Descending the Leadership Mountain: Strategies for a Successful Exit


Are you facing the daunting challenge of exiting a leadership role? Discover key strategies to leave the team, and yourself, better than you found it.

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Thursday, June 20, 2024, at 2:00 PM EST

Have You Ever Climbed a Mountain?

I’ve climbed a little, but I wouldn’t consider it “mountain climbing.” Growing up attending summer camp, we would spend a day in Sand Rock, Alabama, climbing the cliffs and exploring the ravines. It was fun and pretty easy climbing.

The most fun part of climbing was descending. Ascending took a bit of planning and a lot of courage. Descending only required leaning back and trusting the person on belay below you. Descending was easy and fun. You hang onto the rope, sit back in your harness, and enjoy the slow descent back to the ground.

This is not the case for real mountain climbers.

Climbing Everest

Take Everest, for example. People die every year on the mountain. Naturally, you’d think climbing up is the most dangerous half of the experience. In reality, descending Everest is much more deadly.

Climbing up takes careful planning, exacting execution, and patience. Descending requires the same, yet people coming down the mountain tend to become complacent, exhausted, and suffer from poor time management.

Even the term for climbing focuses on the ascent, not the descent, yet both are critical for a safe climb. People don’t just climb up. They also climb down.

Climbing the Leadership Ladder

A long role in a single organization is a thing of the past. According to the research, people change jobs every 4.1 years. Millennials change jobs more frequently. This means people frequently step into a new leadership role and out of roles. To stick with our mountain analogy, people are constantly ascending and descending.

Much like a mountain climber, we tend to plan how to step into a role. We chart a course and work to build our team and organization strategically. I wrote an entire book on this.

Yet, planning and intentionality often wane when a leader transitions out of a role or organization.

Transitioning into a role is like ascending a mountain, but it’s the transitioning out that kills the majority of leaders. Not literally, but figuratively.

“Every New Beginning…

…comes from some other beginning’s end.”

That is a lyric from Semisonic’s song, Closing Time. It’s so true. Every beginning comes on the heels of an ending. The next chapter starts when the current chapter ends. The next step begins as the previous step ends. And the next job really can’t start until the previous job ends.

By “ends,” I don’t mean off the payroll. Ending well requires more than cleaning out an office. Starting strong in your next opportunity requires ending your previous role well.

So how do you descend a job well?

Ending Well

Leaders who transition well understand that transitions are journeys, not moments.

Packing up an office is a moment, but leaving is a journey. Hugging people goodbye is a moment, but leaving is a journey. Transitions your files doesn’t transition you down the descent.

To descend intact, you must traverse the ending journey well. How? Here are 5 suggestions:

1. Start ending well the day you begin.

We should always lead with the end in mind, including our end. As you execute your ascension plan, pay attention to what you learn along the way. You’ll want to eventually descend as carefully as you ascend. From the beginning, work to intentionally develop others, pass along your skills, and replace yourself.

I was the lead pastor of Woodstock City Church for nearly 13 years. My official last day was August 1, 2021, but I began replacing myself seven years prior. Moreover, I worked to pass along my skills and delegate more than I did during my tenure.

2. Recognize the emotions of the descent.

The physical toll of a climb isn’t the only challenge. Leaving a role or organization takes an emotional toll on everyone. You’ll experience plenty of discomfort, grief, and confusion. And just when you feel like you’re past the emotions, they come flooding back.

The human temptation is to ignore and suppress the emotions. After all, who wants to feel all that negative stuff? But it’s important to feel it. If you don’t feel it, you can’t move past it. A critical part of your leaving journey is emotional.

When I left Woodstock City Church, I worked hard to force myself to feel the emotions of the exit. I spent 13 years leading the church. I spent 13 years helping build something – from a couple hundred attendees to nearly 8,000. We grew from four staff to 65. Not to mention the countless stories of life change I experienced. That’s a lot to leave behind. And it wasn’t easy. For over a year, I felt elements of sadness. I missed the team I left behind. I missed the routine. I missed the leadership. The more I recognized and felt these emotions, the better I processed and moved past them.

3. Write down the losses.

Losses fuel many of these descending emotions. Even if you’re excited about the new role, job, and organization, you’re losing many things as you exit. For instance, you’re losing relationships, processes, systems, and culture. You’re losing the comfort of the old rhythm and expectations.

Losses must be grieved to rest in peace. Write down everything you’re losing in the descent. Then, take time to grieve each loss.

As mentioned previously, there were plenty of losses for me leaving the church. Friends, teammates, work, routines, meetings (yes, I missed a few of them), Sunday mornings, and more. I wrote down every loss I imagined I’d feel to help me grieve completely. I encourage you to do the same.

4. Don’t rush the process.

Journeys take time. That’s why we call them “journeys.”

Rushing your leaving often leads to suppressing the emotions of the exit. It’s essential to take time during the process to experience the journey.

I officially informed a few in leadership of my pending exit nine months before I left. I didn’t want this to surprise them, and I didn’t want to keep it a secret. That’s unhealthy for everyone. By bringing my pending transition to light this early, I could design an exit strategy to prioritize the church and the next leader while giving myself plenty of space to take the journey. Remember, your descent doesn’t begin the day you leave but the day you decide to leave.

5. Take this trip with others.

There’s too much happening during the descent to go it alone. I believe we should always have trusted advisors in our corner. These people are especially valuable during moments like this. Find two or three trusted advisors and create a personal personnel team. Use them for wisdom and advice. And when the time comes, allow them to support you during your descent.

At my church, I was blessed to have people in my corner to process my exit and support me during and after. I imagine they would have been harder to find if I had sought these people out after exiting. It’s never too early to build a supporting infrastructure. Serious climbers don’t go it alone. Nor should you.

Starting Your Next Ascent

The best way to thwart your new beginning is to ignore the reality of an ending. When leaders ignore the ending, they begin the next ascent exhausted and emotionally split. I encourage you to follow these tips to help ensure you end well so you can start your next climb strong.

One more thing: If you’re planning to transition roles at any point, pick up Big Shoes To Fill. I wrote this book for you.

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