I am glad you used the term "lawyering". I have been on both sides of this situation.

As the child, I distinctly recall the fun in "outsmarting" my parents. I considered them as incapable of expressing themselves well. The more they argued for me to "get the point", the more I thought they didn't "get the point". They never did succeed in their goal and since my goal was to prove they would fail, I thought for a long time that I had succeeded in my goal.

Today, the more detailed a contract, the more fun I have in finding out where it fails... where the loophole exists. Think you can cover every possible scenario? I love it when you try.

As someone who develops software solutions for merchants, I frequently advise the CSR's that those asking for specific features never know what they actually want... they know what they intend. Find out what problem they are trying to solve and solve that -- they won't care which "feature" solves it, just that it is solved.

With my own child, I do not give specific instructions (except in emergencies), I state the intention. For example, "Your room needs to be clean", "The kitchen needs to be clean", "Select something to do over the summer related to animals and which requires you getting out of the house" (yes, this one has 2 intentions being met [animals is because she wants to be a vet]).

Occasionally I have made a mistake and given a specific instruction. Being her father's daughter, she promptly "lawyered up". My response was direct, "You really want to play that game with me? I enjoy it. Do you think you will?"

It's only fun if it succeeds. However, I suggest that speaking in highly-specific terms to someone of a nature similar to mine will never succeed no matter the threats... it's an internal joy you can't take away by continuing, so perhaps the underlying point they are making without knowing it is of benefit: "tell me what you intend without trying to tell me the steps."

There's a side effect of this, too. "How to Win Friends And Influence People" has a whole chapter on "Give A Dog A Good Name" which concludes with the point "Give the other person a fine reputation to live up to"... namely, by stating your intention and allowing that to be fulfilled in whatever manner they think it should, they are very likely to do more than had you asked something specific in the first place. Where they fall short, giving them "an out" by asking, "Nice job. Did you forget _ _ _ _? It will be perfect when that is done, too" takes away any fight and gets the job done.

Finally, the lesson of speaking via intention instead of by specifics is something which has served me well in life. I may not know how what I want is achieved, but I do care that it is achieved.

One thing you can do is avoid providing opportunities for lawyering by keeping your own wording simple. Use short, concise statements.

Avoid asking open-ended questions like "Why did you do X?"

Explain what he is required to do briefly, and the consequences of failure.

Instead of saying "Please take all the books you were reading that are now strewn around your room to the bookshelf" simply say "Put away your books" or better yet, "Clean your room."

Instead of saying "Why did you hit your sister when throwing that thing? Didn't I tell you to NOT throw it when she's standing in front of you and tell her to move away so you won't hit her?" you say "I told you not to hit your sister, but you did it anyway. Now you must [insert consequences here]."

Don't engage in arguments or debates. If you're sure he knew what you really meant, call him on it. "You knew what I wanted you to do and you didn't do it. I'm disappointed." Then walk away. Disengage. End the conversation on your terms, not his.

It's also important to explain the consequences for failing to follow instructions, and follow through with those consequences consistently. This is one of the hardest parts of parenting.

When I was in college and I wanted a professor to regrade my test, they would regrade the whole thing, not just the one thing I was concerned about. It rarely paid off for me to do so.

I've adapted that tactic with my children who look for and attempt to exploit loopholes.

"Please take all the books you were reading that are now strewn around your room to the bookshelf?"
"OK".
15 mins later, find a bunch of books still in the room.
"Why didn't you complete the task?"
"They aren't books I was reading, they are activity books"
"Do you need me to make a more difficult, specific rule for you to follow, or do you want to try completing the original task to my standard?"

Generally they will choose to finish the task. Sometimes they turn it into a game and see how many loopholes they can find, but inevitably I will continue to give them definitions and rules that actually make their job much harder than it would have been otherwise. I have to be careful to avoid contradictions, but I treat it as a game once in awhile, and when it's not appropriate I tell them, "I'm not in a position to help you understand the instructions better. I believe you understand my standards and instructions, though, and if you choose not to do the work correctly you will lose a privilege or have more work to do later."

I would have a discussion about "spirit of the law" vs "letter of the law" as well as figures of speech. I would then follow it up with a discussion about the golden rule. Does he want someone to do this to him every time he says something using a figure of speech?

When you're dealing with matters of discipline or anything else are you a stickler for the letter of the law yourself?

If you make a promise to your child do you fall back on the letter or the spirit if they accuse you of not meeting it? eg: "But you said we could go to McDonalds!" "I said we could go to McDonalds if you did your homework, we did, we walked in and out again, then we went to to VegRUs and actually got something to eat."

Children can be frustratingly good at copying bad habits their parents don't notice in themselves.

Since the child is 8 and reasonable bright have you tried reasoning with them as you would an adult rather than getting frustrated in an amusing manner?

Also you can simply not accept unreasonable appeals to the letter rather than the spirit. Focus on what they "knew were supposed to do" rather than what they were told to do. If it works without consequence then they'll do it more.

In this situation I merely tell them, "You knew what I meant. You may not make up excuses for not obeying and you are always responsible for obeying correctly." Their consequence is typically a menial task to perform.

Your child is willfully disobeying and drawing you into an energy draining exchange each time. Treat this as you would any other misbehavior.

In our house, we used the 1-2-3 behavior modification method. Any time our kids did something they were not supposed to do, we would name the behavior and say, "That's 1." If the behavior repeated, they would get a "That's 2" and on 3 they got a time out. They knew this, and most of the time, all it took was "That's 1" to get them to shift behavior. So in your case, I would have said, "You know what I meant. That's 1." If he argued, I would simply say, "That's 2." And so on.

I don't know what your preferred method is for behavior modification, but you need to connect a consequence to this behavior and stop talking to him about it, because he KNOWS he's pushing buttons and he's enjoying it. Maybe it's "You know what I meant. Bedtime at 8 tonight." If he argues, "Bedtime at 7:45."

Back in the old days most parents would have smacked their kids for being a wise ass and moved on. All these people talking about how your kid is brilliant and is trying to make you a better parent with his responses is just ridiculous. Your child is 8, he may be precocious, but he's being a smart ass. You need to put your parent pants on and teach him to follow both the letter of your instruction and the spirit of your instruction. Being a smart ass gets you no where except on the internet or in politics.

Very simple. Only ask once. Once only. If they lie, tell them they lied and then take something they like away for a week.

You're negotiating, when you should be giving direction. You'll find you like your child much better as they start acting less stubborn.

Didn't think I would ever post on P.SE, but will give it a go none the less, I will keep it relatively self centered as I will be honest that my experience with parenting and children isn't that great.

My History & Why I Stopped Doing It

I did exactly this as a child and I think I drove my parents and teachers quite crazy with it. Now, at some point - still as a child - somebody (likely my little brother) tried to use this against me and as I hated losing arguments I came up with an argument which in one big swoop invalidated years of arguing:

Language is a ridiculously complex system and literal interpretations are actually incorrect. Not only against the spirit of the original statement (which I did not care about), but actually incorrect, dumb (the one that hit me) and short-sighted.

or when I got slightly older (around 10 I believe) and started programming more actively it changed into the following form:

Humans are not computers and [fill in some language] is not a programming language.

and just to put it into a more modern form as a third alternative

Language is created to facilitate communication. Miscomprehension and/or miscommunication is a failure of one or both parties. If the communicated instructions are of a commonly accepted form, then it necessarily means the fault lies at least partially on the receiving end (and likely entirely except in the very specific case if there is an alternative commonly accepted interpretation of the same instructions).

What I was essentially arguing was not about some weird "spirit" of a rule, law, statement or question, but the fact that language by it's very nature is a complex system rather than a rule based interpreter. So if I take an example like

"Please take all the books you were reading that are now strewn around your room to the bookshelf?"

The way that would have worked with me is pointing out that language works in a way where an example or over specific case can be used to give instructions where the person giving the instruction may have made likely, albeit incorrect assumptions and not understanding so is dumb and stupid. Now, it might sound really harsh to call it dumb and the way this is communicated is up to debate, but the thing is, at least talking for myself, I considered myself smart for years due to my literal interpretations. In other words, the only way to stop behaviour like this in individuals like me is to address this core issue: Interpreting language literally is easy: everybody is able to do that. Interpreting language in it's full scope: that's what's hard. Present it as such that a failure of him to comprehend this is something that shows a lack of intelligence, not an abundance of it.

So, is it Actually Beneficial?

Up till this day I rarely lose an argument, so I would definitely not argue that the mindset allowing literal interpretation and being open for confrontation is not beneficial in some regards. However arguments won going down the literal route tend to be arguments won at the cost of social standing and respect, so do in every possible way dissuade him from this behaviour. Lawyers indeed do use these kind of interpretations, but in every other place in life you need actual debating skill rather than this 'fake' debating.

So my final advice: Act as if he needs help understanding it better anytime he pulls this act ("Oh dear, was my instruction too hard to understand? I am sorry, wait, let me explain it to you better now...") and maybe grant him some victories when he starts to actually debate and for example is able to point out inconsistencies in your parenting (he sounds like the type who might be capable of that).

Put less effort into clarifying your expectations and more into clarifying the consequences of not living up to your expectations. So far it seems that you are providing your son with positive rather than negative reinforcement for his lawyerly behavior.

Have age-appropriate expectations. At age 8, a kid doesn't need to be forced to drink his juice; he is old enough to pour his own drink, and to understand that he shouldn't pour himself something that he doesn't intend to drink, because that's wasteful. At age 8, a kid who throws something that hits his sister is old enough to understand, without being told, that in such a situation, (1) regardless of whether it was really your fault, you apologize immediately, because that's the way nice people behave when they hurt someone else; (2) you need to figure out how to keep it from happening again in the future.

I think that everyone's answers are all reasonable (though very different), but I lean more towards the "it depends on the child" and "it depends on whether he is really causing problems." I also suspect that the best thing to do is wait it out. I agree that this type of thinking can be helpful to an adult, but could just as likely be problematic for an adult. If you can put up with this for a year or two, I think you should, and then you should revisit how to make it less painful.

The best solution might be to provide less guidance and just be outcome focused.

Note 1: I would not consider my answer "advice." It may be helpful, it might not, but it is not guidance as to how you should respond. None of us know enough about the situation to give the right answer.

Note 2: Once upon a time, when my child was about 4, he had trouble remembering to put on clean clothes each day. So every morning, I would ask "did you put on clean underwear today?" He always responded "Yes." About 4 days into this, he needed a swat on the butt, and I noticed it was pretty soft. You guessed it -- he had followed the letter but not the spirit of the law. He had put on a clean pair of underwear each day -- over the dirty one -- so he was wearing 4 or 5 pairs by the time I found out. My point is that I think I can understand where you are coming from, and I sympathize. He is now in his late teens, doing fine in college, and pretty normal. Only wears one pair of boxers at a time.

I get this kind of behaviour too, and found the most effective way of dealing with it is to congratulate my child on spotting the problem with my instructions ("Well played sir!"), asking that they thought I meant (which they almost always know), and asking for them to do that. This seems to defuse the game-playing, as I have acknowledged defeat on the language front, yet stress that I still seek performance of the task. We also take that opportunity to discuss the various frailties, ambiguities and nuances of our language. Both of my kids are delighted by word play and the jokes that can come from it, and I suspect the lawyering is an extension of this.

I also give context to instructions ("Your untidy room is making me grumpy" or "... so that your socks don't get wet walking to school" or "I don't want the other kids calling you 'Stinky McStinkypants', so...") which is usually motivation enough to actually perform said task. I guess you could call the context "consequences".

Anything with time constraints is given time calls ("10 minutes until we leave" and "four minutes"), and if it's not life-threatening I'll let it slide and allow my child to wear the consequences, such as wet socks from not putting shoes on when asked, or wearing pyjamas to school because they weren't dressed in time (they were unaware there was a change of clothes travelling with us, and have not subsequently made this mistake).

These techniques have worked great with our eldest, who's doing the lawyering much less, and will no doubt work well with the youngest, who's doing it increasingly. They were also very interested to hear me name the practice; I now have two children running around accusing each other of being a "language lawyer".

Your son is incredibly brilliant. He is trying to help you become a better communicator.

I must commend you for taking the time to clarify that he does indeed understand the spirit of your words, and that he does in fact know what it is you would like for him to do. This is a testament to his brilliance and his confidence.

Each time he lawyers, consider thanking him for pointing out that what you said was ambiguous (guaranteed he know what ambiguous means) and, given that he understands the spirit of what you were trying to tell him, ask him how you could have better spoken your words to be less likely to be potentially misunderstood. Chances are, if the way you talk to your son is blatantly open to interpretation, so is the way you talk to everyone else. This can wreak havoc on your professional career and stand in the way of advancement, and even make you more likely to be a candidate for dismissal.

English is a language in which it is incredibly easy to be misunderstood, and worse, without even knowing that you were misunderstood! Statements made at the office have the potential to be interpreted in at least as many ways as there are people in your audience -- misinterpretations which can foster ill will, disrespect, blame towards you.

Your son has the gift of confidence. If he weren't self-confident, he would assume that his literal interpretation of what you said was incorrect, and become confused -- and as time goes on, introverted and withdrawn. His continued behaviour in this way is indicative of his self-confidence, and you should not interpret this behaviour as disrespect toward you.

Embracing his viewpoint will turn you into a better communicator, which will in turn work miracles in your life both as a parent, as an employee, and as a human being!