If Delegating Still Feels Hard, Read This
“You don’t have to do it all yourself. Just because you can, doesn’t mean you should.” — Sheryl Sandberg
If Delegating Still Feels Hard, Read This: How to Finally Let Go and Scale
I used to say yes to help... and then low-key panic the second someone else touched a project.
I'd hand off a task, and five minutes later, I'd be hovering in Slack, "just checking in."
Delegation felt harder than just doing it myself. But that wasn't the real problem.
The real problem was that I hadn't trained me to let go.
The Delegation Paradox: When Help Creates More Work
If your team is constantly asking you what to do next, it's not because they're clueless.
It's because you haven't trained them—or yourself—to lead with clarity.
We think we're delegating tasks... but we're actually creating more work. Sound familiar?
A client once told me, "I hired a VA so I could stop doing everything... but now I feel like I'm managing more than ever."
And yeah, she was answering constant questions, reviewing every file, and giving feedback on every post.
Here's the truth: she didn't hire help. She hired a new inbox.
Why Most CEOs Fail at Effective Delegating
The micromanagement cycle is real, and it's killing your productivity.
When you hover over every decision, you're not just wasting your time... you're actively teaching your team to be dependent on you.
Let that sink in.
Letting go doesn't mean giving up. It means setting up systems so your team can succeed without you hovering.
The Breakthrough Solution: Systems Over Supervision
Here's how to fix: it
Document how things get done (SOPs) - Create clear, detailed processes that anyone could follow
Invite them to improve those systems - Their perspective might catch blind spots you've missed
Create a culture of ownership, not obedience - Reward problem-solving, not just task completion
And when they bring you options? Don't take the bait. Ask: "What would you do if I weren't here?"
This builds confidence. It builds autonomy. And most importantly, it builds time for you to actually lead.
Even when they choose a different path than you would've taken—watch how often it still works.
That's the moment you realize: your way isn't the only way. And thank god for that.
From Constant Questions to Complete Ownership
Try this three-step framework to transform how your team operates:
Set the expectation: No question without 3 possible solutions. When someone comes to you with a problem, ask them to bring three potential solutions. This forces critical thinking before involving you.
Walk them through the decision once. Show them your thought process. Help them understand the "why" behind your decisions so they can replicate that thinking.
Then step back and let them handle it. This is the hardest part. You have to resist the urge to jump in and "fix" things.
Over time, it goes from:
"Can I run something by you?" To...
"There was a problem. I fixed it. Here's what I did."
And THAT is how you scale a business without sacrificing your sanity.
The Ultimate Delegation Mindset Shift
You didn't hire a team to babysit them. You hired them so you could focus on what only you can do.
Don't forget that.
The most successful CEOs aren't the ones who do everything perfectly. They're the ones who build teams that can operate independently.
When you shift from manager to true leader, you create space for growth... both for your business and yourself.
TL;DR
Delegating isn't just about handing off tasks. It's about creating systems that let your business run without your constant input.
It's about training yourself to trust the team you've built.
And when you get there, that's when you'll finally experience what you started this business for in the first place... freedom.
The best part is that your business will actually grow faster when you're not the bottleneck.
Now isn't that worth the temporary discomfort of letting go?
