This week in the world’s #1 newsletter on leadership communication:

How to Delegate (and Get Your Life Back)
On the Show: How to Become an Inspirational Leader (According to Science)
Book Recommendation: Is Your Leadership Style Oversized Sweatpants?

How to Delegate (and Get Your Life Back)

Delegation is not just a skill – it is pure leverage. World-class leaders are world-class delegators.

It took me years to develop the skills and to shift my attitude from “I can do it best!” to “who can do this better and faster?”

Today, I have an executive assistant, a virtual assistant, a marketing lead, a designer, a podcast editor, an accountant, and a cleaner. None of them are full time, I rather collaborate with the best in their fields for as many hours as necessary.

When needed, I also have a driver (= Uber) and a chef (apps for food delivery and ready-made, healthy meals).

Must be nice, you may think, and I had the same mindset. But if you earn more than a cleaner, then not having a cleaner actually costs you money.

A lot can go wrong when delegating. Dumb delegation means that you constantly have people asking you for clarification or doing things the wrong way.

Smart delegation allows you to focus on what’s important instead of what’s urgent, so that you can create more impact in your life and career.

Here is my system for smart delegation that I often share with my 1:1 CEO coaching clients. If you implement it, you will have more time and money (provided you reinvest the time), but more importantly, this is about your health and the life you want to live.

I only have so much time left on this planet, but lots of cool stuff I want to do. Tasks that I do not enjoy but other people do are the first to go. Plus: not having to deal with 100 little tasks a day keeps the burnout away.

1/ Eliminate - Automate - Delegate

Eliminate

Does this have to be done at all (now)? What would happen if I ignored this?

Automate

Is there a tool for this? Can AI do it? Can I create a workflow? If you are doing something more than once, chances are you can create a workflow and put it on autopilot.

Delegate

If something needs to get done, ask “who?” not “how?” (h/t Dr. Benjamin Hardy)

2/ Create Systems

Once I know what to delegate, I ask myself:

Do we have a system?

Do we have the right system?

Do people follow the system?

This helps me identify the problem right away.

3/ Four Levels of Delegation

(h/t Jonathan Swanson)

By Task

"Please write this report by Friday." The least powerful way to delegate.

By Process

“Complete this report every Friday and share it with the leadership team.” A step up but you're still not teaching how to do things at a higher level.

By Goal

"Ensure the leadership team is informed about relevant sales data on a regular basis. Architect and execute the system." You're now delegating whole areas and empower the person to build a system.

By Anticipation

The highest level of delegation. The first time you hear about a task is when it's done.

No one starts at Level 3 or 4. You have to build your way up by sharing as much context and your own thinking, and by providing specific and timely feedback.

This is best done in person or via a recording (use Loom or Zoom) because it is more context-rich, rather than via Slack or email.

4/ Vision - Commitment - Execution

This is the best framework to delegate to team members:

Vision: What's the goal or big why?

Commitment: What are you and I prepared to do to achieve the vision?

Execution: What's the plan to make it happen?

5/ 5X Your Output with 10-80-10

Provide a clear briefing and context at the beginning – the first 10%. Then let the person you're delegating to do 80% of the work. At the end, do quality control and bring in your taste and judgment.

You are still involved but only do 20% of the work. As Dan Martell says, delegating “80% is 100% fricking awesome”.

6/ Definition of Done

Instead of saying, "We need a clock for the meeting room," which may lead to an Amazon box on your desk tomorrow, give a clear DOD: “Ensure the meeting room has a visible and operational clock to reduce the need for participants to check their phones.”

7/ How to delegate to AI

Delegate outcomes, not tasks

Don’t say: “Summarize this.” Say: “Produce a one-page brief that a CEO can read in 3 minutes and make a decision.”

Front-load context aggressively

Including why this matters, what “good” looks like, and what to avoid.

Treat AI work as iterative, not transactional

AI improves during the conversation if you let it.

Standardize what you repeat

Create a delegation template or a custom GPT.

Treat AI like leverage, not labor

Use AI's speed and raw intelligence, but keep in mind it has no taste or judgment – those traits are uniquely human.

If you want to be a force multiplier, accept that there are inefficiencies and that things will not be done exactly how you would do it. However, that’s a small price to pay for winning back your time, offloading tasks you hate and growing your career or business.

Get my 1-page cheat sheet “Delegate like a CEO”.

ON THE SHOW

How to Become an Inspirational Leader (According to Science)

I do a weekly show to help you become a top 1% communicator. Subscribe on Spotify, Apple, or Youtube.

Inspiration is not a nice-to-have as a leader. It is what makes you and your organization successful. Infuriating leaders, on the other hand, are unpopular and achieve little. So how can you become more inspirational?

To find out, I'm joined by the world's number one expert in inspirational leadership, Adam Galinsky.

Adam is a professor at Columbia Business School in New York and he's been studying the science of inspiration for over 20 years. His book "Inspired" is one of the best books on leadership in many years, and his excellent TED talk, "How to Speak Up for Yourself," has been viewed tens of millions times.

Three take-aways from our conversation:

The leader amplification effect: what you do and say will be magnified, often more than you realize yourself
Leaders exist on the continuum that ranges from infuriating to inspirational.
You have 3 core roles as a leader that fulfill deep human needs: visionary (leading to a brighter future = optimistic, big picture, values based), exemplar (safety and security), and mentor (belonging, empowering).

Adam gives you scientific yet actionable strategies to become more inspiring as a leader. (note we released this interview last year as audio only but it was so popular that we created a full video version for you for Spotify and YouTube).

Watch and listen to the full episode here:

BOOK RECOMMENDATION

Is Your Leadership Style Oversized Sweatpants?

Most leaders I meet feel stuck in the middle.

They don’t want to micromanage. But they also don’t want to be the nice boss no one really listens to. Their leadership communication feels messy and exhausting.

In The Manager Method, Ashley Herd – a former HR boss at McKinsey & Company and Yum! Brands – puts a name to this dilemma with a metaphor you won’t forget.

She describes three leadership styles:

Tight jeans – overly rigid, controlling, and suffocating
Oversized sweatpants – so relaxed that clarity and accountability disappear
Cozy joggers – the sweet spot: connection AND accountability

If you’ve ever felt torn between being liked and being respected, this book is for you.

Ashley joins me on the Speak Like a CEO podcast next week where she unpacks her simple three-step framework that helps you overcome this dilemma for good.

Have an inspired weekend,

Oliver