Why Delegation Is Hard—and What to Do About It
For high-performing leaders, delegation is a strategic necessity
Most high-achieving professionals know they should delegate more. Yet when the moment comes, many revert to doing everything themselves. The familiar justifications sound like this:
- “I can do it faster myself.”
- “Teaching someone will take more time.”
- “I don’t want to burden others.”
These reasons feel legitimate. But over time, they place a ceiling on your leadership impact. You may get today’s urgent work done, but you don’t scale. Your team doesn’t grow. And the organization becomes dependent on you. If you’re unavailable—even for a few days—everything stalls.
So why is delegation so hard, even when we agree it’s important?
Why Delegation Fails
1. You wait until you’re overwhelmed.
Most people only think about delegating when they’re in over their heads. At that point, they lack the time, patience, and energy to train someone else. Delegation under pressure becomes rushed, stressful, and ineffective.
2. You treat delegation as a one-time handoff.
Effective delegation is not “Here—can you take this?”
It’s a cycle of teaching, observing, coaching, and adjusting. Leaders often underestimate this investment. When early attempts feel inefficient, they conclude, “It’s faster to do it myself.”
3. You see asking for help as burdening others.
This hidden belief blocks many leaders. In reality, high-potential employees want stretch assignments. Delegation gives them visibility, new skills, and a path to the next level.
4. You tie your value to doing, not leading.
Many leaders built their careers on being competent, reliable, and the one who “gets things done.” Handing off meaningful work can trigger a quiet fear:
“If I’m not doing the hard tasks, what is my value?”
This keeps them stuck in execution instead of leadership.
5. You fear losing control—or seeing imperfect results.
Perfectionism (even subtle perfectionism) undermines delegation. If the delegated work doesn’t look exactly like your version, it can feel wrong—even if it meets the actual goal.
6. You’ve been burned before.
If a previous delegation attempt resulted in poor quality or a missed deadline, your brain creates a shortcut:
“Delegation is risky.”
However, often the real issue was unclear expectations, the wrong person for the task, or a lack of follow-up—not the act of delegating itself.
7. You fear becoming less relevant.
A surprising number of leaders worry:
“If I’m not doing the work I know, I’ll have to figure something new… and I won’t feel as confident.”
Research from the Center for Creative Leadership (CCL) supports this. In a study of 498 senior leaders, individuals were 72% more likely to stick with efficiency tasks, such as execution, rather than exploration tasks, like innovating. Delegation often requires stepping into that more uncertain, exploratory space.
What To Do Instead: Practical Delegation Strategies
1. Plan early—before you’re overwhelmed.
Delegation is easiest when you’re not in crisis mode. Identify a few tasks ahead of time that you can gradually hand off.
2. Start small.
Choose low-stakes tasks first. This builds confidence for both you and your team.
3. Choose the right person—based on more than skill.
Consider their:
- Interests
- Growth goals
- Need for visibility
- Capacity
And remember: if you always delegate to the same strong performer, they eventually become the bottleneck.
4. Make time for coaching, allow autonomy, and learning.
For a successful delegation, you’ll need to make time for:
- A brief alignment meeting before they begin
- Check-ins at logical milestones
- A quick debrief afterward
- Allow room to try and learn
5. Normalize that you’re not asking for a favor.
Delegation is a win-win-win:
- You free up time for higher-value work.
- They develop new skills and confidence.
- The organization becomes more resilient because you’re no longer the single point of failure.
What Not to Delegate
- Your self-worth. Delegation doesn’t lessen your value—it elevates your leadership.
- Your boundaries. You don’t need to overextend yourself to prove you’re still contributing.
Partner With Your Management in the Process
Delegation often becomes difficult when ownership is unclear. Leaders sometimes take on responsibilities without understanding that certain decisions or bottlenecks require managerial involvement—not individual heroics.
Remember:
Your boss(s) are part of your “team.”
If something is beyond your scope, looping them in is not incompetence—it’s leadership.
A Real Story: How One High Performer Became a Scalable Leader
One of my clients, Stephan, a VP at a Fortune 200 company, was known as the person who could rescue any project. But that reputation came with a cost—he was exhausted, always “on,” and constantly stepping in when his team struggled.
Through coaching, he realized that his need to protect the work was actually preventing his team from growing. He began experimenting with what he called “controlled failure”—stepping back enough for others to learn while mentoring them behind the scenes.
What he did:
- Stopped rescuing his team in client meetings.
- Set clearer expectations and provide guidance.
- Created room for his team to “fail” and learn.
Here is what happened next:
- The team rose to the occasion.
- Peers became more accountable.
- And for the first time, he felt like he was leading, not firefighting.
It took time and patience, but he was commited. As he put it:
“It was neither easy nor quick. But it was the only way to scale my impact and influence.”
Read Stephan’s full story here.
Final Words
Delegation and coaching are often given as simple advice to high-performing leaders. But they are not quick, one-step actions. They require clarity, planning, and a willingness to shift your mindset.
When you treat delegation as a long-term strategy—not a last-minute maneuver—you not only empower your team, you unlock your own capacity to lead at a higher level.


