The delegator’s dilemma

Have you ever found yourself caught between knowing you must delegate and doubting if your team is truly ready?

Andrea, a composite character from several founders I've coached, faced this tension while steering her growing tech company towards a new market segment.

During our third session, she sat rearranging sticky notes, afternoon light casting shadows across her office. The usual spark in her eyes had dimmed, she looked tired.

"I know I need to delegate more," she began. "But we're mid-pivot, and I'm not convinced my team really gets the vision or can maintain our standards."

I nodded slightly, creating space for her to continue.

"It's like I'm trying to hand over the controls of a plane while changing course mid-flight," she said. "If I let go now and someone steers even slightly off course, we could miss our destination entirely."

Although Andrea expressed concern about this crucial juncture, I sensed something else underlying her words.

"I'm curious—have you experienced a different kind of journey, one where course corrections feel more natural?"

Andrea tilted her head. "What do you mean?"

"Well, when flying a plane, mistakes can be catastrophic. What about other ways of reaching destinations?" I asked.

"Like driving a car on a road trip," she said slowly. "I always did that with my friends. If you miss a turn, you can always find another route."

"Based on your experience, which metaphor feels more accurate?"

Andrea leaned forward, "It's not like it's always been a smooth ride, but I've always felt I had time to course correct."

How is it different this time? I challenged.

"When I started, I had nothing to lose," she said quietly. "Now that something has been built, I'm afraid to lose it. Letting go at this juncture is a real struggle."

Despite her insight, in our next session, Andrea still felt stumped.

"What happens if you continue being the only one who can steer?" I ventured.

"We crash anyway. Either from my burnout or our inability to scale."

During our eighth session, Andrea looked slightly more relaxed than before. When I asked what had shifted, she described her small delegation experiments. "It's uncomfortable. I'm still learning to sit with that discomfort."

"What's helping you stay with it?" I asked.

"Remembering the road trip," she smiled. "Remembering that we are driving, not being launched into space."

A year later, as we concluded our work, I asked what she would take with her.

"The biggest shift was in acceptance. I had to learn to breathe again—to trust the process, even when things are done in a different way. I still suck air through my teeth sometimes, but I'm no longer reaching for the wheel at every turn."

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What metaphors might be shaping your approach to delegation? How could reframing them open new possibilities?