around competence. again, as I talked about in the intro, leadership competence is so much more important than functional area expertise.
We can learn the latter, but when we refined our leadership skills and we know how to move people forward and give them the support that they need, that’s what builds our competence as a leader, not if we know how to do the job. We’ll pick that up over time. In the area of confidence. I loved Adam’s discussion around how those issues that seemed so insurmountable and so stressful early on in his career with perspective over time, he was able to be more calm going into those situations and have more confidence because he knew that despite those challenges that they had in the short term, they were positioning themselves to win for the long term.
And that’s an important lesson for new leaders to understand that yes, it does seem . It’s difficult to overcome in the moment, but believe that you will, and then take the lessons as you go. And then finally, in the area of calm, Adam talked about the concept. He talks about this a lot, about centeredness and just really yourself perspective and being able to be calm in the moment and to be present in the moment and to be confident and have that competence.
And that all comes together for centeredness, which really hits into that leadership competency of calm. Thank you for being part of the Executive Evolution podcast, Adam, and if you would like additional information about Adam, there’s links in the show notes.
And as always, remember you can go from being an accidental leader to the greatest of all time leader. All it takes is developing your competence, confidence, and calm. We’ll see you next time on Executive Evolution.