In my consulting practice, I often work with leaders who are at an inflection point—business has grown, their roles have expanded, and what once felt manageable now feels overwhelming. They’re juggling it all, but beneath the surface lies a common fear: If I let go, will things fall apart? Or even more personal: Will I lose the part of my work I enjoy most?
The shift from individual contributor to leader is one of the hardest transitions to make. I remember the first time I was promoted to lead people who had once been my peers. It wasn’t just about learning to delegate—it was about redefining my value. I had to navigate friendships, redefine expectations, and learn how to coach instead of fix.
As I moved into more senior roles, I often heard, “What got you here won’t get you there.” At first, it felt like a challenge to who I was. I prided myself on being the one with the answers, the person in the weeds with the data. But over time, I came to see that real leadership meant creating space for others to step up.
Letting others try, and even fail, became essential. It wasn’t easy. But when I did it well, I became the conductor, not the violinist. I had space to think strategically, solve operational challenges, and mentor future leaders.
Ironically, now as a small business owner, I find myself doing tasks I once delegated. Technology has changed, and I'm re-learning how to operate in the details. There’s humility in that too.
So how do you know when to step back or when to jump in?
Let go when:
Your highest value lies elsewhere
A team member can learn by doing
The task is repeatable and coachable
You're holding on due to perfectionism, not necessity
Jump in when:
There's no one else to do it (yet)
The task is new or critical to the business
You’re setting an example or training in real time
Start small. Have them shadow you. Let them try. Ask guiding questions instead of giving the answer. And remember: doing it all is not sustainable, nor is it leadership. Empowering others is where your true impact lies.
