Why Delegating Feels So Hard and How to Finally Get It Right

Not long ago, I was coaching a leader who was frustrated by the sheer weight of his calendar. He told me, almost with resignation, “I can’t find time to focus on the big stuff that would really move the needle for the organization.”

I asked the obvious question: How’s delegation going for you?

He gave me the exact look I’ve seen from dozens of other leaders when I asked about delegating - part sheepish, part defensive. Like clockwork, he rattled off the greatest hits:

• “I don’t have time to delegate.”

• “It’s just easier if I do it myself.”

• “My team already has too much on their plate.”

• “I’m not sure I can trust someone else to get it right.”

Sound familiar?

I don’t want to diminish this reality: those reasons all feel valid in the moment. When you’re underwater, stopping to explain a task feels like one more burden. That’s the trap. You keep clutching everything close, and suddenly the work that matters most—the strategic, high-value stuff only you can do—keeps sliding further down the list.

Yet, delegation isn’t just about survival; it’s one of the rare leadership skills that produces a triple win.

• For the employee: they have an opportunity to develop while building trust with their manager.

• For the manager: they get back the one resource you never have enough of—time.

• For the organization: work happens at the right level, with stronger employees and leaders emerging as a result.

That’s the magic of delegation: one action, three wins.

The problem is that too many leaders treat delegation as a quick handoff of undesirable work.  Delegating is much more strategic than that.  Ultimately, effective delegating requires knowing what to delegate and how to hand it off in a way that empowers individuals to achieve success.

So, how do you actually do that?

What Tasks to Delegate?

The first stumbling block for most leaders is simply deciding what’s fair game to delegate. Everything feels important until you look closer. Two tools can help cut through the noise: the Eisenhower Matrix and the FOCUS Model.

The Eisenhower Matrix forces you to step back and classify tasks by importance and urgency. The process organizes tasks into four categories:

• Do it now: Urgent and important. These stay on your plate.

• Decide (schedule for later): Important but not urgent. Protect these from the day-to-day whirlwind.

• Delete: Not important and not urgent. (Yes, some work doesn’t need to be done at all.)

• Delegate: Urgent but not the best use of your time. These are prime candidates to hand off.

The FOCUS Model offers another lens to view delegating. It helps you view tasks not merely as items to delegate, but as opportunities for team member growth. By applying its categories, you can match the right project to the right individual. Thus, turning delegation into a strategic process rather than simply a random distribution of work.

• Flaws: Areas that are not your strengths

• Opportunity: Projects that stretch and develop others

• Confidence: Work you trust others to handle well

• Urgency: Time-sensitive tasks you shouldn’t hoard

• Strengths: Projects that better aligned with your team’s capabilities

When you start running your workload through these filters, you’ll be surprised at how much can move off your plate and how much more strategic space opens up for you.

Below is a one-page document summarizing the Art of Delegating. Feel free to download and share with your network.

How to Delegate Effectively?

Knowing what to delegate is only half the battle. The other half is how you hand it off. A careless handoff usually backfires resulting in rework and trust breakdowns. On the other hand, when done well, it builds confidence and commitment to completing the assignment. Here is the four-step approach I teach leaders to delegate effectively:

1. Clarify the Assignment

• Provide a clear description of the task or project

• Define the decision-making authority they have

• Explain the outcome you’re hoping they will achieve

• Allow time for questions and discussion before starting

2. Build Excitement

• Share why you chose this person for the task

• Emphasize how the assignment supports their growth and development

• Highlight the positive impact their work will have on the team or organization

3. Set Expectations

• Agree on what success looks like (specific outcomes or deliverables)

• Establish the method and frequency of updates (e.g., weekly check-ins, draft deadlines)

• Clarify how potential challenges or obstacles will be addressed

4. Provide Support

• Ask what support or resources they need to succeed

• Notify others affected by the handoff so roles are clear

• Reinforce your confidence in their abilities (“I trust you with this”)

Delegation for the Win

Delegation isn’t about offloading the work the manager doesn’t like. It’s about multiplying your team’s capacity, building trust, and regaining the bandwidth to lead at the level your role demands.

Now it is your turn, spend some time this week reviewing your calendar and identify one task/project/assignment that you have been holding onto and should delegate? Use the process outlined here to practice becoming a master delegator!

Let me know how it goes. Good luck.

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Andy Noon, PhD

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Andy