New School IT
We laugh about the stories of how we discovered the unpredictable dynamics of corporate operations as we move beyond simplistic "machine" metaphors.
Collaborating with diverse co-hosts, we explore and analyze organizations as complex, living systems. Our show challenges the "people, process, technology" cliché to help leaders navigate the gap between ambition and operational reality in the era of AI, data-driven decisions, and digital operations.
New School IT® is affiliated with SODA™, the Systemic Of Disciplined Adaptability. SODA is the operations framework for companies to cultivate and strengthen the needed discipline and adaptability to thrive in the age of AI, data-driven operations, and digital markets.
New School IT
Cheryl Haggerty, Shalion's CCO: How A Nontraditional Leader Builds Trust, Purpose, And AI Readiness
With Cheryl Haggerty, Chief Client Officer at Shalion, we explore nontraditional careers, values-driven leadership, and how AI reshapes teamwork and trust.
From progress over perfection to building cross-team flow, Cheryl shares honest stories and practical tools:
• nonlinear career path and authenticity
• values as a compass for purpose
• progress over perfection as a team norm
• cross-team communication and effectiveness
• trust beyond titles and honest leadership
• AI for productivity with human empathy
• designing customer success from first principles
• practical ways to learn AI together
• advice at 15, 30, and last year
Follow the show, share it with some of those building teams, and keep an ear out for Cheryl's return after she finishes her London School of Economics degree, which she started just this year.
Hello, this is New School IT. How can I help you?
SPEAKER_01:Hi, everyone, and welcome to New School IT. I'm your host, Roland Hoffman. Today is our first special guest episode. My guest is Cheryl Haggerty. She is the Chief Customer Officer at Shalyon. She built a remarkable career without a college degree, but is now studying at the London School of Economics to get a degree in AI leadership. Let's jump straight in.
SPEAKER_03:Please hold.
SPEAKER_01:Most of us were taught that success has a playbook. Study hard, get the degree, climb the ladder. My guest today, Cheryl Haggerty, has built a remarkable career without a college degree, rising all the way to chief customer officer at Shalion, which is a high-flying startup out of Barcelona that recently has been signing world-class companies. And not only that, now she's also studying at the London School of Economics to master the next big shift, which is leading in the age of AI. Hi, Cheryl. How are you?
SPEAKER_00:Hello, hello.
SPEAKER_01:This has been a huge year for you. New role, new study, new chapter all the way around. How do you feel about it all?
SPEAKER_00:I feel good. I feel uh very good, very happy, very pleased. There's a small part of me that still feels like an imposter, but no, it's it's been a good year. A year where I can truly be me.
SPEAKER_01:Nice. Okay, I want to ask you a few questions. You've built a powerful career without following the traditional route. Looking back, what gave you direction when there wasn't a clear roadmap?
SPEAKER_00:Okay. So honestly, I would mirror people. If I saw someone doing well, if I saw someone getting promoted, if I saw someone being celebrated, I would try and mirror them, their style, their behavior, their way of working. That was my early roadmap. And then I realized, do you know what? I'm not gonna get anywhere unless I'm me. So trying to be the best version of whatever it was I was doing was my roadmap.
SPEAKER_01:I like in the beginning you chose people that could mentor you, whether they were actually aware of the fact that you recruited them or not.
SPEAKER_00:Exactly.
SPEAKER_01:And then after that, the best thing I can do to be happy in my life is just to be myself. And what I also heard you say is a third thing is adaptability.
SPEAKER_00:Yeah, totally. There's one thing I won't adapt though, which is I will never stop wearing leopard print. But apart from everything else in my life, I am adaptable.
SPEAKER_01:Our listeners can't quite see that you're actually wearing leopard print right now. It's my trademark. Yeah, nice. Okay, in all of that, was there ever a moment when you thought, this is the ceiling, this is as far as it's gonna go, and something shifted in how you saw yourself or your path?
SPEAKER_00:Yeah, I'm I mean, honestly, I still don't know my path. People say to me, what was the kind of direction? And my answer was always, when I grow up, I'll tell you what my my path's gonna be, but I'm not there yet, and I still feel the same. I'm doing something that I love, I'm doing something I'm passionate about. Will that be the same thing in a year or five years? I don't know. But I will only choose things that mean something to me or will give me some kind of joy. So it's really hard to answer that question because I don't really have a path.
SPEAKER_01:Life's so dynamic that there's always going to be uncertainty, and what's important today is unlikely to be the most important thing forever.
SPEAKER_00:Exactly. If you'd have asked me in my twenties or even my thirties, what would I be doing now at nearly 50? I would not be saying that I have a role that's a global role, that I would be travelling the world to try and help brands and organizations. I mean, that sounds quite corporate, but I've never grown up in a corporate world. My mum and dad have blue-collar jobs, and that's just what we did. So I pinch myself. I'm definitely one of these people that um when I go on a flight and maybe I've got a free upgrade. I mean, I am celebrating, I am drinking all the champagne that they give me.
SPEAKER_04:I love it.
SPEAKER_00:A lot of the other business professionals are very corporate about it and very calm. I look like I've won the lottery. So I like to celebrate and savour them.
SPEAKER_01:It's one of the things we love about you, Cheryl.
SPEAKER_05:Please hold. Every twist and turn the game the letter. Every doubt, just push me to the bottom. It's the right of the word to get it done.
SPEAKER_01:Purpose. How do you define purpose? Not necessarily what your purpose is, but how do you define purpose?
SPEAKER_00:So I've had some really great mentors through my career, and one of them pushed me to think about my own personal values, and that's kind of driven my purpose. So trust, integrity are really important to me, honesty, genuinely being kind. And those are the things that drive me in helping other people. Right. So for me, everyone has to win, which isn't always possible. But we need to be able to kind of celebrate things together. And it's more important that my team feel supported and that they have my trust and I have their trust. Yeah, and I need my team to do the same. So my purpose is about if everybody can grow a little bit further, then I've achieved something.
SPEAKER_01:There's an internal purpose, something that looks inward, like I want to be a better person. And then there's an external purpose, something that serves somebody else. And the external purpose that serves somebody else tends to be more powerful than the one that is about the internal focus.
SPEAKER_00:Yeah, I'm much more satisfied when that happens.
SPEAKER_01:Yeah.
SPEAKER_00:Don't get me wrong, I celebrate something that I've done that maybe I hadn't hadn't done previously. But yeah, it's more important for me, the team.
SPEAKER_01:It's a good segue to the next question I was going to ask you.
SPEAKER_03:Please hold.
SPEAKER_05:Be yourself and let the real life show.
SPEAKER_01:When you're helping others grow, how do you help them find direction when things feel uncertain?
SPEAKER_00:There's one phrase I use in all of my sessions with the team: progress over perfection. The blocker for momentum is doing something. And we try and get this perfect idea or perfect scenario of what we want to try and get to. And we spend so much time, sometimes, trying to define and create that perfect version of something that we don't start. And for me, not starting is as bad as not having a strategy, because you need to get that momentum. So, again, if my team are listening, they will be laughing and chalking it off the board, I'm sure, of their kind of work bingo uh words for me. But it might not be brilliant, but start.
SPEAKER_01:You have worked across so many fast-moving organizations. What have you learned about keeping things flowing between teams and departments?
SPEAKER_00:I've learned it's really hard.
SPEAKER_01:Yes, it is, isn't it?
SPEAKER_00:I think the first thing I would say is uh we sometimes forget that nobody comes to work to do a bad job. And it's really easy when communication is breaking down between a a team or a department or a project, that there's always the assumption that someone's not doing something or someone's doing a bad job to cause something. But it tends to be just the lack of any decent communication. The conversation's key. What I mean by that is sometimes we spend our time ticking off the list of things that we should have done or have done, but it hasn't driven anything in any kind of flow between teams that we haven't said, actually, has this delivered anything? Has it changed something? Has it given you more insight? Has it changed the way we operate? So compliance versus effectiveness, I think talking out loud is probably the thing for me.
SPEAKER_01:If you don't have connections between people, then the information doesn't actually flow. Connections have strengths. I sent you an email, it's a weaker connection than you and I are talking right now.
SPEAKER_00:I'm smiling because my head has gone back however many years it is. I remember the first couple of interactions that we had, and I'd sent you some emails, and we couldn't have been further apart in the understanding of that comms. Your interpretation of what I'd written. I remember and what I'd actually written.
SPEAKER_01:But look at us now. We ended up in conversation, you work these things out. Real progress and real change in innovation happens because people are talking to each other about new ideas.
SPEAKER_03:Yeah. Please hold.
SPEAKER_05:Progress over perfection.
SPEAKER_01:So give me an example of something when everything clicked. Wow, I can't believe how well this is going.
SPEAKER_00:I think it's when people come together and think about the overall problem that's trying to be solved rather than just their part in it. The handcuffs have been taken off people to say, I only want you to focus on this part. Yes, you might represent different departments, but the whole point of bringing this team together is because we want to try and solve the problem. We don't want to try and solve department problems. We might do that along the way, but that's not their kind of aim. So I think taking the handcuffs off so people feel like they have the ability to give their input and their ideas and their thoughts and not worry if it sounds odd or weird or stupid. Those are the good kind of connections.
SPEAKER_01:Yeah. Give me a specific example.
SPEAKER_00:Oh so I I remember being part of a startup and we won this huge, huge, huge global client and had absolutely no idea how we were going to deliver it. Um and I say that with some jest because of course we had a brilliant team, we had brilliant tech, we had brilliant solutions, but we'd never dealt with a client that was this big and the expectation was very different. So how we approach that project internally was a huge challenge for us. But the one thing that we didn't do was ask the client.
SPEAKER_01:Okay. I want to go back to asking for a specific example of when everything clicked.
SPEAKER_00:Oh, yeah, sorry, I'm always good at getting bad stuff rather than good stuff. So I'm responsible for the customer success team where I where I am. And one of the things that we do is build capability, we build knowledge, we help educate teams. And as a team, we spent some time together really understanding and pulling apart what does the next version of that look like with AI, with everything else coming through. And I think the moment that clicked is once we said, forget what a CS kind of type role is, just forget it. Pretend it's never existed. How would we actually operate? And the feedback and the input and the ideas were heartwarming sounds wrong, but like you I just thought like, oh my god, people have really thought about this.
SPEAKER_01:There is a it's a joy when it happens. Yeah.
SPEAKER_00:And it's those kind of moments that I I love because then we're all doing something different as a team together. And it clicks. Please hold. Okay, that's an interesting and relevant topic for me. It's important for me personally, it's important for us as a business. How do we incorporate this? I think on one side we have the ability to remove some of the mundane and be more productive in our work. I think on the other hand, the human element, the empathy, the questions, the listening, the seeking to understand is as important as the productivity. I think my team fear when they hear that something AI-related is going to be introduced because there's an assumption that jobs will be reduced. And that's not the case. We want to be able to scale better. We want to be able to deliver better value quicker, not just to have efficiencies in the people that work within the business. One of the challenges I feel with AI at the moment is not necessarily the use cases, but we talked about trust earlier. How much do people trust what's coming back? And you spend more of your time working out whether something's real than actually absorbing whatever the information is that you're trying to take.
SPEAKER_01:Yeah. I'm also curious how you will answer this question after you've been studying at the London School of Economics, because I'm sure academically and scholarly there are many more considerations to go into this. So, how do you go about building trust as a leader?
SPEAKER_00:Yeah, it's a it's a good question. I don't see being a leader associated with a title, so everyone has has that inbuilt in them. However, what I will say is in my career throughout my journey, sometimes people will choose to have a conversation with me or not based on my title. But that has stayed with me. So I've been really conscious to make sure that as I come through my career that I treat people as people and as humans, not as the job title. The thing I would say on top of that though, is I do sometimes suffer a little bit with the imposter syndrome, and that is a good leveller for me.
SPEAKER_01:It takes courage to admit the weakness, but as a leader, especially that creates that trust.
SPEAKER_00:Yeah, and that and I think that's you know, if I've got something wrong, I'll tell you. If I'm not sure about something, I'll tell you. Not to the point that I want anyone to feel that there's no direction or that they are not being supported. But for me, it's a good balance between if I expect the team to trust me and me trust them, we've got to have a level of openness. Please hold.
SPEAKER_05:Some days you win, some days you're guessing. That's the dance of doing what you love. Keep adapting, keep connecting.
SPEAKER_01:In the context of the curriculum that you're pursuing, how does AI affect this trust equation between people?
SPEAKER_00:It comes back to that continuous kind of openness in conversation because this week I've been testing some AI tools with my team, and we're getting some brilliant results, and we're all in this together and we're seeing the information. But some of the things are not quite coming back as they should be. And the team are looking to me to provide some leadership and knowledge, and that's really hard when it's a space that's not your makeup, your bag, your experience, your kind of DNA. So I think leading through this kind of time of change with AI, you just have to be open. But also, it's my responsibility to educate myself, to help educate my team and educate the clients on what it could do, what it means, what it does do, how it will affect the leadership, how it will change our processes. Do we need to second guess? Do we need to double check? Is there a quality element? There's lots of questions that come out, but we're trying to navigate it together. So that's not a brilliant answer because I don't know. One of the reasons that I'm spending and so much time of my own personal time on this course is to really try and understand and get experience from either people that have tried it, done it, started it, um, or people that are in the same situation as me. And how do we try and learn together?
SPEAKER_01:Let's agree right now that we're going to do a second episode after you're done. I can't wait to hear your thoughts about this. Exactly. You have given a lot of thought-provoking ideas and stories. I want to switch gears here to the last question. I'd like to ask you if you look at how much you've achieved, if you could give yourself advice at three different moments in your life, one at when you were fifteen, the other one when you were thirty, and the third one last year, what would you tell yourself?
SPEAKER_00:Wow.
SPEAKER_01:Okay, so at fifteen Everybody should see the Cheryl smile right now.
SPEAKER_00:I think I would say the future version of you is so proud that you didn't give up.
SPEAKER_04:Don't give up.
SPEAKER_00:Don't give up, yeah. I think the second thing would be as a 15-year-old, just do it. Doesn't matter what it is, if you're being asked to travel or do something different, just do it. Motivation really only comes when you've actually started something. So as a 15-year-old, I would always say to myself, Oh, I need to motivate myself to do something, or I need to find the motivation. But motivation comes when you start. So I think those are the things that I would say to myself at 15.
SPEAKER_01:What do you tell your 30-year-old?
SPEAKER_00:I would say don't listen to other people's version of you. Trust that you know your capability. And and maybe that could have held me back. It it it hasn't, but maybe it could have. So I would definitely say, you know, don't listen to other people's version of you. You know what you're capable of, so just go for it.
SPEAKER_01:Trust yourself.
SPEAKER_00:Yeah. Always remember your values.
SPEAKER_01:Interesting. Explain that a little bit.
SPEAKER_00:Yeah. I think as you as I get older, as I take on different responsibilities, work with different people and roles and different cultures. And I think I had to remind myself of the things that were important to me. As I left one organization and joined another, I didn't want to start somewhere that didn't align with my core value set. So I think last year that's the thing.
SPEAKER_01:To me, it sounds like you've made a difficult decision, but are happy that you did because it aligns with your values.
SPEAKER_00:Yeah. Yeah. That's a good a good summary.
SPEAKER_01:It's clear that you follow your own advice.
SPEAKER_03:Yeah, yeah.
SPEAKER_01:Very proud of you.
SPEAKER_03:Please hold.
SPEAKER_01:Okay, so in the spirit of wrapping this up, any words of wisdom?
SPEAKER_00:Uh just be yourself. You know, whether you're talking about AI, whether you're talking about career progression, whether you're talking about education, just be yourself. Be you.
SPEAKER_01:On your behalf, I will add, wear a leopard print.
SPEAKER_00:Wear a leopard print. It is essential. Everyday item, regardless if you're in a board meeting or out with friends. It's it's the uniform.
SPEAKER_01:I want to thank you so much. I think you reminded everybody that the most important thing about leadership is not that you know everything. I mean the level of honesty is inspiring. Thank you for that.
SPEAKER_00:Thank you. Thank you for having me. It's been awesome. Lovely to chat to you for a bit. Thank you.
SPEAKER_01:Thank you. That was Daryl Hagley. A 15 takeaways worth keeping. Start now. Favor progress over perfection. Build trust through openness. Lead with purpose, and stay adaptable. Oh, and most importantly, UBU. This has been useful IT. Follow the show, share it with some of those building teams, and keep an ear out for Cheryl's return after our LSD program. I'm Roland Hoffman. Thanks for listening. Stay curious and stay focused.
SPEAKER_05:That's the dance.
