229: How to Be a Better Delegator
Jul 24, 2025
Entrepreneur Leadership: How to Master Delegation and Build Real Leverage
If you're serious about entrepreneur leadership, you must learn how to delegate. Period. You can’t scale your business, your impact, or your time without it. And if you don’t get this right, I promise you—growth will stall.
I spent 10 years as a military officer and over a decade as an entrepreneur. I’ve led all types of teams. One of the biggest shifts in my own leadership came from understanding how to delegate well—and more importantly, how to think about what should and shouldn’t be delegated.
Let’s break it all down.
The Delegation Matrix: A Framework for Entrepreneur Leadership
When I think about delegation, I use a simple matrix of four quadrants to help make decisions:
1. Unique Skill + High Value
This is your genius zone. For me, that includes creating content. It’s high-value, and no one else can replicate it exactly how I do it. These are the last things I’ll ever delegate.
2. Unique Skill + Low Value
For example, I’m good at graphic design. But just because I’m good at it doesn’t mean I should be doing it. It's a unique skill, sure—but not one that moves the needle the most. Delegate it if the quality tradeoff is minimal and you don’t love it.
3. General Skill + High Value
Things like scheduling social media posts or email marketing fall here. These are general skills—but the outcome is high value. This is where delegation with training and systems becomes critical.
4. General Skill + Low Value
This is an easy yes—delegate it. Scheduling meetings, admin tasks, etc. Important? Yes. But they don’t need your brain.
The 5 Don’ts of Delegation
Delegation isn’t just dumping tasks on someone and walking away. Let’s hit the most common mistakes.
Don’t skip the why – Explain the reason behind the task so your team is invested.
Don’t neglect training or standards – If you want quality work, you need to set the standard and train to it.
Don’t start with high-value tasks – Earn trust first. Don’t throw someone into the deep end with your most critical work.
Don’t forget to follow up – Delegation isn’t abdication. Circle back and check in.
Don’t fear holding a standard – Leadership means having hard conversations when people aren’t meeting expectations.
The 5 Do’s of Delegation
Great entrepreneur leadership is more than offloading work. It’s about empowering others to win.
Do empower your team – Give them the tools, access, and authority to succeed.
Do challenge them – Show them what "done" looks like, but let them figure out the path.
Do give feedback and compliments – Praise publicly, critique privately, and always be clear.
Do encourage self-critique – Ask how they could have done better. Create a culture of improvement.
Do provide a growth plan – Show team members a future with your business, or they’ll find one somewhere else.
Entrepreneur Leadership Is a Never-Ending Climb
There is no finish line here. Delegation and leadership are Sisyphean. But the reward is leverage—getting back your time, building a team that executes without you, and growing a company bigger than yourself.
No one said it would be easy. But you can absolutely do it. You just have to try harder.
Show Notes
00:30 – Why delegation is key to entrepreneur leadership
01:12 – The 4-quadrant delegation matrix explained
02:30 – When to keep tasks vs. delegate them
04:22 – What general + low-value work you should always delegate
05:05 – 5 common delegation mistakes to avoid
06:55 – Why follow-up and holding standards matter
07:50 – 5 strategies to lead and delegate effectively
08:22 – How to challenge and grow your team
10:10 – Creating a company culture of ownership
11:00 – Leadership is a leverage game—if you do it right
