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I didn't know I was the problem until I wasn't anymore. For years, I operated under the idea that being a good leader meant being involved in everything. Every email that went out. Every meeting agenda. Every decision, big or small. I told myself it was about maintaining standards, but really? I just couldn't let go. The breaking point came on a Tuesday afternoon when I found myself in my fourth meeting of the day about font choices for a slide deck. I remember sitting there

I worked with a founder after they lost a multi-year deal. It wasn't a dramatic failure—no botched demo, no pricing mishap, nothing that would make for a cautionary tale at a conference. They lost it because they took too long to answer a superintendent's question. Five days. That's all it took for trust to quietly walk out the door. After four decades in this business, I've watched hundreds of deals succeed and fail. I've seen products win that probably shouldn't have, and b

A superintendent went quiet during one of my presentations. Not the bad kind of quiet. Just different. I was walking through our implementation process, showing timelines and explaining support structures. She stopped asking questions. Started nodding politely. The old me would've kept going. Finish the presentation and call it a win. Instead, I stopped. Reading the Room "What's on your mind?" Long pause. "My teachers are exhausted. I'm worried about adding one more thing, ev

I used to think good leadership meant knowing all the answers. Spent years proving I knew more than everyone around me. Made sure my team understood I was the expert. The result, I lost a lot of good people that way. The Pattern I Created Would give my team direction. Assume they understood. Get frustrated when they don't execute the way I expected. Focus on high-value opportunities. Target the right stakeholders. Prioritize likely deals. Made sense to me. It should've been o

A founder I worked with was drowning in his own business. Doing every sales call. Reviewing every proposal and contract. Answering every customer question himself. Kept saying: "I can't find anyone good enough to hire." Turns out that wasn't the problem. The problem was that every time someone on his team tried something, he took it back. Rewrote their proposals from scratch. Jumped on their calls. Overrode their decisions. His team gave up trying months ago. I told him what

Background: From Classroom Teacher to Ed‑Tech Founder Adam spent years in the classroom, working directly with students and witnessing the daily challenges that come with large class sizes and limited time for meaningful conversation. In 2017, he joined forces with a colleague to launch Bloomsights.com , an online platform designed to capture student voice and provide educators with actionable insights into school climate and student well‑being. The goal was simple: help teac