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Transcript

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[00:00:00] Kimberly Boyd: Welcome to Pragmatism In Practice, a podcast from ThoughtWorks where we share stories of practical approaches to becoming a modern digital business. I'm your host, Kimberly Boyd, and I'm here live at Paradigm Shift with one of our incredible speakers, Darren Smith, Chief Technology Officer at MYOB. If you're not familiar with MYOB, they're a business management platform providing solutions in finance and supply chain employee and project management. Fun fact, they were Australia's first unicorn. Darren has made the journey to join us here in LA all the way from Sydney, Australia. We get him fresh off the plane. We're excited to dive in and have a conversation today about Darren's leadership journey and what's brought him to our paradigm shift stage today. Darren, thank you so much for joining us.

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[00:00:45] Darren Smith: Thank you for having me.

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[00:00:47] Kimberly: Maybe we can just kick off and you can tell us and our listeners a little bit about yourself and a brief overview of what your leadership journey's been so far.

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[00:00:57] Darren: Sure. Well, as you said, I've been a CTO at MYOB for the last three years. Before that, I spent a lot of time as a consultant at a company called ºÚÁÏÃÅ.

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[00:01:07] Kimberly: We might have heard of them.

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[00:01:08] Darren: Yes. Where I really started out was as a developer from university, grad developer working on a mainframe type of system called Tandem, it's high availability, that kind of stuff. Within those first few years, I got to ride the dot-com boom in the late 90s, got to learn Java and really even travel around the world working in different places. I think for me, as part of the leadership journey that I saw early days, people were always being pushed forward into new roles, expanding. If you had any talent or any capability, it was like you're a leader kind of thing.

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I found early on for my whole journey that I kept on getting pushed into leadership roles, even though I didn't think I was quite ready for it at that time. I think that stuck with me for a while. I think that stuck with me through, well, probably up until the last couple of weeks even. [laughs] What that meant for me was, I probably get pushed into different roles of leading a team through to working with a friend of mine who brought me in to lead the delivery organization in a small little startup business as well through to coming back and forth between being an individual contributor back in the leadership roles until I really felt comfortable in my own skin.

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When I look back at that journey myself, I think about how I was lucky in terms of being in the right place at the right time, that there was always something that was opening up. It wasn't something that I sought, but a lot of times I got pulled into those roles. I think it's only on reflection that I realized that people would give me opportunity. It wasn't just, yes, all luck. It was a lot of people around me that supported that role too.

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[00:03:19] Kimberly: I'm sure it wasn't all luck, it was largely based on their experience working with you and your capability. Well, one of the things I want to dive back into is you mentioned there was a couple instances that you got pushed into roles that maybe you didn't feel ready for at the time, and it sounds like you had a couple of those experiences in your career. How did you adjust and take on the role and assume the leadership? Are there any reflections that now that you've done this a couple of times that you've said, "Wow, this is probably something I'm going to take and take with me to whatever comes next?"

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[00:03:54] Darren: Look, I think early days I had huge imposter syndrome, so I probably first thing I did was just pick up any book that I could just to learn the craft, and while they were helpful, they didn't necessarily help me in that moment. I think it wasn't until I took that lead role where I was working with a friend of mine and understanding the switch from being an individual contributor where I could see at the end of the day, running a whole bunch of code, you knew how productive you were. You could see it, you could stare at it and start say, "Yes, I've done something." Moving into a leadership role, you start to feel at the end of the day, "All I've done is spend time in meetings."

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That was a real important shift for me to learn and start to value the change in what I was doing. The coping mechanism that I developed at that time was starting to think not about the things that I needed to do today, but they're the seeds I needed to sow. Because a lot of the things that you do really don't pay off for days, weeks, months. [crosstalk] Yes. I think that was a really important thing for me and it actually gave me a chance. I think at the end of that role, I stepped back out of that and went back to just to being a developer for a while. Really, as I then moved back into leadership roles and really set me on the path that I am on today, I was able to use that moment and reset myself and start again to start to say, "Okay, I'm valuing this. I can understand what I'm doing." I think that one of the most important times for me was really understanding that I had to shift my mode and value the work that I was doing but in a different way. That was probably one of the most important leadership lessons I learned.

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[00:05:39] Kimberly: Yes, there's a value that comes in many different forms, right? It looks a little different for every role. I think we all have experiences that have an impact or really resonate with us in our career journeys. Can you talk to any experiences that you've had in your leadership journey that have had a significant impact on you and have influenced how you approach being a leader?

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[00:06:04] Darren: I would say some of the moments that are going to stand out to me was, I remember once being on a client site doing some work, installing a system back in the times when you still had to install things in the data center or on their servers, Things are going wrong with the system and it took me a while. It's taken me ages to work out what was going wrong with this.

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I was getting a call from my manager at the time, reaching out to me and trying to just get hold of me, work out what's going on, what's taking so long, and all that. I just wanted to be in the moment. I really wanted to focus on what I was doing. I was a little bit embarrassed that I couldn't fix this thing, right? It wasn't a trivial thing, but I always had that sense that I always should be able to fix anything. It wasn't until he got through to me that he taught me a valuable lesson. He said that "You've got to pick up the phone. You've got to be available," not because he was checking on me to see if I was doing a good job or not, but he was checking on me to see if he could help. He said, "I can't help you if you won't talk to me." I think that was one of the most valuable things I learned as a leader, that you need to be able to reach out.

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Be there in that moment when you start to work with the people that you're working with. Later on, I realized that it's like being a parent. I've got quite a few children now, and so I've learned a lot of leadership lessons there too. I think that when you think about it, being a leader is a lot like being a parent for a toddler.Ìý

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One of the things that having little kids did for me was teach me risk management. When you think about it, every time that a child's walking past you and picked up something, you're doing it like a blink risk management assessment at that moment.

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[00:08:11] Kimberly: What are they going to do with that? What are the possible permutations?

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[00:08:14] Darren: Exactly. Should I take that off them? Are they going to break it? Are they going to hurt themselves? Are they going to cry? You're weighing up. Is it worth taking off it because it's going to do more damage or is there a learning opportunity? Those kinds of things. I think that that's another big role of the leader is starting to recognise when you can step in with that into each situation. One to let someone learn and grow by themselves, and others where it's a little bit more risky that you want to step in and help them learn and grow together with you.

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I think those are some of the more valuable lessons that you learn with time, is that the role is enabling others to do their role better, not driving them to a better outcome, but you're giving them the tools that they need to be better today and into the future.

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[00:09:02] Kimberly: Yes, helping remove the roadblocks from those team members. I really like the point that you made about being a leader also requires being able and being comfortable to ask for help yourself, because I feel like a lot of times people probably feel like, "Well, I'm a leader. I must have all the answers." That's never going to be the case. I think that's a really important point to reinforce with our team members, our peers, our colleagues that no one has the exact right answer. As we're all striving to be leaders, we should all be striving to be open for that feedback. I think tied to that point, I know that your paradigm shift talk really emphasizes the significance of authenticity and that self-awareness at the heart of what you're building for the customer. I think we're continuing to see and hear a lot about the role of authenticity when it comes to leadership. maybe you could talk a little bit about how you view authenticity playing a really pivotal role in building teams.

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[00:10:05] Darren: For me, and what I would talk about in this context is not just about your values and who you are. It's actually what you do and what you do time and time again. I think that's a big thing in authenticity and in terms of being able to deliver to your customers, to your team, to the people around you. I think that being authentic means that you are clear on what you are willing to do for those that are asking and not always bending to the whims of others because that's what they want and because you're trying to be employee-led or customer-centric. Those things are important, but they're in the context of what you can truly follow through and execute on. It's kept on peeling that onion back in a sense that the heart of that is trust. Building out a strong team is really about creating an environment where you trust each other.

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One of the tricks of trust though and I've seen it play out time and time again, is when people start to think that trust is something like you should just trust me to be left alone and to do my job. I don't think that's the right thing. Trust is not something that you want to draw down on. It's something you want to keep on replenishing. I think that's what authenticity is about, is being about being clear, being honest, having that follow through, being consistent. Those are the kinds of things that I think that as a leader or as any contributor to a team, really needs to bring with them to be able to build the trust to be a highly performing team overall.

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[00:11:42] Kimberly: I really like the idea of refilling or continuing to fill that trust pot and not drawing down on it, like you said. You mentioned that that can be a challenge when you're really striving to be that authentic leader between getting pulled for the team, getting pulled towards the customer, while you're trying to maintain that authentic path that you're on. How do you strike that balance between seizing opportunities and maintaining that authentic path? Are there strategies or ways of working that you applied at to help you do that?

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[00:12:29] Darren: I think in the first instance, being authentic doesn't mean being stagnant and just being the same thing forever. I think there you do need to have growth, you do need to have ambition and it's following through on those things that are important. In the talk, I talk about three things you need to think about around authenticity. First is actuality, what is going on around you? What is the reality around you? What's informing, what's driving you to the next thing? The next is ambition. The idea of ambition there being that you can see an opportunity that customer's asking you for something, there's an opportunity to develop and to grow or your own, in a sense that you want to go out there and do something different. Those are all good things.

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Then I think it then comes down to having an authentic response. What is the thing that I'm going to follow through on? What that means for me is, each of those things it's almost a continual loop that you keep on feeding back through and starting to understand what's important. Then I think as you start to engage with your customers and as your staff and with the people around you, you start to have those frank conversations. I think that when I've had my biggest regrets in losing an opportunity or saying the wrong things, I will get this wrong quite often, is that it's when I've been inauthentic or when I've bent to someone else's desire and I've not been true to my values that I can't walk away and start to say, "I should have helped and stuck my guns there because I lost out the opportunity anyway and I missed the opportunity to be authentic with someone else."

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I think it's really coming back there and giving yourself permission to do those kinds of things. I think that's part of the reason why I actually want to have talk about this so much is it's not about what I do and it's not about a process. It's actually about giving people permission. I think that's something that we forget to do. We forget to be honest, we forget to be clear, we forget to be consistent because we're being told we've got of be all these other things too. I think that's really the heart of the message.

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[00:14:48] Kimberly: I think that's a great point. That was really what was resonating with me with what you were saying is I think people, when there's challenging situations or crises or they perhaps want to speak up. They don't like the direction that something's going, but they feel like they can't and then they have those regrets. If you're reframing that around, "Well, I really need to be authentic", maybe that gives people more purchase and freedom to act in that way, so they don't have those regrets about at least how they showed up and led. Darren, we've talked a bit about your leadership journey, and some of the things you've learned along the way, and really the big role that authenticity plays for you as a leader. When you're thinking longer-term and what's next, and perhaps reflecting back on your career someday, what is the vision and legacy that you individually hope to leave as a leader?

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[00:15:48] Darren: I'm not sure I really have anything huge or anything specific about me. I think that there's probably two things. One is that idea that we've got to be respectful for each other. I think that when I have led into leadership roles and even when I've been in just an individual contributor role, one of the things that's really hit me at the core is when I feel that there's a lack of respect in a workplace, amongst a team, and others. A big part of what I hope that the legacy I leave behind me is not about anyone remembering my name or saying I've done this amazing thing or not. It's just that I've created a culture of respect and that I've contributed to others being respectful to each other.

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It's amazing. I'm not someone who gets overly emotional about things and that's the one thing I do. When I see a lack of respect around me, that is something that just really drives me to action. I think that when I think about the legacy, it's really about that. It's really about creating that moment for others and probably not messing stuff up for the next person to come along.

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[00:17:08] Kimberly: Leave the place better than you found it, and then creating an environment where people can feel great.

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I think that's a pretty great thing to aspire to. Well, thank you so much for joining us today, Darren, and joining us at Paradigm Shift, making the trip from Australia. We really do appreciate it.Ìý

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Thanks so much for joining us for this episode of Pragmatism and Practice. If you'd like to listen to similar podcasts, please visit us at thoughtworks.com/podcast. If you enjoyed the show, help spread the word by rating us on your preferred podcast platform.

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[music]

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[00:17:43] [END OF AUDIO]

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