📬 In This Week’s Issue:
Why delegated tasks keep landing back on your desk
The hidden pattern behind stalled execution
The three phases of work every leader must understand
How to delegate without work boomeranging
How to help someone who gets stuck without redoing the work yourself
Setting the Stage
Every leader knows this pattern: you delegate a task, get a confident “Got it,” walk away feeling good… and a few days later the work is sitting back in your inbox.
Not because you asked for it.
But because it couldn’t move forward without you.
It’s frustrating, draining, and quietly erodes confidence in the team. I hear versions of this every week on coaching calls, in workshops, and from leaders who swear delegation “just doesn’t work” in their world.
And here’s the twist:
Most of the time, delegation doesn’t fail for the reason leaders think.
Before we get into the real cause, quick heads up: I’m hosting a free online version of my delegation + work-alignment workshop on Friday November 21. Enroll here.
Now let’s unpack the boomerang.
🔎 THE BIG INSIGHT
Delegation doesn’t fail because expectations are unclear. It fails because the work silently shifts into a stage the person isn’t built for.
Why Delegation Breaks (Even with Good People)
Work doesn’t move in one smooth motion. It moves through three phases. If you read last week’s newsletter, you saw how the middle of a project can fall apart. This week is another example of what happens when those phases get out of sync.
Ideation → Activation → Implementation
Different people thrive in different phases, and that’s the real source of most delegation problems. Some people love imagining and exploring possibilities. Some naturally organize, plan, and structure. Some get energy from pushing work forward and finishing.
Problems start when the task you delegated change phases… but the person doesn’t.
You delegate something that starts in a phase they’re comfortable with. Then the work moves into a phase where they struggle (usually without warning). Momentum slows. Confidence drops. They hesitate. They try to keep up, but they can’t create forward motion.
And that’s when the work returns to you.
It’s not intentional.
It’s not malicious.
It’s not laziness.
It’s misalignment.
The Boomerang Pattern
Here’s what it looks like in real life:
You assign a task.
They start strong.
Progress stalls.
They ask for a quick check-in.
You step in to “help.” You take a little more.
You finish it because the deadline is close.
Then you think: “I guess it’s just easier if I do it myself.”
But the real issue was never effort. It was the phase of work.
When someone gets assigned a phase that drains them, the work always boomerangs:
They don’t know where to start
They can’t build momentum
They wait for more clarity
They overthink the next move
They avoid the task
They quietly hope someone notices they’re stuck. They almost never say it out loud. They just hand the work back to the safest place it can land: you.
How to Delegate Without the Boomerang
Here’s how to change the pattern without micromanaging or doing it all yourself.
Match people to the right phase of work. Before delegating, ask yourself: “Which phase is this task in and who thrives there?”
If the task is early-stage, give it to someone who loves exploring possibilities.
If it’s planning-heavy, give it to the person who thinks in systems and structure.
If it’s near the finish line, give it to the person who finds joy in pushing things across it.
Delegation works when the phase and the person match.
Be clear about which phase you’re handing off. Most leaders delegate tasks. Great leaders delegate stages. Say something like:
“Here’s the phase you’re leading. Here’s what ‘done’ looks like before it moves to the next stage.”
That one line removes 80% of boomerangs.
Build cleaner handoffs. This is where most teams fall apart. A strong handoff answers three questions:
What exactly has been completed?
What is the next action?
What decision needs to be made before work can continue?
Good handoffs keep work moving. Bad handoffs send it straight back to you.
When someone gets stuck, don’t take it back. Instead, diagnose the phase If someone is stalled, resist the urge to jump in. Simply ask:
“Which part of the work is unclear or draining for you?”
They will tell you the phase. Then you can adjust ownership or walk them through it without owning the whole thing.
💬 READER QUESTIONS
Q: “How do I get comfortable delegating things I know I’m better at?”
Start by delegating based on stage, not skill. If the person thrives in the stage the work is currently in, they’ll often outperform you because it energizes them. Skill can be coached. Natural wiring can’t be forced.
Q: “How do I avoid redoing someone’s work?”
Set the checkpoint earlier. Feedback after the work is done almost always leads to redos. Feedback during the stage they’re responsible for creates alignment without rework.
Q: I feel guilty delegating work I don’t enjoy. Is that normal?
Yes, but misplaced. Work you dislike is usually work someone else loves. Delegation isn’t dumping. It’s aligning.
~ Chad Todd
Delegation doesn’t fall apart because people aren’t capable. It falls apart because the work moves into a phase they’re not built to lead. Match the work to the person, tighten the handoffs, and the boomerang stops showing up in your inbox.
P.S.
I’m hosting a free online version of my Working Genius workshop on Friday November 21. I will walk through the three stages of work, explain the 6 types of people that work for you, diagnose where delegation dies, and give you tips to delegate in a way that everyone wins.