Insights on Building Mission-Driven Organizations

Practical lessons from 15+ years of leadership across nonprofits, real estate, and healthtech. Topics include AI implementation, nonprofit operations, business systems, and what it takes to scale organizations without losing your mission.

Listening to Your Emails and Messages Makes You a Better Communicator

Listening to Your Emails and Messages Makes You a Better Communicator

For most of my career, I’ve moved fast. I’ve relied on instinct, momentum, and the ability to figure things out on the fly. In small teams or early-stage environments, that approach works. You don’t have to explain every step or provide perfect clarity—you just build, adjust, and keep going. But as the organizations around me grew, the cost of unclear communication started to show up in ways I couldn’t ignore. I’d send a message that made perfect sense in my head, only to realize later it didn’t land the way I intended. Or I’d fire something off quickly and it would accidentally create more work or confusion for someone else. That’s when I started using a small Mac feature that unexpectedly became one of the most effective productivity habits I’ve ever built: Speak Selection.

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Technology & Digital Strategy Kenny Kane Technology & Digital Strategy Kenny Kane

Why I Stopped Chasing Inbox Zero (and What I Do Instead)

For a long time, I thought Inbox Zero was the goal.

If my inbox was empty, I felt clear. In control. Productive. Like I had actually finished something.

But eventually I noticed the pattern. The cleaner my inbox got, the busier my days felt. More replying. More sorting. More “just one more thing.” I wasn’t doing better work. I was just better at moving emails around.

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