Why Smart Leaders Still Struggle to Delegate

“How do I delegate more effectively?”

If I had a dollar for every time I’ve heard that question from brilliant, accomplished professionals, I’d be writing this from my yacht. (Spoiler: I’m not. I’m sitting in my kitchen, procrastinating from folding laundry.)

But here’s the truth: most of the time when people ask how to delegate better, they aren’t struggling with the mechanics of delegation. They’re struggling with… not wanting to be disliked.

Yep. That’s the real blocker. Not delegation. Not communication. Not even prioritization. It’s the old, familiar fear of coming off as “too much,” “too bossy,” “too demanding,” or “not nice.”

The Real Symptoms of Delegation-Phobia

Let’s look at some of the telltale signs that a leader is masking people-pleasing with a delegation “challenge”:

• They assign a task but say, “No rush, whenever you can get to it,” even when it’s actually needed by Thursday.

• They give feedback that sounds like a compliment sandwich inside a compliment burrito: “I really love what you did here, and honestly it’s amazing, I just had one super tiny thought… but if you disagree that’s totally fine too.”

• They hesitate to follow up—because they don’t want to “micromanage.”

• They tell themselves someone else should know how to do something, but they don’t actually ask or clarify.

Sound familiar?

Here’s the kicker: these behaviours aren’t about a lack of knowledge. Most professionals know how to delegate. They’ve read the books. They’ve taken the trainings. They get the process.

What they’re really asking is: “How can I get others to do things without them thinking I’m a jerk?”

The People-Pleasing Trap

Here’s what people-pleasing does in leadership:

It creates vagueness where clarity is needed. It sacrifices the health of the team to preserve the comfort of the leader. And ironically, it leads to exactly the thing you were trying to avoid: people being frustrated with you.

People pleasers in leadership roles often convince themselves they’re being kind by not setting deadlines or clearly stating expectations. But kindness without clarity creates confusion. And confused people don’t perform well.

A Few Gentle Wake-Up Calls

If you’re struggling with delegation, ask yourself:

• Am I avoiding a direct ask because I fear how the other person will feel about me?

• Am I softening expectations so much that they’ve become invisible?

• Do I use vague language to “keep the peace” rather than create alignment?

If yes, congratulations—you don’t need a lesson in delegation. You need a little self-coaching in confidence.

So, What Can You Do?

Here’s what works:

1. Be Kind and Clear: Saying “I need this by end of day Thursday” is not aggressive. It’s respectful of everyone’s time.

2. Say the Quiet Part Out Loud: If you’re worried about tone, say so: “I want to be really clear here, not pushy.”

3. Practice Discomfort: Delegation will feel uncomfortable at first. Do it anyway. Growth rarely feels cozy.

4. Remember: Likeability Isn’t Leadership: Great leaders are respected, not just liked. Focus on impact over approval.

The Bottom Line

You don’t need to be more capable to delegate. You need to be more willing to be clear, even if it risks a raised eyebrow or awkward silence.

Delegation is not about unloading tasks. It’s about owning your role as a leader, and letting others own theirs.

And yes, sometimes that means you won’t win “Most Popular” at the office party. But you will win back your time, your sanity, and maybe even your weekends.