Career and College Readiness: Questions to Ask Before Locking In a Student’s Plan

I didn’t start my career in the classroom. I started as an athletic trainer.  

That role gave me something I didn’t fully understand at the time, but now shapes everything I believe about student planning. More than anything else, relationships matter.

When you’re rehabbing an injury with a student, you see them at their most vulnerable. You’re there early in the morning, and late at night. You’re not grading them. You’re not evaluating them. You’re just there to support them.

That changes how you see kids.

Later, when I moved into teaching and then into career and technical (CTE) administration, that perspective stayed with me. I could see very quickly that the students who had strong relationships with the adults in the building were the ones who thrived. Not just academically, but in knowing who they were and where they were going.

That’s where I think we get student planning wrong. Schools try to treat it like a checklist.  

But you can’t plan a student’s future without understanding the student in front of you.

Why This Moment Matters More Than People Realize

There’s a reason student planning has become such a high-stakes moment in schools.

Part of it is accountability. Districts are required to show that students have plans. They have to report outcomes. They must prove they are preparing students for college, careers, or the military.

But here’s the tension. Just because a plan exists doesn’t mean it’s right.

I’ve seen plans created just to check the box. And on paper, they look complete. The courses are there. The credits are aligned. Everything “works.”

But that doesn’t mean it serves the student. And when we miss that, the consequences follow students long after they leave high school.

What Goes Wrong When Plans Move Too Fast

Most of the time, when a plan goes wrong, it’s not because educators don’t care. It’s actually because they’re overwhelmed.

Counselors today are managing hundreds of students. And they’re not just planning schedules. They’re supporting mental health, handling emergencies, sitting in meetings, coordinating services, and trying to keep everything moving forward.

Unfortunately, because of this, planning can become transactional.

• You look at the transcript.
• You move the student forward.
• You check the box.

But there are two major problems with that approach.

1. The data is often outdated.
You’re making decisions based on last semester’s performance, not who the student is today.

2. You’re missing the student’s voice.
Just because a student took a class doesn’t mean they want to continue in that path moving forward.

That’s how students end up in programs that don’t fit them. And by the time anyone realizes it, it’s often too late.

The Risks Are Bigger Than Graduation

When people think about student planning, they usually think about one outcome, and that’s graduation.

But the risks go far beyond that.

For example, students can miss scholarship opportunities because they weren’t placed on the right diploma plan. They can miss certifications, dual credit, or advanced coursework that would have saved them time and money. They can graduate technically “on track,” but completely unprepared for what comes next.

And sometimes, the impact shows up years later.

I’ve known students who spend thousands of dollars and multiple years in college trying to figure out what they want to do, backtracking through majors, retaking courses, and carrying financial stress that could have been avoided.

Not because they made bad decisions, but because no one helped them ask the right questions early enough.

The Question That Changes Everything

If there’s one question I wish every educator would start with, it’s this:

What experiences are shaping what this student thinks they want to do?

Not: What do you want to be?
Not: What’s your plan?

Instead: What have you experienced so far in your life that is influencing your thinking?

I’ve learned students don’t make decisions in a vacuum. Their interests are shaped by classes they’ve taken. By people they’ve met. By what their families expect. By what they think is possible for them. By their culture.

If we don’t take the time to understand those influences, we’re building plans on assumptions.

The Questions That Actually Matter

The right questions are crucial. And they should evolve as students grow.

In middle school, the goal is exploration.

You’re asking:

• What kinds of classes or environments seem interesting to you?
• Do you like working with people, or more independently?
• What work, learning or volunteer experiences have you had that you did not enjoy? Why?

At this stage, it’s not about locking anything in. It’s simply about helping students start to see possibilities.

In early high school, the goal is exposure.

You’re asking:

• What experiences have you had that are shaping what you want to do?
• What have you tried that you didn’t expect to like?
• What are you interested in exploring next?

This is where students begin to connect experiences to potential paths.

Later in high school, the goal is alignment.

You’re asking:

• Does your current plan actually reflect what you want to do?
• Are there opportunities you’re missing, like certifications, dual credit, or advanced coursework?
• What could this plan mean for you after graduation?

This is where planning becomes more concrete. But it should still be flexible.

What Happens When We Ask These Questions Early

When schools ask these questions consistently, students stop feeling like they are just being moved along. They start to feel like they actually have a voice in the process.

That matters, because this work should not be about locking a student into a decision too early. It should be about helping them learn more about themselves over time.

When we take this approach, students start to figure out what they like, what they do not like, and what kinds of opportunities actually fit them. They can make adjustments earlier, when there is still time to change direction and when the stakes are much lower.

By the time they graduate, the goal is not just for them to have a diploma in hand. The goal is for them to have some direction and a clearer understanding of what comes next in their lives.

I have witnessed students take one course that completely changed how they saw their future. I have also seen students realize that a path they thought they wanted was not actually a fit. That kind of clarity is just as important, because knowing what you do not want can be just as valuable as knowing what you do.

Where Systems Make the Difference

This is where systems really matter, but only if they are helping people do their jobs better, not trying to replace the human part of the work.

At the end of the day, the most important thing is still the counselor sitting with the students, understanding what matters to them, and helping them make informed decisions. That face-to-face aspect cannot be taken out of the process.

That’s what I love about Pathways. It is focused on the counselor. It does not try to take the human part out of planning. It helps take away the administrative noise, synthesize a lot of data, and put the right information front and center so counselors can spend less time chasing details and more time with students. It even allows students themselves to have the autonomy to see their plan and even adjust it through MyPathways, a mobile-friendly student and family portal.  

That is the real value to me. The system is not the point. What it makes possible is the point. When counselors have better visibility and cleaner data, they can catch issues earlier, have better conversations, and help students make decisions that actually fit who they are and where they want to go.

The One Thing I Wish Educators Understood

I want every counselor, and every educator, to understand that there is more than one version of success.

Not every student needs a four-year degree. Not every path should look the same. And not every decision needs to be final.

Student planning should not be about locking a kid into one future too early. It should be about helping them see what is possible.

Our job is not to decide for students. It is to help them explore their options, understand their opportunities, and make informed decisions as they learn more about themselves.

To me, that is the real goal. Not just building a plan, but helping students leave with direction, clarity, and the freedom to adjust when they need to.