Advice on Evaluating Positions and Doing Something About It?

How do I improve my ability to:

1. Evaluate a chess position like the engine/stronger players

2. Make a plan that will do something about it and take advantage of the weaknesses?

I have a coach, so I can suggest things to work on if I have ideas.

I'd love to study this idea in my off time too, since I believe I need a lot of time to digest material like this.

Ideas?

Why don't you ask him? That's why you have him, no?

There is a famous book about your question. 

Iossif Dorfman "The-Method-in-Chess"

The only problem, it's not for beginners.

I remember giving you free lesson once and contact me back if you need more help. But never heard back from you lol. But yeah 50kg is 100% correct.

If coach asks you to evaluate position like stronger player he isn't a coach just some random player. There is this video course "Evaluation of Positional mastery by FM Zaur Tekeyev. 

But most of the time problem lies in not calculating tactics on empty square or irrational candidate moves. You can pick up Muller's Chess Cafe Puzzle Book 1,2,3. They are very good and you will learn a lot you don't know yet. Its hard don't expect to cakewalk through them as they are long consequential tactics that changes motif single puzzle that requires calculation up to move 4-6. Sometimes up to move 8 or 9 but its rare. 

Plans: For plans to work you need motifs.

Question to ask is:

Are you playing Queenside, Kingside or Center? 

Is there any tactical motif I can exploit? Such as Backrank issues, Interrupt piece co-ordination for opponent, deflect the piece that you are playing on to some random place by exploiting tactical motif such as pin, forks, etc. 

Here is an example FYI. This below is homework I got from FM for my lesson. This exercise in particular is very advanced. 

@1

"1. Evaluate a chess position like the engine/stronger players"
++ In order of descending priority: king safety, material, endgame prospects

"2. Make a plan that will do something about it and take advantage of the weaknesses?"
++ Occupy weak squares, preferably with a knight outpost or a king invasion. Assail weak pawns so as to win it and win the endgame.

Watch Naroditsky’s speedrun videos.  He explains his thought processes very well.