Getting out of the weeds by delegating.
Oct 03, 2025As an entrepreneur, delegating work to other people is a superpower.
It gives you huge leverage to get more things done, better, or faster than you would have going at it alone.
But it’s not that easy.
In fact, I’ve failed miserably at parts of delegation over the years.
- Not sharing clear expectations
- Handballing things to the wrong person
- Not measuring the progress or quality of outcomes
On the other hand, I’ve done a couple of things well enough to enable us to grow the team to 130 people fairly quickly.
And thought those couple of things might be worth sharing.
So over the next two weeks of emails, I’m going to share two simple ways delegating has transformed my business and my week.
Hopefully, they’ll help you get way more done:
The first one is:
How. Then Who.
(Not… who, then how)
Let’s break it down…
HOW
I’m a big believer in doing the thing first before asking others to do it.
The reason isn’t so I can be the hero and show that I’m better; it’s to understand the job well enough to recruit for it, set expectations, and hold people accountable.
You’re not trying to master it. That’s for the next person to achieve.
Doing it first lets you see what’s involved in the role, what challenges pop up and what good looks like.
The problem is, most business owners either spend too long here or not enough time.
What I mean is:
- You own the role for too long and eventually become the expert you should have recruited or;
- You don’t do it and have no idea what the role involves therefore you under, or overvalue it.
The perfect length of time depends on the complexity of the job and your current understanding of it.
So you need to be honest with yourself and do it just long enough to fully understand it.
The next step is to find someone else to do it (and master it).
WHO
The simplest step is to find someone on your current team who has the capacity to take on the work you need done so you can free yourself up.
In many cases, just asking other people to help will get you the result you need.
But often we sit there telling ourselves that; other people won’t do it properly, or they’re already busy enough, or that it’s weak to ask for help…
The reality is, other people want to do new things as much as you do.
The boring stuff that you’ve had to do for years is new and interesting to them.
So allowing them to learn, acquire new skills, and work on new challenges is exactly what they’re looking for - Your job is to help them, help you.
If you don’t have anyone to handball things to you’re going to need to recruit for the role.
And in that case, you’re back at writing a job description, recruiting and onboarding people to help with the work you need done - A conversation for another day.
PUTTING ‘WHO. THEN HOW’ INTO PRACTICE
The question you should start asking yourself is:
- What new skills do you want to learn that you don’t have time for today?
- What old things are you willing to hand off in order to make time for it?
If you’re anything like me, you’re great at adding things to your list (not subtracting them).
But the key is to REMOVE SH*T!
I’m not saying to stop doing it.
You can’t afford to do that... Someone has to do it.
But it doesn’t need to be you!
I hope this is the nudge you needed to handball work to others keen to do it.
It's been a huge leg up for me over the years and it's so simple that many people overlook it.
Take care and have a great week.