An Open Door That is Never Knocked
At your current or previous workplace, there probably is some senior leader who said that they have “Open Door” policy; anyone in the company can come to their (zoom) office to discuss any problem. Laudable, but what followed, I assume, is a tepid response: an initial surge of requests to meet and rapid fallback to the status quo.
So, why does this happen?
First, it would feel to the person, going to senior leadership, that their direct line of management would be surprised—in the worst case, offended—that they failed to answer the questions of their reports. And, if the feedback raised—is a surprise to the direct line of management—puts everyone in uncomfortable position and the power dynamic between the person and their manager, makes it more complicated.
Second, the person doesn’t know what level of context or problems a senior leader is well positioned to help with: “Should I talk about my daily struggles with source code management, friction working with a different org, or why the company is doing X vs Y?” In most cases, the most valuable feedback is provided by the leaders you directly work with because they have the most context (as they ideally should). So you preemptively decide it’s not worth talking to the senior leader.
How to counter this?
If you are on the direct line of management, explicitly stress and repeat multiple times that it is not only okay, but highly encouraged for their reports to approach the leaders during such sessions. If your ultimate goal is to let your reports grow, their ability to escalate and talk to senior leaders is an essential skill. So it is best for both of you that they are willing to take the first step.
The senior leaders, who initiate these programs, should explicitly clarify what kind of topics their advice will be most helpful. At the same time, not preemptively restricting the conversations to a narrow set of topics, which would exclude the majority of their intended audience. In fact, in my experience, folks who just joined the company, often tend to have insightful and fundamental questions—since they are not beholden to the current constructs of the how company operates.
PS: I came across Ed Catmull’s recounting of similar experience in his book — Creativity Inc: