Not sure where to start?  Take the free 3-minute Operator Assessment →

Podcast Episode · S3E12 Notebook of a COO

Hire Your Headache First

When owners finally hire, they hire a mini version of themselves, another set of hands doing the thing the business already does. It feels like growth, and it usually caps the business instead. The first job you should hire out is not the work you are best at, it is the work you hate: the recurring, draining, below-your-pay-grade work that eats your week and does not need one ounce of your genius. In this episode, JT breaks down how to hire your headache first with three moves: find the headache where what drains you meets what does not need you, turn that headache into a playbook before you delegate it, and hire someone to own the outcome instead of perform the tasks. Ends with a simple five-day exercise to find your first or next hire, whether that hire is a person, a part-timer, or a piece of software.

Three Moves

Hire your headache. Keep your genius.

You cannot out-produce a bottleneck by adding another one just like it. These three moves are how you hand off the work that drains you without handing off a mess, so the hire actually frees you.

01

Find the Headache

The work to hire out first lives where two questions meet: what drains me, and does this actually need me, the specific human? Offload your drains, do not clone your strengths. That list is your first hire, whether it is a person, a part-timer, or a piece of software.

02

Turn the Headache Into a Playbook

You cannot delegate what you never documented. Spend one week as a narrator: every time you do the draining task, write down what you did and why, the steps and the decisions. A playbook is the only thing you can actually give away.

03

Hire the Outcome, Not the Hours

Do not hire help, hire the owner of a result. Define what good looks like in a number: not someone to answer phones, but the person who owns a full book and zero missed calls. Then they make the small decisions, and you stop being the answer to every question.

Previous Episode

You Own a Job, Not a Business

If the business stops the moment you stop, you own a job, not a business. The 30-day test to find your real org chart, and the three moves that turn a job that owns you into an asset that runs without you.

Listen to S3E11  →
Take the Free Assessment

Are you still the person every task routes back to, or have you handed off the work that drains you?

The Operator Assessment takes three minutes and tells you which operator profile you fit right now: Foundation Builder, Stuck Operator, or Scale-Ready Operator. It points to the next operational move based on where you actually sit.

Take the Assessment  →

The delegation playbook, the SOP templates, and the system for hiring people who own outcomes are inside The Small Business MBA.

The headache-audit worksheet, the one-week playbook-documentation framework, outcome-based role scorecards, and the full operator course library. Everything you need to hand off a system instead of a headache.

Join The Small Business MBA  →

Free forever • All pillars and bonus courses included • No card required