Delegation Tips

When a CEO meets their board, they tell them “here’s what I’ve been doing” (a 7) and I’m about to (5).

When an entry level person starts as a waiter, they say “tell me what to do”

Everyone else sits on in between on “rungs” of the ladder.

To get promoted, naturally take yourself up the ring by understanding what is most valuable to the company and providing it

Look at your last 10 emails to peers or senior people.

Now jump up 2 rungs in your next 10 emails.

If you’ve been asking “what do I do?” start saying “I think I should,” instead of “I see” start saying “I recommend”

Watch your career soar, now let’s flip to the manager:

You’re an expert twitter🧵 writer and starting a twitter agency. You are a 7.

You hire an entry level person and it’s not working out.

You’ve been managing them at the 5/6 level asking “what did you do?”

Instead, they need you at the 1/2 level: “do this.”


Ensure they consistently deliver what you tell them at “level 1.”

I call this the ‘triangle of success’: do they deliver what you asked, on time and above the quality bar indicated?

Once they do, start to stretch them!

Ask what they think. Ask what they recommend!

Inviting your reports to move up the ladder gives you leverage and helps them grow.

It’s the ultimate win win.

“But Jesse, I hired a VP and managed them at 5 and it didnt work!”

“I hired a new VA managed them at a 2 – they quit!”

It turns out very senior people can be total beginners for some tasks.

On the flip, junior people may be didn’t experts in specific tasks.

The key concept here is: Task Relevant Maturity

TRM is a simple concept with a long name: how well does the person know how to do the task they’ve been given?

Every single person is at a different place in their development.

And that development level is unique for each and every skill!


I am an expert in growth marketing – I could easily fly at level 6/7 and just update people on what I’ve been doing.

I am a total beginner in setting up a 3PL – someone tell me what to do!

If someone senior or mid-level isn’t delivering, ask them about their TRM!

The key to making this work in a fluid way is to make talking about the LL and TRM a normal part of everyday work discussions.

Examples of what this will sound like:

“Jump up on the LL and make a recommendation!”

“I’m new to TikTok. Can you jump down the LL for me?”

The last item on the list is “the situation”

At times, there’s either an opportunity so meaningful that the leader wants to operate with total control.

This is rare and temporary (~1/year). Communicate it clearly to your team.

Then follow daily check-ins and be hands on.

So to review the secrets of delegation:

+ Learn and study the LL and TRM

+ Make both normal vocab in your org

+ For any given task, discuss the persons TRM and agree on where you both want to be on the LL

+ Stretch people by jumping up 2 rungs

+ Make space to calibrate/grow