A little over 2 years ago, I had a decision to make. My IT consulting firm (Alliance Technologies) was going through multiple transitions. I was moving from a COO to a CEO, I was navigating three separate buy-outs and my flagship company Alliance was seeing growth that was outpacing our capacity. I was hiring new people, going through process improvement, and implementing new technology for the team.

I was making a lot of moves and really maturing the organization. But there was one aspect of the business that blindsided me. Looking back, I would have spent way more time and attention on this decision.

My operations team approached me with a new tool that would replace our existing system that was slowly becoming out-dated and very limited. The new software would fix a lot of those limitations and add additional capabilities that I know we would eventually need. It was a step in the right direction and would help make our organization more sophisticated. My team did their due-diligence, the software checked the boxes, the contract looked good, and we were excited to implement.

Fast forward 2 years and we had to go back to the drawing board on the software. It was evident that something was wrong. My team was fighting the tool that was supposed to make our lives easier. Instead… way more complicated. Employees frustrations grew to a boiling point and our clients were also not happy with all the hiccups. We were spending more time fixing our internal tool than supporting our clients.

This is the failure point that doesn’t sit well with me. I fucked up.

I saw this new software as a replacement for our old system, basically like buying a new car. (better, faster, more options) What I failed to realize is that this software exposed some glaring gaps in our process maturity. I bought a sports car and tried to drive it on a gravel road. My failure to understand that this purchase was more than new software meant my team was being setup for failure. They needed me to guide them on the business implications of the software and NOT just the technical feasibility.

I learned a valuable lesson the hard way, and what’s even more insulting is that for the last 16yrs I have been advising clients to avoid the very trap I found myself in! It was a monumental mistake, and I am not out of the woods just yet, but making some stellar progress. The unlock to fixing the problem came only when I realized I wasn’t solving a technical issue; I was solving a business issue. That reframe put the answer into focus.

There are countless lessons I can derive from this mistake. One of the biggest is something that I have known but never experienced first hand. Blindspots.

I am usually the guy that is exposing the blindspots, this time, I experienced one. It is a terrible feeling, and something I never want to go through again. I have changed my environment to ask better and broader questions and to seek advisement, even if it’s a decision that is well within my expertise. I think my failure here was partly derived from the fact that I was too close to the problem. Not an excuse, but an observation that is going to make me a better leader in the future.

Coaching and advising should not be taken for granted. A different perspective could have saved me years of anguish and tens of thousands in consulting fees. If you are at a pivotal decision, a fresh set of eyes could help you avoid my fate. I offer on-demand consulting because I have years of experience helping clients achieve successful outcomes and advising them through my own failures. You can take advantage of that by booking a convenient time with me here:

Until next week,

—Jared

Text Me: 314.806.3912

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