We tried not to sound judgmental. We didn’t mean to be judgmental. But the kid still felt judged, so they got defensive or shut down in shame.
We’d hoped for a productive conversation. We just wanted to help them be more successful. We tried to tread lightly because we knew it could be a touchy subject.
But we still fell into the judgment trap.
Murphy’s Law Revisited
I’m sure you’re familiar with Murphy’s Law:
“Anything that can go wrong will go wrong.”
This is often said in jest, when you experience a series of unlikely misfortunes. And it’s funny because it’s very much not true. Usually, most of the things that could go wrong don’t go wrong.
But when it comes to talking with teenagers, this version of Murphy’s Law is almost always true:
“Anything that can be interpreted as judgment will be interpreted as judgment.”
Where the Judgment Trap Lurks
Parents, teachers, tutors, and coaches all fall into the judgment trap. Bosses, especially those of young adults, do too. I know about it because I’ve fallen into it more times than I can count.
The good news is that you can learn to side-step the judgment trap if you see it coming.
It’s there anytime you’re correcting someone’s behavior – anytime you’re pointing out choices they could have made differently.
The judgment trap is there whenever you give advice, especially if they didn’t ask for your advice.
It’s waiting for you to use the wrong tone or the wrong words, or even just bring up a sensitive subject at the wrong time.
How to Avoid the Judgment Trap
There’s no silver bullet that will ensure you never fall into the judgment trap, but there are some strategies that lower your odds.
- Start the conversation by telling them, explicitly, that you’d like to understand their perspective and engage in collaborative troubleshooting.
- Then really listen to what they have to say. Make sure that you’ve understood them.
- Normalize whatever they’re struggling with, so they know they’re not the only one.
- Share your own failings, so they know that you’re in no position to judge. Tell them that you’re in no position to judge.
- Get them to give themselves advice by asking guiding questions.
- If you do give advice, don’t do so without permission. If they turn down the offering of advice, respect that.
- Your advice should not be what they “should” do; just say what has worked for you or worked for some other people. You’re just sharing things they might choose to try.
In general, the image to keep in mind is this:
If you’re giving a top-down lecture, they’ll feel judged, and you’ll get nowhere. If you’re having a collaborative dialogue, you stand a chance of avoiding the judgment trap and actually helping them move toward their goals.
P.S. This was just a taste of the ideas we cover in class #2 of our Parenting for Academic Success series. Motivation and Behavioral Change: What Really Motivates Teenagers is this Wednesday, August 20th, at 7pm.

Chris Loper has been working as a tutor and academic coach since 2014, racking up over 13,000 hours of experience supporting students.
Along with Greg Smith, Chris is the co-creator of Parenting for Academic Success, a series of classes that create empowered parents, confident students, and harmonious families.
Chris writes the popular self-improvement blog Becoming Better, where he also offers habit coaching, helping busy adults with habit formation and productivity.
Chris’s most recent endeavor combines his academic and habit-formation expertise to help students thrive in college. Visit SmartCollegeHabits.com to learn more.
In 2021, he published a humorous memoir titled Wood Floats and Other Brilliant Observations, a book that blends crazy stories with practical life lessons.
He lives in Issaquah, WA, where he is the owner of South Cove Tutoring.



