How Can I Prepare My Child for the Transition to Middle School?

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In this episode featuring a listener question, executive function coach Seth Perler joins Debbie to discuss how to prepare a fifth grader for the transition to middle school. They emphasize the importance of proactive planning and open communication with the child, provide strategies such as creating a study space, using calendars and planners, touring the school, setting up meetings with teachers, and decluttering and organizing, and discuss the possibility of homeschooling certain subjects.


About Debbie Reber

Debbie Reber, MA is a parenting activist, bestselling author, speaker, and the CEO and founder of TiLT Parenting, a resource, top-performing podcast, consultancy, and community with a focus on shifting the paradigm for parents raising and embracing neurodivergent children. A regular contributor to Psychology Today and ADDitude Magazine, and the author of more than a dozen books for children and teens, Debbie’s most recent book is Differently Wired: A Parent’s Guide to Raising an Atypical Child with Confidence and Hope.

About Seth Perler

Seth Perler is an Executive Function Coach and Consultant with extensive experience addressing extraordinarily diverse learning needs. Seth was a teacher for 12 years, working with a diverse range of Gifted and Twice Exceptional (2E) students in charter schools for 8 years, and teaching students with ADD, ADHD, Dyslexia and other executive function challenges, as well as students with developmental disabilities. He’s been an Executive Function coach for middle, high school and college students since 2010. He coaches parents through his Executive Function Lab.


Resources mentioned


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Episode Transcript


Hey everybody, I am here with Seth Perler, my friend, my colleague, who is generously joining me for this Parent Lean In episode. If you’re not familiar with Seth, he is an executive function coach and consultant with extensive experience addressing extraordinarily diverse learning needs. He’s been on the show a bunch of times before. We talk a lot about executive function. My kid has interviewed Seth for a conversation before.

And Seth is really passionate about meeting the unique needs of students and he places heavy emphasis on addressing social, emotional, lifestyle and executive function issues to really help students create amazing lives for themselves. I know that’s kind of your big picture mission. So you guys, if you’re not familiar with Seth, he has a ton of resources on his website, which is Sethperler .com. He also recently launched this awesome community called the Executive Function Lab. He coaches people there on how to get results. He offers a ton of tools and it’s just a great community. So you can find out more about that at So hello Seth.


and the summit which is coming up this summer, executivefunctionsummit .com in August. I think it’s the sixth year. Crazy.


And how many years has that been running now? Oh my goodness. Tifos. Yes. That’s another amazing event. So check out Seth for all the things, but as you’ll hear from this episode, he’s also, yeah, I learned every time I talked to Seth, he’s got a lot of great insights. So welcome to the show, Seth.


Hey, Debbie.


All right, so this question was called in from a listener. I’m going to play it for you all and then we will get to some ideas. 


My name is Ashley and I have a question about my son who’s currently a fifth grader. I’m already thinking ahead to him going into sixth grade and middle school and the sheer amount of changes that will happen with multiple teachers navigating different classrooms. He’ll go from not having homework to having homework. It’s a lot to be honest, I’m feeling overwhelmed at that prospect. Fourth grade was really challenging. Fifth grade year has actually gotten a lot better as we’ve made adjustments to his IEP. I’m wondering what are the ways in which we can prepare him? How can we get him ready for that? And I’m curious to know if you’ve experienced or have recommendations to get connected with people who do like part -time school, maybe go to partial days and do more schoolwork at home. I’m worried a full day in middle school is going to be too much. 


Seth, do you want to take this first or do you want me to take it first?


I want to hear you take it first.


Okay. Okay. So I have some thoughts. I’ll kick us off and then Seth will hear what you have to say. So, gosh, as I read this, I really like, I felt this parent’s anxiety. I have been there. Like at every stage, I’m always kind of looking at the future, the next six months, the next year, the next school year, and trying to anticipate all of the potential problems so that I can proactively plan for all of them so that I can prevent anything bad from happening. So I get into this like really, you know, kind of hyperactive control mode. I want guarantees essentially. So I just wanna put that out there to start with that it is actually impossible to plan for every potential possibility to kind of force this, you know, ideal or perfect future to unfold and to control what’s gonna happen. And I know this because I’ve tried many, many times. So it’s impossible to do and it can be very stressful and put a lot of pressure on ourselves to think that we have to figure it all out. So just putting that out there. With that said, a couple of things. One is, first of all, I’d start by talking to your kid and not right now, because you wanna do this as the school year gets closer over summer break and not one big conversation, but just kind of check in with your kids here and there. Find out what is he worried about? If anything at all, this might not be on his radar at all, but get a sense about what does he think it’s gonna be like? Is there anything he’s concerned about? Anything he’s really excited about? So I would be having these ongoing small conversations to kind of get a sense of where he’s at. So that if there are some specific concerns that he has, or some, I guess, blind spots is the word that’s coming to mind, like he might think, this is gonna be easy, but you as a parent know this is not gonna be that easy. So kind of identify those things and then start to kind of proactively plan for some of those things. Like you’ll start to get a sense of where the gaps are, where you anticipate there being some challenges. And so thinking about, okay, what are some things I can put in place? What are some ways we can maybe pick one or two skills to start building right now? Again, in collaboration with your child and in a way that your child can feel some agency over it and excitement over learning those things. So that’s one thought. 

My second thought, and then I’m gonna pass the baton to you, Seth, is while we can’t plan for the future, we can again anticipate this might not go well or I could see this happening and we can come up with some if this then that ideas just to kind of help our mind quiet down. So we’re not going to be able to plan for every potential outcome. There are some things going to happen that we could never have predicted. That’s just the way life is. But we can kind of say, okay, if all the crap hits the fan, then this is what we’ll do next. You know, and just kind of give yourself a limited period of time to come up with, okay, if this, then that, a couple of options. So you can quiet your mind and say, you know what, I know you’re anxious about this, but we’ve already discussed it. We have a backup plan. And now I’m just gonna turn off the anxiety or try to be gentle with that part of myself and just be curious and let this unfold because I don’t know what’s gonna happen. We have no idea what’s gonna happen. So those are some initial thoughts. All right, Seth, so tell me what came up for you when you first heard this question.


The first thing that came up for me was I was super excited that they’re being proactive because I hear so many parents that say, you know, we saw red flags when they were in third or fourth grade and didn’t do anything about it. And now they’re in 10th grade and blah, blah. So it is so good that they are being proactive. Uh, and I also thought that, you know, they’re wondering if it might be too much for their kid. Well, it probably will be on the other hand, sometimes we find out that they really step up. Especially if the parents are proactive and your child can feel capable and like they have a toolkit. So I want you to imagine a toolbox in your garage and that toolbox has a bunch of tools in it. And you know how to use most of them. A little bit. That’s what you want to start sixth grade with. Now I taught fifth and sixth grade for six or seven years, five, six combo. I love that age, by the way. It is probably my favorite age. I think it’s such a cool age and it’s such a great opportunity. Uh, it’s such a great opportunity to have a big influence on these kids as they’re coming into who they are. Um, but they can, if they can really, as I said before, they can really step up to it if they feel like they have a little bit of a toolbox that way when they go in on the first day, there’s a foundation and stuff makes sense to them. They, they, they under, they have a much better idea of what’s going on. So I love that the parent asked this. So in terms of figuring out how to do that. There’s a couple of thoughts. There’s a lot of thoughts that I’ll get into in a minute, but first of all, in my summit and my executive function lab and my course, the UGYG course, like I, especially the course, I go through really everything that you need for that foundation. So there’s that shameless plug there. And then the second thing is that we must plan. And this is exactly what you were talking about. We can’t do everything. It’s not going to happen. It’s not realistic. But we can take steps to plan and there are specific concrete things that your child will need. And I love the if then then that approach. But that allows you now to be proactive during the summer and to use the summer to write up a plan, hopefully with buying an ownership, hopefully with your child for the summer, where you spread it out, the different things that you’re going to do to plan and get some buy -in right now to write it on a big giant wall calendar, which I love that on this day we’re going to work on your SSS, what I call the sacred study space. On this day, we’re going to research your teacher’s websites and learn about them. On this day, we’re going to set up a tour. On this day, we’ll do school shopping, et cetera. So set up several times during the summer when you can have fun, when it’s relaxed, when you can, but set it up now on the calendar with your child and then follow through, take time to do those things. And like Debbie said, discuss what it’s gonna be like, get by in an ownership, ask them what they think. And then here are some specific things. Can I share some specific things that, so as somebody who taught this grade and has worked with all these families, so things that you can do.


Please. Yeah.


I would really encourage you to use the big giant desk calendar on the wall and a planner over the summer with your child. And that when your child says, when are we going to so -and -so? That your response should always be, oh, it’s right there on the calendar. And not rescue them and tell them, get them looking at the calendar, make it so that it’s, it’s, there’s no resistance to it. It’s just an easy thing for them. They’re used to working with calendars or planner either way, but something to start scaffolding that I cannot tell you how important planning and planners and calendars and calendaring and learning skills around that are. Uh, so start doing that now. Next thing, uh, just think of outside the box ideas, but one outside the box idea I had with this one is, um, you know, your kid’s going to be going from class to class to class is to have a quote locker at home, meaning that you can have a little box or a space at home that is you can even call the locker just for the summer that where they’re just sort of getting used to, oh, this is where I have to go to get the thing. So again, like with the calendar, when your kid says, when are we doing this? You can say, well, look at the calendar. When they say, where’s this? You can say, well, go check your locker. And you can be using that as a place to leave things for them. Um, like if they’re going to summer camp and they need things during there, et cetera. So.

Another thing I did want to say when they were asking about the different class schedules and different types of options around that, that if there is an opportunity to take fewer classes, I’d really rather see the child take fewer classes and be able to get their skills down during that first year. So that’s really wise if there are different kinds of creative options, like what they’re asking about. Next thing is, is if they can tour the school, do the tour, ask if you can do a tour, go early, like if kids can go into middle school and walk around, get familiar with it, if you can go to the playground during the summer several times and they can start understanding the layout, it is really overwhelming for kids when they’re coming into sixth grade to understand, especially with all these big kids walking all around and where their locker is and how the bell’s working, all that. So do tour tours and then set up meetings proactively with the teachers. Don’t wait for conferences. Say, hey, can we pop in and say hi for five minutes? If you can, bring your child with you and just say, Hey, we wanted to know a few things and this leads into the next one. The few things that you might ask them in a meeting with them is what you can also put in an advocacy email proactively to the teachers to one, ask about certain things and two, to share about your kid. You do not want to write a giant email to the teachers. They have a lot going on at the beginning of the year. Just a quick, hey, here’s three things that my kid responds well to and three questions for you.

But some of the most important questions that I have for teachers are, when do you post homework on your portal? How accurate is it? What if we need an extra copy? Where do we turn things in? How reliable are you about posting the grades? Like, do you do it? Some teachers post right away, and then teachers are really aware. And some do it once every month or month and a half. It’s really random. And then you find out your kid is failing the class and has a bunch of zeros. So I’d want to get some clarity around some of those things, like how long should homework take, whatever your questions are. So I would not ask them 50 questions. If you meet them, that’s one thing, but in an email, keep it short. And then you can set up accountability proactively, like, hey, maybe we can start study groups with one of your friends every Sunday or every Wednesday, and we just have a study party and make it fun and like that can be some sort of accountability. A tutor, you can set it up now, things like that. Setting up a homework routine during the summer, talking through your child. What would a homework routine look like? Let’s set up our study space, the SNO, which is my Sunday night overhaul. Let’s figure out what we’re going to do once a week to overhaul your systems. Start using a timer during the summer and model it. Whether or not you’re using it with them, use a timer a lot, then this can help with them understanding how the bells are working there and how long three minutes is or whatever, but also just helping them grasp how long things take more effectively so that they can anticipate the gravity of the homework because the hand holding stops a lot of times in sixth grade and the wheels can fall off. Declutter during the summer. And then my last thing is, is after the decluttering is organized and label things with your kid, make it fun, make it a party, get cool boxes and stuff like that, put big giant labels on it so that they have a decluttered space of their own for their studying, for their own personal stuff, and that they’re really ready to hit the ground running. That was a lot.


Oh my gosh, such good, such good insights. Like every time I hear you talk about this stuff, I’m like, oh, I should have done that. Oh, I missed that window. But I love all those specific strategies. I love the locker at home. I’ve never heard that before. So I love it. I love that.


I just made that one up today. But think weird creative thoughts like that, you know?


Yeah, no, it’s great. It’s brilliant. And I love what you said, just to kind of wrap up that our kids also can surprise us. So just staying curious and open, your kid’s gonna be a completely different kid six months from now. So just kind of really trusting in the process and just being present for what is happening. In addition to this planning and like all the stuff that Seth just shared, but again, trying to find that balance between trying to control what’s gonna happen and creating the right support and the right conditions and then being open to how things are gonna unfold. And then I do wanna just touch upon, and you mentioned this briefly, the homeschooling piece, it really, I’ll just say it depends on your state, like how flexibility, how flexible schools would be for you to like take some classes at a local public school and then do the rest homeschooling. So I think you’d have to do a little investigating to see what is possible. But depending on the state, certainly that is an avenue some people take. They might have their kids do math or science or gym or PE or other things at a local school. But then they can do these kind of deeper areas of interest, these concentrated interests in a different way that would really kind of play to their kids strengths. So that might be possible.

So much wisdom in here. I want to just highlight, Seth mentioned his UGYG, that is his online course. It’s called Upgrade Your Grades. And you can learn more about that at SethPerler .com. So definitely check out the show notes for this page. There’ll be a ton of resources on how you can learn more about executive functioning and the executive function lab and connect with Seth. But Seth, thank you for joining me today and for sharing all this. And thanks to the listener for this great question. Anything you want to say before we wrap up?


Thanks for what you do, Debbie, and thank you everybody for listening and just taking that active role, taking action to support your kids.


Awesome alright bye everybody.


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