Why Can't They Just 4—Finishing the Job (and the Series): How Real Engagement Happens

Missed the easier installments? Start here!

If you’ve ever given someone an assignment—only to watch it go sideways—you’ve probably thought: Why can’t they just do what I asked?

It’s a common frustration. But more often than not, the issue isn’t with the employee—or at least, we haven’t given them a fair opportunity to show us. Instead, the problem lies in how we frame the conversation.

We tend to default to telling. Sometimes we clarify. Sometimes we over-explain. But rarely do we pause to ask first.

That pause—the choice to lead with curiosity instead
of control—is where the most significant shift in
leadership begins.

Engaging vs. Instructing

At the heart of the Engagement Model is a simple but powerful rhythm:

ASK → ANSWER → AGREE → ITERATE

"Most performance 'problems' aren’t rooted in capability—they’re rooted in clarity and connection."

"It's not about making work easier. It's about making work...work."

Each step builds the clarity, ownership, and follow-through most leaders wish they had—but rarely design for. Here’s how it plays out in practice:

ASK: Start with meaningful questions

Once you’ve set the Foundation (see Installment 2)—clarifying where we are, where we’re going, and the expectations tied to the role or task—it’s time to invite their thinking. Instead of jumping straight into instructions, start with questions that let them surface context, priorities, and perspective for themselves:

“What do you see as the most important part of this project?”
“What challenges do you anticipate?”
“What would success look like from your perspective?”
“How do you think you’ll get started?”

This doesn’t mean you never share your own point of view. But when you start by listening, your input becomes part of a dialogue—amplifying their ideas, not replacing them.

You might say, “Ah, I see why you’d go that direction. In my experience, X has worked well—how do you think that would apply here?” That kind of response surfaces gaps in understanding, exposes assumptions you didn’t realize you had, and opens the door to development.

ANSWER: Make their questions truly welcome

Many leaders complain that their team “never comes to me with questions.” Some assume the employee is too confident. Others chalk it up to intimidation.

But often, the problem isn’t confidence—it’s how we’ve trained people not to ask.

After giving a long list of instructions, we barely pause (and often look like we're ready to be done with the conversation) and say, “Do you have any questions?” If you’re the employee, what’s the risk of saying yes? Will you look like you weren’t listening? Will you be met with impatience?

This is why I always ask leaders: What’s the difference
between “Do you have any questions?” and
“What questions do you have?”

It’s subtle—but powerful. The former implies that questions
are optional or might be unwelcome. The latter assumes that questions belong here—that they’re a normal, expected part of ownership.

Then, of course, you have to follow through: listen carefully and answer thoughtfully. It tells your team that curiosity is not only welcome—it’s part of the job.

AGREE: Confirm shared understanding

Before ending the conversation, make sure you’re aligned. Ask the team member to say back what they understand their next steps to be.

If it matches what you intended, great. If not, don’t just correct—circle back to Ask and Answer until agreement is truly shared.

You might say:

“Hmm, okay—if we go that direction, how will you address ___?”
“My concern about that is ___. In the past, I’ve found success with ___. Do you think that might work here?”

You’re still leading—but through conversation, not correction. And that sets the stage for much smoother follow-through.

ITERATE: Create the feedback loop

Engagement isn’t one-and-done. Once the work is underway or complete, the cycle begins again:

What worked?
What didn’t?
What should shift next time?

But again, start with questions—not just Feedback with a capital F. Try:

“Tell me about how you decided to take that approach.”
“I heard ___ from the client. Were you able to incorporate that?”

You may learn things you didn’t know—about what changed or evolved as the work as progressed, what emerged through trial and error, or what was misunderstood. And by asking about the why behind their choices, you open up space for real development—not just judgment.

Three Common Questions

1. How long should I leave for this cycle?

It depends on the scale and complexity of the task. But I typically plan for three scheduled check-ins:

Rough draft — early enough to see whether they’re headed in the right direction.
First draft — where the shape is clear but there’s still room for meaningful course correction.
Final draft — what they believe is finished, with just a little time held back for polish or adjustments.

This rhythm avoids both micromanagement and last-minute fire drills.

2. What if what they bring back is completely wrong?

That’s when it’s time to revisit the Foundation.

If the result is wildly off-base, chances are the why of the assignment wasn’t clearly understood. Go back. Ask what they thought the goal was. What the Foundation meant to them. Often, a simple realignment there will reshape the entire effort.

Then re-enter the cycle—starting with new questions, clearer answers, and more aligned agreement.

3. When is it okay to just tell them what to do?

Sometimes, it does need to be done a certain way. In those cases, I recommend a mental decision tree:

First, ask: Are there functional implications?

Does their approach fail to meet the objective?
Does it create unmanageable or irreversible risks?
Is something critical missing?

Then, ask: Is this just a stylistic preference?

Is my preference essential to the outcome?
Do I lack trust in their skills?

If the answer to those questions is no, then guide, discuss, and support—but let them choose how to proceed.

If the answer to any is yes, then be honest. Say:
“This is one of those times where I need you to do it a specific way. Here’s why.”

Give clear direction, but still highlight where they have room to contribute or take ownership.

Pulling It All Together

And one more time for good measure, here's the full model showing all the pieces we've worked through during this series.

"What’s the difference between “Do you have any questions?” and “What questions do you have?”

When I started this series, it was with a simple but frustrating question: Why can’t they just…?

We began by naming the cycle of high expectations, vague instructions, disappointing results, and the downward spiral that follows.
We explored how shame creeps in and makes the cycle even harder to break.
We introduced the Foundation: clarifying the starting point, expectations, and shared definition of success. And in this final installment, we’ve explored what real Engagement looks like in action—and the feedback loop it creates:
ASK → ANSWER → AGREE → ITERATE. It’s a rhythm that transforms conversations into clarity, ownership, and results.

The through-line is this: Most performance “problems” aren’t
rooted in capability—they’re rooted in clarity and connection.

When leaders stop defaulting to control and instead lead with
curiosity, conversation, and shared ownership, everything
shifts. Work gets done. People grow. Cultures strengthen.

So the next time you feel that familiar thought rise— “Why can’t they just…?” —pause.

Ask. Listen. Agree. And walk through it together.

It’s not about making work easier. It’s about making work work.