What To Do With A Sneaky Teen

I got a wonderful e-mail recently from a parent who is struggling with "sneakiness" from her teenage son. Do I hear a chorus of "me too". This is a classic parent-teen struggle. You work hard to set reasonable rules, and your teen works just as hard to wrangle him/herself around them. Here is what this parent wrote: "I believe he senses me becoming "paranoid" and questioning things because I don't trust...and he then becomes sneakier. How do I break that cycle and how do you convey confidence and trust when they have broken that trust?"
Let's play this out. You make a rule. This mom had a rule about no food in the basement. She goes down the basement and finds cans and wrappers stashed behind furniture. This a relatively minor infraction but a great example of how these small things build up, create niggles of doubt, until full out distrust and paranoia develop. Fill in the blank here with the smaller rule breakers that your teen challenges you with. 
Here is your "I Get It" moment: "Hey honey, I just found (fill in the blank) wrappers and cans in the basement. Clearly you think this is a rule worth breaking. Give me an alternative. I'd rather we come up with something together, that we both can agree on, rather than you disagreeing with something and sneaking around to do what you want anyway." The work is always to encourage truth-telling. When you include your teen in the rule-making, at least you get them to have partial ownership of the problem. Here is how you can do this. Using the above example, 
Your teen will probably say: "its stupid that I can't eat downstairs where I hang out."
Parent says;" What do you think I am worried about when you ..........." 
In this case kid will say: "that I will trash the basement." 
Mom can say: "Yes that's right, so what will you do to assure me you won't trash the basement, and get rid of your trash."
 Now the owness is on the teen to come up with a plan that makes you happy.
Final question from parent: "What will the consequence be if you don't follow through on your plan."
The consequence is in place. If you aren't satisfied with the consequence your teen comes up with, offer one up yourself. Maybe in this case, you are banned from the basement for 24 hours if I find trash down there. 
As your kids get older, they will disagree with you more and more. Your choice is to set your rules, and watch your kids dance around them, or engage them in the process so they feel a part of the process. They want to manage their life, they are driven to manage their life, even if they don't do it well. It's called practice! It is up to you to give them opportunity to practice, by including them in the process. They will screw up. But I think it is less about trust, and more about temptation. Teen''s are impulsive, and don't think things through for very long. They need help in that department. So when you find the beer can in the basement, what you want is use that to open conversation. So rather than getting angry, and going with a "how can you betray my trust like this" You might say" I was surprised to find this beer. I know we don't have any in the house, so either you or one of your friends brought it in. What are you going to do to make me feel OK about being in the basement and sneaking in beer or booze.?" Again, using the words trust can be loaded. Teens are tempted by all the fun stuff teens want to do and try. They need your help to stay safe and trustworthy, not just your anger.  
Have you seem my new short film about the power of understanding:
https://www.youtube.com/watch?v=MzpwSYP-Id0&t=11s