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How to Know It’s Time to Hire Your First (or Next) Team Member

April 10, 20255 min read

Why trying to "do it all" is costing your business more than you think.

You didn’t start your business to burn out.

But if you’re like many business owners, you're wearing too many hats, working weekends, and waking up at 2am thinking about overdue invoices or client follow-ups.

Hiring help might feel like a luxury, but here’s the truth: if you're still doing low-value work that someone else could do for a fraction of your hourly rate, you're holding your business back—and possibly yourself along with it.

So how do you know it’s time to hire? Let’s break it down.

1. The Real Cost of Doing It All Yourself

Most business owners underestimate the opportunity cost of tasks they’ve outgrown.

If you’re charging $200–$300 per hour but spending hours on admin, chasing invoices, or formatting documents, you’re not just wasting time - you’re burning profit.

It’s not noble to wear every hat. It’s inefficient.

2. Use the Skills/Fun Box to Audit Your Time

Here’s a tool we use in coaching to create clarity fast: the Skills/Fun Box. It helps you classify your tasks by two axes:

  • How skilled the task is

  • How much you enjoy doing it

You’ll end up with 4 quadrants:

quadrant

Tasks in the bottom row? They’re the first ones to go.

Here are a few examples to get you thinking - your own version will vary depending on you and your business:

  • Low skill / low fun: Chasing invoices, formatting reports, updating your calendar

  • Low skill / high fun: Social media posts, Canva designs (still a delegation candidate!)

  • High skill / low fun: Proposal writing, technical reporting - delegate with Standard Operating Procedures (SOPs)

  • High skill / high fun: Sales conversations, strategy, vision, leadership, team coaching - your zone. Protect it.

Pro tip: Spend 80% of your week in the top right box. That’s where leverage, joy, and growth live.

3. You’re the Bottleneck (And You Know It)

Here are a few signs you’re long overdue for a hire:

  • You’re the only one who knows how to do critical tasks

  • Things sit in your inbox because no one else can “just do it”

  • Projects slow down (or stop) when you’re away

  • You’re rescheduling family time to “catch up” on admin

This isn’t sustainable - and it’s not how you grow a business that can run (mostly) without you.

4. You’re Stuck in the Wrong Quadrants

Borrowing from Stephen Covey’s Time Management Matrix, tasks fall into four types:

  1. Urgent and Important: Crises, deadlines (firefighting)

  2. Not Urgent but Important: Strategy, planning, leadership (growth zone), preventative activities, recreation

  3. Urgent but Not Important: Distractions, interruptions

  4. Not Urgent and Not Important: Time-wasters

When you spend too much time in Quadrants 1 and 3, you burn out. When you shift your time to Quadrant 2, you build a business that lasts.

Hiring frees up space for you to live in Quadrant 2.

5. Hire for the $30/Hour Tasks—Not the $300/Hour Ones

One of the most common mistakes business owners make?

Hiring someone junior to do what they love doing themselves.

Don’t start there.

Start by offloading what you’re not good at or what drains your energy.

Common examples:

  • Bookkeeping

  • Invoicing and accounts payable

  • Chasing up debtors

  • Updating Xero or MYOB

  • Managing your inbox or scheduling

If it’s not in your “Zone of Genius,” it’s a candidate for delegation.

6. "But I Can’t Afford It" - A Reframe

Here’s the most common hesitation we hear:

“I’m not sure I can afford to hire someone right now.”

But here’s the better question:

Can you afford not to?

Imagine freeing up just 10 hours a week. What would you do with it?

  • Call more qualified leads?

  • Build a sales pipeline?

  • Launch a new offer?

  • Spend time with your kids, without guilt?

When used wisely, a new hire is not an expense - it’s a lever.

7. Where to Start: Use the Skills/Fun Box to Prioritise

Still not sure who to hire next?

Use your Skills/Fun Box audit to create a shortlist of tasks to delegate. Then ask:

  • What tasks drain me but still need to be done?

  • What’s holding me back from getting to $300/hr work?

  • Where would 5–10 hours a week make the biggest difference?

From there, decide:

  • Is this a part-time VA?

  • A local admin assistant?

  • A bookkeeping or financial services partner?

  • A contractor with specialist skills?

8. You Don’t Need to Hire a Team Overnight

Start small.

  • Delegate one task

  • Then a small project

  • Then a routine responsibility

Build trust. Build rhythm. Build systems. All of these are learnable skills.

Before you know it, your business will no longer depend on you doing everything - because it won’t have to.

9. Final Thought: Be Before You Can Do

One of the most powerful ideas we teach is the Be → Do → Have model.

Most business owners get it backwards. They think:

“Once I have more time, more money, or more help… then I’ll do things differently… and finally be the successful business owner I want to be.”

But that mindset keeps them stuck.

The shift happens when you flip the script:

“I choose to be the business owner who protects my time and focuses on high-value work. So I do the things only I can do - and learn how to effectively delegate the rest. That’s how I have the growth, freedom, and balance I’ve been chasing.”

You don’t wait for freedom.
You lead with it.
That’s the difference between staying busy and building something that lasts.

Be first. Then do. Then have.

Hiring isn’t just a task. It’s an identity shift.

You’re not just the technician anymore. You’re the owner. The leader.

Time to start acting like it.

Ready to Reclaim Your Time?

If you’re feeling stretched too thin, overwhelmed with low-value tasks, or unsure how to take that next step toward freedom - let’s talk.

Together, we’ll map out your Skills/Fun Box, identify what to delegate, and help you build the support structure your business needs to grow without burning you out.

 Book a Complimentary 15-Minute Brainstorm Call
https://www.butleradvisory.com.au/time-with-trent

You don’t need to do it all. You just need to take the next right step.

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