Based on what you're describing, it sounds very similar to issues I have had with my children. In particular, I have had this issue with my 3yo who is the middle child out of 5. The crying and lack of communication sometimes persists, but we have systematically improved the situation.
I think the key thing is for you to introduce structure. It sounds like you're giving your child too much freedom and responsibility to take care of things on his own, when he is perhaps not ready. This is challenging to recognize, particularly for parents with more than one child, where the older one(s) might be more independent than the younger one(s). It is sometimes hard to mentally separate what each child is capable of doing on their own.
While @nGinius has some good points about quizzing and demonstrating with examples, from my experience, this type of behavior modification strategy on its own is generally of little value (with all due respect). It sounds nice, and it is good to introduce ideas, but in my experience taking the approach of quizzing and demonstrating independence does not generally modify a child (or an adults) actions.
Behavior modification only happens through consistent long-term one-on-one coaching. You have to spend more time with your child, do more hand holding, and give them more structure. Maintain consistency so they know what, where, when, and how to do a given task. Consistency helps them know when they are supposed to mentally shift from one task to the next.
What worked for us is to have more structure and predictability in our house:
- Try to follow a structured schedule and post your schedule so that your child can see it
- Give your child notice of events in your schedule. For example, "Son, in five minutes we're going to get our shoes on".
- Lead your child where they should be. If they're supposed to be tying their shoes, lead them to find there shoes in the location they should always be.
- Work closely with them to accomplish the activity they are supposed to be doing. If they're supposed to be tying their shoes, sit down and help them get them on. Work with them for weeks, months, or sometimes years until they can do a given task independently.
- Give them a high five and compliment them for accomplishing each task so well.
Above all value consistency over independence. Sure, your child may know how to tie their shoe on their own, so its easy to say, "Go get your shoes on, you know how to do it on your own". But, they may not have internalized the idea that it is their responsibility or that its time to do it (even though you told them its time). Lead them and sit down with them and coach them through it, even if you know that they know how to do it on their own. Make sure they are doing what they should be doing the way that they should be doing it. Make sure you're supporting them. Independence will come with time, but don't rush it.