© All rights reserved. Powered by Techronicler
In Conversation with
A Techronicler interview with Mike Gibson, Chief Technology Officer, Planet DDS
Techronicler: Everyone has an origin story! What was the first piece of technology you ever broke, built, or fell in love with?
Mike Gibson:
I’m old enough to remember when PCs first became a household thing. One computer, maybe, if your family was lucky. And there wasn’t really an IT person you could call when something went wrong. You just figured it out.
My early jobs in tech were like that too. Nobody handed you a manual. You opened up the beige tower, looked at all the chips and hard drives crammed in there, and started poking around. That hands-on curiosity was how most of us learned.
The most memorable “breaking” moment came when I swapped out a CPU chip and forgot to put the fan back on. The chip overheated almost immediately. Embarrassing? Yes. But also formative. That was the moment I realized that understanding how something is built isn’t just interesting, but also the difference between knowing what you’re doing and just hoping for the best. That itch to dig in and figure things out has never gone away.
Techronicler: A lot of careers look like straight lines on LinkedIn. How was yours different? Was there a pivotal moment or ‘happy accident’ that actually steered you toward your current role or niche?
Mike Gibson:
Mine wasn’t a straight line, but it was intentional in its own way.
I graduated with an electrical engineering degree, which was actually pretty common for people entering tech at that time. I started as a developer and spent a few years writing code, but I kept noticing something about myself: I was more energized by the problem-solving layer than the code itself. Translating messy business requirements into something a system could actually do was the part I couldn’t stop thinking about.
About three or four years into my career, I stepped away from being a full-time keyboard jockey and started moving through different layers of leadership. Development management, product management, PMO at a large organization, even running a support org for a while. By the time I reached executive leadership, I’d touched almost every part of the software lifecycle — not as a specialist, but as someone who’d actually delivered and supported the work at each level.
There was no single “happy accident.” But the willingness to move sideways, to learn a different function instead of just climbing straight up, is what gave me the skills I rely on now. A CTO who’s only ever done one thing tends to optimize for that one thing. I’d rather understand the full system.
Techronicler: What is the one problem or project that is taking up 80% of your brain space this month?
Mike Gibson:
It’s a question a lot of engineering leaders are wrestling with right now, even if they’re not saying it out loud: how do you evolve your organization’s people, processes, and tooling for an AI-powered world without grinding everything else to a halt?
We’ve been moving our teams from traditional Scrum structures into smaller, tighter pods composed of a designer, a product person, and one or two developers, with much more frequent client interaction and AI embedded throughout. The designer is actually delivering code the developer refines. The whole workflow has changed. And that’s before you get to the cultural side of it.
Here’s the honest challenge: change management used to move at a pace that gave people time to adjust. That’s not the reality anymore with how hyper-accelerated everything is. So my job right now is figuring out how to push people down the change management curve without knocking anyone off it. We can’t put the plane on the tarmac and rebuild it. We’re building it while we fly.
That tension of continuing to deliver against a roadmap while fundamentally reshaping how the team works is where most of my bandwidth is going. Six months in, it’s as complex as I expected. And still worth it.
Techronicler: If you were given $10M to start a company today in a niche outside of your current field, what problem would you solve?
Mike Gibson:
The classic technologist answer to this question is to buy an HVAC company. AI-proof, recession-resistant, unglamorous in the best possible way. I get the appeal.
But I’d take it a step further. Rather than just buying a trades business to escape the technology wave, I’d invest in one specifically to bring that wave in through the front door. The HVAC, plumbing, and electrical industries are facing a real workforce crisis. The skilled workforce is aging out, and you can’t just drop new people in without serious training. The knowledge gap is enormous.
That’s where I’d focus: using AI to accelerate apprenticeship and training programs, streamline procurement, and help these businesses run with leaner teams without losing quality. You still need the hands-on expertise, the tools, the job site experience. But there’s a lot of work that AI can absorb on the operational side, and almost no one is building for that market seriously yet.
Techronicler: What specific ‘quality gates’ or documented pathways have you built to help individual contributors make their first leap into leadership?
Mike Gibson:
The first thing I’d push back on is the assumption that strong technical skills automatically translate to leadership potential. It’s one of the most persistent myths in our industry, and acting on it is how you lose great engineers and create struggling managers at the same time.
What we try to do is give people real ownership before they ever get a title. Not “tag, you’re it” moments, but structured opportunities with clear expected outcomes. Early client conversations are a big one, including the uncomfortable ones. There’s nothing that develops empathy faster than sitting across from someone whose system isn’t working the way they need it to, and having to navigate that honestly.
When something goes wrong internally, we’ll often have a more junior engineer lead the postmortem by owning the investigation and then owning the recommendations. That kind of exposure to pressure, to accountability, to communicating findings to the team, builds something that no amount of code review can replicate.
The other thing I always try to get to with people who are eyeing leadership is the “why.” If the answer is just compensation, that’s a conversation worth having, but it’s not a strong foundation. The question I want them to be able to answer is: what problem do you think you can help solve that you can’t solve from where you are now? That’s what separates a manager from a leader. One has a title. The other has a reason.
Techronicler: What is the one book every leader in tech should read this year?
Mike Gibson:
One that I’ve had on my list and intend to read this year is The Crux by Richard Rumelt.
The premise resonates with me. Tech leaders, especially at the senior level, tend to be very good at execution. We can ship, we can scale, we can manage crises. But strategy — real strategy, not just a roadmap with quarterly OKRs — is harder to practice, and easier to let slip. Rumelt’s work is focused on identifying the core challenge at the heart of a problem rather than just responding to surface-level symptoms. That’s a muscle that needs regular exercise at any level of leadership.
The reason it’s relevant right now specifically is that AI is compressing the execution layer. Things that took months are taking weeks. If your edge was purely operational speed, that edge is shrinking. The leaders who stand out will be able to identify the right problem before racing to solve it. That gap between execution and strategic thinking is where I think the most growth opportunity lives for most tech leaders right now.
Techronicler: What is a piece of ‘common wisdom’ in the tech industry that you completely disagree with?
Mike Gibson:
“Move fast and break things.”
I don’t fully disagree with the spirit of it. The concern behind that phrase is legitimate: bureaucratic processes and excessive governance can slow innovation to the point where it stops happening. I’ve seen that too, and it’s a real problem.
But using it as a blanket philosophy in a business-critical environment is a mistake. In healthcare, if we move fast and break things, our clients can’t see patients. That’s not a metaphor, but the actual consequence. Stability, security, and compliance aren’t constraints you work around — they’re the foundation everything else sits on.
What I’d say instead is that speed and caution aren’t opposites. You can ship fast on features that don’t touch core stability. You can iterate quickly on user experience without touching security architecture. The skill is knowing which category you’re in at any given moment. “Move fast and break things” works when the thing you break is recoverable. The problem is that people often don’t stop to ask whether it is.
Techronicler: How do you create ‘leadership moments’ for junior team members before they officially have a title?
Mike Gibson:
Intentionally. That’s the key word. Not accidentally, not reactively, but structurally.
We try to be deliberate about pulling junior people into situations that are just slightly outside their current comfort zone, with enough context that they can succeed, but not so much scaffolding that there’s nothing to figure out on their own. Retrospectives are a good example. We’ll call out a junior engineer and ask for their perspective directly. It sounds small, but it does two things: it gives the team a fresh angle, and it forces that person to think beyond their specific component and consider the broader system.
The other piece is making sure they understand what success actually looks like before they go in. I’m not interested in pop quizzes. My job is to make my people successful — not the other way around. If I hand someone a leadership moment without equipping them for it, that’s on me.
The last thing I’ll say is that the best indicator of someone’s readiness for leadership isn’t how they perform when things go well. It’s what they do when something breaks. Do they hide? Do they escalate immediately without a recommendation? Or do they dig in, figure out what happened, and come back with a point of view? That instinct tells you a lot more than any formal evaluation.
Mike Gibson is the Chief Technology Officer at Planet DDS, where he leads product development, cloud infrastructure, and security strategy for a suite of SaaS solutions serving enterprise dental organizations. With over 20 years of experience in software engineering and executive leadership across industries including finance, insurance, education, and dental technology, Mike specializes in driving scalable, secure, and user-centric platform transformations. He is passionate about empathetic leadership, building resilient systems, and making innovation feel accessible.