One thing I've been striving to do - often unsuccessfully - is remove moral judgments from my observation of situations.
Most people don't distinguish between observing and judging.
They say, "It's bad that it's raining outside." Well. Maybe, yeah. But there's two things going on there - first, it's raining. That's either true or false. Then there's that "bad" - which is an opinion, a moral judgment on the situation.
I think most people aren't aware of when they're making moral judgments and when they're making observations. That's not good for being able to think clearly.
Analysis and observation needs to be separated from moral evaluation to do it straightforwardly, or else you get blind to effects you don't expect and don't want to see.
Thus, I'd recommend you strip your observations down to cause and effect. "X seems to have happened, what caused it? Perhaps Y, perhaps Z... let's observe some more."
That's observing and then moving into analysis.
You can judge after that - that's fine, I judge things all the time - but for clear analysis, you've got to be able to separate the observing from the judging. And yet, it's hard. Look at the this sentence here - "that's fine, I judge all the time... for clear analysis, you've got to separate observing from judging." That sentence fails its own recommendation.
It's complicated. It's maybe impossible to completely remove judgment from observation. But I'd recommend you try, because you're more likely to figure out what's actually happening to do that. To do that, look for what effects are actually happening, and then try to figure out the causes. Refrain from judging whether the causes/effects are good or bad until you've figured out what causes produce what effects.
In the book "Warrior Mind" the author mentions one of the 6 pillar energies - curiosity. It is very similar to what you call observation. He suggests this quality to be developed by mindfulness and recommends the works of Jon Kabat-Zinn but there are others who can help in developing mindfulness.
What a strong negative connotation! Judging. Judging things, judging people, being judgmental... these are not pleasant things that polite and civilized people do... right?
But if judging is such a fault, perhaps we should learn what exactly it is. Hmm... I don't know exactly. Maybe Merriam-Webster can enlighten us:
Judge. Transititive verb. "to form an opinion about through careful weighing of evidence and testing of premises"
Hmm. That's... not what we expected, now is it? Judging is bad. But forming an opinion through careful weighing of evidence and testing premises... that doesn't sound so bad. Hmm.
What does that sound like to me?
You've probably heard that if you want to find out what you are most insecure and ashamed of, listen to how you judge people.
If you tend to say, "His shirt looks so tight on him!!" then you're probably most insecure of your body.
Thing is, I've always considered this statement one of those...
"Hmmm makes sense but nah"
At least not for me.