Delegation: Why Planning Starts With Letting Go

I’ve heard leaders describe their calendars like a loop they can’t escape:

“I don’t have time to plan.”

“Because I don’t plan, I spend all day reacting.”

“And because I’m reacting, I don’t have time to delegate.”

"And because I don't delegate, I don't have time to plan."

Round and round it goes.

The problem isn’t that they don’t know how to plan. It’s that they’ve filled their day with work that someone else could be doing. And every day that loop spins, strategy takes a back seat.

The mistake I see most often is that leaders try to do more when what they really need is to do less.

Letting go through delegation isn’t just about efficiency. Rather, it’s how you create the margin to think, anticipate, and lead. But if you’re the kind of leader who jumps in and solves problems the moment a team member asks, you’ll never break free of the loop. You’ll always be in the weeds.

One client of mine admitted he couldn’t stop himself from diving in when asked a question. So we tried something different: he scheduled time on his calendar for strategic work. Not a vague “catch-up block,” but specific time to review the market data to map out next quarter’s goals.

That shift mattered. When a team member came with a question, instead of dropping everything to do the work himself, he had a reason to say, “Let’s walk through this together” or “Can you take the first pass?” He was less tempted to jump in because he had somewhere else important to be by leading the business.

A few key things to remember as you schedule your own specific time:

• If you don’t let go of the urgent, you’ll never have time for the important.

• Every task you keep on your plate is one less development opportunity for someone else.

• Delegation works best when you fill the freed-up time with strategy, not more busywork.

If you want to break the loop, don’t just delegate. Schedule what matters most. Because the most strategic thing you can do this week might be blocking time to stop doing everything yourself.