Assessing the Technology Landscape Good strategy requires honesty. Before deciding where to go, leaders need a clear picture of where they are. Every organization carries a mix of strengths and weaknesses in its technology environment. Some systems work well. Others exist mainly because replacing them feels inconvenient. At several points in our growth at eGroup, we stepped back and asked a difficult question. If we were building this organization from scratch today, would we

Understanding the Business Context One of the most common mistakes executives make with technology strategy is starting with the technology. The starting point should always be the business. Early in my career I saw how easy it was to fall into the opposite pattern. A team would discover a promising new technology and begin imagining how it might be used. The discussion quickly became technical instead of strategic. The better question is always this. What problem are we solv

Why Technical Strategy Matters Introduction to the Series This post is the first in a six-part series on mastering technical strategy as an executive. Over the years, leading and scaling a technology services organization, I have seen how technical strategy can either accelerate a business or quietly slow it down. Many organizations invest heavily in technology but struggle to translate those investments into meaningful outcomes. The difference usually comes down to clarity,

Building and scaling technology teams is one of the most rewarding challenges in business. It is also one of the most demanding. Growth creates energy. It also creates pressure. Expectations increase, priorities multiply, and the pace of decision-making accelerates. If leadership is not intentional, that growth can create confusion just as easily as it creates opportunity. Over the years, as we built and scaled our technology services organization, I have learned that leading

We were recently named to the 2026 CRN MSP 500 list. I am proud of that recognition, and our team should be. But awards are the byproduct. They are not the objective. The real work happens long before anyone publishes a list. The managed services market is evolving quickly. Clients expect more than uptime. They expect predictability, security that is embedded from the start, and strategic guidance that helps them move forward with confidence. They want a partner who thinks ah

Ideas matter. They spark possibility and set direction. But what transforms possibility into progress is the steady, deliberate work that follows. Over time, I’ve come to believe that the most innovative organizations are not defined by moments of brilliance, but by their commitment to doing the right things, the right way, over and over again.   As I’ve built and scaled a technology services business, I’ve learned that a lack of resources is no excuse for a lack of resourcef

Are you prepared? Are you sure? In the early minutes of Saturday morning, April 2011, a water main broke underneath the street in...

The big gain in adopting cloud-based services is certainly financial, but not always “directly” - I have a suspicion that as soon as I...

Love that headline quote from Stephen Denny - author of "Killing Giants" - it's simple and sensible - and certainly representative of...