As a young individual contributor making a transition to managing a direct report of my own, I am finding myself in somewhat of a conundrum.
We are a relatively flat organization which does not have much in the way of processes and control. In my division, both my manager and her manager are what one would call visionaries: leaders rather than managers; people who are better at imagining than implementing; people who inspire rather than break things down into milestones and concrete deliverables.
Unfortunately, this has now led to several instances where I feel my work is often reviewed on the level of "what looks good" rather than "how much sense it makes". For example, a recent risk analysis I submitted to my own boss was sent back to me on the grounds that it's way too detailed and she wants bullet points instead.
Setting aside the obvious fact that she's the boss and I do what she says, I feel that this is impeding my own substantive development. Any set of sufficiently generic bullet points will "look right" - what counts in a risk analysis (or, indeed, in any substantive document) is not only whether it "looks right" (it's important, yes) but also whether the underlying logic behind it makes sense. For example, "damage to the organization's image" is a point that can look right in any risk analysis - but if I got there by reasoning that the image of the organization will be damaged by triggering an invasion of little green men from Mars if we proceed with this project, then the reasoning that had led to that bullet point is flawed and, therefore, so is the conclusion. And yet my boss insists on looking at conclusions alone, rather than at the reasoning that had led to them.
As a result, I end up in a situation where I produce an imperfect level quality of work (owing to my own inexperience) which is never reviewed neither by my boss nor by her boss - because both of them are far too visionary and focused on the big picture to worry about things such as fine detail, logic, and reasoning. In the end, we consistently end up with situations where my work - which is full of errors despite the best of my intentions - end up being accepted, endorsed, and implemented across the organization. And it is only much later that everyone realizes - after me actively pointing it out for six months! - that there are glaring issues in it that need to be addressed: issues that were there from the start, had my visionary bosses bothered to look.
What am I supposed to do? I feel that having a vision is all fine and good; but if you don't know how to break that vision down into concrete milestones, deliverables, objectives, and tasks, you're no better than a raving lunatic on the street corner preaching his message to anyone who'd listen. Without receiving constructive feedback, I cannot improve; but you just cannot give meaningful constructive feedback on a big picture summary - you have to involve yourself in the detail.
On a side note, my own direct report has thanked me repeatedly for providing detailed feedback on his work - he said it made him feel that his contribution is read carefully and assessed on its merits. To me, that's just something that I, as his manager, am obliged to do if I am seriously about recognizing the effort that has gone into his work.