A highly technical leader is an asset. Depending on one is a liability.
If you are a CTO, this may sound familiar. A critical technical leader takes a vacation, and only then do you realize how much of the day-to-day operation depends on that person. You assumed there was coverage, but you had no visibility into whether anyone else could make the same calls. If production breaks while that person is holding a drink on a beach, does the team know who decides?
The skills issue in tech is bigger than AI or whether people can do the work. Often, the capability is already inside the business, but people have not been given the opportunity to practice it. A company can have technical leads who are excellent at delivery and still fail to develop the next group of senior engineers. The leader is still an asset, but the dependency the business created around them is a liability.
A durable technical team needs people who can solve the hard problem and people who can help someone else develop the judgment to solve it next time. Some leaders can do both, while others are not natural coaches. Either way, transferring knowledge and judgment eventually has to become an explicit part of technical leadership.
Microsoft's research on software engineering managers found that sufficient technical knowledge was necessary, while people-management skills were critical. Great managers guided engineers to make decisions. That distinction matters because a handover cannot be reduced to a document written before someone goes on leave. Future leaders need to make real decisions while an experienced person is still available to guide them. I have seen firsthand how quickly confidence drops when that practice never happened.
If you sit on the board, you are responsible for requiring and overseeing that transition. Management must create the conditions for it. Require tested cover for every critical technical responsibility, then name the accountable executive and the alternate. Give the alternate real decisions and check whether the operation can continue without calling the usual escalation person.
Short-term delivery may slow down while the next group of leaders gains experience. That is the honest tradeoff. The goal is to keep delivering this week while building an operation that can still work a decade from now.
Is your compony dependent on one person or you don't have that visibility as an executive?
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