Technical people looking up from the bottom often expect some type of meritocracy where being good at your job earns you promotions and responsibility, but that isn't really how leadership works. When you are trusted, you get promotions. For exactly the reasons stated above - leaders delegate to people they have worked with before and trust that the needs will be met.
So as a leader, decide who you trust. As someone lower down the chain, work to build that trust.
If you're a CTO, do you trust your person A or B? If you're not technical what do you base it on? What are you judging?
Are you judging based on their personality? The number of brownbag talks? The feedback from peers?
What you want is for someone to know how things work. And if they don't know, know what to ask. You want someone who's done it before. They have to be technical.
You want your chief of plumbing to know how to plumb. You don't want them to just be familiar with plumbing. If so, the next thing you know a good salesperson will talk them into replacing all the pipes with new wonder-pipes with space-age wonder-clamps.