Is it time to hire a new team member?

Employee, freelancer or outsourced, what's right for you?

There’s nothing like an upcoming new financial year to give you the kick up the bum to revisit and/or reset your Big Hairy Audacious Goals (BHAGs).

As the name suggests, you want to be thinking big, these are your 10X goals! And if you are thinking big, you probably won’t be able to achieve these goals on your own. You will need your dream team, or maybe even a small army!

Business owners often ask us ‘how to know when to outsource’ or ‘when is the right time to bring someone into your team’?

Unfortunately, there is no one-size-fits all response, no magic time or revenue figure which definitively tells you it's time for a team member. But, of course, there are some questions you can ask yourself to help you work through what you might already know in your gut.

Six key questions to ask yourself if you’re considering growing your team:

1. Is there a gap in your knowledge or skills that is holding you back?

Reflecting on your BHAGs, is there key pieces of the puzzle that you can’t fit into yourself? Do you need a new website, or guidance around raising capital? Don’t know what help you might need?

These are all reasons why you might consider having someone else help you, whether that is a business coach, a mentor, an accountant, a specialised consultant (or team of consultants) or an employee!
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2. Are you doing tasks that are pulling you outside your zone of genius (and/or happiness)?

If you find yourself bogged down in tasks that don’t light you up, or don’t directly bring in the bacon, maybe it’s time to chunk those off and say sayōnara! Weigh up whether the time, and heart ache, you are spending on these tasks may be better spent elsewhere while a VA, administration whizz or bookkeeper lightens your load!
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3. Could AI or digital automation help bridge the gap?

In 2026, it would be remiss not to also have you consider whether AI and automation can play a role in providing you with the extra capacity you need.

Exploring the use of AI agents or other systems might be an important first step, and your first foray into expanding your team might be someone to help you digitise and reconsider your workflow, before you jump into getting a full-time human on board!
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4. Should you hire an outsourced provider/freelancer or an employee?

The lines between employee and outsourced team members are growing increasingly blurred, and gone are the days that only employees commit or get excited about your business (in fact many consultants and outsourced teams probably care more!).

If you need a physical presence (for example taking charge of a reception or storefront), or someone to be consistently focused on your work, though, then an employee may be the best option. On the other hand, it’s generally easier to start and stop a relationship/engagement with an outsourced business or freelancer, than it is an employee. And the costs are more all-inclusive (although most often higher for this reason).

Personal preference will play a part in this choice too!
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5. Do you have consistent income to support a team member (or freelancer) and associated expenses (now and for the foreseeable future)?

As we said before, enlisting help is going to be an investment so it's important to consider if you have the cashflow to support this right now, and ongoing (depending on the arrangement). Most advisors will say to have 3 months salary and expenses up your sleeve before bringing on an employee. This is a good guide and allows you and the employee a little runway to start seeing a ROI.

Many coaches or consultants will tell you to jump before you’re ready to invest in their services, and that the cash will follow. What is right for you will depend on your business and risk profile but the old saying is true – you gotta spend money to make money!
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6. Are you ready to manage expectations of someone else’s work?

This doesn’t only apply to having someone working for you as an employee! When you bring on a freelancer, or even a flashy business coach to assist you, you need to be clear on what you expect from them, and make sure they deliver! Managing these relationships and outcomes takes time.

Make sure you are aware up front the time investment you will have to make up front to get the most out of that employee/freelancer/consultancy. You don’t want to be left feeling like you could have done a better job yourself, and saved yourself time and headache!
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Ready to grow your team but not sure where to start?

Our HR Partners can help you figure out the right structure for your business, identify where the gaps are now, and map out what roles you might need in the future.

If you're considering outsourced HR support or fractional technology leadership, find out how we can help.

Get in touch.