The short answer
The cost of hiring too late, my five tips for a first hire, and the three-step interview process I use.
In short: Hire when the work is costing you your headspace, not when you finally feel ready. Know why you’re hiring, decide where the role sits in your structure, write a clear position description and interview questions, give candidates a paid test task, and agree how you’ll work together before day one.
Prefer to watch? The 60-second version is on YouTube.
Hiring is the hardest thing in business. But the most chaotic period for me wasn’t a bad hire. It was not hiring fast enough. I felt pressure that we weren’t hitting our goals, pressure because all the delivery was on me, and pressure at home because I was taking work home and wasn’t being the husband or dad I wanted to be.
What does hiring too late cost?
Your headspace, mostly. Many founders say “I’m too stressed, but I’m not ready to hire.” A business is built through people. If you want to get out of the weeds and grow, you have to protect your headspace, and the best way to do that is to hire the right person for the right role. Taking a bit of risk with a methodical plan is what kick-started my growth.
What are my five tips for a first hire?
1. Know your why
Is this hire to free up your capacity? To do something you’re not good at? To bring a technical skill you don’t have? Or to be your 2IC? Each one is a different hire.
2. Decide where they sit in your structure
As a founder you wear every hat: sales, marketing, admin, finance. Decide which stream the new person sits in. Sketching your org chart, even a rough one, sets the boundaries for their success.
3. Nail the position description and interview questions
Write a solid position description and list the tasks you expect them to do day to day. Then prepare your five or six key interview questions. It’s easy to finish a great conversation and realise you never asked what you needed to know.
4. Test them
You only get 30 to 40 minutes in an interview. Ask candidates to do some real work, and pay them for the hours if you need to. Look at how they approach it and whether it fits how you work.
5. Agree how you’ll work together
Do you like meetings and talking things through, or instructions over email? Define how you’ll work with them day to day. It shapes their KPIs and the feedback loop, and sets them up from day one.
What interview process do I use?
At the start, I hired based on how tired I was or how nice the person was. That can work, but it slows you down later when mistakes show up. Now we keep it short but detailed, in three steps:
Get to know you. Background, fit, whether we like each other.
Technical interview. Questions about the problems we need solved.
Coffee or lunch. The personal side, and how they’d fit.
Don’t cram it all into one sitting. Spreading the steps over a week or two gives you time to sleep on it and reflect.
Is “hire fast, fire faster” good advice?
I can’t stand it. When you hire someone, they’re leaving a job, a career path or another business to join you. Bringing them in just to “see how they go” is unethical. Hiring quickly is fine if there’s a detailed plan behind it. Put the right person in the right role with the right structure, and the test is simple: your day should get easier.
Frequently asked questions
How do I know it’s time to hire?
When you’re too stressed to grow, taking work home, and the pressure is all on you to deliver. Waiting until you feel ready usually means waiting too long.
What should my first hire do?
Decide which hat they take off you: sales, marketing, admin, finance or delivery. Where they sit in your structure defines what success looks like.
How many interviews should I do?
I use three: a get-to-know-you chat, a technical interview, then a coffee or lunch, spread over one to two weeks.
Key takeaways
Not hiring fast enough was the most chaotic thing that happened to me.
Know the why: capacity, a skill you lack, technical help, or a 2IC.
Spread three interview steps over one to two weeks so you can reflect.
“Hire fast, fire faster” ignores the person leaving a job to join you.
Last updated: 26 October 2026.
Leader of the herd. Shehan's career has spanned professional services, finance, banking, and strategy. He started Elephant to connect busy, ambitious people with the proactive financial advice they need to make great life decisions. He built the kind of firm he always wished existed - and then showed up in trackie-dacks to run it.
