12 Stoic Questions to Transform Your Leadership

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As coaches, executives and leaders, our time and energy are in constant demand.

There’s always something pulling us in a different direction — whether it’s a meeting, an urgent decision, or simply managing relationships.

In the whirlwind of these responsibilities, it’s easy to get lost in the chaos and wear our busyness as a badge of honor.

But amid the noise, Ryan Holiday, one of the world’s best-selling philosophers and authors, encourages us to pause and ask a simple, yet profound, question: What do you actually value?

Holiday, who has worked with the NBA, NFL, Special Forces, and even sitting United States senators, has spent over a decade studying ancient philosophical practices.

His message is consistent.

“When you know what you value and know where you’re going, it makes it easy for you to ignore what doesn’t matter and focus on what does matter,” Holiday said.

“I think we often look for answers, but it’s really the questions that teach us the most. The question at the right time can totally change the direction of your life,” he added.

This insight is particularly relevant for us as leaders. Whether we are shaping a company’s culture, guiding a team, or navigating personal transformation, the questions we ask can serve as a compass.

Holiday offers 12 in particular to help us reflect on our path:

1. Who are you spending time with? Your environment and relationships shape your mindset and behavior. Are you surrounded by people who lift you up or bring you down?

2. Is this in my control? Leaders often feel responsible for everything. But recognizing what’s within your control can help you manage your energy and expectations more effectively.

3. What does your ideal day look like? If you’re not intentional about how you spend your time, you’ll end up living someone else’s agenda and dreams. What does excellence and doing your best look like to you daily?

4. To be or to do? Are you more focused on appearing successful, or on the actions and habits that genuinely bring value and deeper fulfillment?

5. If I am not for me, who is? If I am only for me, who am I? This ancient question forces us to consider the balance between self-care and service to others.

6. What am I missing by choosing to worry or be afraid? Fear and worry can paralyze us. What opportunities are you neglecting because you’re stuck in a cycle of fear and self-doubt?

7. Are you doing your job? Leaders wear many hats, but sometimes the simple question—“Am I fulfilling my role?”—is the most grounding.

8. What is the most important thing? With competing priorities, asking yourself this question daily can help you stay aligned with your larger mission and vision.

9. Who is this for? Are your decisions serving you, your team, your ego or a greater purpose?

10. Does this actually matter? As leaders, we can get caught up in the urgency of the moment. Step back and ask: Will this matter a few months or year from now?

11. Will this be alive time or dead time? How are you using your time? Are you actively learning, growing, and contributing, or just going through the motions?

12. Is this who I want to be? Our actions shape our identity. Are you becoming the person you aspire to be? And what habits will allow you to be that person?

    BONUS: What is the meaning of life? The ultimate question, one that every leader should return to periodically. Reflecting on your purpose can provide clarity during challenging times.

These questions are more than just philosophical musings. They are tools that can drive deeper reflection, action, and ultimately transformation in our personal and professional lives.

Whether you’re building a company, leading your team, or designing your self-leadership strategy, the right questions at the right time can unlock new insights and guide us toward meaningful progress.

So, as the demands of life and leadership press on, remember to pause and ask: What do you actually value?

The answer may lead us exactly where we need to go next.

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