I first met him years ago, in a windowless room, back when we were both grinding through tech support tickets. I’ve watched him climb, and I’ve cheered for him as he stepped into his first real leadership role. But when he sat across from me yesterday, he looked like a man who had lost his map.
His team wasn't just struggling. It was stalled. He was fighting to keep his head above water, not because he lacked the drive to lead, but because he was trying to protect his team from the discomfort of expectations. “I don’t want to be the bad guy,” he told me. It was a well-intentioned trap. He wasn't failing. He was just stuck in a cycle of triage, mistaking silence for harmony and clarity for cruelty.
We began to pull at the threads of his daily struggle. We looked at the team member who never prepared for 1:1s, the quiet ones who sat motionless during strategy sessions, and the deadlines that seemed to evaporate into thin air. I asked him, “Do they truly know the difference between what you’ve requested and what is actually required?”
He paused, a look of realization dawning on him. They didn't.
He hadn't been empowering them. He had been withholding the one thing they needed to succeed: the clear, sometimes uncomfortable truth of what success actually looks like. He was stuck in the weeds, trying to compensate for their lack of direction by doing the heavy lifting himself. He wanted to be a leader, but he was acting like a safety net.
I leaned in. “Next meeting, don’t leave the floor open to whoever feels like speaking. Assign each person a specific piece of the update. Force the structure so they have the room to be prepared.”
He hesitated. “Won’t that feel forced?”
“Clarity is kindness,” I replied. “You don’t get to the 30,000-foot view by carrying your team. You get there by trusting them to stand on their own two feet.”
He left that afternoon not with a heavier workload, but with a new perspective: accountability isn’t the enemy of a positive culture. It is the framework that allows it to exist.
To my fellow leaders: if you find yourself dreading the hard calls, ask yourself if you’ve actually given your people the best shot to shine, or if you’ve just been letting them wander in the dark. Accountability isn't your burden to carry. It is your ladder out of the weeds.
And if you’re nodding along, wondering how to lead with that kind of precision and empathy, well, that is exactly what I’m here for. 👍🏼
One last thing.
Good leadership writing does not spread the way other content does. It moves through trust. Someone reads it, recognizes it, and quietly passes it to the person they think needs it most.
If that person came to mind for you today, this is your moment.
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Some background on this post for those who don't know me:
Early in my educational leadership path, I was a Coordinator of Instructional Tech. My office was a converted closet. No windows and a door that felt like a coffin lid.
My friend was the IT tech, so our work collided daily. Tickets unsolved meant I couldn't do my job so we often tackled them together so that I could establish trust with teachers and get them to adopt new tools and teaching methods.
He went on to become an IT leader at an international construction firm, and I went on to lead systems and initiatives well beyond edtech. 😊