Realizing what matters way too late

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I have just had a vivid memory of a situation at work years ago.

My boss had asked me to create a new thing and when I showed the finished system to him and walked him through its capabilities, he asked me to demo it to a group of higher up managers.

They had asked for a system to meet certain ends with clients and the system I created achieved all their goals at almost no new cost. It was easy to use and immediately ready...

But it went over like a lead balloon. I have been wondering why ever since. They finally started using it a year later and have been using it ever since...

It has just now dawned on me what my boss did wrong and what I did wrong that morning. I can't believe it. The whole approach was wrong. We should have presented it in the most simplistic way, as if we were showing the thing to very young children.... It's almost physically painful to remember this and realize how stupid I was.

I don't think I will ever be able to read that kind of situation in real time. The best I can hope for is to maybe figure it out long after the dust has settled. I am intelligent in certain ways, but I am also a moron.

I relate to this. I seem to only figure something out way after the fact. I too am reasonably intelligent yet sometimes I have failed so badly to "see the wood for the trees" that it's often years later -- years of ruminating and chewing over a situation like a dog at a bone -- that I suddenly see where something went wrong or I went wrong.

It can happen on a big and small scale -- it can be for big things like your presentation, and even for smaller things like realizing later something you should have said in an encounter earlier. When I spoke to a friend about this, she told me there's a French saying for the principle of this: l'esprit d'escalier -- a conversational remark or rejoinder that only occurs to someone after the opportunity to make it has passed.

It can apply to not just a remark in a conversation but to entire approaches, situations, anything where we can't seem to think of the right way to go about it until much later, after we've agonized and examined and re-examined.

It's so frustrating to operate this way; it's been the bane of my existence in big and small ways.  

Yes, this is why it is actually a good thing for an important decision maker like the POTUS to get away from the office and spend time on the golf course--so he can step back and figure out what really matters.