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I talk to hundreds of EdTech CEOs every year. Across many of them, I feel a recurring, quiet dilemma: the rumination over what a CEO “should” actually do.

There is a nagging sense of guilt that hits when you dive into the details of a product launch or a sales script. You’ve hired great leaders—experts in marketing, product, and success—to drive those functions. So, you tell yourself to stay at 30,000 feet. You focus on “strategy.” You delegate. You empower.

But then, you feel disconnected. You worry you’re losing the pulse of the business. You’re caught in the False Dichotomy: Are you a visionary leader, or are you a micromanager?

My recent conversation with Sara Leoni, CEO of Ziplines Education, offered the perfect antidote to this struggle.

The Player-Coach Mindset

Sara doesn’t see a conflict between vision and execution. She views leadership through the lens of her time as a D1 softball player at UNLV—a top-10 ranked team that fought its way to the College World Series. In that world, the best coaches weren’t just standing on the sidelines with a clipboard; they were “player-coaches” who knew exactly what it felt like to be in the dirt.

For Sara, being a CEO means:

• Aligning the Vision: Not just stating a goal, but making sure every person understands exactly what that vision looks like for them.

• Showing Up Off the Field: Building a team-first culture where “I’m only as good as my team” is a daily operating principle.

• Radical Transparency: Sharing the “brutal truths” alongside the wins. If you don’t share the bad, you aren’t leading a team; you’re kidding yourself.

Harmony in the “Dirt”

The “False Dichotomy” suggests that getting into the details is micromanaging. But Sara’s approach suggests that you achieve harmony by doing both.

You hire experts to lead their disciplines, but as the CEO, you are the bridge. You are the one who ensures that the 20-mile march—a principle from a book Sara recommends, Jim Collins’ Good to Great—is happening every single day, regardless of the “weather” in the market.

Respecting the Traction Gap

In the growth stage, many CEOs try to build a “rocket ship” overnight. They push for scale before they’ve truly crossed what Bruce Cleveland calls the “Traction Gap,” also the title of a book that helped inform Sara’s practices.

Sara’s leadership is built brick-by-brick. It’s about executing the basics day in and day out. It’s about having the discipline to stay in the “Player-Coach” role until the foundation is unshakable.

The takeaway for my fellow EdTech leaders? Don’t be afraid to get a little dirt on your uniform. If you’re ruminating on whether you should be in the details or in the clouds, the answer is usually: Yes.

Real leadership isn’t about choosing between strategy and tactics; it’s about the “harmony” found in doing both.

These are the same themes we'll be exploring with a small group of CEOs, investors, and operators at the StartEd CEO Summit at EdTech Week 2026.

If this is relevant to what you're building, you can learn more or request an invite here.