When we talk about digital transformation, it often brings to mind system upgrades or new platforms. But in my experience, the most meaningful change doesn’t start with the tech. It starts with people.
Across my roles in higher education, enterprise systems, and immersive tech, the most valuable lesson I’ve learned is that real transformation comes from asking the right questions, not having all the answers.
What really makes the difference is good communication, listening properly, and asking the right questions early on.
Start with the conversation
Before I start looking at solutions, I start with a conversation.
Workshops, chats with staff, feedback sessions, all of that helps uncover what’s really going on. Not the surface-level issue, but the everyday friction points. The workarounds people rely on. The things they’ve quietly put up with for years.
A few questions I always come back to:
- What’s slowing you down more than it should?
- What do you wish worked better?
- What would make a noticeable difference in your day?
Getting clarity here helps shape everything that follows.
You don’t have to control everything to lead it
One of the most important lessons I’ve learned is that leading a project doesn’t mean controlling every part of it. It means helping other people succeed, steering when things go off track, and giving space for the right ideas to surface.
At CQU, I led the GenAI Taskforce and supported the rollout of appropiate GenAI tools. We didn’t just switch things on and hope for the best. We tested real use cases, worked with teams to shape what they needed, and adjusted as we went.
I’ve found that the best outcomes come when the people affected by the change help design the solution. It’s not always clean or quick, but it works.
Build systems around people, not the other way around
Too often, digital projects focus on delivering the new system without looking at whether it actually helps. For me, the real value comes from making sure the tools enhance the way people already work, or want to work.
When I led the SharePoint Online migration and the rebuild of the internal service desk at CQU, the priority was on improving day-to-day experience. That meant mapping out real workflows, simplifying them where we could, and involving staff in the process early.
It wasn’t just about moving to a new platform. It was about making the new one more useful than the old.
What Makes It Stick?
From product delivery roles to XR and AI side projects, the theme I keep returning to is this:
Change that sticks is built through clarity, collaboration, and the courage to ask questions early.
No single person controls transformation. But good leadership brings people together, gives them space to contribute, and helps move the vision forward, step by step.
A few things I try to stick to
Every project’s different, but here are a few things that have served me well:
- Start by listening. Don’t assume you already know the problem.
- Ask better questions. What people tell you up front isn’t always the whole story.
- Build with others. Co-design gets buy-in, and usually better ideas.
- Be flexible. Things change, make sure your approach can too.
- Keep the goal in sight. Fancy features mean nothing if the basics aren’t right.
Final Thoughts
Digital transformation isn’t about launching tools and calling it done. It’s about making real improvements to how people work, solve problems, and get things done.
In every project I’ve led the same approach has helped: talk to people, understand the need, and let the solution grow from there.
You don’t need all the answers on day one. Just start with the right questions, and go from there.
Thanks for reading. If you’re exploring similar spaces or wrestling with how to lead tech-forward teams, I’d love to connect. You can find me on LinkedIn or check out more of my work at matthewaisthorpe.com.au.