Leading when it hurts
Recently, I visited my mother in the hospital. I sat by her side and watched her in pain, realizing that her best days were behind her. There is nothing quite like seeing the person who once carried you now needing to be carried. Walking out of that room, I felt the weight of grief pressing down on me, grief not just for what I was seeing, but for all the things I knew I would miss. The laughter around the dinner table. The little inside jokes only the family knows. The comfort of her voice on the other end of the phone.
I left that room trying to hold it together, but as soon as I stepped into the hallway, life rushed back in. My phone lit up with notifications. Missed calls. Voicemails. Text messages waiting for answers. Emails piling up. People needing advice. Problems waiting to be solved. Fires that needed to be put out.
Listen to this column:
There are moments in leadership that no one ever prepares you for. They do not fit into leadership manuals or development seminars. They do not show up on the highlight reels. But they are real. And they test the very core of who you are as a leader.
That is the part of leadership most people never see. They see the public moments, the speeches, the meetings, the headlines. What they do not see are the moments when your heart is breaking but your leadership is still in demand. They do not see the quiet pain you carry while still being expected to encourage others. They do not see the way you push forward for your team while privately grieving the things you cannot fix.
Leadership does not pause for our pain. It keeps calling, even when our hearts feel empty.
Later that same day, I heard from a leader I deeply respect. She was in Texas, sitting at the bedside of her 97-year-old grandfather as he prepared to leave this world. In her own moment of grief, she sent me a text that stopped me in my tracks:
Henry, what do you need from your community right now?
It was such a simple question. But in that moment, it was one of the most selfless acts of leadership I had seen. She was hurting, and yet she thought to ask what I needed. That is what leadership should look like. Not “What can you do for me?” but “What do you need?”
We rarely ask that question of our leaders. We ask them to perform. To solve problems. To be strong. But rarely do we pause and ask, What do you need right now? How can we carry some of the weight for you? Imagine how different leadership could feel if that question was asked more often.
These are the unseen parts of leadership. The nights when you are drained but still have to encourage your team. The mornings when you are grieving but still need to check on your partner who is stressed about the bills. The moments when you want to retreat but instead you keep showing up because people are counting on you.
And yet, something unexpected happens in the middle of the pain. Serving others gives purpose to the struggle. Pouring yourself out does not erase the grief, but it reshapes it into something meaningful. Pain without purpose can feel crushing. But pain tied to calling has the power to make you stronger.
That is why doing what you are called to do matters so much. If you are leading in a way that is just about a paycheck, a title, or someone else’s expectations, those heavy moments will break you. But if you are leading from calling, from that deeper place that says, “This is the work I was made to do,” then even in the hardest days, you can keep moving forward.
The Selfless Way of leadership is not about pretending you have it all together. It is not about perfection or polish. It is about showing up when no one sees the cost. It is about asking better questions, like my friend did for me: What do you need right now? And it is about remembering that service itself has a way of steadying you.
Leadership is not about escaping pain. It is about finding the courage to serve in it. And when you do, you discover something remarkable: even in the deepest grief, you can still give. Even in weakness, you can still lead. And sometimes, it is in those very moments that your leadership becomes the most real, the most human, and the most impactful.
About the author
Henry Sanders is the CEO of Madison365, founder of the 365 Leadership Summit, and an executive coach who helps leaders navigate transitions, build trust, and lead with lasting impact — not just surface-level performance. Just stepped into a new leadership role — or preparing for one? Start with a free 15-minute Leadership Audit: a no-pressure session designed to help you clarify your next 100 days and lead with presence, not panic. To schedule your session or learn more about executive coaching, email Henry@365nation.com. And don’t miss the 365 Leadership Summit on November 3 — where real leaders come together to build what lasts. Visit 365Leadershipsummit.org to register.
Instagram: @Henry_Sanders_Jr