Rethinking Struggle: Why Adaptive Leadership Beats "Figuring It Out Alone"

This weekend in the kitchen, my son picked a recipe that required chiffonading basil. He read up on the technique, determined to try it on his own. When I asked if he wanted me to show him first, he said no. A few attempts in, he realized it wasn’t as easy as it looked—and asked for help. I guided him through the motions, and within minutes, he had mastered the technique.

This small moment in the kitchen made me realize how often leaders push struggle as a growth tool, even when guidance would be more effective.

The Problem with “Just Figure It Out” Leadership

Some leaders equate struggle with growth. They believe withholding guidance builds resilience. But too often, this approach leads to frustration, wasted effort, and—ironically—less learning.

A senior leader once told me, “You have to let less experienced team members learn through struggle.” While I understood the intent, I disagreed. Struggle without direction doesn’t teach—it frustrates. Learning happens when people are challenged, but also supported.

I once had a manager give me a high-stakes project and imply that my promotion hinged on its success. I asked for expectations, but none were given - except to get it done. So I dug in, worked hard, and delivered what I believed was a strong outcome. At the end, I was told I had missed the mark—that my work didn’t meet expectations. Expectations I was never given. And just like that, I was deemed not ready for the next level.

Was I capable? Absolutely. Was I given the right conditions to succeed? No. Because struggle isn’t what makes someone grow—clarity, feedback, and the right level of challenge do.

Struggle isn’t inherently bad—what matters is whether it’s purposeful and supported. When people are left to flounder without clear direction, it’s not growth—it’s unnecessary friction.

Great Leaders Adapt to How People Learn

True leadership isn’t about throwing people into the deep end—it’s about assessing what they need and adapting accordingly. Here’s what that looks like in practice:

✅ Clarify Expectations Early – Learning isn’t a guessing game. Make sure people know what success looks like before they start.

✅ Gauge Readiness & Offer Support – Some people learn by doing, others by watching first. Ask: “How do you want to approach this?” and support accordingly.

✅ Encourage Problem-Solving, Not Isolation – Letting people struggle within a structured framework leads to growth. But making them operate without guidance only breeds confusion.

✅ Give Feedback Before It’s Too Late – Don’t wait until the project is over to say it missed the mark. Course-correct early so learning happens in real time.

One leadership team at a high-growth startup encouraged new hires to ask for clarity rather than struggle in silence. The result? Execution speed increased by 30%, and onboarding time was cut in half. By fostering a culture where seeking guidance was a strength—not a weakness—they accelerated success.

The strongest teams aren’t built on struggle alone. They thrive because leaders provide the right balance of challenge and support.

Final Thought: Struggle Should Have a Purpose

Struggle in itself isn’t the goal—learning is. The best leaders don’t let people flounder. They create environments where people can stretch, grow, and thrive.

So next time someone on your team takes on something new, ask: Do they really need to struggle through this? Or do they need a guiding hand to accelerate their growth?

How do you balance challenge and support in your leadership style?