Delegation Is Difficult. And What Makes it Easier.
Delegation is one of the most complex leadership skills you'll develop.
There are multiple moving parts, lots of places it can go wrong, and most of the advice out there makes it sound way simpler than it actually is.
"Just delegate more." "Empower your team." "Let go and trust."
Right. Thanks for that.
Meanwhile, you're juggling a dozen different variables:
Is this person ready?
Will they understand what I need?
What if they mess it up?
How much guidance is too much? How little is too little?
And underneath all of that is the real problem nobody talks about.
We're guessing what people can handle. And guessing isn't a strategy.
Think about your last delegation attempt that didn't go well.
I bet it wasn't because you gave bad instructions.
It was probably because you misjudged something fundamental: either what the task actually required, or what the person could actually deliver.
Maybe you thought they could work independently, but they needed more check-ins.
Maybe you thought it was straightforward, but there were more moving parts than you realised.
Maybe you thought they'd take ownership, but they just completed tasks.
The result?
It lands back on your desk. Your stress goes up. And you think, "I'll just do it myself next time.".
What if you could stop guessing?
Here's what I've learned working with frontline leaders: delegation gets dramatically easier when you can accurately assess two things:
What the task actually demands
What the person is actually capable of
Not what you hope the task requires. Not what you think the person can do. What's actually true.
Most leaders skip this step. They look at a task and think, "Sarah could probably do this." Then they hand it over and hope for the best.
But every task has invisible requirements. Every person has specific capability patterns.
When you can see both clearly, delegation becomes strategic instead of hopeful.
A quick example
Let's say you're thinking about giving the monthly team newsletter to Sarah.
First - does she have the basic skills?
Can she write professional communications? ✓
Does she know our company communication standards? ✓
Can she use the design/email software? ✓
Does she understand what content to include? ✓
Skills check: Yes. This is delegation, not training.
What does the newsletter actually demand?
Working independently for weeks at a time
Coordinating with multiple people for content
Making judgment calls about what to include
Taking complete ownership of quality and deadlines
Managing monthly pressure and visibility
What can Sarah actually handle?
She works well alone but likes regular check-ins
She manages multi-step projects effectively
She makes good judgment calls consistently
She always follows through on commitments
She stays steady under normal business deadlines
The match? She can handle this. Her capabilities meet what the task actually requires.
The conversation:
Sarah, I’ve been thinking about our monthly newsletter and I’d like you to take it over.
You’ve shown you can handle this kind of coordination work - the way you managed the training logistics last quarter, and how you stay on top of the client reports, tells me you can juggle the moving parts and follow through reliably.
What I need is a quality newsletter delivered on time each month that keeps the team informed and engaged. You know our communication standards, and you’re good with the systems, so I’m confident you can run with it.
Let’s plan for you to check in after you’ve done the first content outline, probably next Friday and then we can set up a regular rhythm from there.
What questions do you have before you get started?
Done. No guessing. No crossed fingers.
When the match isn't there
This is where most delegation advice falls apart. It tells you to "just delegate" but doesn't help when the person isn't quite ready.
Your assessment might show Sarah has the skills for the newsletter, but her independence is LOW while the task needs MEDIUM. She completes tasks well but always waits for direction on next steps.
Now you have options instead of just hoping:
Option 1: Add structure
Give her the newsletter with more check-ins and clearer milestones: "Sarah, I want you to handle the newsletter. Let's break it into phases - content planning by Monday, first draft by Wednesday, final version by Friday. Check in with me at each stage and we'll review how it's going."
Option 2: Start smaller
Give her part of it first: "Sarah, I'd like you to handle gathering the content for the newsletter this month. Once you've got all the articles, bring them to me and we'll work on the layout together.
Option 3: Wait and develop
If the gap is too big, keep the task but create opportunities to build her independence first with smaller projects.
The key is you're not guessing why it might not work, you can see exactly where the gap is and adjust accordingly. Instead of delegation mysteriously failing three weeks later, you can set it up for success from the start.
This changes everything
When leaders learn to assess accurately instead of guessing, delegation becomes a strategic tool for building capability, not just a hope that someone else can help with the workload.
Ready to stop guessing?
This systematic approach to delegation is one of seven modules we cover in Leadership Essentials - practical frameworks for the complex leadership challenges frontline leaders face every day.
Next cohort starts 3 February 2026 - let me know if yo’d like to join the wait list and early bird pricing.
Because figuring out delegation through trial and error is exhausting. And expensive.
