Delegation Should Feel Like Relief — Not Another Headache

If delegation doesn’t feel relieving for you, you’re not actually delegating — you’re just assigning tasks and hoping for the best.

I’ve worked with many clients who thought they were delegating, yet still felt overwhelmed, uncertain, and mentally burdened. The reality? They weren’t getting the full power of their assistant.

Sometimes the problem is having the wrong person in the seat (rare with our team, but it happens). More often, it’s how someone approaches delegation.

In this post, I’ll walk you through:

• 3 warning signs that delegation isn’t working

• 4 common mistakes that make it a you problem instead of a them problem

Relief Is the First Sign Delegation Is Working

The very first and most important indicator that delegation is working is relief.
It’s not just about freeing up hours in your day — it’s about clearing mental space. Even if you’ve had a bad hire in the past, the right person combined with the right approach should leave you feeling lighter.

If you don’t feel that relief, pay attention to these warning signs.

3 Red Flags Delegation Is Failing

1. You Still Mentally Own the Task

If it’s still circling in your head — wondering if it’s done, checking the status, or worrying about the outcome — you haven’t truly delegated.

2. You Don’t Feel Confident Adding New Tasks

Your assistant should be able to take on new responsibilities, even without a process in place. If you hesitate because you think they “just won’t get it,” that’s a problem.

3. Your To-Do List Is Shorter, But Your Brain Is Still Busy

Delegation isn’t just about doing less — it’s about creating white space for strategy, creativity, and leadership.

Is It a You Problem or a Them Problem?

If delegation isn’t working, the next step is figuring out why. Here are 4 signs it might be you:

1. You’re Delegating Only Low-Leverage Tasks

Passing off 5–10 minute admin tasks is easy — but it won’t give you real relief. Instead, hand off high-impact tasks that don’t require your expertise.

2. You Haven’t Given a Runway of Context

If you want someone to take initiative, they need to know the big picture. Share your goals, your “why,” and even your random thoughts via quick voice notes.

3. Your Expectations Aren’t Clear

Don’t just say “I need the numbers.” Say: “I need these numbers by end of day tomorrow so I can review them before my presentation.” Context + clarity = ownership.

4. You Have Unrealistic Timelines for Proactiveness

Assistants need time to learn your business.

• First 4–6 weeks: Build rhythm and trust

• 6–12 weeks: Expect small suggestions

• 3–6 months: True proactiveness emerges

The Bottom Line

If you’ve handed something off but still feel burdened by it, run through this checklist. Ask yourself:

• Are they the wrong person?

• Or do you need to shift how you collaborate?

Effective delegation isn’t just about saving time — it’s about increasing your capacity for high-value work.