How leaders inspire change at every level

I’ll start where I often start, with two lines.

Back in 2011, I drew two lines on a piece of paper. They might be the most important lines I’ve ever drawn.

Not because they were artistic (they weren’t) but because they gave structure to something we all feel and rarely name: the gap between where we are and where we want to be.

On the left, I wrote, “Where I am.”On the right, I wrote, “Where I want to be.”

At the time, I was working with middle school and high school students in the suburbs of Chicago. I loved my job, I truly did.

But I felt a pull toward something else: the marketplace, business, entrepreneurship.

Discovering business as a force for good

This was 2010, 2011, right after the financial collapse. People were rethinking capitalism and asking what companies were really for.

I stumbled into the world of social enterprise and realized that business could be a force for good.

On the left side of my line, I was a communicator. I was young. I was financially constrained (okay, broke). I had grit and drive. I was purpose-driven and career-curious.

But I lacked tools. I lacked credibility. I lacked network. I lacked access.

The obvious path was an MBA. But it was expensive, and for someone not making much money and coming from a family where college itself had been a stretch, it didn’t make sense. It wasn’t just about cost. It felt misaligned.

So I decided to build something different.

Designing my own master’s degree

I called it the Leap Year Project.

Instead of enrolling in graduate school, I structured twelve internships in twelve months, all with companies around the world.

To fund it, I created a newsletter people could subscribe to for ten dollars a month to follow the journey.

About two hundred people signed up. This was before crowdfunding really took off. And those subscribers didn’t just fund the project, they helped shape it.

They introduced me to companies creative enough to take a chance on a 25-year-old who wanted to be a one-month consultant.

I downsized my life to a roller bag and a backpack. I worked at NBBJ in Seattle on experience design projects for Microsoft.

I became interim community manager at Threadless in Chicago. I helped organize the largest Thanksgiving dinner in the country at the Los Angeles Mission.

And I completed nine other internships that stretched me beyond what I thought I could handle.

But the bigger shift wasn’t geographic.

Inviting others to take their own leaps

All year long, I kept asking people one question: What leap would you take if you could learn, grow, or try something new?

People responded in ways I didn’t expect. They started businesses. Fostered children. Improved their health. Designed family trips. Deepened community involvement. We documented their stories alongside mine.

At the end of the year, I staged my own graduation at a TED conference in Chicago. Cap and gown included. It was playful, but it pointed to something serious: experiential learning deserved credibility.

That question became my life’s work.

Launching Experience Institute

At 26 years old, I launched Experience Institute as an alternative to graduate school.

We created a fellowship model built around apprenticeships: three immersive experiences over the course of a year, combined with in-person learning intensives in Chicago.

The tagline was “Harvard meets The Amazing Race.”

We eventually partnered with the University of Pennsylvania, Stanford, and UC Berkeley. We built programs for high school students, gap-year learners, and early-career professionals.

The premise was simple: real learning happens when you roll up your sleeves.

But something interesting happened as we placed fellows inside companies.

When companies started asking for more

The companies themselves were hungry.

They were used to “sage on the stage” learning: PowerPoints, outside experts, one-off workshops. But they wanted something deeper. They wanted experiential learning inside their organizations.

So we adapted the LEAP framework into project-based learning for teams.

Leaders worked on real company challenges (innovation initiatives, management redesigns, storytelling projects, AI tools) while receiving coaching and facilitation.

For over a decade, I operated between academia and industry, helping organizations rethink how transformation actually happens.

And then I realized something uncomfortable.

Taking my own leap into the executive suite

I had helped many leaders navigate transformation, but I hadn’t lived inside their seat.

So I stepped aside as CEO of Experience Institute and installed our COO into the role.

walked the Camino de Santiago across Spain for reflection. And I joined NextGen Growth Partners in Chicago as Chief Talent Officer.

Rethinking private equity through leadership first

NextGen isn’t a traditional investment firm. Instead of buying companies first and installing leaders later, we start with leaders. We identify exceptional operators, then acquire companies aligned with their strengths.

We often partner with founders navigating succession, a phenomenon sometimes called the “silver tsunami,” with millions of business owners lacking succession plans.

Now I work alongside founders and CEOs in industries like IT services, HVAC, and commercial cleaning. Transformation here isn’t theoretical. It’s payroll, culture, operations, legacy. It’s messy and deeply human.

Which brings me back to those two lines.

Vision begins on the right side

Transformation starts with vision.

Harvard researcher Daniel Gilbert found that when we vividly imagine our future selves, our brains begin responding as if that future has already happened.

So I ask leaders:

What do we hope to know?
What do we hope to feel?
What do we hope to do better?

Then we return to the left side.

Where are we really?

What are our strengths? What are our constraints? What’s holding us back?

Too many teams jump to action without understanding their starting point. It’s like using GPS without enabling location services.

Once both sides are clear, we can LEAP.

Listening before leaping (L)

The L stands for listen.

Transformation doesn’t start with action. It starts with listening (interviewing the people living the challenge). Getting out of the boardroom and into real conversations.

Often, teams return with a refined or entirely different understanding of the problem. And they return energized.

Expanding the field through exploration (E)

The E stands for explore.

At Stanford’s d.school, we talk about flare before focus. Exploration widens possibilities before narrowing them. It requires clarity about mode: are we generating ideas or evaluating them?

Bring in diverse voices. Not just executives. Include analysts, frontline staff, emerging leaders.

Exploration creates ownership.

Acting through constrained experiments (A)

The A stands for act.

Choose experiments worth running. Set constraints: thirty to ninety days, defined budgets, measurable outcomes.

Transformation isn’t one sweeping move. It’s consistent, intentional action. Improving by one percent daily compounds dramatically over time.

Reflecting to turn action into growth (P)

The P stands for present.

John Dewey said we don’t learn from experience, we learn from reflecting on experience.

At the end of each LEAP cycle, participants deliver short talks sharing what they tried, what worked, what failed, and how they changed. Those moments crystallize learning.

And yes, even senior executives get nervous before presenting.

Why belief must anchor transformation

Beneath the LEAP process sit three deeper foundations.

The first is belief.

Dan Pink writes about purpose as a driver of motivation. Viktor Frankl reminds us that those with a why can endure almost any how.

For me, that why is helping people flourish: helping leaders find clarity and confidence in difficult moments.

The second foundation is belonging.

Google’s Project Aristotle found psychological safety to be the most important predictor of team performance.

Belonging looks like remembering a colleague’s child’s soccer game. Sending flowers. Hosting informal gatherings. Pulling someone aside when they’re struggling.

These moments aren’t small. They’re structural.

The third foundation is becoming.

Transformation isn’t only about company metrics. It’s about who people become in the process.

In LEAP Talks, when someone shares how they changed (not just what they produced) you can hear a pin drop.

That’s growth.

Embracing the messy middle

Let me be clear. Transformation is not a clean diagram. It’s a spaghetti bowl of twists, false starts, executive debates, and hard conversations.

And now, sitting inside companies rather than advising from the outside, I feel that mess firsthand.

Transformation isn’t a reorganization. It’s not a slide deck. It’s not a two-day offsite.

It’s consistent, intentional leaps by teams brave enough to try, fail, learn, and try again.

Fifteen years ago, I drew two lines because I felt a little lost. Today, I draw them because I understand that feeling lost is often the beginning of being found.

The space between those lines is messy. It’s beautiful. It’s terrifying.

It’s where individuals become teams. Where companies become trusted brands. Where work becomes meaningful.

The market will force transformation on all of us eventually.

The real question is whether we will transform together and whether we’ll find a little joy along the way.

This article is based on Victor Saab's brilliant talk at our Chief People Officer Summit in Chicago. Check our upcoming events.

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From here to there: What real transformation actually requires