As my friend and I jogged through the tree-lined streets of Barcelona, the warm Mediterranean sun on our faces, our conversation pierced deeply into our dreams, desires, and struggles.
I shared my internal conflict about taking a sabbatical amid shifting company dynamics and uncertain economic conditions. My friend listened intently, then shared a personal story that completely reshaped my perspective on developing leaders.
The Lessons of the Sea
He loves to go sailing, but what he enjoys even more is taking out first-timers and letting them take the helm. For him, nothing beats seeing the unbridled joy on their face when feeling the pure power of harnessing the wind for the first time. He described the crisp sea air and the exhilarating feeling of the boat cutting through the waves, with the first-timers’ faces alight with a mixture of excitement and nervous anticipation as they took the helm.
He’d sit back in the captain’s chair letting them fully own the experience with very little guidance…even as, while peeking over their shoulder, seeing the shoreline creeping a little closer, the waters starting to get a little more shallow.
“How are things looking?” he’d ask.
“Everything’s great, this is fantastic!” they’d respond, obviously not seeing the encroaching shoreline
He’d let them go a bit longer before checking in again, noticing the shore getting even closer and the waters even shallower. Yet again, the same response and the same lack of directional change ensured. Finally, he would either have to tell them to start turning or take control of the wheel himself.
One day, he tried something different.
After they settled in, “Hey, I need to go below deck for a few minutes. You’ve got this.” Once below deck, he would peek out through the little porthole window only to have his mind blown.
The boat began turning away from the shoreline much earlier than when he’d been sitting behind them looking over their shoulder.
Without the comfort of him being there to jump in if something went sideways, the responsibility of captaining the ship became all all too real, so navigation decisions were made with much more focused intention.
Just as there’s an ocean of difference between steering a ship and captaining it, so there is between managing a team and truly owning the team’s success or failure.
Where in your life have you felt the difference in weight between responsibility and ownership?
From Steering to Captaining
In the silent strides we took together upon completion of his story, the moral of his story washing over and around all the doubts and conflicts I was grappling with, it all snapped together with (now) obvious clarity
With me going “below deck” during my sabbatical, I left the team at the helm of the business. My friend reminded me with his story that true leadership isn’t about constant oversight but about stepping back to let others lead, make decisions, and grow.
As I was transitioning back in, I shared this story while on a walk with my second-in-command. She stopped in mid-stride, looked at me with her eyes widened in realization, “Oh my gosh, Derek, that is spot on,” reflecting on how the dynamic had shifted in my absence, bringing a newfound depth to her role.
She shared how, in my absence, the weight of the team’s decision-making had shifted. Before, when the final call needed to be made, or the answer was unclear, everyone would look at me. Now, those weightful, expecting eyes all turned to her.
This experience taught me an invaluable lesson about leadership. It’s not just about steering the ship; it’s also about knowing when and how to step below deck and trust your crew to navigate. This act doesn’t just empower them, it transforms them.
Have you ever felt the subtle shift from steering to truly captaining, in work or in life?
Where have you experienced this transformative moment of taking or giving true control?
Trusting the Crew
It made me wonder: where else was I unintentionally holding my team back by ‘sitting right behind them’? Where could I ‘go below deck’ giving them the real sense of ownership they needed to grow?
These questions weren’t about disengaging but about trusting my team to steer the ship, to make decisions, to fully own their roles. It was about understanding that sometimes, true leadership means taking a step back to let others shine.
How often do we delegate to our team and then metaphorically (or perhaps literally) stand behind them, looking over their shoulder, thereby robbing them of full engagement and growth?
Where in your life or business can you step below deck to provide the space for others to grow, to fail, to lead, and ultimately to shine?
Our Greatest Impact
As leaders, our greatest challenge and reward lie in stepping back, in trusting the potential we’ve nurtured. It’s in these moments, when we dare to let go, that we truly learn the depth of our impact and influence.
Because ultimately, being a great leader is not just about steering the ship, but about developing more leaders, more captains.
Lead With Energy,
Derek
If you aren’t already, sign up here to get experiences like these in your inbox each month.