Why delegation keeps turning into a time sink

If you want to get better at delegation, stop saying so much!

That line usually makes managers uncomfortable, because most of them believe the opposite. They assume clarity comes from explanation, context, and thoroughness. If they just explain it well enough, the other person will understand, align with it, and execute.

But the popular approach to delegation gets them into trouble, and I see this pattern frequently in clients.

A manager wants help with something that is perfectly reasonable to delegate, but instead of starting the conversation cleanly, they start with a story. They explain why the task exists, how it came to be, what happened last time, who else was involved, what might go wrong, and how busy everyone is right now. Five minutes later, they finally get to the ask.

By that point, the other person is dazed and confused.

What should have been a simple delegation turns into a rambling download of context that blurs the point of the conversation. The manager believes they were helpful, but the delegate feels like they were sprayed with a firehose, and confusion sets in.

Here’s what this typically sounds like.

Instead of starting with: “Hey Bob, I need your help.” 

The manager starts with: “So, as you know, we’ve been trying to clean up this process for a while, and last quarter we ran into some issues because the timeline slipped, and there were a few stakeholders who weren’t looped in, and I don’t want that to happen again…

Can you see how unnecessary all of this background is?

A far more effective opening sounds like this:

“Hey Bob, I need your help. Can you do the X by Friday?”

That’s it.

That sentence does three important things immediately. It signals respect. It creates clarity about what is being asked. And it establishes a commitment before anything else gets layered in.

Once you get a commitment, you can stop.

Or, if they ask for context, you can provide it.

That sequencing matters more than most leaders realize.

When you lead with backstory, you force the other person to process information before they know what they’re responsible for. They’re trying to listen, interpret, and guess where the conversation is going all at once. That’s when meaning starts to drift. They latch onto details that don’t matter and miss the ones that do.

Word count is the hidden enemy here.

When you use too many words upfront, you dilute the point of the conversation.

Constraints feel fuzzy. Decisions seem provisional, and the delegate isn’t sure what’s fixed and what’s flexible, so they come back with questions, half-solutions, or requests for reassurance. The manager then explains further, trying to clear up the confusion they just created.

That’s how delegation turns into a time sink.

One of the most useful rules I give leaders is simple: 

Your job is to delegate the work with as few words as possible.

Do NOT overexplain, check in a million times, clarify, re-clarify, and hover.

Make a request, confirm commitment, pin down a schedule, and STOP TALKING!

There’s a massive benefit to saying less.

When you stop over-explaining, you save yourself a ton of time. You give the other person space to think. You allow them to engage with the work rather than react to your narrative. You communicate trust, whether you intend to or not. And over time, people become more capable because they’re not being walked through every decision in advance.

This is a subtle shift, but it’s powerful.

Move your attention away from how clearly you are explaining to how cleanly commitments are established. 

And resist the urge to tell the whole story.

Start with the ask.

Get the commitment.

Pin down the schedule.

Then get out of the way.

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Matt Cross

Matt Cross is a speaker, author, and advisor with expertise in leadership, change, and teamwork. He is the author of Subtle Shifts: Simple Strategies for Sustainable Success, which explores the power of small, intentional adjustments to inspire lasting change.
 Matt regularly speaks at Fortune 500 companies and works with executives, entrepreneurs, and emerging leaders from some of the world’s leading non-profits. His popular email newsletter, The Subtle Shift, helps leaders get to the next level and unlock new possibilities for leading with clarity, confidence, and composure.