When you work in public safety, transportation, and cybersecurity, you quickly realize that technology itself can’t meet every challenge in such high-stakes environments. Tools and platforms matter, but lasting solutions depend on people—building trust, showing empathy, and asking the right questions. For me, customer success has always been about something deeper: building trust through empathy and curiosity.
The only way I know how to do this is to put myself in the customers’ shoes. I want to understand not just what they’re asking for, but who they are, the pressures they face, and those they serve. You can’t assume you understand their world—you must see it from their side.
Leading with Empathy
In most projects, the toughest challenges rarely come from the technology itself. They come from navigating the different perspectives, priorities, and pressures of the people involved. One project that stands out involved a large metropolitan customer that had two groups with very different priorities. The customer’s operations team was focused on uptime and technical performance, while leadership was focused on strategy and long-term outcomes. On the surface, their goals didn’t conflict, but the conversations weren’t moving forward.
Instead of treating them as one audience, I met with each group separately. I asked questions like, “How does this project tie into your long-term vision?” and “What does success look like for you on a daily basis?” These questions got to the heart of their concerns, and I also listened to what wasn’t being said. What I found was that they cared about the same thing—protecting their community—they just expressed it in different ways. Once we reframed the discussion around that shared goal, progress came quickly.
That experience reminded me that empathy isn’t just soft, it’s strategic. It’s what allows us to uncover the real drivers of success and keep everyone aligned.
Staying Curious
Throughout my experiences, I’ve found that empathy is a core component in making sure customers are satisfied; however, it’s only one piece of the equation. Curiosity is the other. Curiosity drives me to ask questions, even when a request seems straightforward.
I remember a public safety customer who needed help integrating video feeds. On paper, it was a simple task. But I asked, “How do you actually use these feeds during an incident?” That one question uncovered critical information: during emergencies, a neighboring agency also needed access. By discovering that early, we built a secure, multi-agency solution from the start instead of trying to retrofit it later.
Moments like these are why I love this work. Curiosity protects us from solving the wrong problem. It helps us design systems that meet requirements and effectively support the people on the ground when it matters most.
From Vendor to Partner
When empathy guides how we listen and curiosity shapes the questions we ask, trust grows. That trust turns a vendor relationship into a true partnership. In my role, I’ve learned that partnerships start with listening, not pitching. Projects shift dramatically when we slow down to understand a customer’s culture, pain points, and the mission behind their request.
When we do that, the relationship changes. It becomes more than transactional, it becomes enduring. Together, we solve challenges, discover opportunities, and measure success in outcomes that matter to everyone.
That’s what partnership looks like, and it’s what we strive for every day at Skyline.
Why the Human Side Matters
At the end of the day, technology will keep evolving. The tools I work with today may look completely different five years from now. But the need for the human side—empathy, curiosity, and trust—will never change.
Technology is only as good as the trust behind it. When customers know we understand them and not just their systems, we can create solutions that make a real difference.
This Customer Success Week, I’m proud to celebrate the people at Skyline who bring that human side to every conversation, every meeting, and every project. For us, that’s the whole point.
About Skyline Technology Solutions
Skyline Technology Solutions delivers innovative public safety, transportation, and enterprise technology services with a people-first approach. From designing secure, reliable systems to building trusted partnerships, we help organizations solve complex problems and create lasting impact in the communities they serve.
Learn more about how we partner with customers across the country at skylinenet.net
Kurt Welling, Director of Customer Success