Delegation is hard.

When wrong tasks are entrusted humans or AI who don’t deliver, you end up drowning in work. Bad delegation leads to more work (fixing leaks) than you had in the first place.

But when leaders delegate correctly, they gain leverage and build great companies.

I use a 5-level ladder to match each job with the right owner and win back my time.

The Delegation Ladder

Level 1: The Instruction Follower

These are people (or AIs) that need explicit direction for every step you want them to take when performing a task.

Detailed Loom videos are your friend here. When you ask them to fill out a Google Sheet, you need to create the column headers and tell them which data goes where.

You: "Turn the wheel 30 degrees left at the stop sign."

Them: Turns exactly 30 degrees left at the stop sign

This is how McDonald's built a $200B empire. They have everything laid out to a T — from French fry cooking time to the exact script for greeting customers.

Ray Kroc developed a 75-page manual that detailed everything in precise specs.

Level 2: The Navigator

Amazon's two-pizza teams operate here.

Jeff Bezos would give teams a clear destination (reduce checkout friction by 50%) but let them choose the path.

The result leads to features like 1-click order. It helps Amazon generate billions in revenue because teams have autonomy within boundaries.

You: "Get us to the airport."

Them: "Should I take the highway or back roads?"

Level 3: The Trip Planner

When Brian Chesky was scaling Airbnb, he hired Belinda Johnson as their first executive.

His directive was simple: "Fix our legal problems."

They didn't know what legal challenges they would face or how complicated solving them would be, but Belinda built an entire government relations strategy that turned regulators from enemies to partners.

You: "We need to be in Boston by Friday."

Them: Book flights, arrange transport, handle logistics

Level 4: The Co-Pilot

Netflix's famous culture deck describes this perfectly: "We don't seek consensus, we seek excellence."

When Reed Hastings noticed declining DVD rentals, Ted Sarandos didn't wait for instructions. He proposed investing $100 million in original content — a strategy that transformed Netflix into a $240 billion company.

You: "We're losing East Coast market share."

Them: "I've analyzed three expansion strategies. Here are the trade-offs..."

Level 5: The Radar

This is Susan Wojcicki at Google.

Before YouTube's acquisition was even on Larry Page's radar, she was already analyzing the threat and building the business case. She saw the $1.65B opportunity before her CEO did.

You: Don't even know there's a problem yet

Them: "I noticed our competitor's hiring pattern suggests they're entering our market. I've prepared our response."

Delegating To AI

AI is climbing this same ladder right now.

Today's AI operates at Levels 1-3:

• ChatGPT can follow exact prompts (Level 1)

• Claude can draft emails with general guidance (Level 2)

• Workmate autonomously manages your calendar (Level 3)

Tomorrow's AI will reach Levels 4-5:

• AI teammates will identify opportunities

• Systems will make strategic recommendations

• Agents will solve problems before you know they exist

3 Simple Truths

1. Not everyone needs to reach Level 5

A Level 2 support person might be perfect for that role.

But your head of engineering has to be operating at Level 4-5.

2. People operate at different levels for different work

Your CMO might be Level 5 on strategy but Level 3 on budget management.

That's normal and, in many cases, optimal so they can focus on their areas of strength.

3. Mismatched levels kill productivity

Giving Level 5 autonomy to someone who needs Level 1 structure creates chaos.

Providing Level 1 instructions to a Level 5 performer can create resentment and lead to turnover.

Bottom Line

In order to grow fast and build leverage, everyone needs to learn the art of delegating.

If you try to implement delegation on the fly, you will stall your own growth and that of the person you are delegating to.

Start thinking about it as a ladder where you match the right level of autonomy to the right type of work and the right person's capabilities. And see the output grow beyond your imagination.

Until next week,

David Lobo

Head of Growth, Workmate

P.S. Where do you see AI climbing the delegation ladder in your organization? I'd love to hear your examples.

P.P.S. Workmate is building toward Level 4-5 delegation for executive assistance. We're starting with calendar management (Level 3) and expanding from there. Join the waitlist.