You became CEO because you were exceptional at something. Maybe it was product intuition—you could see what customers needed before they did. Maybe it was rallying people around a vision, or making bold bets when others hesitated. Whatever it was, it worked. You built something from nothing, scaled from 10 to 50 to 100+ people.

But somewhere along the way, the thing that made you successful started slipping away. Your calendar filled with back-to-back meetings about org charts, budget approvals, and putting out fires. The work that energized you—the deep thinking, the customer conversations, the product decisions—got pushed to evenings and weekends, if it happens at all. You’re working harder than ever, but you feel less effective. You’ve become the bottleneck everyone needs to get through, yet you’re too buried to think strategically about anything.

This erosion happens gradually, then suddenly. One day you realize you haven’t done the work you love in months. The work that made you successful, that made this worth doing, has been crowded out by the demands of running a larger organization.

The Inquiry

Sit with this question. Don’t answer it immediately. Let it work on you for a few days:

If you could reclaim just three hours a week to focus on what only you can do—the work that made you successful in the first place—what would you do with that time, and what are you tolerating right now that’s preventing you from claiming it?

How to Work With This Question

This isn’t a productivity question. It’s a question about what you’re willing to let go of, what you’re willing to stop tolerating, and whether you still believe the thing that made you successful actually matters at this stage.

Here’s how to engage with it:

Spend time with the first part: What would you actually do with those three hours? Not what you think you should do, but what would genuinely move the business forward in a way only you can. Get specific. “Strategic thinking” isn’t an answer. “Mapping out our AI product strategy for the next 18 months” is.

Then get honest about the second part: What are you tolerating? The meetings that don’t need you. The decisions you could delegate but don’t trust anyone else to make. The standards you won’t compromise on even when they slow everything down. The narrative that you have to be involved in everything because “that’s what a CEO does.”

Notice what comes up: Resistance. Guilt. Fear. “If I’m not in all these meetings, what am I actually doing?” This is the real work. The question isn’t just about time management. It’s about identity, control, and whether you trust the organization you’ve built.

What This Reveals

Most CEOs discover one of three things when they sit with this question:

1. They’ve lost touch with their actual role. They’re doing the job they had two years ago, not the job they have now. Reclaiming those three hours means fundamentally rethinking what “CEO” means at this stage.
2. They don’t trust their team. The reason they can’t reclaim the time isn’t about the calendar—it’s about delegation, development, and whether they’ve built a team capable of running without them in every meeting.
3. They’re avoiding the harder work. Sometimes the fire-fighting and meeting overload is a way to avoid the uncomfortable strategic questions: Are we pursuing the right strategy? Do I know how to lead at this scale? What if I focus on the big stuff and discover I don’t know how?

An Invitation

If this question landed with you—if you felt the weight of what’s been lost and the pull toward what could be—I’d love to continue the conversation.

I work with CEOs navigating exactly this transition: from founder-CEO who does it all, to leader-CEO who builds the systems and team that free them to focus on what only they can do. Sometimes that happens through a 12-month coaching partnership. Sometimes it starts with a focused 3-session program to gain clarity on what’s driving your patterns and what needs to shift.

Either way, the work begins with a question like this one—and the willingness to sit with what it reveals.

Let’s talk | Schedule a 15-minute call

---

This is the first in a series exploring the challenges CEOs face across three dimensions: You, Your Team, and Your Strategy. Each post offers a powerful question to deepen your thinking and a practice to strengthen your leadership.