“I Know I Need Help, But I’m Scared to Hire” - How to Know When You’re Ready to Bring Someone On

If you’ve found yourself thinking, “I know I need help, but I’m scared to hire,” you’re not alone. It’s a common moment of hesitation for small business owners - and understandably so. Hiring can feel like a big leap. The pressure of getting it “right,” the financial commitment, and the responsibility of supporting someone else can be daunting.

Often, this hesitation comes at a time when things are already stretched. You're fully booked, struggling to keep up with messages, spinning all the plates, and deep down, you know you can’t keep doing it all alone. But the idea of bringing someone into your business feels overwhelming, and there’s no clear guide on how to decide if it’s the right time.

In fact, this is something many accountants won’t advise on in detail. But from a finance and strategy perspective, it’s one of the most important decisions you can make - so let’s talk about it properly.

First, this isn’t a sign that you’re bad with money.

If you’re spiralling at the thought of hiring, it’s likely because no one has ever shown you how to assess if your business is truly ready. Without clear checks in place, two things tend to happen: you either hire too soon and panic when your cash flow dips, or you wait far too long, trying to do everything yourself and heading towards burnout.

Hiring doesn’t have to be a shot in the dark. There are a few clear financial markers that can help you decide whether now is the right time — and if not now, what needs to change before it is.

Let’s break it down, step-by-step

1. Know your average monthly revenue.

Start by looking at your average monthly revenue. Not your highest month ever, but your baseline. What does your business consistently bring in, and how stable is that income? Hiring adds an ongoing cost to your business, so it’s important to make sure your regular revenue can support that commitment, not just occasional spikes.

2. Get clear on the full cost of hiring.

Next, consider the full cost of the hire - not just their hourly rate or monthly fee. Think about the time it will take to onboard them, the systems or tools they might need access to, any software subscriptions that may need to increase, and, depending on the structure of the role, potential tax or legal implications. If you’re hiring a freelancer, it’s wise to factor in a buffer in case their hours grow or their rate changes down the line.

3. What’s the return on investment?

It’s also important to understand what you expect the return on that investment to be. If you’re hiring someone to take tasks off your plate, how are you going to use the time that gives you back? Will it allow you to take on more client work, build new income streams, or invest time in marketing and growth? Hiring is only a good investment if the time and energy it frees up translates into something that benefits the business - whether financially or operationally.

4. What happens if a client pays late?

Finally, assess whether your business could still function smoothly if your next major invoice took 60 days to get paid. It’s not uncommon for payments to be delayed, and even in those moments, your team needs to be paid on time. A bit of cash flow planning here can make a huge difference in your confidence and resilience as a business owner.

Hiring doesn’t need to be fearless - just informed.

If you’re at the stage where you know you need help but aren’t sure whether now is the right time, take that as a sign to slow down and look at your numbers. You don’t need to jump in without a plan, but you also don’t need to stay stuck out of fear.

Making your first (or next) hire can be one of the most exciting and empowering steps in your business journey when it’s done with clarity and confidence.

If you’re considering hiring but still feel unsure, I’d love to hear from you. I’m always happy to help you explore the financial side of growing your team, without the jargon or judgment.