The Mindset Of Delegating Imperfectly

Ever catch yourself hesitating to delegate because your assistant "might not do it right"?

That hesitation actually costs a good amount.

Instead, the most skilled delegators have shifted their mindset from “Is this done perfectly?” to “Did I get any value from this?”

Hidden Math of Delegation

Here's a simple way to think about it:

→ If you delegate 3 tasks per week with 100% success, you get 3 wins.

→ If you delegate 20 tasks per week with 50% success, you get 10 wins.

The more you delegate, the more leverage you get - not just from the sheer number of tasks handled on your behalf, but also in compounding your assistant’s knowledge and skills by giving them more feedback.  

Why Perfectionism Kills Productivity

There are two big ways to look at delegation: Perfectionism and Value-First.

A perfectionist mindset resembles this:

❌ "Is this done exactly right?"

❌ Delegates 3 tasks per week

❌ Spends hours reviewing work

❌ Progress is glacial at best

A value-first delegator has a different mindset that looks more like:

✅ "Did I get any value from this?"

✅ Delegates 20 tasks per week

✅ Makes quick yes/no value judgments

✅ Progress is compounding

If only 20% of delegated tasks create value, but you delegate 5x more tasks, you're still ahead.

Why Most People Get Stuck

The vast majority of fear isn't about perfection, but about risk.

Some tasks can create negative value:

• Sending wrong information to clients
• Making incorrect financial decisions
• Mishandling sensitive data

But what separates skilled delegators is that they know how to categorize tasks.

For example, here are task categories sorted by risk level:

1. Zero-Downside Tasks
   • Research summaries
   • Data organization
   • First drafts
2. Limited-Downside Tasks
   • Internal presentations
   • Process documentation
   • Project updates
3. High-Risk Tasks
   • Legal documents
   • Financial transactions
   • Client deliverables
   • Strategic decisions

How to Start Delegating Imperfectly to Get More Done

Imperfect delegation takes time and practice to feel comfortable. To begin, we'll break down the transformation into manageable steps.

Start with Zero-Downside Tasks

• Question: "What's the worst that could happen?"
• Answer: "We waste some time"
• Action: Delegate freely

Set Value Thresholds

• For research: "Find me 3 useful insights"
• For analysis: "Identify 2 actionable recommendations"
• For summaries: "Capture the main decision points"

Create Quick Feedback Loops

• 2-minute review: Scan for value
• Binary decision: Use/Don't use
• Fast iteration: "Try again with this angle"

Measuring Success

What gets measured, gets managed. What gets managed, gets done.

While this might seem like a purely qualitative skill, these key indicators help you track your transformation and identify areas for growth. Track these:

1. Number of tasks delegated
2. Time spent reviewing delegated work
3. Valuable insights gained (even small ones)
4. Tasks that led to action

Your aim shouldn’t be a 100% success rate, but rather positive expected value over time.

Conclusion

Progress isn't about perfection. It's about momentum. Even a "bad" delegation might surface one insight you wouldn't have thought of. That alone makes it valuable.