Looking for Wisdom? Go to a Middle School Open House

The best leadership advice I ever received didn't come from a Fortune 500 CEO or a management guru.

It came from my kids' middle school principal.

At an open house years ago, the principal said something that I've carried with me ever since: "Our goal here is to stretch our students, not stress them." She went on to describe their approach to guiding pre-teens through one of life's most turbulent phases, what the curriculum entailed, how the classrooms were structured—but all I could do was sit with that phrase: Stretch, not stress.

You might be skeptical about applying middle school wisdom to executive leadership, but trust me when I say that "Stretch, don't stress" has transformed how I think about growth, leadership, and transformation. 

Over the years, I've developed three practices to help teams and organizations shift from stressing to stretching. 

1️⃣ Shift Your Language, Shift Your Mindset

When I work with executives, I often talk about "growth muscles" rather than "change muscles." For me, this shift in language is subtle but meaningful. I’ve been asked many times, "When do I get to stop changing?" This question is always a clear indicator that the teams I’m working with are exhausted by constant transformation. 

Consider how this question sounds if we talk about growth muscles instead. Would you ever want to ask, "When do I get to stop growing?"

This reframe changes everything. Growth feels natural, organic, something we do by choice rather than necessity. It opens us to possibility rather than shutting us down in fear.

2️⃣ Start From Zero, One Step at a Time

Two years ago I stretched towards something that was totally unfamiliar to me: Generative AI. The mere thought of it felt overwhelming. Most people would stress about that knowledge gap—feel paralyzed by how much they didn't know. But instead of stressing about my lack of knowledge, I decided to stretch, step by step. I gave myself permission to be a complete beginner, and I started at 0.

I began by asking ChatGPT to help me write a simple app. 

(True story: When it gave me the code, I had to ask, "Now, what do I do with this? " 😅)

I had a lot of work to do.

So, I built my scaffolding slowly. I asked my computer science major son a few basic questions. I used ChatGPT as my (very patient) teacher. I failed repeatedly (check out my early AI avatars—yikes!). Above all? I kept experimenting.

Stretching means being okay with imperfection. It means building your capacity one small step at a time.

3️⃣ Turn Up Wonder, Right Through the Mess

One of the biggest reasons we stress instead of stretch is fear. I've found it helpful to think of our emotional states like a switchboard. When you raise the dial on curiosity and wonder, the fear dial naturally lowers. It's not about eliminating fear entirely—it's about balancing it with something more powerful.

The most successful stretching happens when we lean into curiosity—and embrace imperfection. Even two years later, I still marvel at what AI can do, and that feeling creates exactly the kind of openness that sustains learning and growth—even when things get messy.

… And things will get messy. They always do. But the messy middle is where success is born. Leaning into wonder and curiosity is your best way to keep putting one foot in front of the other. 

The beauty of stretching versus stressing is that it creates sustainable transformation. Maybe it's not so surprising that this wisdom came from a middle school principal after all. The journey of pre-teens discovering who they are isn't so different from organizations navigating disruption. Both require the same fundamental ingredients: The courage to take small steps forward, permission to be imperfect, and the confidence that wonder and curiosity will carry you through the messy middle.

Your turn: How are you stretching (not stressing) yourself and your team? Hit reply and let me know!

-Charlene

What I Can’t Stop Talking About: 

• Two sides of the same coin. Order and change aren't enemies—they're partners in transformation. Discover how great leaders create the container for both, driving unstoppable organizational evolution. Save this for when you need a reminder to take the long view. 

• Choose your AI bias wisely. Think AI fairness means eliminating bias? Think again. Learn how choosing the right biases—and having diverse teams make those choices—builds trust in your AI initiatives and strengthens your organization's ethical foundation.

• Feed Your Mind … Mindfully. Just like we curate what goes on our plates, shouldn't we be intentional about what fills our digital space? I’m all about treating social media consumption like a nutrition plan. Here’s how I’m transforming my online well-being—and not falling down cat video rabbit holes.

My Latest: 

• Catch up on my webinars! You can still review the slides and recordings of my two new webinars. In “Unlocking The Power of Generative AI,” I explain how to set up a generative AI “playground,” three ways to elevate your leadership with step-by-step instructions, and the broad outlines of creating a strategy. In “Developing a Winning Generative AI Strategy for Competitive Advantage,” I walk through the steps needed to create a cohesive AI strategy. 

• Are you asking the right questions? When it comes to AI, the answer might be … no. In last week’s Leading Disruption, I’m challenging use cases and encouraging us to think bigger, more strategically. Are you ready to join me? 

• How do you determine the “right” AI tech stack? Let’s be real: How do you determine the “right” AI tech stack when the ground is shifting beneath your feet? Join me tomorrow, November 19 at 9 a.m. PT / 12 p.m. ET, where I’ll answer this question (and others!). And for even more on this, be sure to sign up for early access to my upcoming book, which is all about how to create a winning generative AI strategy. 

My Upcoming Appearances:

If you want me to speak at an upcoming event or conduct a workshop with your executive team, please drop me a note at [email protected]. 

• Nov 19: Private Workshop, Aventura, Florida

• Mar 20: SHRM, Philadelphia, PA

• Aug 29: SHRM, Indianapolis, IN

If this information was helpful, there’s plenty more!

📌 Sign up for updates and early access to my upcoming book, co-authored by Katia Walsh, which is all about creating a winning generative AI strategy.

📌 Want more? Check out my weekly publication, Leading Disruption, on LinkedIn.

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