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Issue 013 November 3, 2026
If you lead anything that matters, someone is quietly asking what happens if you're gone. For executives it's the board, and the term they use is key person risk. For everyone else it's your boss, in a succession conversation you aren't invited to. Either way, the answer is probably not the compliment you think it is.
For a long time I took being needed as the highest praise there was. Every decision that routed through me felt like proof that I mattered, and every late call where someone said "we couldn't move without you" landed like a thank you. I'd built work that ran beautifully, and it ran beautifully because I was in the middle of it.
Twenty years ago I worked for a boss who saw it differently. She had a master's degree in psychology, and she spent a lot of time teaching me how people think and what actually motivates them, which was not something they covered in engineering school. As the shuttle program's end came into view, she brought me behind the curtain on something most people at my level never saw. She stood at a whiteboard and mapped the entire operation, every role and every critical skill, then worked through who held each one, who could step in, and what would happen if no one could. What stayed with me wasn't any single name on that board. It was how deliberate she was about all of it, and how rarely I'd seen anyone treat people with that kind of rigor.
What she understood, and what I didn't yet, is that being needed is one of the strongest motivators there is. People don't hoard knowledge because they're selfish. They hold onto it because it feels like proof they belong, and the best people feel that the most.
The same instinct that makes someone your most dedicated performer may make them your biggest risk.
I was on that whiteboard. I'd been marked as critical skills, and I took it as the best performance review I'd ever gotten, proof that I was doing a great job and that the program needed me. It took me longer than I'd like to admit to realize that the pattern she was teaching me to see in other people was sitting in my own chair.
The same behavior gets read two different ways depending on who's looking. Your boss sees responsiveness and ownership. Someone thinking about next year sees a single point of failure with a good attitude. Both of them are right, and only one of them is planning for what happens when you're not there.
From that second seat, indispensability isn't loyalty or excellence. It's a constraint, the slowest point in the system and the place where everything waits. If every important decision waits for you, your team moves exactly as fast as your calendar allows. You'd never accept that from a machine on a production line, and most of us accept it from ourselves because it feels like dedication.
I ask every leader who reports to me the question she taught me to ask. If you were gone for thirty days, what would actually stop? Not what would get harder, because everything gets harder, but what would stop. Most leaders find two or three things they expected and one they didn't, and the one they didn't expect is usually the one that matters most.
If you were gone for thirty days, what would actually stop?
So run the test on yourself before someone runs it for you. Write down everything that would stall if you disappeared for a month, then write the name of the person who would pick each one up. Leave the blanks blank. Every one of them is a person you haven't developed yet, and that's your real job for the next quarter, more than anything on your calendar this week.
The question is easier to answer on paper than in your head, so I built the Key Person Risk Self-Audit to walk you through it. You'll map what stops without you, find the skills only you hold, and pick the first blank to fill in the next ninety days. It's free, and you can download it below.
See you every other Tuesday.
~ Alicia
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