Why Delegation Feels So Hard (and How to Know When to Let Go)
Delegation comes up in almost every coaching conversation I have — whether I’m working with an executive or a team. Team members want more autonomy so work can flow more efficiently. Leaders want to hand things off, but worry the work won’t meet their standards. Regardless of whether the pressure to delegate comes from above or below, the core issue is almost always the same: control.
Most of us like to feel in control — at home, at work, everywhere. Control gives us a sense of agency. It convinces us that if we’re the one doing the work, the outcome is more likely to align with what we want or need. Sometimes we’re simply tired of having to reroute our work through someone else — especially if the feedback we get feels nit-picky or doesn’t add meaningful value. And as leaders, we often believe that the smallest details matter: the word choice, the nuance, even the font. (I promise I’m not kidding.)
The stakes can feel even higher at work. Our output is tied to our reputation, so relinquishing control can feel risky. But here’s the tension: your best work requires focus, and focus requires that you don’t do everything yourself. Delegation isn’t a luxury; it’s a leadership skill.
The real challenge is knowing when to hold onto control and when (and how) to let go. That answer will always be unique to your role, your team, and your goals. So instead of giving generic advice, here’s a simple framework you can use with your coach or thought partner:
Think of control as a weight.
Sometimes you need the weight — it grounds you, stabilizes you, and keeps you upright. But other times, the weight becomes too heavy. It doesn’t hold you up; it drags you down.
If a task, decision, or responsibility is holding you up, strengthening your leadership, or allowing you to contribute uniquely — hold on.
If it’s pulling you under, draining your capacity and impact, or blocking your team’s growth — let go.
Now it’s your turn to reflect:
Where do you need to hold onto control because it supports you?
And where do you need to let go because it’s sinking you down?
If you want to talk through your specific situation, I’d be honored to serve as your coach and thought partner. Send me an email and we’ll set up time to connect.
