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Are You REALLY Ready to Hire? 5 Questions to Answer Before You Jump In

So, you think it’s time to hire? Congratulations!

Investing in support for your business is one of the greatest gifts and most powerful levers you can give yourself.

But before you dive in, it pays dividends to do some real-talk due diligence to make sure it’s 100% the right move.

Leading a team is a privilege – so set yourself and your new team member/s up for success from the get-go! Ponder these questions and find your answers before you begin:


The Role Question

Teams need direction, transparency and clarity to be effective. If you are expecting your team to be psychic and know exactly what you want without taking the time to lay out priorities, give them direction etc – you’re in for a rough ride.

Having a clear idea of what they will be doing is crucial – without it, you’ll both end up feeling frustrated.

Before you bring someone onboard, make sure you truly understand the key pieces that are currently missing in your business. A good starting point is to consider what your major stressors are right now.

What processes or areas of your business are you spending way too much time on?

Where are the crunch points stopping your business from growing / preventing you from taking advantage of opportunities?

Conversely, which areas do you love to noodle and waste time procrastinating in (my examples: making pretty graphics in Canva, financial tracking, playing with Notion dashboards). 

It’s important to note that not all roles will directly contribute to the bottom line… but they can free you up to do so. What I mean by that is, for example, a VA organising and managing your inbox might not translate exactly to more money in the bank – BUT it will free 5-10 hours a week of your time and reduce your stress levels so you can focus on money-making activities rather than wrangling outlook. Plus, she might find that important client enquiry that you missed from last week… 😉

Clear on exactly who you need? Let’s progress…


The Money Question

Teams can as expensive… from three to five figures plus each month. Team costs are often the biggest percentage of a business’ expenses – but don’t let that put you off. 

The key is to get SUPER intentional about how to budget and pay for them. Whilst it might seem glamorous to be able to say “oh yah, I have a team of 15” at your next networking meeting, in reality, big teams need to be very carefully managed.

So, putting our professional hat on for a moment, you need to ask yourself – do you have the cashflow for the role you want to hire?

You need to act responsibly and ensure you’ll be able to meet your payroll commitments. Your cashflow problems are not your team’s problems. 

If possible, have a clear 3-6 month runway of predictable income that will cover expenses including their pay before considering taking on a new team member. I also advocate building a ‘Business Buffer Pot’ – a savings pot that allows you to continue paying the team (and yourself!) in the event of revenue dropping unexpectedly.

If your budget is tight, consider these options:

  • Hire for a project / individual piece of work, rather than commit to a retainer
  • Start small with just a few hours per week (perhaps five), so you can focus on a high-value, money-making activity without interruption. As your business grows, you can always request further support
  • Consider ‘offshore’ VAs or agencies, who generally have lower per hour costs
  • Compare and contrast rates for roles with similar levels of experience and select the candidate closest to your needs within your budget

Money stuff all good? Let’s go onto…

The Control Question

Are you actually willing to give up some control?!

Your business has been your baby for soooo long – and although it’s been exhausting trying to do everything alone, it’s also given you complete control over Every. Single. Aspect.

In order for a  new team member to help you and do their job, you must be willing to let go!

You will need to accept that they may not do it exactly the way you would… but that’s actually a good thing. Remember you’ll be hiring for your gaps, not recruiting someone who is just like you!

And you will need to adjust your working practices to make room for other people.

This means moving all notes, tasks, digital assets, logins and tools to an accessible place – NOT leaving them languishing in random draft emails or on post-it notes on your laptop.

Accepting support also means being willing to be transparent about aspects of the business you might have kept private up til now.

Team members need to understand the current situation in order to work their magic and bring value. So are you comfortable sharing your goals and priorities? Communications with clients? The current pain points in your business? Inefficiences in processes and systems? Finances? The level to which you share is of course up to you, but you’ll need to get comfy with the idea that information now needs to be in a common realm, not just your head.

Open to all that? Great! How about…



The Time Question

Getting a new team member up to speed takes longer than you’d think (or hope). In my experience, most new hires need a month or two to learn the ropes, and anywhere between 3-6 months to really nail their role.

So do you have the time / willing to make the time to onboard and train your new team member/s properly, so they can do a great job?

At first, it’ll seem like they ‘don’t know anything’ – and in a sense, they don’t – you’ll need to teach them all aspects of the business, how things need to get done, your expectations of them, and how they fit into the overall picture.

I recommend blocking out a few hours each week for 1:1 time with your new hire in the initial couple of months, then regular check-ins and meetings as needed.

Reckon you can factor that in? Then, last but not least…



The Leadership Question

Are you ready and willing to step up into the CEO role, be a visible leader and take responsibility?

Having a team is not something to be taken lightly. You are now becoming a critical part of each team member’s income streams, and their own business.

You have the power to make their life miserable, or be their favourite client to work with.

So are you willing to lead with integrity, do the hard things, be firm but kind?

Are you ready to allow your thinking and messaging about your business to become a ‘we’ rather than ‘me’?

Really think about this – it’s a biggie and where I see most team issues stemming from.


So how did those questions sit, friend?

Remember – none of this stuff magically appears. We all need to learn how to be a great boss… and it’s something I’m deeply passionate about.

During my 17 years in the trenches of building businesses from solopreneur startups to billion dollar corporates, I’ve seen the good, the bad and the downright ugly of team building.

I’ve recruited dozens of roles, ranging from high-level managers and specialists to interns, freelancers and entry-level positions and have managed and coached teams of 20 people. 

So if you need some help with this, I got you!

Jump on a Coffee Chat with me and we can talk through the options for support with this process.

           Chelley x

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Hi, I’m Chelley

Let’s make like Marie Kondo and streamline your business so it feels peaceful, profitable and totally on-purpose.

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