At the end of each semester, I read every course evaluation of the undergraduate courses I teach.

Not because I’m looking for praise, but because I’m looking for patterns.

Across several years and hundreds of students, the pattern has been remarkably consistent.

Students tell me:

• the expectations are clear 
• the material is relevant
• the feedback is helpful 
• the real-world examples make the course come alive

And yet, there’s always a counter signal.

A smaller group asks for: 

• more templates
• more examples 
• more step-by-step instruction

At first glance, that sounds reasonable. But it points to something much bigger.

This Isn’t Trade School

Undergraduate education is not trade school.

By the time students reach a 4000-level course, they’ve already learned how to learn. They’ve been given structure, repetition, and clear instruction. That foundation matters.

Early in any career—whether in the military, business, or academia—instruction should be crisp, clear, and structured. That’s how competence is built.

But if you never move beyond that, you create a different problem. You produce people who are excellent at following direction, and uncomfortable operating without it.

Where Structure Breaks Down

At some point, the model has to shift.

Because the environments students are about to enter do not look like their coursework.

In executive roles, in government, in complex organizations, you are not handed step-by-step instructions.

If anything, the opposite is true.

I’ve previously written of how Steve Jobs captured it well, “We don’t hire smart people so we can tell them what to do. We hire smart people so they can tell us what to do.”

That requires something different. Not just knowledge—but judgment.

What the Textbook Gets Wrong

In my federal budgeting course, we walk through the formal process. It’s clean. Sequential. Logical. Then we compare it to what’s actually happened over the past several years.

The reality is:

• Deadlines slip
• Continuing resolutions dominate
• Political theatrics override process

Media coverage often misstates what’s happening procedurally. Students quickly see the gap. 

The system they’re reading about and the system they’re watching unfold in real time are not the same. If they leave the course only knowing the textbook version, they’ll be unprepared.

If they leave understanding how to recognize divergence and apply judgment, they’ll be ahead of most professionals.

In my lobbying course, we explore something similar. So much of what shapes outcomes in Washington is visible. But very few people know where to look, how to interpret what they’re seeing, or which signals matter.

The result?

A lot of smart people consuming poorly curated sound bites of information, and very few understanding it.

The Skill We Don’t Teach Enough

We talk a lot about critical thinking. We don’t talk enough about operating under uncertainty.

The ability to interpret incomplete guidance, separate signal from noise, recognize when reality diverges from theory, and making a decision anyway is the difference between a strong student and a ready professional.

It was once referred to as The Manager’s Dilemma in business school is – the deferral of a decision while awaiting just a little bit more information. 

It’s also worth acknowledging something else. Today’s students have grown up in a very different environment.

They’ve consistently known:

• Smartphones and constant connectivity
• Instant access to information
• Rapid advances in computing power
• A global pandemic that disrupted normal expectations
• Ongoing geopolitical instability
• Active shooter drills as part of the school experience

And alongside all of that, they’ve been told that high academic achievement is the pathway to success. That creates capable, informed students.

But it also creates an expectation that answers should be available, accessible, and precise.

The Illusion of Certainty

Now we’re watching the next phase unfold.

AI tools can generate structured responses, provide immediate feedback, and suggest what appears to be a confident answer. Students have been understandably quick to adopt these tools.

But there’s a risk. AI can create the illusion of certainty.

It can produce an answer that looks complete even when the situation itself is ambiguous, evolving, or misunderstood. That’s where the gap widens.

Because the environments students are entering are not becoming more certain; they are becoming less certain.

Letting People Think

One leadership technique I’ve used, on active duty and in my corporate work, is simple. I don’t always tell people how to do something. I give them the objective and then I let them get there.

Sometimes:

• The path they suggest is different than I would have chosen
• Sometimes it’s less efficient
• Often, it’s better.

Because when people are given room to maneuver, many will surprise you. They bring creativity, efficiency, a different way of seeing the problem, and the ability to synthesize across inputs.

Not everyone thrives in that environment.

And that’s the point. It becomes a natural sorting mechanism.

This approach doesn’t work for every role. There are times when precision matters, time is constrained, and the process must be followed. But when the objective is to identify higher-level talent, this approach is revealing.

Some people interpret the objective, take ownership, and move toward a solution. Others look for the template, wait for more direction, and seek certainty before acting.

The difference becomes clear very quickly.

The Team You Know You Have

In the military, we didn’t always get to choose the team.

People are assigned. You make it work.

In business, you have the ability to build the team—and the responsibility to get it right.

In strategy sessions, I sometimes run a simple exercise by asking,

“If I asked each of you to privately write down the name of your A player—and your least helpful player—you’d all ace the test.”

They laugh nervously because they know it’s true.

The issue isn’t awareness.

It’s action.

There’s always a reason:

• Bob has a medical issue
• Joe saved us four years ago
• It’s not the right time

So “best available” becomes permanently embedded in your culture.

Some organizations hire for best available. Others hire for best in class. Best available solves for speed. Best in class compounds performance. Both have their place.

But the mistake is knowing the gap exists and choosing not to act.

The Market Is Sorting Differently Now

Students graduating today are entering a more competitive and less predictable job market. There are more qualified candidates on paper than there are opportunities.

So, the question isn’t: “Who has the right degree?”

It’s: “Who stands out?”

When I help place students into internships—or speak with executives hiring into their teams—the criteria are rarely what students expect.

We’re not just looking for GPA or coursework.

We’re looking for early indicators:

• Can they communicate clearly, especially in conversation?
• Can they show genuine intellectual curiosity?
• Can they synthesize what’s supposed to be happening with what’s actually happening?
• Can they operate without constant direction?

Those are the differentiators and they’re visible quickly.

What AI Can’t Do (Yet)

AI can generate content.

It can structure, summarize, and accelerate.

But it cannot yet replicate:

• Intellectual curiosity
• The quality of thinking that emerges in conversation 
• The ability to reconcile conflicting signals
• The judgment required when the answer isn’t obvious

Technology can give you an answer. It cannot (yet) tell you whether the answer makes sense.

What Endures

The people who stand out tend to share a few traits:

• They communicate well
• They stay curious
• They do the work when no one is watching
• They don’t wait for perfect clarity before they act
• They’ve learned how to learn
• They’ve learned how to apply learning in ambiguity

This is why I structure my courses the way I do. Not to make things harder. But to better reflect the environment students are about to enter. Because once the syllabus disappears, the expectations don’t.

So, where should the line be drawn?

How much structure is enough?

At what point does more structure stop helping and start holding people back?

Because the goal isn’t just to help students succeed in a course.

It’s to prepare them to succeed when there is no syllabus, no rubric, and no clear answer.

Your Hiring Process

You don’t get hired for how well you followed instructions in school.

You get hired for how well you think when the instructions run out.

So, one more question:

Are you sure you’re hiring for the right thing?