When you're working with a student but find yourself on opposite sides of an issue with the parent, a good way to get back on the same side is to share your concerns rather than to debate.
For example, imagine a parent wants her student to add several more highly selective colleges to a list that you feel already has too many reach schools. If you tell her that this is a bad idea, if you share statistics to show her that these are reach schools, if you tell her that her son has too many reach schools and needs to find some more realistic options, it creates a conflict. It doesn't matter how gentle you are in your communication. Even though you're confident in the advice you're giving, she hears you dismissing her request and maybe even feels like you aren't supporting her son.
Instead, just tell her what your concerns are.
"Dan is a good kid and he's worked hard. He deserves to get a lot of acceptances and to have college choices he's excited about next spring. But he's got a lot of reach schools on this list right now. And if we add more, my concern is that he'll receive too many rejections and not enough acceptances. And I don't want to see that happen to him."
Now she hears that you're just trying to protect her son from too much disappointment. She's going to want the same thing. Sharing your concerns instead of trying to win a debate puts you back on the same team. Now you can work together find a solution that's best for her son.
Sometimes parents make suggestions about what their kids should be writing in their college essays. If you're worried that the parents' suggestions wouldn't serve the student's best interest, don't dismiss the idea. Don't create an argument. Just tell the parent what your concerns are.
"I understand your suggestion and I actually agree with you that it could be an interesting story. But sometimes parents notice things about their kids that kids don't notice about themselves. Stephen didn't mention the community service experience as being important to him. When I asked him about it, he didn't seem to have much to say. I want the admissions officers to get to know the enthusiastic, likeable
kid that I know. My concern is that if we push him to write about community service, his heart won't be in it and they won't get to see the same kid that we see."
We teach our counselors at Collegewise that it's virtually impossible for a parent to be upset with you when you are genuinely, dutifully looking out for the best interest of their student. Even if a parent disagrees with your recommendation, if they know that you're personally invested in the success and happiness of their student, they'll be appreciative of your intentions.