The Leadership Challenge of Delegation

By Christina Hassan

One of the most common challenges I see in my work with leadership and executive coaching clients is delegation.

It’s a struggle that comes up again and again—and with good reason. Most leaders don’t get to where they are by being passive or hands-off. They’re in leadership because they’re committed, passionate, driven, and hard-working. Many of them have built successful careers by being the ones who always come through, who figure it out, who go the extra mile to get it done—and done well.

But here’s where the challenge begins.

That same work ethic and attention to detail that helped them rise through the ranks can make it hard to let go. It’s not uncommon to hear leaders say, “By the time I explain it to someone, I could have just done it myself,” or “What if they don’t do it to my standards, and I have to redo it anyway?” There’s a real fear of wasting time, of compromising quality, or of missing something critical.

In the early stages of a leader’s career, being hands-on made sense. They were often responsible for managing projects, delivering results, and ensuring every step from A to Z was tightly controlled. They learned that staying on top of every detail meant fewer mistakes and more success. Control wasn’t necessarily about ego—it was a strategy for survival and effectiveness.

Even in mid-level management roles, there’s often a need to maintain close oversight. But as leaders step into higher-level leadership and executive roles, the game changes. Suddenly, they’re not just managing people and projects—they’re shaping strategy, setting vision, and driving the organization forward.

This shift from operational to strategic leadership is where delegation becomes critical—and where many leaders get stuck.

You can’t do both at full capacity. There simply aren’t enough hours in the day or enough bandwidth in your brain. Continuing to lead like you always have—personally managing the details while also trying to operate strategically—just doesn’t work.

Delegation is no longer optional. It’s essential.

And yet, it often feels like a loss of control. Not in the “I need to control everything” sense, but in the “I need to make sure things don’t fall through the cracks” sense. For many leaders, letting go feels risky. What if deadlines are missed? What if the quality drops? What if the team doesn’t deliver?

These are valid concerns. But the truth is, the only way to grow into a more strategic, visionary leader is to build trust in your team, invest in their development, and let go of the day-to-day control.

Delegation isn’t about abandoning your standards—it’s about equipping others to meet them. It’s about creating space for you to do the work only you can do.

It’s hard. And it’s worth it.