Shaun is a thought leader in Digital Journal’s Insight Forum (become a member).
When I step into a new organization as a technology leader, my mindset isn’t “what’s broken?” It’s “where are we, really?”
I recently joined a company that, like many others, is reassessing the role of technology across its operations. It wants to move beyond seeing IT as a utility and start thinking of it as a lever for business strategy. That’s what drew me in. I have always been energized by transformation — the kind that starts not with assumptions, but with honesty.
That kind of honesty takes vulnerability. It is something I spoke about last week during a panel at the mesh conference, and it keeps coming up in my work. Vulnerability is not a weakness. It is a leadership skill. It opens the door to real conversations, builds trust, and sets the stage for change.
The first 90 days are about earning trust
When you enter a new organization, it is tempting to jump in and start fixing things. I learned early in my career that experience alone does not give you the right to make sweeping changes. You have to earn that.
In this role, one issue stood out immediately: Wi-Fi problems in one of our offices. It was mentioned in interviews, echoed in early meetings, and flagged by multiple people. Is Wi-Fi strategic? Not necessarily, but I knew that until the “plumbing” was working, nothing else I proposed would resonate.
Solving early problems like this is not about checking boxes. It is about building credibility. When people see that you listen and deliver, you earn the right to go deeper and start addressing more complex systems and structures.
At the same time, you have to be careful not to reinforce outdated perceptions. Someone recently asked me to fix their VPN. I could have jumped in, but that would have signalled that I am still a support contact. Instead, I helped connect them to the right person and used the moment to reinforce what I am here to do, which is to lead, not troubleshoot.
Listen first, act second
The most important thing I do in a new role is listen. I start with the organization’s strategic documents — the vision, the goals, the values. Then I talk to my team. Do they understand the strategy? Are their efforts aligned with it?
From there, I meet with people across the organization. I listen to their frustrations, their aspirations, and how they see technology playing a role in their work. Then I reflect that back and confirm what I heard. That simple step builds trust and often reveals gaps between the official strategy and the lived experience.
You can’t fix those gaps unless you understand them. And you can’t understand them unless you create space for people to share openly.
A broader view comes with responsibility
It’s often overlooked that technology leaders typically have the widest view across the business. While other departments focus on specific functions, technology connects them all. That perspective is powerful, but only if the organization treats the role accordingly.
Too often, technology roles are treated as operational rather than strategic. In this case, the company had already started shifting expectations before I arrived. My predecessor had been more focused on steady-state operations. Now, the organization wanted someone who would help shape vision. That made a big difference. Not just for me, but for the signal it sent across the company.
Still, I have to live up to that shift. I have to reinforce the message in how I show up. If I start fixing VPNs and printers, I am doing more than helping, I am resetting expectations in the wrong direction.
Small conversations can unlock real change
You will not fix everything in your first few months. But you can shift how people see what is possible.
That starts with conversations.
I make time for one-on-one conversations with as many people as I can. Not to check boxes or collect updates, but to hear what they are thinking. You never know who has been waiting for an opportunity or quietly building skills in an area like cybersecurity. You don’t get that insight from a dashboard, you get it from listening.
Transformation rarely begins with a massive initiative. It begins with trust, curiosity, and consistent follow-through. If you want to move the needle, start by showing people you are here to listen, and then follow through with action based on what you learn.
