Between conversations with several mother’s, a few books on the subject, and talking to boys directly, I have come up with what I think are the eleven most important things… 
Here they are:
1. A safe place to figure themselves out:
It happens almost every day, and sometimes many times a day: Teenagers are always changing. They will change their clothes. Their mood. How they walk, talk or what they’re into. Some days they just need to figure out what feels right. Some days nothing feels right. Being a teenager is hard. Sometimes the greatest job as Mom is to act like you don’t even notice.
2. Boundaries:
Our boys need to know what is absolutely okay, and what is absolutely not. They may resist rules, but deep down they feel safe when there are clear-cut rules without exceptions. Make them clear and consistent, and have absolute consequences in place for when they break rules. Boundaries = Security.
3. Freedom:
Within those boundaries, teenage boys need the opportunity to stretch their wings. Teenage boys should be encouraged…Even pushed–to try new things, to take some risks, to find adventure. Given enough opportunities for healthy adventure, they will avoid a lot of trouble. (Remember–“Idle hands” and all of that…) Keep them busy doing character building, exciting activities and watch them become men before your eyes.
4. A Listening Ear:
Boys need to talk. Even the quietest ones will open up when given the chance. Get them alone, in the car or wherever you can, and make it clear that you want to hear about their interests, and their lives. Be patient, and try different times and places until you figure it out. Push through the ‘awkward,’ and bring up subjects that make boys squirm (hello puberty!); it will be a challenge but don’t give up on this subject matter. This makes it clear that you’re OK with any and every topic, and will always be available and comfortable talking. Listen more and criticize less.
5. A Sense of Humor:
This is the good stuff. Teenagers…are hilarious. This may be one of their very favorite thing’s about these years. No more knock-knock jokes or bad made-up jokes that never seem to come to a conclusion. Teenagers actually GET STUFF. There’s hardly anything like the bond of a good joke or a hardy laugh.
It’s a hard world: A good sense of humor will get your kid through many trials in life–So encourage it.
6. Touch:
Your teenage son will likely pull away from you physically, and that is normal, albeit painful. But even the most rigid, sulky teenage boy needs hugs from Mom; Dads should make this a practice as well. Don’t get awkward and keep a distance. Create a “hug a day” rule or something that makes it routine and normal. He’ll love it even if he refuses to show it.
7. Genuine interest:
What does your teenager love? Learn to love it too. Know at least enough about what they are passionate about so that you can have a decent conversation. This will keep doors open greater than any other gesture you can make.
8. Forgiveness:
Teenagers will make mistakes. Lots of them. They’ll act selfish. They’ll space out. They’ll get insecure and do stupid things because of it. They are going to mess up so much you’ll wonder where you went wrong. If you know it’s coming, it won’t throw you off. Consequences may be in order, but so is a whole lot of grace.
9. Direction.
Listen Mom: Your teenager actually WANTS you to give them guidance. Sure, they’ll act like they don’t, but they do. Keep it relevant, and as brief as possible, but when you see them facing forks in the road, go ahead and speak some good solid words of advice to them. Share a Bible Verse that fits their situation. Quote someone they might respect. You are their greatest resource they have, and they need your direction. They’ll thank you, even if it takes twenty years.
10. Encouragement:
It’s hard to be a teenager. (remember?) The world will yell and scream all kinds of negatives to your son. So be his greatest fan. Be his cheerleader. Believe in him with your heart, and tell him that you do. Every. Single. Day. I’m not talking about phony, contrived encouragement (Everyone is a winner!) but the authentic kind that finds their greatest attributes, and it speaks to them boldly.
11. An example:
Our kids are watching us. They get a lot more of an idea about what is right, wrong, good and bad from what you do than what you say. So take your position seriously. No, you’ll never be perfect, and you can tell your kid that–but don’t use that fact as an excuse to be lame. If you don’t want them to swear, don’t swear. If you teach them to speak well of others, make sure you do the same. Probably the greatest thing you can do for your son is to model the kind of person you want them to be.
A common key to pretty much everything that’s been stated here is that Mom is involved in the teen’s life. To listen, or discipline..to share a joke, or a hug…you need to be in close proximity to your kids. For those moms that work long hours or cannot be physically involved in your children’s lives, I encourage you to creatively find solutions for this. You will never regret making sacrifices or adjustments so that you can be present for your children when they need you. And the thing with parenting is–you’re never really sure when they’ll need you. So being there as much as possible is key. Do what you are able, rely on others to help when you’re not able, and put your job as parent before anything that you possibly can.