Better Humans, Better Leaders: A Conversation with Ali Schultz (Reboot.io)

Alexis:

Welcome to Le Podcast on Emerging Leadership. I'm Alexis Monville. And today, I'm honored to have Alison Schultz with us, the co-founder of Reboot.io, an organization that's been reshaping the landscape of leadership coaching and organizational development. This year marks a significant milestone for Reboot.io as they celebrate their 10th anniversary. A decade of empowering leaders and teams across various industries. Hey Ali — how do you introduce yourself to someone you just met?

Ali:

Well, I guess I would say, Hi, I'm Ali. I'm one of the co-founders of Reboot. How are you?

Alexis:

That's nice, that's direct. Could you walk us through the inception of Reboot?

Ali:

Yeah, so Jerry and I met in 2013 and we began doing the CEO bootcamps together. We did three bootcamps, including one in Italy, which is not too far from you, before we formed Reboot with our partner Dan Putt. The bootcamps proved that our instincts were right and that we were onto something. And so Reboot really came out of a vision to create a coaching and leadership development platform that would support people not only in better leadership, but also in the work that it takes to become a better human.

Alexis:

I think that's the part I'm very impressed with in all your communications with Reboot. Sometimes when you look at leadership development, there's that kind of thing that is really technical, that seems to forget that behind all those skills, all those things that we learned to do, there's a human being. And that's probably something really important. I feel that you are really touching that regularly very well, and that's something I really appreciate.

Ali:

Hmm. Thank you.

Alexis:

What were some of the initial challenges you faced and how did you overcome them?

Ali:

Yeah, so this is a great question. We had to build a brand for the company that was bigger than Jerry. So we had to build something that went beyond just Jerry Colonna. And by the end of our first year we had that, which was pretty cool to see. People were searching for Reboot, they weren't just searching for Jerry Colonna. And in the process of building that brand, we took advantage of Jerry's notoriety and his reach and the work that he had been doing in the space for over a decade at that point. We carefully crafted a brand and a voice that could stand on its own.

I would say another thing that we wanted to do, which kind of relates to that, is we wanted to build a company that wasn't built around just one coach, one personality, or one method. We wanted to bring together a team of coaches that were distinct and unique in their experiences and in their styles to better serve our clients. Internally, Jerry kind of refers to this as wildflowers. I have a biology minor going decades back, but if you know anything about biodiversity, there's an inherent strength in that. It serves our clients better when our coaches are unique, so people can come to Reboot and really get fit with a coach within our herd of coaches, I say lovingly. You have a variety of humans that can meet the variety of humans that come to us for help and support. Can you imagine going to a therapist or a coach that just tries to fit you into their style or their method without really meeting you where you are as a human? It just doesn't match. So we wanted to create something that was really a unique coaching experience that was in service to anyone that would come to us for help.

Alexis:

This is very interesting. And a quick question about the brand. Does Jerry's book Reboot was already out when you created the brand?

Ali:

No, no. We started in 2014, so we started Reboot in 2014. So we were doing this before Jerry's first book came out. His book came out in 2017 or 2018, I believe. So it was further down the line. We had already had a brand and a larger platform established. The book came out and it had a place to be. It was kind of cool.

Alexis:

It's very tempting to use Jerry's notoriety and the work he did in the past and say, OK, that's the one method we will propose. And I really like what you're saying now. No, that's not what we are doing. We are uniquely different and you can find a good match for you at the right time for you. I really like that approach. You will celebrate the 10-year anniversary of Reboot.io. What are the significant milestones that stand out for you?

Ali:

Yeah. I've got a couple of handfuls I jotted down. I think pulling off our first bootcamp was a big deal. And then I lost count after 25 bootcamps. That's a significant thing to successfully produce that many events year after year. Another really big memorable event was getting the Reboot podcast out and shipped. That happened pretty quick — it was probably September of 2014, three months since we had started, and we had the podcast out. It was cool to have Jerry listen to it for the first time and to see his reaction. So that was really special.

And then after that we just kept putting together products and services that were really on our roadmap and that we had wanted to put out in the world, including our peer groups, our circles, and we had put together a 360 review process for clients. So a lot of services that were really in support of one-on-one coaching, but expanded and complemented just the one-on-one coaching work. Internally we had produced some really fun things too — we had a chapbook of poetry that we would use at events, we had made a branded journal. So it was cool to have some tangible takeaways that we would give Reboot clients in our work with them. And then of course, Jerry's first book, Jerry's second book, which is coming out soon — tomorrow actually, it launches.

On top of what I think is also kind of celebratory for us, and maybe for me, because I hold this seat a little bit more than some of my colleagues — I've just been the one kind of defaulted to being the brand voice — the amount of content that we consistently put out into the world for free, because we know that not everybody can afford our coaching rates, but everyone should have access to frameworks or ways of thinking or questions for reflection that can help them become a better leader if they're interested in this work. It's nice to be able to provide such a rich library of resources for folks to come to our site and mainline our content and get a taste for what we're about. We really put a lot of good content out in the world as a service to the entrepreneurial community and the emergent leaders, to use your language — the emergent leaders that are there because they need support. They need to recognize what are the practical skills that I need, what's the radical self-inquiry piece that I need, what's the inner reflection piece that I need to bring into this leadership space. And then what are the shared experiences? How can they then find their people or their communities or places for support, in order to give them greater resiliency and enhance their leadership.

Alexis:

Yeah, that's beautiful. And among all the resources you are exposing to the world, I really like the journaling prompts.

Ali:

Yes.

Alexis:

That's so simple and so helpful to help people start with journaling. Some people told me, but I don't know what to write. I said, write what's on your mind. They said, no, I'm stuck, I cannot write anything. I said, OK, let's start with some prompts. And when I discovered your journaling prompts, I said, oh yeah, that's really cool.

Ali:

I'm glad you think so. I think so as well. Journaling takes work, and it's personal for everybody. There's no right way or wrong way to do it. It just has to support you. Margaret — who's my partner in content creation and the brilliant editor to our podcast — and I sat down and I was like, we have enough journaling prompts from all the content we've put out in the world and from all the events that we have done where we could just do an email course, even though it's zero cost. Sign up, get a daily email in your inbox. The questions that we pulled together are very rebooting, and they're applicable to anyone in leadership or management, or even people who don't think of themselves as CEOs or founders. They can be really handy in helping someone establish a journal practice or giving them that external prompt so that they can sit down and do some self-reflection. It's such an important piece of being a leader. I'm really delighted that we re-released that this year.

Alexis:

Over those 10 years, how has your role evolved within the company?

Ali:

Oh yeah. I've been around, done a lot. I started in ops primarily, so I was making sure that the trains ran on time and taking care of a lot of the internal structure, the business structure of what we are doing, and really leading the marketing and content efforts. We've been very lucky as a company that because of Jerry's notoriety, the PR efforts and the traditional marketing efforts we really didn't need so much of, but we could be really creative and specific with the content we put out.

After five years, we came to a moment in the company where we were no longer a loose consultancy of coaches, which is kind of what we began as, as we tried the experiment of, what is this company and what does it need to be? We began employing our coaches. So that was a slight shift in the business model. Not too bad, but it was at that point that I handed over the operational reins to a small ops team within the org and I just stepped into coaching full-time. So it was a big shift, but it was also welcomed.

Alexis:

That's a big one. But that's probably very satisfying to have built something, build a team that can run on its own and enables you to do something that has a different kind of impact.

Ali:

Yeah. Yeah.

Alexis:

What does emerging leadership mean to you, and how does it align with the mission of Reboot?

Ali:

Yeah, this was another really great question. We believe that better humans make better leaders and better leaders create more humane organizations. And we love working with emerging leaders because we can instill in them during those emergent years the soft skills that are so important. And we can also stress the importance of doing the radical self-inquiry work alongside the practical skills. It's a way to really support what's emerging in each individual as they're stepping into their leadership.

Anyone who takes a leadership role that has not done that before is going to run up against a host of issues, including self-doubt, imposter syndrome — all these things that really stem from who am I and what am I bringing into this role. But it also stems from, I've never done this before, what do I need to know to do the job? Kind of the formula or the bet that we take at Reboot is that practical skills plus radical self-inquiry plus shared experiences equal greater resiliency and enhanced leadership.

It really fits that emerging leadership sensibility. When I think about emerging leaders, there's something emerging. It's emerging in you. It's emerging from a need in the world. It's emerging from a need in the organization. And how are you going to meet that? How are you going to listen for what's showing up? How can you be attuned to that? And how can you meet what's emerging and be agile about it?

Alexis:

I love it. Can you share with us an example of a time when your leadership skills were put to the test?

Ali:

Yeah. When I operate, I'm really transactional. Like, when I go in, I go in to just get shit done. That's why we're here. So I think it took a while for me to really pause or trust that holding space for everything else that's in the room is actually going to get things done more smoothly and potentially more quickly. Because you're not just meeting with people who are always ready to go, tracking the same agenda items that you are, seeing everything the way that you want to see them.

I would say learning to just kind of sit back, not drive so much with the get-shit-done mentality, but to really create enough space for the humans in the room and be able to meet that humanity, right? Personal check-ins, how are we doing, how are we feeling about these things, and then moving into what may be the agenda items. It's realizing what are the other issues that aren't maybe so tactical or get-shit-done oriented that are also in the room that need to be unpacked and talked about. For early leaders, and a lot of clients that I work with too, it's like learning that shift can be really impactful.

And it's hard, I think, during early startup days when everybody's kind of doing everything and there's an urgency to just get everything done as fast as possible, because it feels like there is no time to pause or to take things slow or to ask big questions. I guess my invitation is, and my learning was, to create the space for that way of being with the to-do list. It's more powerful in the long run.

Alexis:

Yeah, thank you for sharing that. I have the tendency also to look at the time we have allocated to do something and to say, OK, I don't want to waste the time of anybody, so let's get to it immediately. That's kind of that urge that is there. And it's hard to pause. So it's very helpful to say, yeah, but make enough space for the human being in the role. If we look at the startup environment, what are some key qualities you look for when you are building a team?

Ali:

Key qualities. I think there's a lot of power in finding people that are good people. You just really want good people. As far as qualities — a willingness to dive in and face problems, that's key. And a willingness to be a little bit obsessed and dedicated also goes a long way at first, especially when teams are small and new and there's a lot of exciting stuff happening. The obsession or the dedication can really help focus and small team cohesion a little bit. Yet that certainly doesn't scale — it can, but it needs to be named, checked in on, and maintained in a healthy way.

You want people that are engaged in the work, like they want to be there. They're eager to solve these problems. They're eager to show up every day and solve these problems, and they get a little bit of aliveness out of it. You're going to get so much more out of the team. It's just hard to work with people whose heart isn't in it. Someone who's willing to put their heart into it makes things kind of fun at the beginning.

You also need a balance of contextual thinking and execution, especially at first, because at first everybody's kind of doing everything, and it's a little bit like a kindergarten soccer team where everybody's on the field and not everybody has a defined role. As things grow and roles scale and the company scales, there's more clear parameters and more clarity around what your key role is. It's really great to have people that can execute, but you also need people who can create something from nothing, because in a lot of startup spaces, that's art really, to be able to create something from nothing.

When it comes to hiring people, there is no sociopath filter. However, sociopaths exist. You have to trust your gut when hiring. And you have to be quick to really get toxic people off the team. One of the ways to test for this — it's not foolproof because there are some really charming and toxic people that can wreak havoc in your organization — but we always say the Sunday test here at Reboot. Would you want to hang out with this person by choice on a Sunday? Like, it's a non-work day. You don't have to be in their presence, and yet you would choose to hang out with them on some relaxing non-work activity. If someone passes the Sunday test, that's a pretty substantial thing. And you can tell a lot too about people and how they make you feel meeting in person.

As teams scale, I think it's key to also know that not everybody scales with the organization. So natural turnover in many ways can be celebrated. Like, oh, we have reached this point in our organization where we need to bring in a CFO, not just a director of finance. That can be really hard, especially as teams grow, because you get attached to people. But there's ways to also build it into culture and say, we're bringing you in, we know this might be a short-term thing, but we want this to be the best place that you've worked, and we're going to celebrate what's here.

Alexis:

I really like your answer and setting the right expectations also for people. There are people who can grow with the team or with the company. That's celebrate what they brought to the team. And there are people who don't want to go to the next stage. They prefer the infancy in the incubation mode. And that's okay. How do you approach your own personal and professional development?

Ali:

An ongoing process really of discovery from within me, but also a commitment to being curious about what's showing up for me and my work. I believe we need guides in this life. We can't do this alone. I've got a great body worker. I've got a great therapist. I have a small herd of beautiful horses where I get to go and decompress. I have great colleagues that I get to share my work with and they share their work with me. So there's this cross-pollination that happens. And I have a very loving and wonderful partner with whom I'm lucky to share both life and work.

That's a big part of what supports me in my work. I live a pretty cloistered life on purpose, so that I can hear my own voice clearly, stay attuned to what's emerging within me and within the world. That quiet life really ensures that I have the resources that I need to do the work that I do with my clients.

Alexis:

Are there any books, mentors, experiences that have profoundly impacted your style, your leadership style, or your way of doing your work?

Ali:

Yeah, there's probably too many books to mention. But I'll say that it's probably been informed by three things that are really important to me, and that is deep ecology — this belief that the world, in order to really amend the climate crisis or the ecological disaster that is impending, we really need to tune into a shift in consciousness, which helps people awaken into self-actualization versus a less aware way of being in the world. So I'm a deep ecologist at heart. It's kind of cloaked in all of my work at Reboot. I don't speak about it that directly most of the time, but for me it's right there every day.

Another practice that's really informed the work that I do is art. I've been an artist for my whole life. I'm not formally trained, nor do I think you need formal training to really be an artist — same with leadership in many respects. But there's something about the practice of art where you are alone with yourself and this idea, or you in a blank page or a blank canvas, and it's like, what am I going to bring to this? And it's much less about what am I going to be creating, and it's more about how am I with that creative force that's arising in me, and how do I trust my intuition and my instincts? I think there's something about beauty and truth in that whole process. It's really personal and intimate, but I think it's key to leadership.

And then hands down, horses have definitely impacted my beliefs about leadership and probably my leadership style. There's so much there for me in the horse aspect, like I can't even talk about it. I just start crying. But there's something about learning to be in relationship with another being that is not a power-over relationship, really. It's power-with. That goes a long way into anybody's leadership or management role. In my small herd of beautiful horses, they don't put up with anything really other than the best me, the most authentic me that I bring forward. Every moment spent in the barn is — I'm not going to knock my therapist, because I love her, she's fantastic — but it's immediate feedback. If I am off base or if I'm not owning some state of mind, or I'm bringing some really grumpy state of mind into the interaction with them, they know it. And they're like, you don't feel great about yourself right now. Why should I feel really great about you? They demand really the best of us in order to really have a good relationship with them. It's a really wonderful attunement practice.

Alexis:

That's absolutely perfect. You brought me back many years, when we had horses at home. When you spoke about that, it brought me to when I was a small kid. When I was approaching the horses, they were always trying to smell through the nose. You approach your head close to their nose and they don't move and they smell slowly, and it's warm and you feel something is happening.

Ali:

Yeah. Well, I'm really glad you brought up that memory, because if the horse industry really needed to convert people, all you need is to just have a horse blowing on your face or your hand. There's something really potent about that. You're hooked. Anyway.

Alexis:

Let's take a look at what will happen in the future. How do you see the landscape of leadership coaching and organizational development changing during the next five to 10 years?

Ali:

I think the trajectory of the last five years has been important just to look back a little bit, because it put the emphasis on the importance of leadership development within any startup or any organization. I sense that's going to continue. There was a time when it was a hard sell to get an executive coach or bring in L&D work, and now it's kind of a norm, especially in startup companies that have been funded and other organizations too, in other verticals and industries — not just tech. Which is really great to see, because now that coaching and L&D are part of budgets, they're seeing the impact as well. The payoff of those line items are so great for the individuals and the teams and then the organization and business as a whole.

The thing is, work is a very human place. I really don't think AI is going to shift that too much. There are still going to be humans doing human work, and humans need tending to, and those humans that are working in relational spaces need tending to, whether it's their teammates or their customers or the service that they're providing. So I would hope, if I look into that crystal ball, that the landscape of L&D or leadership coaching will just become more and more human.

Alexis:

I love it. And you guessed that my question was also connected with AI, because it seems everything is related to AI nowadays. I've heard a lot of people thinking they will solve everything with a little bit of AI. I would love us to use the time that we gain to engage in more meaningful relationships.

Ali:

Well said.

Alexis:

What's next for Reboot? Any exciting projects or initiatives you can share with us?

Ali:

We've got a lot of ideas in the hopper, but I think the big and easily ready to share tidbit is Jerry's second book launches tomorrow. So you can find it on bookshelves everywhere — for real, not just in pre-order. We're excited to see how that emerges. Tomorrow we were aiming for some bestseller lists with a lot of presale efforts. The book industry is a really crazy space, so we'll see what happens.

Alexis:

Excellent. Where can people learn more about Reboot and connect with you?

Ali:

Reboot.io is the easiest place to start. You can find all of our resources, our podcast, the journaling prompts, our newsletters. I'm on LinkedIn. And of course Jerry's books, Reboot and now Reunion. Thank you so much for having me, Alexis.

Alexis:

Thank you very much, Ali, for joining the podcast today.