Teaching Chess

I recently convinced my brother to create an account on lichess and I am now attempting to teach him how to play chess better. He knows the basic rules, we played a bunch as kids. The only problem is I have spent the last couple of years trying to get better at chess, and he is still just trying to not hang pieces. As you can see from my account I am not a complete noob, but there is a big difference between playing and teaching the game. I am looking for any advice on a general teaching plan so as to not completely overwhelm him, take the fun out of playing, or leave him with gaps in his knowledge since I have forgotten what it was like to be a complete beginner.
How do I go about teaching him? Where do I start? How do I progress? I figured this could be helpful information later in life when I teach my children how to play as well so quality answers are appreciated.

@AlexandeRufus Well what I will tell you certainly won t be original, but If he is trying his best not to hang pieces than he needs to do some chesstempo or lichess puzzles to learn some cheapos for starters, than you may teach him some very basic and most played openings like Queen s gambit declined/accepted (this is a must, probably most popular opening on lichess, particularly at medium levels) and some way to fight off e4, I am a fan of sicilian opening, used to play Petroff but it s quite boring for my taste and it is very difficult to defend when you play against someone who knows what he s doing.

@gayweather I should have really clarified. I am not asking what he needs to do to improve, I went through that process myself so I can tell him all sorts of things to improve. I don't think that he will be anywhere as obsessed as I have been about chess though, and in fact may not seek to develop himself outside of what we do together. I think that chess for him will be more about the socialization than mastering the game. Since almost all of his improvement will come from our time spent together, and I don't think he's even going to pursue basic mating patterns without me, how do I help him improve? What should be the progression of things I teach him?

The logical path is to start from the endgame, i.e. with fewer men on the board. KQ-K, KR-K, KBB-K, KBN-K, KQ-Kp, KR-Kp, KR-KN, KR-KB, KQp-KQ, KRp-KR etc. There is much beauty in some simple positions. My favorite teaching position is Saavedra's.

>> I think that chess for him will be more about the socialization than mastering the game.

Then I wouldn't worry about teaching him. I'd say enjoy the time together and don't stress over the game he could be playing.

@AlexandeRufus That s a tough one, I guess I would stick to playing limited number of openings or at least similar ones, If you will experiment you probably won t teach him much, this way he should be able to play some openings you like playing on a decent enough level

Hello, Age is important. I think that for kids playings with friends is interesting. As you say socialize and not being discouraged.
Three phases: opening, middle game, end.

Opening I prefer general aspects, i.e. the center, development, castling.

Middle game, you have TACTICS, better understable for kids. work with each one of the aspects, double attacks should be the first, then continue with each one. Encourage to protect pieces!! and take a look at undefended opponent ones. AND STRATEGY, begin with easy aspects of strategy, open files.

Ends. Begin with pawn endgames.

Use a general book as guide, it will help you.
I prefer not to explain opening, but this is a personal bias. explaining opening and the general aspects of the different openings, will help anyway

Hey, Im 2000-2100 with the new formula, was 1900-2000 before summer and im teaching chess to beginners up to about 1800 rating. I started teaching long time ago, but with big pauses. Ive had maybe 10 students(each student avarage learning/training time of 2months, ranging from 2 sessions to 6 months) in last 8 years, but since about this year's June or July i teach to 2 groups of people (group of 3-6 and group of 4-7). I have also spoken with more then few chess coaches that do this every day for years.

What youre asking is very difficult thing to answer you. Youre not asking a quickfix to a certain problem, but rather how to teach him so that hes learning optimally fast, not being overwhelmed and what methods to use. Thats a pedegogy. People study 3 years in highschool to learn that:)

Maybe thats why answers youre looking for arent what people are writing. How can you tell - what is too much, what is too little? And for every person its different.

I can give you following advices in hopes that it will help:
1) Most important job of a teacher or trainer is to find a bridge from your brain to your students brain. When you find that, you can feel when the student understands what you are talking about when not. Then you can tell him in such a way that he understands and learns the quickest.
2) Second most important job is creating a study plan and excercise difficulty level. You need to teach him things that hes missing the most at first. It can be creating opening repertuare (but very shallow one, you dont need to teach him variations to 10th-15th move if hes haning pieces every move and doesnt know that rooks like open files and knights like central squares), or it can be basic strategy, it can be tactical ideas, or maybe hes scared of his opponents and thats what is stopping him to win games, maybe he needs to learn to control his time more and not get into zeitnot every game.
After that you need to give him excercises that he likes. If he thinks that hes an intelligent person, give him a little harder level excercises then his level, to keep him motivated. If he thinks that chess is only played by smart people and doesnt consider himself one, then give him very simple excercises. Mate in 1 move, to evaluate position when someone doesnt have a minor piece, rook or a queen, he has to understand that such positions are winning and when theres only 1 pawn advantage it can easily still be a draw, some fork tactics, some piece development excercises, that knights has to go to center and bishops to e3/d3, c4/f4, b5/g5 - from white perspective.
3) Look what hes confortable with. Maybe he likes playing more, maybe hes a scientist and likes to read a lot and create teories, maybe he is scared of playing and wants to solve puzzles more, but in that case make him play every once in a while as well, or he will never get out of his confort zone if he only solves puzzles all the time and after a while lose motivation to chess, because playing is more fun in the end.

Other then that, just try to have fun with him. Teacher is not only about learning as effective as possible, but also about socializing and having fun with students:)