Why Many Students Need a Boss: Executive Functioning and the Hidden Struggles of “Working for Yourself”
In the working world, most of us have a “boss.” That boss sets expectations, outlines priorities, creates accountability, and checks in on progress. For better or worse, the presence of a boss helps keep us on track. It gives structure to our day, deadlines to our work, and often, a helpful nudge when we’re falling behind.
Now imagine a world where you had to manage all of that yourself. Every project, every deadline, every organizational system depended on your own internal motivation and planning. Sound stressful? Welcome to the life of many students today.
The Student-as-CEO Problem
In school, especially as students reach middle and high school, there’s an unspoken expectation that they will manage their own academic lives: keep track of assignments, plan long-term projects, self-motivate to study, prioritize tasks, manage distractions, and adapt when things don’t go to plan.
In essence, they’re being asked to be their own boss.
And for some students, those with strong executive functioning skills, this works just fine. They naturally plan ahead, stay organized, and manage their time well. But for many others, this is a recipe for being overwhelmed. It’s not because they’re lazy or unmotivated. It’s because being your own boss is really hard. (I should know! I do it every day, and I’m 51.)
Sure, middle and high schoolers have their teachers who do certainly have boss-like qualities. Buts still, juggling five different subjects, extracurriculars, social pressures, and the unpredictability of adolescence… that’s a lot.
What Are Executive Functioning Skills?
Executive functioning refers to the set of cognitive processes that help us plan, organize, initiate, and complete tasks. Think of it as the brain’s management system. It includes skills like:
· Time management
· Task initiation
· Working memory
· Self-monitoring
· Flexibility
· Goal-setting
· Prioritization
These are the same skills we expect from successful adults in the workforce. And yet we often expect young people to develop them without much guidance, support, or practice. There is no class in school called, “Executive Functioning 101.”
Why a “Boss” Can Help
When students work with an executive functioning coach or academic tutor, they’re often gaining more than just help with math or English. They’re gaining a boss, someone who sets clear expectations, helps create a plan, follows up, and holds them accountable. And students respond.
The “boss” doesn’t need to be authoritarian. In fact, the best ones aren’t. They’re steady, supportive, structured, and consistent. They help students learn how to break big tasks into small ones, how to anticipate obstacles, and how to build habits that actually stick.
Eventually, with the right guidance, students begin to internalize those systems. The goal is not lifelong dependence. It’s to build the internal boss over time.
Partially the best bosses I've ever had are the ones who try to set their employees up for success. The best bosses get excited when their employee becomes a boss themselves.
We All Need Accountability
Adults don’t usually function in total isolation. We have supervisors, colleagues, deadlines, check-ins, and meetings. We have spouses, friends, mentors, or therapists who nudge us toward our goals. We rely on structure to keep us balanced.
Why wouldn’t we expect students to need the same?
When a student is struggling to stay on top of their workload, it’s easy to chalk it up to disinterest or poor motivation. But more often, what they need is a little management help. They need someone to step in and say: "Let’s figure this out together. Here’s what we’re going to do today, and I’ll check in with you tomorrow."
It’s not about micromanagement. It’s about giving students the same support systems that adults rely on every day.
Because even the most successful CEOs didn’t get there alone.