This is based on a flawed premise. How does the CEO of Tesco understand the value of the marketing, quality management, or other talent that they hire? This is thousands of people. Once you go past 10 employees management significantly changes. This is well understood management science.
They understand their direct reports, and probably have enough interactions with up to 150 other people to sort of know how they are doing. That's the scope of who they understand. They don't get to talk to all of their suppliers individually, and while they probably make some PR efforts once a year to work in a store, there is just not time to do this!
What CEOs have to do is delegate. They try to have trusted lieutenants who'll run areas well and have good up and down communication. When people who are more in the know talk about problems in the club, this is what they are getting at. You can think you have the best staff below you, but are people too with their own motivations. Our relationships with Raiola or other agents are driven at these lower levels and at some point a CEO can't be in every discussion. It is however his responsibility to fix things from the top down which is not as easy as you may think. Imagine if the head of scouting is actually a family friend of Sir Bobby. Sir Bobby and the CEO may know that the scout is not doing their job and even talk about it candidly. This does not change the fact that they are still bound by good management (try to rehabilitate the scout), employment law (contract may make it difficult to shift him), and the fact that there is a personal relationship that needs to be managed.
