Over almost three decades in technology, I’ve learned that the knowledge that gets you through one chapter won’t carry you through every chapter that follows. I’ve watched tools, platforms, and entire ways of working change. What has helped me move forward is perseverance, a willingness to learn, and a desire to keep expanding what I understand. Those habits have shaped both my career and the way I lead.
Before technology became my profession, I worked as a carpenter while attending school. You learned from people with experience, practiced your craft, and took responsibility for what you built. Better tools could make the job easier, but you still needed to understand the materials and recognize when something wasn’t right. That respect for craftsmanship has stayed with me throughout my career.
I brought it into web development during the dot-com and Y2K years, then into infrastructure, software, product, security, and leadership. Every expansion of responsibility gave me more to learn. Understanding the technology was part of the work; understanding the business, the customer, and the people doing the work required just as much attention. I had to keep broadening my perspective as the decisions became bigger.
Learning became part of how I lead
As my responsibilities grew, I became accountable for decisions that reached beyond my own work. A product decision could affect customers, an infrastructure decision could affect operations, and a shortcut could create a problem another team would inherit. Leading across those areas taught me to ask better questions and listen to people whose expertise differed from mine. It also reinforced how much there was still to learn.
Working directly with customers helped me understand what people actually needed from a product. Working with developers helped turn those needs into something practical. Working through security requirements and audits reinforced the importance of being able to demonstrate that our processes worked. Each experience added context that I could bring into the next challenge.
I’ve also learned that people need clarity when they’re being asked to change. They need to understand why a different approach matters and have an opportunity to contribute what they know. My responsibility is to help establish that direction, coach people through the unfamiliar parts, and keep working with them when progress takes longer than we hoped. Perseverance becomes a shared effort when a team understands what it is working toward.
There have been plenty of opportunities to get comfortable with what I already knew. But I enjoy discovering something that changes how I think or helps me solve a problem more effectively. I want to understand the next tool, hear a different perspective, and learn from the people around me. That curiosity has helped me navigate change and given me more to offer the teams I lead.
Faster answers still require informed judgment
Today’s technology gives us extraordinary opportunities to accomplish more. Work that once required considerable manual effort can happen with a few instructions. I welcome that progress, and I want to help people put it to good use. My experience also makes me ask what we need to understand before we rely on the result.
That question connects much of what I’ve written about: fixing root causes, improving processes before automating them, building sustainable products, and sharing knowledge across a team. A completed task tells us something happened. We still need to determine whether it solved the right problem and whether the result will hold up for the people depending on it. Leadership requires staying interested in those answers.
AI makes this especially relevant. A confident explanation can be persuasive, even when it is wrong. If we repeat it without understanding or checking it, we can build our own false confidence around the system’s mistake. Our ability to recognize missing context and questionable assumptions matters as much as our ability to get an answer quickly.
Better data, clearer instructions, and relevant business knowledge can improve the results, but they don’t guarantee correctness. We need to keep educating ourselves so we can evaluate what the technology tells us. Otherwise, our ability to produce work can grow faster than our ability to judge it. That is a gap leaders need to pay attention to.
Experience gives us something to build on
As we give AI agents more responsibility to carry out work, I see an opportunity to apply lessons earned through years of leading technology teams. Define the outcome, make responsibilities clear, check the results, and learn when something goes wrong. We still need people who understand the customer, the process, and the consequences of a decision. Those fundamentals give us a way to move forward thoughtfully.
I want the time we gain through automation to create room for better conversations, stronger mentoring, deeper investigation, and continued learning. I want experienced people sharing their judgment and newer colleagues bringing questions that challenge our assumptions. That exchange helps a team grow and gives us better knowledge to build into our systems.
Looking back, perseverance has meant continuing through difficult work while staying open to a better way of doing it. My leadership experience has given me perspective, and my willingness to learn has helped me keep that perspective useful. I’m grateful for the people who have taught me along the way, and I expect to keep learning from others throughout whatever comes next.
After almost three decades, I still want to know more than I did yesterday. That desire has helped me move through each chapter of technology change, and it remains central to how I lead.
As technology expands what we can accomplish, are we putting the same effort into expanding what we understand?
Thanks,
Michael Cronin
Website: https://www.michaelcronin.info
LinkedIn: https://www.linkedin.com/in/michaeltcronin/details/experience/
