Most high-achieving leaders know they should delegate.

But when it comes time to actually hand something off, they freeze.

“What exactly should I delegate first?”

“Will it really save me time?”

“Can someone else even do this the way I do it?”

In my years of coaching and working with business owners, I’ve noticed this pattern again and again: Leaders recognize they’re overloaded, but struggle to identify which tasks are worth handing off.

And more often than not, they’re stuck in the loop of “it’s faster to just do it myself.”

That mindset makes sense when you’re in a reactive state–putting out fires, answering emails, chasing deadlines. But staying in that loop is what keeps you there. Delegation isn’t about short-term relief. It’s about long-term clarity and scale.

Why You’re Probably Overthinking It

The biggest mistake I see is when someone finally decides to delegate–but then does a massive info dump on a new assistant and expects it all to run smoothly. There’s little context, little structure, and the handoff becomes another fire to manage.

Or the opposite happens: they don’t delegate at all because they’re expecting the assistant to immediately do things exactly the way they would. Here’s the truth: you’ll rarely get 100%. But 80% is often more than good enough–especially when you consider what you’re gaining in return: time, mental space, and momentum.

Delegation takes intention. And it takes a little planning.

But the good news? You don’t have to overhaul everything at once.

Start with the Delegation Matrix

One of my favorite tools for helping people decide what to delegate first is the Delegation Matrix–a simple but powerful way to map out tasks based on their urgency and importance.

Here’s how it works:

	Urgent	Not Urgent
Important	Do it yourself (strategic priorities)	Delegate it (important but not time-sensitive)
Not Important	Delegate or automate (admin, busywork)	Eliminate or defer

The sweet spot? Important but not urgent.

These tasks are often valuable but easy to push aside–things like onboarding follow-up, CRM upkeep, internal process documentation, or customer support tracking. They’re crucial to smooth operations, but they don’t scream for attention… until they’re suddenly overdue or broken.

By identifying tasks in this quadrant, you can begin delegating in a way that supports your business and your sanity.

A Personal Example from My Founder Journey

For a long time, I held onto customer success management at Trusty Oak. I was personally handling every new client match, every support request, and every check-in. And for a while, that made sense. I knew the business best, and I cared deeply about the client experience. But eventually, we were serving nearly 100 clients–and I was buried in the weeds.

I wasn’t leading. I was reacting.

The turning point came when I trained and empowered a team member to take over client success. It took time, yes. But once it was in place, I could step back and see the business again. I was able to focus on growth, strategic decisions, and the bigger picture.

And something else happened, too: my team leveled up. Delegating that role wasn’t just a relief for me–it was an opportunity for someone else to lead.

What’s Really at Stake

A lot of leaders assume that delegating means stepping away. Losing control. Diluting quality.

But in reality, delegation is what gives you the bandwidth to stay in your zone of genius–and evolve.

Because if you’re still doing the same tasks you were doing three years ago… chances are, your business isn’t growing the way it could be. And you probably aren’t, either.

When you delegate well, you create space.

And in that space, your creativity, leadership, and impact can expand.

Want to Know Your Delegation Style?

If this is resonating, you might also enjoy the Delegation Style Quiz. It’s a quick way to identify your delegation tendencies–and get personalized insight into how to improve your approach.

Because the first step in better delegation?

Self-awareness.