How to Stay Adaptable as a Startup CTO

[00:01:45] Welcome and Introduction

Andrew Murphy: Hello, everybody, and welcome to Tech Leaders Livestream. For those of you who don't know, I'm Andrew Murphy, the founder of Tech Leaders Launchpad, which helps technology leaders learn to be better. I started my career as a software developer before moving into leadership and then coaching. What I found when I became a technology leader was that there weren't a lot of resources for people like me fifteen years ago, so I made it my mission to help others in the ways I wasn’t helped. Part of that is sharing the people I learn from with you, so today I have Chris Simon with me. Chris, say hello.

Chris Simon: Hi, everybody, and thanks for having me, Andrew.

Andrew Murphy: You're very welcome! Chris is a startup CTO coach. We'll talk about his career highlights and history, but first, my favorite icebreaker: What's your favorite tech gadget that's not your computer?

[00:06:17] Icebreaker: Favorite Non-Computer Tech Gadget

Chris Simon: I've got a lot of tech gadgets I like, but my top pick this last year is the Pixreal Air augmented reality glasses. They're like sunglasses, but with tiny screens inside that project down and through a lens, so it looks like a screen floats in front of you while you still see the world. I travel a lot and love watching movies on them—it feels like sitting in front of a cinema screen, even in the back of an airplane. They're amazing.

Andrew Murphy: We were just saying in the pre-show that we've got lots of flying coming up, so having a massive screen right there is appealing. Awesome! Let's dig into your potted history, Chris. Why are we talking to you today? What's your background?

[00:07:28] Chris Simon's Career Journey

Chris Simon: I've always been in technology. I taught myself to code as a teenager, studied electrical engineering at university (because I got a random scholarship), but my heart was always in computers and programming. Nearly twenty years ago, I co-founded a company called FlexiSchools in Sydney—it lets parents order kids’ lunches from school canteens, and it’s still operating. Startups existed then, but the ecosystem was totally different; VC and onramps hardly existed. My journey taught me a lot about being a startup CTO and how that title can be misunderstood or debated in the tech world.

We launched a second business, Lantern Pay, a healthcare insurance payment platform, and I got to build a bigger team and see it through to acquisition by one of Australia’s big four banks. After that, I moved into independent consulting, coaching, and training. With startups, I coach technical leaders on strong foundations; with bigger businesses, I focus on architecture and domain-driven design. I’m also on a few advisory boards and steering committees. My real passion is working with first-time CTOs, especially in startups, and tackling tricky domain and design problems.

[00:10:42] Engaging the Audience & Topic Introduction

Andrew Murphy: Brilliant. We've got an hour with you, Chris, so if you're watching, remember to ask questions in the chat—we'll try to get to all of them. If not, we'll answer them later. If you have to miss some, there’s a replay. If you’re not on YouTube, I suggest you move there for the best experience. Now, when I bring guests, we pick topics they’re passionate about. Straight away, Chris, you chose “how to stay adaptable.” Why is this so important to you?

[00:12:11] Why Adaptability Matters for Startup CTOs

Chris Simon: Startups change rapidly. You're building something new, sometimes innovating for the first time, and that requires constantly shifting your mindset and approach as your role and what the company needs from you changes. I’ve seen businesses outgrow their early people because those folks couldn’t change with them. If you’re self-aware enough to realize when you need to step aside, that’s great. But I also think it’s an exciting growth opportunity to evolve and stay with the company as it scales. It’s very rewarding to see a journey from a few people and no processes to selling to a major company. I want to help other CTOs have that experience—seeing a company through, rather than being replaced.

[00:14:05] The Challenge of Continuity vs. Change

Andrew Murphy: Whether you keep adapting or someone new comes in, someone always has to learn—a learning curve for both incumbents and newbies. Why not keep the ones with domain and cultural knowledge if you can?

Chris Simon: Exactly. Continuity is valuable, but people have had bad experiences seeing folks hang on too long. If someone can’t adapt, bringing someone else in is best, but you get the best of both worlds if the original person can grow and adapt as needed.

[00:15:43] Roles, Titles, and Functions in Startups

Andrew Murphy: Daryl raised a good point—roles/titles vs. functions. As a CTO, whether you have 3, 20, or 200 people under you, your job title stays the same, but your actual job changes.

Chris Simon: Yes! I split titles into three buckets: how your company understands/uses your role, how you represent the business externally (candidates, prospects, etc.), and the title you want on LinkedIn for your next job. Those are often at odds and can cause confusion. But more to Daryl's point, your responsibilities shift hugely as you grow—from wearing all the hats at first, then delegating out as you scale. Being adaptable means understanding your own strengths and knowing when to delegate to others with complementary skills.

[00:18:24] Delegation and Learning Through Adaptability

Andrew Murphy: Feel free to add your own observations in the chat. We did a live stream with Michael Lopp (Rands) on “Delegate Until It Hurts,” which was about pushing yourself to delegate more than feels comfortable. On that note, can you share a story where focusing on your adaptability made you a better CTO?

[00:19:30] A Story of Adaptability—and Its Challenges

Chris Simon: There’s a time I hired someone into a role, and I was so keen not to be an overbearing CTO that I gave them too much freedom. I failed to provide enough expectations and structure—there’s a fine line between delegating and leaving people dangling without guidance. I learned that people often need clarity and some boundaries, especially when they don’t have all the context. I didn’t get this right, and the person ended up leaving, but it taught me to balance autonomy with support and structure.

[00:21:39] Learning from Mistakes—Reflection and Moving Forward

Andrew Murphy: As leaders, our mistakes impact people. We have to find safe spaces to learn, but sometimes we just have to act and learn from the outcome. The key is to reflect, learn, and do better, not hide mistakes.

Chris Simon: 100%. But let’s not forget—learning from mistakes isn’t the only way. Read books, find mentors, take training courses—you can also avoid some mistakes entirely by learning from others. We should use all these modes, not just trial and error.

Andrew Murphy: As someone running an online learning platform, I completely agree!

[00:23:31] Balancing Long-Term Strategy and Short-Term Adaptability

Andrew Murphy: As startup execs, change is constant—markets, people, business priorities. How do you balance long-term strategy with the need to respond and adapt quickly?

Chris Simon: I frame objectives by timescale—strategic (long-term) goals versus tactical (short-term) actions. Strategic goals should be outcome-oriented (what impact or outcome do we want?), which lets you adapt your day-to-day tactics without losing that alignment. Problems happen when long-term goals are too prescriptive. If you focus on outcomes, you can change tactics as needed while staying aligned. Agile and feedback loops are about zigzagging toward the real goal, testing, and adapting as you go, instead of following a rigid plan that may not land you where you want.

[00:27:05] OKRs vs KPIs—Their Role in Adaptability

Andrew Murphy: This relates to OKRs versus KPIs—OKRs are those long-term, outcome-based goals, KPIs are health metrics to make sure everything's running well. KPIs can help flag issues you need to address tactically, while OKRs keep you focused on the bigger objective.

Chris Simon: Agreed! There's a good analogy to tech monitoring—KPIs as monitoring metrics (like SRE metrics for reliability), OKRs as service level objectives (what matters to the business). Both are important: KPIs give you tactical signals, OKRs show you’re delivering on outcomes.

Andrew Murphy: I like that analogy! Sometimes it’s less about the metric itself and more about the direction or trend.

[00:30:59] What Are the Skills/Behaviors Needed for Adaptability?

Andrew Murphy: Let’s give people some actionable advice. What are the skills or behaviors leaders need to develop to be more adaptable? Are there common signals or indicators when they need to change how they work?

Chris Simon: Great question. I use a framework with coaching startup CTOs: growth stages tied to team size.

• Early days (founding team): You need to be entrepreneurial, build tech, think like a business leader, get involved in sales, manage risk, and understand the financials. If someone is only coding, maybe don't call them CTO yet; but if they're involved in all these areas, they really are.
• Growing team: Add engineering manager and tech lead duties. Recruit and build a team, set and protect culture, energize people, start implementing processes.
• Multiple teams: You need situational awareness (political acumen), attend to system architecture, play a role in talent branding, and be accountable for process scale and people utilization.

The crucial skill is noticing when you need to change—being situationally aware. Are you meeting the needs of the wider org? Do you have relationships and trust with other leaders? Those relationships are your early-warning system for when adaptation is needed.

For team leadership, use models like Tuckman (forming, storming, norming, performing) and dynamically adjust how directive or supportive you are based on team maturity and challenges.

[00:39:06] Developing Awareness and Noticing When to Adapt

Andrew Murphy: So, it's about constantly asking: What should my role be? What are the gaps? Who should fill them? Should I, my team, or do we hire?

Chris Simon: Exactly! It's cultivating awareness (situational and organizational). Most people are too inward-focused. First, develop that awareness; then use frameworks to help decide how to adapt.

Andrew Murphy: If you don't have time to be situationally aware, that's the first thing you need to fix.

Chris Simon: It's not just time, but appetite—especially for technologists. Many developers want to be CTOs, thinking it’s about being the best coder, but it's actually about building trust and relationships across the business. If you don't want to do that, CTO may not be for you. These relationships are your feedback channels for when to adapt.

[00:42:25] The CTO Role and Alternative Career Pathways

Andrew Murphy: Some CTOs prefer to remain hands-on technologists, hiring others to handle the business side. Does that work?

Chris Simon: A couple of examples—New Relic’s founder hired a management team and continued coding, staying hands-on and letting them run the business. Mitchell Hashimoto at HashiCorp stepped back fully into an IC role. It's complex but can work, depending on clarity of roles and egos. I did this myself too—transitioned from CTO to a kind of chief architect/trainer, reporting to the new CTO. It worked for me.

Andrew Murphy: I've been there—transitioning away from technology is really hard, especially if it's your identity or comfort zone. Learning things like accounting or business reporting is a big leap.

Chris Simon: That's why I tell startup CTOs to start learning business fundamentals from the beginning. It's valuable to understand runway, fundraising, board reporting, and outcome-driven reasoning early. Even when your team is small, your investors want to know what you’re doing with their money. People leadership becomes important later, as you grow.

[00:48:56] Value of Business & Outcome Understanding for All Leaders

Andrew Murphy: Even if you’re not a CTO—say, a tech lead or EM—understanding these strategic concepts will make you better at your job. Knowing why you’re building something, being able to talk outcomes, building those cross-department relationships—those skills are valuable everywhere.

Chris Simon: Absolutely! That’s why I love domain-driven design—it always connects tech to business value. I train people in strategic DDD, and we spend a whole day on business models before touching the tech. It makes you a better technologist at any level to really understand the business side.

Andrew Murphy: Talk to your PMs, UXers, product owners—they’ll love to share this with you, and it’ll make work easier all around. As you rise, your job becomes more about coordination and trust than engineering specifics.

Chris Simon: Agreed. Trust is built by consistently doing what you say you’ll do—it’s the foundation. Deliver what you promise, and people will trust you.

[00:52:30] Building Trust and Wrapping Up

Andrew Murphy: And trust is built in drops but spent in buckets—so be intentional. We're nearly at the hour, so if you have questions, send them in. Chris, what's an actionable thing someone can do on Monday to build adaptability?

Chris Simon: On Monday, pick someone outside your engineering team and ask about their role, their challenges, what matters to them. Start building those relationships and make it a habit. It’ll drastically improve your ability to make decisions and contribute. It's more important than learning another language or framework.

Andrew Murphy: For startup CTOs, that might be your cofounder or early hires. When their answers start changing, it’s a sign it’s time for you to change too.

Chris Simon: Exactly.

[00:55:38] Closing and Next Livestream

Andrew Murphy: Thank you, Chris! Next time, I’ll be joined by April Lee to talk about embracing neurodiversity as a tech leader—from team dynamics to being a neurodiverse leader yourself. If you’re new, scan the QR code or check the chat for links to my newsletter and more. Chris, anything else to share?

Chris Simon: Check out my website, chrissimon.com.au. I’m especially passionate about allyship and promoting diversity and safe workplaces in tech. If you want to talk about improving as an ally—especially around addressing bias and accessibility—I've set up a section on my site, and I offer free 1:1 peer chats. Peer support, not expert advice; let’s learn from each other.

Andrew Murphy: Thanks Chris. It's hard to know where to start in allyship, but even talking about wanting to start is super valuable. Thanks to everyone who joined us today. See you in a couple of weeks!