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how I went from a**hole to master delegator
Published 9 days ago • 6 min read
Read Time: 3 minutes
10 Lessons That Completely Changed How I Delegate
I want you to remember one thing: if you don’t learn how to delegate in business, you better prepare to drown.
Early in my career, I was garbage at delegating.
I had trouble asking for help. And I probably came across as an asshole.
I insisted on doing everything myself, working insane hours and micromanaging everyone. I thought that was what it took to succeed.
But as my business grew, I quickly hit a wall.
I felt overwhelmed, burnt out, and could hardly get out of bed.
But then, a mentor told me something:
"People are the ultimate leverage in your business. It's the only form of leverage that removes you from decision-making. Learn how to get others to grow your business for you."
That resonated deeply with me. It wasn't easy unlearning old habits, but with time and a lot of mistakes, I'm now less of an asshole delegator.
Jokes aside, business schools don't teach you how to delegate (most business schools are scams). But these 10 hard-earned lessons will:
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Delegation is an art and science. It requires a blend of:
Mindset shifts
Practical systems
Emotional intelligence
But among these tactics, there's a principle that outweighs all the others-
Whole-heartedly caring about your people.
Delegation doesn't happen in a vacuum. It happens between humans. (Click to tweet)
Yet, too many leaders treat their team like a number. They don't take the time to actually get to know their team, to hang out with them, and to connect with them.
But when you don't care about your people, they're not going to care about you.
Lesson 1: The greatest gift you can give to any relationship is time
Hang out with your team outside of work.
Enjoy time together. Do experiences together. Find a way to tap into the humanness behind all this and forge a real connection. Because when people are friends and have a good time, you got their back, and they got yours.
The chemistry works without words.
Lesson 2: Go skydiving with your CRO
And you don't need to formalize hanging out with your team. They'll notice if you just "spend time to spend time".
Instead, simply have fun together.
For example, we had a Founder OS offsite exploring Mexico City together.
I met up with my Director of Customer Success in Laguna Beach two weeks ago.
Last week, I went skydiving with my CRO in San Diego.
When you're just buddies and hanging out, you're making stuff happen together.
Lesson 3: Hire people smarter than you, then get out of their way
Hiring people more intelligent and skilled than you is the fastest way to grow.
Your job is to give them the:
Tools
Resources
Environment
...to do what they do best.
Perceived autonomy enables flow and flourishing.
Give your smartest people space to surprise you, and they will.
Lesson 4: Follow "Servant Leadership"
Amateur managers think their team works for them.
Pro managers know they work for their team.
You are an enabler.
Remove roadblocks, coach your team, and point them to the right resources.
Lesson 5: Tell your team the Why behind the What
How I used to delegate:
"How" first, "What" second, "Why" third.
I got it in the wrong order. When your team understands the purpose behind their work, they:
Feel more important to your big mission
Make better decisions
Take more initiatives
Always start with "Why," then "What," then "How."
I do this by sending a weekly Loom report in the Founder OS Slack:
Lesson 6: Default to trust
Hire amazing people, set them up for success, then trust them to deliver. (Click to Tweet)
Micromanaging screams "I don't trust you." When you don't trust your team, they don't trust themselves, and they deliver worse work.
Extend trust generously and you'll be surprised how people rise to meet it.
If a person you look up to trusts you, you'd do anything to maintain their trust.
Lesson 7: Give advice, not feedback
When delegating, focus on giving advice rather than feedback.
Feedback looks backward at what went wrong.
Advice looks forward at how to improve.
Don't critique past mistakes - share specific ideas on what to do differently next time.
Lesson 8: Delegate authority, not just responsibility
Delegating responsibility without the authority to make decisions still creates bottlenecks.
Push authority to make judgment calls down to the front lines.
I love this one of Tim Ferriss' "17 questions that changed my life":
"What if I let [my team] make decisions up to $100? $500? $1,000?"
Ferriss said it helped him cut his workload from 40-to-60 hours per week to less than 2 hours per week.
I've noticed the same with Herb - I only spent 37 minutes running the business last month. I give my Executive Assistant the ability to make decisions that cost us below $5,000.
Lesson 9: Show your team that it's okay for them (and you) to fail
Failure is a core ingredient in innovation. If you aren’t failing, you aren’t pushing the boundaries of what’s possible.
Punishing failure discourages people from stepping up.
So create a culture where it's safe to fail. Encourage experimentation, normalize iteration, and frame mistakes as learning opportunities.
Creating a fail-safe culture starts with allowing yourself to make mistakes.
I've seen leaders that tell their team "It's okay to fail"...
...but then, beat themselves up over mistakes they made.
That doesn't work because your team imitates your behaviors.
Just like children, they don't do what you tell them to do, but what you do.
Treat yourself like you want your team to treat themselves.
Lesson 10: Create SOPs and systems
If you want to travel the world - build systems.
If you want to sell your business - build systems.
If you want to work 4 hours a day - build systems.
You can't truly delegate a task until it's out of your head and onto paper.
That's why you need systems.
At Founder OS, our minimum-viable SOP has 3 components:
A Loom video of how to do the task
A Google Doc with written step-by-step instructions
Many examples of what "excellent" looks like
If you don't want to spend 100s of hours building SOPs yourself, there's a shortcut -
I share all the systems that got me to 2 million social followers and $10M+ a year in Founder OS. We share them with a curated group of founders. Only 2% get admitted. If you want to see if you're a fit:
Delegation buys you time, freedom, and infinite scalability as a founder.
It's not easy, but it's a skill that will transform your life and business when you commit to mastering it. At least, it did mine.
Let's win together,
Matt
P.S. Whenever you're ready, there are 4 ways I can help you:
#1: The price to join Founder OS will increase permanently on October 15th. Book a call now to save $1,000+ by becoming part of the best community of founders in the world — before the price goes up!
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