So is it possible to learn good judgment?
The single most important factor in developing good judgment is getting in the habit of thinking in terms of cause and effect. Do you stop and reflect before making decisions and taking actions? Do you project likely outcomes of decisions and actions in advance? Do you look at each decision and action as a set of choices, each with identifiable consequences?
Think of playing chess. The key to success is thinking ahead. Before you make a move, you play out in your head the likely outcomes, often over a long sequence of moves and countermoves: If you do A, the other player would probably respond with B. Then you would do C, and he or she would probably respond with D. Then you would do E, and he or she would probably respond with F. And so on.
This is what strategic planners call a decision/action tree because each decision or action is the beginning of a branch of responses and counter-responses. In fact, each decision or action creates a series of possible responses, and each possible response creates a series of possible counter-responses.
You can start being more strategic by using decision/action trees in your thinking at work. Get in the habit of thinking ahead and playing out the likely sequence of moves and countermoves before you make a move: If you take this decision or action, who is likely to respond, how, when, where, and why? What set of options will this create? What set of options will this foreclose? How will it play out if you take this other decision or action instead?
Maybe the most important thing you can do to jump-start your own development of good judgment is getting in the habit of scrutinizing your own experiences during and after they actually occur. Stop and reflect after making decisions and taking actions. Stop and reflect on outcomes and consequences.