(Do you have a question about your child's education? Email it to Leanna@aplusadvice.com. Leanna Landsmann is an education writer who began her career as a classroom teacher. She has served on education commissions, visited classrooms in 49 states to observe best practices, and founded Principal for a Day in New York City.)

Q: My son Gavin is now in middle school and totally disorganized. He loses papers, forgets assignments and their due dates. While he's never been organized, it was never this bad. Any tips?

A: Disorganized elementary students often have trouble when they hit middle school. The transition from a self-contained classroom, where one teacher issued assignments and frequent due-date reminders, to switching from classroom to classroom, with different teachers, takes a more organized brain.

When it comes to teaching these essential skills, "readiness is everything," says psychologist Richard Selznick, director of the New Jersey-based Cooper Learning Center, a part of Cooper University Hospital in Camden.

Gavin's middle-school muddle may signal that he's ready to learn some basics. Don't expect, however, that he'll master these skills overnight, advises Selznick, the author of "School Struggles" (Sentient Publications, 2012).

He suggests a "study skill of the month" approach. Make September's skill "learning to use a planner." Talk about a planner's function to record assignments and reminders, and why it's important to update it with every class. Each night, without nagging, review how it went. Offer pointers for improvement and reinforcement for a job well done.

"On a calendar, keep track of times the skill was practiced with reasonable success," says Selnick, "using a plus sign for doing the task and a minus sign when it wasn't done. Offer an incentive for a week of pluses."

Organized students have mastered two kinds of skills -- cerebral and physical, says Donna Goldberg, a learning coach and author of "The Organized Student" (Touchstone, 2005).

Cerebral skills help organize information mentally, Goldberg explains, "filing it in our brain so we can access it, act on it and sequence events over time. Physical skills refer to the way we manage our space and work tools."

Look at the physical aspects with Gavin. Ask yourself: Is there one place for his backpack when he comes home? Is there a distraction-free place for homework that is well-stocked so he doesn't waste time looking for a pencil? Does he have a folder system to hold papers he needs for future review? Does he have a three-ring binder or accordion file, labeled by subject, to carry worksheets, quizzes, spelling lists, assignments and so on?

One important cerebral skill is visualizing time. Many kids raised on digital devices "see 'time' as a number -- not hands going around a dial -- and may not know what practicing the trumpet for 20 minutes feels like," says Goldberg.

For some students, an analog clock can help estimate time.

In addition, "a daily planner can help him visualize his workload so he can gauge how much time he needs to complete it," says Goldberg.

Sequencing, another important cerebral skill, helps establish routines and habits to stay on task, says Goldberg. Help Gavin establish a predictable sequence each day -- come home from school, hang up backpack, grab a snack, do homework, 30 minutes of video games, prepare backpack for the next day, and so on.

Work with Gavin a little each day. "Praise progress and reinforce systems you've set up together until he owns them," says Goldberg. "Expect trial and error. Change what doesn't work, and don't worry when it falls apart. Learning to be organized is a process that's perfected over time."

Q: My son, Ezra, just entered kindergarten and is one of the youngest in his class. He's really unhappy, so I want to hold him back a year. My husband says he'll get used to it and his teacher isn't concerned, but two friends who held their sons back agree with me. Is there research about this?

A: The research on holding back a "young 5" is mixed. You can find studies to support it. Researchers Kelly Bedard and Elizabeth Dhuey found that the youngest members of kindergarten classes scored 4 to 12 percentiles lower than the oldest members in grade four, and 2 to 9 percentiles lower in grade eight. Other research shows that any academic benefits of starting a child later often disappear after middle school.

Recent research by professors Kevin Kniffin and Andrew Hanks looked at persons who received doctorates and found that holding kids back has little influence on those who earn a Ph.D. and may have negative influence on post-graduate salary.

The National Center for Education Statistics reports that depending on the region, approximately 6 percent of 5-year-olds eligible for kindergarten are held back each year. (The practice is often called "redshirting," a reference to college coaches who bench a freshman for a season, hoping that an extra year of practice yields a better athlete.)

Alia Wong covers education for The Atlantic. She reviewed several studies and concludes, "It's far from clear whether relative age has much to bear on a child's future success. And absent a consensus, it may be best to hold off on redshirting, if only in the interest of playing it safe." (Find her report at theatlantic.com.)

Every teacher can tell you of a 5-year-old who didn't demonstrate kindergarten readiness and benefited from "the gift of time." And that's really the question: Is Ezra unhappy because kindergarten is a new experience and he hasn't yet made the transition? Or is he unhappy because he's developmentally unprepared and struggling?

"Parents will do whatever they believe will help their children compete in school and life. But they need to remember that not all children progress in the same way and at the same rate or benefit similarly from the same opportunity," says literacy researcher Michael Milone.

"My advice," he continues, "is to be patient, observant and supportive. Don't hover, but try to find out why he is unhappy and address these concerns with his teacher and others at school and listen to what they say."

Meg Meeker, pediatrician and author of "Strong Mothers, Strong Sons" (Ballantine Books, 2014), advises against holding back a 5-year-old who doesn't need it. She says it "can grow into a devastating parenting philosophy," sending a message that high achievement is the only thing that matters.

The transition to kindergarten, says Milone, "is often stressful simply because it is a child's first experience with a perceived major life change.

"Helping Ezra make a successful transition can strengthen his ability to adapt to new situations -- an ability that will be incredibly important to his future."

(Do you have a question about your child's education? Email it to Leanna@aplusadvice.com. Leanna Landsmann is an education writer who began her career as a classroom teacher. She has served on education commissions, visited classrooms in 49 states to observe best practices, and founded Principal for a Day in New York City.)

Q: I just transferred my second-grade son Caeden to a new school. He's easily distracted; in first grade, he got labeled as a troublemaker at his old school. I refuse to have his first-grade problems define him. Should I meet his new teacher right away or wait until parent-teacher conferences?

A: Life doesn't offer many do-overs, but the beginning of each school year gives every child a chance for a fresh start. This is especially true when entering a new school.

If you don't want his previous record to define him, first make sure that he enters the new school with appropriate behaviors -- fix those that may have generated the labels (fair or not) in the first place.

"Second grade is not too young to have a good heart-to-heart talk about how to take advantage of a fresh start," says Allison Parker, a Texas educator with years of second-grade experience. "Sure, teachers look at a child's records to get a sense of how well that student has mastered content and behaviors that will make for a successful school year. But most teachers prefer to make up their own minds about a student: They observe carefully and get to know their new students during the first days of school.

"If his new teacher doesn't see the inappropriate demeanor displayed in first grade, the teacher assumes he's making progress with positive social interactions."

Be proactive about improvement; help Caeden master the comportment teachers expect in school. Can he listen intently, or does he talk or tune out while you're talking? Can he follow a sequence of directions? Does he have basic organizational skills, such as knowing how to gather, store and care for his school materials?

Give him opportunities to practice and be rewarded for behaviors that count in class, such as: respecting adults and other children by listening; raising a hand to ask a question or make a comment rather than blurting it out; focusing his eyes on the teacher when she is speaking; keeping his hands and feet still at his desk; following rules for walking in hallways.

And, yes, make an appointment to see his new teacher soon.

"Don't wait until the first conference," says Marissa Gehley, founder of the consulting group KNOW (Kids Need Our Wisdom). "Tell her you want to meet, so together you can get Caeden off to a great start -- that you want to make sure that you support the teacher's goals for student success."

Ask the teacher to suggest reinforcement strategies to try at home, and be sure to stay in touch with the teacher so that you both can monitor Caeden's progress and know of any problems right away, Gehley advises.

"Make sure you let Caeden know that you're talking to his new teacher and that the two of you will communicate regularly about his good work," she says. "Then ask him to make a list of three or four things that he will do (and that you'll review from time to time) to make sure second grade is the beginning of his best year ever!"

(Do you have a question about your child's education? Email it to Leanna@aplusadvice.com. Leanna Landsmann is an education writer who began her career as a classroom teacher. She has served on education commissions, visited classrooms in 49 states to observe best practices, and founded Principal for a Day in New York City.)