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Succession Planning

by | 12 May 2026

A few months ago, I was seated at dinner across from an executive coach, who in a very business-like way asked, “have you begun succession planning for your role and for the team of the Discerning Leadership Program?”

I’m sure he meant well, but at that moment, I felt the muscles on my face contract into a mask and my stomach clench. I took a breath and then forced myself to stay curious rather than close down. “A good question,” I said. “Why do you ask?” 

He responded as you would imagine, explaining that most founders stay around too long, don’t prepare for their own obsolescence by mentoring others, let alone leaving well in a way that sets their successors and their organizations up for success.  

“I’m aware of all that, yes. But I’m curious why you ask?” By that point, I was calm, but aware of my defensiveness, my attachment to the role I’m in, to this organization and its mission, and to my team. And to be entirely honest, I can’t remember what he said in reply, after which, we changed the subject. But I did walk away thinking about his question. 

It’s not easy for many of us who serve in roles of leadership, let alone as the founders of organizations, to walk away from these roles and what we’ve created. And it’s not easy to walk away well, responsibly setting the stage for those who come after us. We might have good cover stories about how passionate we are for the purpose we’re serving, how committed we are to the mission inspired impact we’re generating, or how much we value the people we’re working with and for. And of course all this is true. At the same time, attachments naturally come into play, and fears. Simply stated, inner freedom around how we plan to move on isn’t so easy or so common.

So, perhaps we can imagine what was going on within Jesus’ heart as he was nearing the fulfillment of his mission, and quickly moving toward those fateful days of Passover before his Passion, suffering and death? Of course, Jesus had more inner freedom than any of us. And he was also fully human. He knew the pain of letting go, the uncertainty of what would come next, and his doubts about the readiness of his disciples to pick up his mission and carry it forward.

The farewell discourses in the Gospel of John, where this Sunday’s Gospel is situated, provide a window into Jesus’ preparation for what happens next. We hear his preoccupation with assuring his friends that he will not leave them alone, that the Father will send the Holy Spirit to them, and that as they do what he has instructed them to do, he will be truly with them, always.

In our leadership, let us pray for the freedom of Jesus to let go when the time is right and in a good spirit, to prepare our people and our organizations well, and to make space for what and who will come next. (And just in case you’re wondering, I’m very happy where I am!) 😉

In sibling spirit,

Tags in the article: On the Road Reflections
Executive Director of the Program for Discerning Leadership

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