Five Questions Every Leader Must Ask
Over the last year, I’ve been reflecting deeply on my own leadership. It’s easy to discuss leadership in theory, but harder to pause and consider how it truly shapes our lives and the lives of those we influence. I’ve been blessed to learn from exceptional leaders—mentors, teachers, and coaches—who have profoundly shaped my approach to leadership. The more I reflect on their impact, the more gratitude I feel. I want to be the kind of leader many of them are or were. I want my leadership to mean something when all is said and done. I want to know that I not only received from great leaders but also passed along the blessings that were given to leaders who came after me. On one hand, I’m reflecting on the leadership lineage that has shaped me. On the other hand, I’m considering how my leadership today will help me be a good ancestor to the future.
Through this reflection, five key questions emerged—guiding questions that help us honor the past, maximize the present, and cultivate the future.
What is my leadership lineage—the people, traditions, and experiences that have shaped my approach to leadership? Who are the key figures—personal, historical, or spiritual—who have contributed to my leadership identity?
Who is on your personal board of advisors—the people who actively invest in your growth, well-being, and flourishing? Do you have a mix of mentors, teachers, leaders, and those who challenge and support you?
Who are the key people in your leadership circle? Leadership is never a solo journey—do you have a mix of these five essential roles? Where might there be gaps?
Mentors – Those who have gone before you and offer wisdom.
Coaches – Those who refine your skills and push you forward.
Accountability Partners – Those who hold you to your values and commitments.
Peers – Those who walk alongside you, offering support, perspective, and inspiration.
Pupils – Those you invest in and help develop."
What do you want your leadership legacy to be? How can you be a good ancestor to the future in the present?
At your core, what do you truly desire as a leader? Beyond roles, achievements, or expectations—what is the deep longing that fuels your leadership?
I had the privilege of sitting down with my dad to discuss his answers to these questions. It was interesting to see him process these questions from a very different place in his life, and it was beautiful to hear his reflections on his leadership legacy.
These questions aren’t just for personal reflection—they’re a way to learn from those you admire, just as I did in my conversation with my father.
In the coming weeks, I’ll explore each of these questions in depth, sharing my own reflections along with insights from others. I’d love to hear your thoughts—what do these questions reveal for you?