Delegate It

Why Delegation Keeps Breaking (and What to Do Instead)

By Scott Drake
Founder

Delegation is often treated like a simple handoff. The task gets passed along. The expectations seem clear. The deadline is on the calendar.

And then something goes sideways. The result misses the mark. A question stalls progress. The timeline slips.

Eventually, the work returns—partially done, off-course, or back in the delegator's lap.

There's no shortage of advice about delegation. But what rarely gets addressed is why it fails.

Most teams treat delegation as intuition, not a structured skill.

Here are three of the most common breakdowns in delegation.

1. Delegation Strategy Doesn't Match the Situation

Most managers use one default approach to delegation: assign the work, step back, hope for the best.

But there are different types of work. Delegating a routine task is one thing. Delegating a problem to solve or a project to lead is something else entirely.

That's where the 12-Strategy Delegation Framework comes in. It categorizes delegation across two dimensions:

  • Type of work: Task, problem, or management
  • Level of trust: From low trust (needs direction) to high trust (can lead with autonomy)

When delegation isn't working, it's often because the strategy didn't match the moment.

Try This Today:

Before handing something off, ask:

  • What type of work is this? Is it a simple task? A problem to be solved? An on-going management responsibility?
  • How much do I trust the person? Do they have experience doing this kind of work? Have they delivered well in the past?
  • Which of the 12 strategies is best for this type of work and my level of trust in the person?

Example:

  • A team member new to client-facing work might need you to stay more involved.
  • A seasoned ops lead handling a recurring task needs you to give more space.

See all 12 strategies here→

2. Delegation Happens Without Real Agreement

Delegation often begins with a simple question:
→ "Can you take this?"

And just as often, it ends with confusion:
→ "This isn't what I expected."
→ "I thought we were aligned."
→ "There was no plan for when things went off track."

These are signs of missing agreements.

Most delegation stops at logistics: the task, the deadline, maybe some background.

That's an assignment, not an agreement.

Try This Today:

Instead of assigning the work, take a moment to co-create an agreement.

Ask:

  • "What does success look like?" → Focus on the outcome, not just the activity.
  • "What could make this harder than it looks?" → Identify risks early while there's still time to shape the approach.
  • "What support will be needed—when, and from whom?" → Agree on where autonomy is expected and where input is available.
  • "When should we check in, and what will we review?" → Set a rhythm for alignment without hovering.

Five focused minutes of agreement-building can prevent five hours of cleanup later.

More importantly, these conversations signal respect. They tell the person receiving the work: Your success matters enough to be defined well.

3. Delegated Work Gets Pulled Back Too Soon

Even when delegation starts strong it can still quietly fall apart.

Many managers step back in the moment something feels off:
→ Progress slows
→ Questions pile up
→ Results look different than expected

They reclaim the work. Sometimes directly. Sometimes subtly.

Not because it can't be done. Because it doesn't feel like it's working.

This is where most delegation quietly dies. Not at the start, but at the first sign of friction.

The Real Issue: Want-To and Follow-Through

What's often misdiagnosed as a skill gap in the worker is actually a desire- and discipline- gap in the manager.

Letting go of work—especially meaningful, high-stakes work—requires:

  • Want-To: a belief that working through others is worth the tradeoffs
  • Follow-Through: a willingness to stay with the discomfort when things aren't smooth

Managers must be taught to expect discomfort.

→ Workers will have questions.
→ Workers will make mistakes.
→ Workers will go through learning loops, especially in delegated problem solving.

Managers go through learning loops too. It's just more obvious when someone else is doing the work.

These are areas where managers need discipline and workers need support.

Instead, this is exactly when many leaders lose patience and take the work back.

Try This Today:

If the urge to take work back kicks in, pause and turn the attention inward.

Ask:

  • Why is this uncomfortable right now? → Is it about the quality of the work or the loss of control?
  • Did I delegate this using the right strategy for the situation and trust level? → Was this a task, a problem, or a management responsibility, and did I match that?
  • If I had kept this work, would I be hitting the same questions or roadblocks? → Is what's happening now just part of the normal learning curve?
  • What story am I telling myself about what this means? → That this person can't handle it? That I'll be blamed if it fails?

Discomfort doesn't mean delegation is failing. It's a learning opportunity for the manager to resist the urge to step in.

Taking over is easy. Restraint is the skill that makes delegation stick.

Closing the Loop

Delegation isn't a single act. It's a system of choices—about what to hand off, how to support it, and whether to stay with it when things wobble.

The patterns that break delegation are often predictable. But so are the ones that make it work.

With the right strategy, clear agreements, and follow-through, managers can delegate better.

If that's the goal, check out Leadership Made Real. It gives managers a step-by-step path to grow the habits and mindset that actually work.

No fluff. Just practical, tested tools—and the space to build real momentum.