An Interview With Super Hero Tutor David May

tutortutoring tipsbusiness advice

An Interview With Super Hero Tutor David May

Full time tutoring wasn’t always David May’s plan. As graduate student and sommelier at a French restaurant, he needed another gig to make ends meet. Growing up, David’s mother was a special education teacher and, during college, David volunteered with autistic children and really enjoyed it. He was interested in continuing his work with special needs students but didn’t have the schedule for a full-time teaching job. Tutoring seemed to be a natural fit, combining his love of this work with a flexible, efficient, side job. It’s been 14 years since David started his part-time gig, and it’s grown into his full-time job. Now, David May is a “power tutor” seeing 20 or more students a week across different schools, neighborhoods, ages and even works with students trying to stay on track while undergoing treatment in the hospital.

The committed and diligent tutors like David are those that are so deserving of our appreciation during National Tutoring Week. His work throughout his career embodies all that this week stands for.

Clark CEO Megan O’Connor sat down with David to learn more about his career path, the challenges of the job, the importance of student-tutor relationships, and more.

Megan: Can you give some background on the different types of students you work with?

David: I’m usually the guy who gets a phone call from a parent who got my name from their child’s school. I also get a lot of calls from parents who recently had a psychologist-conducted evaluation and are looking for help. In either case, my clients are students who need extra support to get through school.

There’s always a challenge with my clients, like a puzzle but with different players. For one, this is a puzzle for the parents. Say, for example, a parent’s child has been diagnosed as having a nonverbal learning disorder, or ADHD, or dyslexia. No parent is expecting that. They’re thinking “what do we do as parents to support our kid? How do we educate ourselves?” Suddenly, as a parent, you are faced with a different parental role than the one you had previously imagined. Then, you have the kid. All of those questions are multiplied to nth degree when you think of it through the eyes of the student himself or herself. What does this diagnosis mean? How is that relevant to me sitting in class this afternoon or doing my homework or writing my paper tonight? That’s how I frame it to my new clients.

Megan: Do you have any specific approach when taking on new clients?

David: I find that humor is a great way to get students and parents comfortable when I’m first taking on a client. For example, I’ll say something like “alright, you’ve got this challenge. That means you probably stink at something, so let’s take a look at that first.” To be really direct like that in a humorous kind of way is a great way to establish connections and unlock that relationship right off the bat. I first help students get comfortable with the idea of “I may never be able to use the correct instance of ‘there’ because there are three ways to spell it and it will simply always be an issue for me throughout my life. It doesn’t mean I can’t be wildly successful someday because those things are not mutually exclusive.” I want to help them understand their challenges and teach them how to work with their challenges. My goal is to play a small part in helping special needs students figure themselves out.

Megan: Do you work with a vast age range of students?

David: Yes, I do. My new clients are usually 4th, 5th, and 6th graders, and I really try to be a short-term relationship in their life because that intention helps me to always be pushing students to use these lessons on their own. You know, I’m going to teach them something that they can do without me sitting next to them in the future. Sometimes, that short-term relationship can be 5-6 years depending on what their needs are, and now those 5th graders are working on their college applications. That’s why the age range of students I work with ends up being vast.

Megan: What is your favorite success story of a student you’ve tutored?

David: One of my favorite stories involves a client who was in 9th grade when I first met him. I showed up to his house and his mom answered the door. She told me that her son didn’t know I was coming. It was an uncomfortable moment. I was thinking this was a bad situation to be in, considering he would probably have a bad reaction, which is likely why she didn’t tell him. Anyway, of course he had a bad reaction and got mad at his mom when I walked in. In that instance, I stood up and said “mom, I think you made a mistake in trying to surprise your son.” Then, I looked at the kid and said “this wasn’t fair to you and, as uncomfortable as I am right now, you’re probably even more uncomfortable. I’m going to leave, and if I ever see you again, it’s going to be because you are giving me a chance.” Then, I left, thinking I wouldn’t hear from him again. The next day, his mom calls me and says “I don’t know what you said, but he wants to meet with you.” I helped him through 9th, 10th, 11th, and 12th grade. He got into Tufts and he would send me his papers all through college. He graduated and got an amazing job. Whenever he’s in town to see his parents, he reaches out and we meet up for coffee. It’ll be a lifelong relationship.

Megan: That’s amazing, I love that story. I think the bread and butter of a successful relationship is when the kids are part of the decision making process.

David: That’s absolutely right.

Megan: This might be related...what’s the biggest challenge you face as a tutor?

David: Actually, it’s usually the adults! Whether it’s the parents or the teachers. I mean, not to create a false adversarial dynamic, but one thing I like about that story is that it really helped me define whose side I’m on. I’ve got the luxury to just be on the side of the kid. For parents, it’s such an emotional thing to have a child who perhaps isn’t living up to the ideal that they thought they would. In a lot of these cases, you’re dealing with super high powered NYC folks who are used to being wall street sharks or movers and shakers who haven’t failed at anything they’ve put their minds to and it can be a very difficult thing to understand that your kid is different than you. I’ve got two kids and, on some level, I don’t think I’ll be immune to that myself – but that’s the point. I’m not these kids’ parent, I’m not emotionally wrapped up in them, and I can just enjoy being their biggest fan. On a similar note, because I work with kids one on one, they get 99% of my attention. I don’t have to manage a classroom with a bunch of different kids as teachers do.

So, it’s a challenge when I see this vicious cycle of the student being set up to fail over and over again. I believe bad habits can be broken and new ones can be learned. You really need the parents to be on board with setting up new systems at home and, sometimes, the teachers need to be on board for the same reason. The way I talk to the kid is different than the way I talk to the parent is different than the way I talk to the teacher. Parents can get really defensive if you’re telling them something they don’t want to hear about their child. Teachers have so much to do that, if I’m not careful, I come across in a way that also makes teachers defensive. I have to be savvy and set things up correctly between all involved parties.

Megan: So, what it seems like you’re saying is that it takes a village to educate a child. It’s the parents, it’s the teachers, and it’s you.

David: Yes, and It takes a little bit of charm to help people see you’re on their side.

Megan: Did you work with a tutor growing up?

David: No, I did not.

Megan: Do you feel like you should have or that you would have benefitted from it?

David: You know, maybe. I definitely had trouble with those long-term, unruly assignments and figuring how to break it down into smaller chunks to get it done. That’s something I’ve learned to help kids learn how to do well but it’s something I was never able to do well by myself. I was often scrambling at the last minute. So, I guess there was never some sort of alarm for me that said “hey, this kid needs something,” but that doesn’t mean I wouldn’t have benefitted from it. I look back sometimes and I think it would have been great to have a relationship with someone who taught me how to organize those things that aren’t clear.


Join Clark in celebrating National Tutoring Week and read more stories about incredible tutors.