Delegation: Letting Go to Lead Forward

What am I holding on to that someone else could take on, learn and grow from?

One of the most surprising themes that consistently emerges in my executive coaching work—even with seasoned, senior leaders—is delegation.

You might assume that leaders who have reached the upper echelons have mastered the art of delegation. And yet, when I sit down with these high-performing executives, the struggle is real. Why? Because the higher they go, the more they carry. Not just responsibilities—but habits, perfection standards, and deep attachment to work they’re great at.

In fact, delegation often surfaces as the hidden key to unlocking time and energy for the very strategic initiatives and bold ideas they dream about but never have the bandwidth for.

The Starting Point: What Does Successful Delegation Look Like?

I begin with this deceptively simple question:“What does successful delegation look like for you?”

After some reflection, leaders usually respond with clarity:

• Being strategic in knowing what to delegate,

• Understanding when to delegate,

• Figuring out how to delegate so outcomes remain high-quality, and

• Creating space for me to focus on more strategic, visionary work.

So Why Is Delegation Still So Difficult?

When we dig into this, common themes emerge.One big one: perfectionism.

Executives often say:

“I’ve honed this process to a fine art. What if someone else doesn’t do it as well?”

The worry isn’t trivial—client outcomes, team performance, and reputational risks are at stake.

So I ask:“What might still be possible if your team does the work—but you preserve quality and client trust?”

This unlocks new thinking:

• “I could oversee the blueprint and review before final delivery.”

• “I could coach the team member along the way.”

• “I could proactively delegate early to allow time for iterations.”

• “I could proactively manage client expectations.”

What begins as resistance shifts into designing delegation, not just defaulting to it.

Beyond Skill: The People Dynamics of Delegation

Another area where leaders stumble is understanding who to delegate to.

They share scenarios like:

• “My team member isn’t skilled yet, but has great attitude and wants to help.”

• “This person has the skill—but lacks commitment because they’re bored or disengaged.”

So we explore:“How would you know which situation you’re facing?”

Often, the answer is intuitive—they already know, based on their relationship and history with the individual.

Then my clients developed strategies:

• For the motivated learner:“I’ll shift into teaching mode, provide support, and use this as a development moment.”

• For the skilled but reluctant:“I’ll reframe the task, involve them in solutioning, and spark ownership through empowerment.”

Delegation becomes not just a transfer of tasks—but a leadership move that balances empathy, inspiration, and stretching.

Who You Need to Become to Delegate Well

Ultimately, my clients walk away realizing that successful delegation isn’t just about others—it’s about who they need to become.

To delegate effectively, leaders must embody:

• 💡 A teaching mindset

• 🧭 A strategic lens

• 💬 A coach’s curiosity

• 🧘🏽‍♂️ Tolerance for imperfection

• 🛠️ A thoughtful balance between monitoring and trust

They realize:You don’t stop being involved—you evolve your involvement.You don't relinquish quality—you reengineer how it's ensured.You don’t lose control—you gain capacity.

The Payoff: Leadership That Multiplies

When leaders make this shift, three things happen:

1. Their teams grow—capability, confidence, and accountability.

2. Their clients benefit—from deeper, more strategic engagement.

3. They themselves finally create space—to work on the business, not just in it.

The journey is challenging—but the return is exponential.

If you're an executive wrestling with delegation, pause and ask yourself:

What am I holding onto that someone else could grow from?What could I gain if I let go?

Call to Action: Is strategic delegation to improve your bandwidth critical for your leadership success? Feel free to book a complimentary Discovery call, using that option from my website: www.SuccessSupport.ca

Back to my LinkedIn post