Zen emphasizes rigorous self-restraint, meditation-practice, insight into the nature of mind (見性, Ch. jiànxìng, Jp. kensho, "perceiving the true nature") and nature of things (without arrogance or egotism), and the personal expression of this insight in daily life, especially for the benefit of others. (Wikipedia)
First of all, I'm not a student of Zen and I know very little about it.
I got in contact with the term (and the concept) while reading Zen in the Art of Writing, by Ray Bradbury, a revered and prolific writer. I also read the book that originated Bradbury's: Zen in the Art of Archery, by Eugen Herrigel, a German philosophy professor that lived in Japan in the 1920s.
I can't deny his book is a very interesting read, with a lot of good concepts about the death of the ego and the forgetfulness of the self, of being able to do things for the process instead of aiming for the target. It has a good amount of things that made me think a lot about life, work, and, well, this blog. I even got a nice motto that follows Herrigel's Zen style:
Writing for the writer, not the reader.
The book also talks briefly about death with a simple passage (that I paraphrase): the soldier that does not fear death needs no training, as the sole reason for training is leaving the fear of the outcome aside. When the soldier embraces the truth that death will come one way or another, he pays attention to his craft instead of to the result of it.
The whole concept in Bradbury's book, derived from Herrigel's, is based on the idea you should care more about doing the work than what the work will become. It's more important to write than to get something finished, because writing will, eventually, result in something usable. Like Herrigel's arrow will meet the target one way or another if he understands that shooting the arrow is more about shooting the arrow than hitting the target (and if he tries constantly to do it).
A way to philosophize this is: you should care about the journey and the result will come.
PS: I don't say "don't care about the result" because that's useless advice. We all care about the result, but as an anxious person, I know I think about the result even before typing the first letter. It's good to plan, but not good to stress that way on something that you haven't even touched yet. Patience, young grasshopper.
In Star Trek, there's a training exercise called "Kobayashi Maru".
The notional goal of the exercise is to rescue the civilian spaceship Kobayashi Maru, which is damaged and stranded in dangerous territory. The cadet being evaluated must decide whether to attempt to rescue the Kobayashi Maru — endangering their ship and crew — or leave the Kobayashi Maru to certain destruction. (Wikipedia)
If the cadet chooses not to rescue the ship, all the crew of the Kobayashi Maru dies. On the other hand, if they choose to perform the high-risk rescue, an enemy force attacks their vessel, resulting in the loss of the whole crew.
This test tries to teach about no-win situations, those in which any choice would or will lead to unfortunate results. It does not matter: death and destruction will happen independently of the cadet's choice.
What's not said in most places that analyze the Kobayashi Maru is the power to teach something more valuable than "some situations can have no good result". In my opinion, it's much more about living with the consequences of your decision, as it's impossible to know what the other decisions would result in.
So, I've introduced two nerdy concepts, one from (allegedly) real-life and the other from fiction. What do they have in common?
Comparison aside, a leader has to Kobayashi Maru on a daily basis. Their job is to make decisions without knowing the exact outcome. Hiring, firing, choosing one thing over another, talking about the problems, or waiting for a better moment.
All of these decisions are impossible to be rewinded and done again. There's no test interface or known results. It's life, plain and simple.
The Zen interacts with the Kobayashi Maru concept when the leader understands their job is not just about making decisions, but living with them. It's not about hitting the target, but releasing the arrow.
When acting, the leader has to understand there are no-win scenarios and they should be prepared for that, using all the available skills and tools to avoid the worse result. Usually, a good leader already has the skill and the tools for dealing with unforeseen consequences, so they learn to deal with consequences and live with the result of their decisions, turning bad results into good ones.
Sometimes there are no-win scenarios. What can you do to turn a no-win scenario into a, at least, acceptable-draw scenario? An it-could-be-worse scenario? Also, how are you training and preparing yourself, as a leader, for the outcome of your actions?
The Kobayashi Maru concept talks with the Zen concept when they both are about dealing with whatever consequences life handles you, independently whether they are good or bad.
When you lead without the fear of making mistakes, embracing the reality that you will make them and will handle the consequences, you then need no more training.