Monica Davidson runs Creative Plus Business, a social enterprise that provides education and support for creative professionals who want to develop their entrepreneurial skills.

She is the director and the doyenne. After years as a freelance writer and filmmaker, Creative Plus Business was Monica’s way of expanding her already robust advice and guidance skills into a formal offering and sustainable business model.

In the Freelance Jungle Facebook group, we often see questions about how to manage the relationship between the freelancer and the contractor, how to attract good quality contractors, how much of the arrangement needs to be shared with clients, and what to do when things go pear-shaped.

The following advice for managing contractors is based on an interview with Monica Davidson by the Freelance Jungle.


What are your four top tips for making sure hiring the subcontractors and managing contractors is as prosperous and stress free as possible?

1.      Be prepared for that before you think you need to be. Prepare for the possibility that jobs will come, work will come, and things will start to work. And that you’ll need help to carry this load and be prepared for that before it actually happens.

2.      Start thinking before you need to about the kinds of people that you’d like to work for you and create a job description. Start looking around early for people that you’d like to work with and let them know that you’d like to work with them.

3.      Be very clear with yourself about what you need from other people, in terms of skills and experience, and what you want, in terms of culture fit. To make sure the person fits, I have developed something called the van test. When my production company was first starting out, we were tiny and a bit poor, and we had to drive everywhere in a van. And if I can’t tolerate being in a van with you for a couple of hours, then I will not hire you. For me, culture fit means I can tolerate being stuck with you, and that you’re fun and interesting, and you make me laugh, and you make me think because when the shit hits the fan, and we all have to muck in, I know you will not be weird about it. Decide what your culture fit looks like.

4.      Start incorporating the idea of hiring, managing, and maintaining contractors into the fabric of your business. Think about how you do things and what sorts of people you’d like to see join in, how you will train them and when, and so on.

Interview on freelancers managing contractors in long form

At the Freelance Jungle, we see a lot of freelancers look to hire contractors because they’re doing well and their work volume is increasing. What skills do you believe a freelancer needs to manage contractors?

The most important thing about the contractor management process is to take someone on before you get too busy. One of the biggest mistakes that I see with people when they’re hiring subcontractors is that they do it out of desperation. They don’t properly think about exactly what they need help with, or what that person’s job is going to be.

It can even stop them from hiring someone because they think, “if I’m going to hire someone, I’m going to have to show them how to do it, or they’re going to have to learn how to do it my way, or what if I don’t like the way they do it?”

If you’re thinking like this, you’re talking yourself out of hiring someone.

You need to manage people. And that means that if you don’t have this set of skills to manage people, then you need to learn them. And there are courses you can do to learn how to manage people.

Also, it’s easier to manage contractors if you found the right people for the job.  And by the right people, I mean people who are the right fit for you and what you’re doing, the clients that you have, and who have the skills that you need.

And I don’t mean necessarily every single skill for the role. Ask yourself how much can I teach when you need to find the right person.

So, it’s a balance between nurturing someone’s potential and also knowing that they’ve got the skills to do the job?

It depends on the contracting model you use. My contracting model is a mix of what I refer to it as inside and outside work.

Outside work is work where your contractors and freelancers are hired for the project. Once that project or job is gone, that position is gone. They get paid from the money that I am making on that project.

As a freelance filmmaker producer for 20 years, that was most of the people that I hired. Sometimes, they were the same people that I hired repeatedly. But I could never afford, nor would it have been sensible for me, to have a camera operator sitting there waiting for projects to come in. It’s much more fun for her to go out and get other jobs with other people.

In comparison, the inside jobs are administrative work, the marketing, financials, and jobs that can’t necessarily be passed on as an expense to a single client and need to be absorbed as a business expense. That person is going to be working all the time, even when you don’t have a lot of work coming in.

Those two contractor groups (inside and outside jobs) are very different hires in terms of skill. For outside jobs, if I’m hiring a consultant or a freelancer to come in to subcontract on a on a job, they do already need to have a pretty high skill set. I don’t really want to spend a lot of time teaching them how to do their job.

When it’s an inside job, though, I’m quite happy to train because the culture fit aspect of it is going to be far more important if that person is actually working with me in my office or at my home in a more intimate way on the deeper meaningful stuff that I’m trying to achieve.

What tools to do you use when managing contractors?

Interestingly, probably your best tool to track what everybody is doing is called the phone. It’s an amazing piece of technology.

A regular check in with yourself and your team is something I like to do. I have given it the very creative title of Monday morning meeting. It includes activities like works in progress, what bills do I have to pay, what deadlines are coming up this week, or what meetings we have to attend, etc.

As my team has grown, or if I’m on a bigger project, that happens with more people. Scheduling a time when you can talk to your entire team using Zoom or using good old-fashioned conference call, so everybody has a chance to talk is really important.

My current team is tiered.

Because I’m a filmmaker, and film runs very much along military lines, I’m not personally a fan of a flat structure. I like a bit of accountability, and a bit more of a waterfall approach to managing people. I’m at the top of that tree. And then I’ve got people underneath me, that manage the consultants and another that manage the other admin and marketing team.

It may sound overly complicated, but it works well because then I’m not having to worry about who’s having a sick day and whether an email was sent. It gives me space to have other tasks to think about.

There’s an adage that if communication is likely to fail, it will. How do you keep the communication going on between yourself, the contractors, and the team?

Having the regular check-in is vital.

In terms of software and apps:

·        Asana –  to help us track different projects and different tasks that we’re working on.

·        Trainual – we put all of our processes and training documents and basically we’re uploading everything that you need to know about how to do your job in a central place.

·        Google Workspace ( – this is an absolute savour for file sharing, emails, and a bunch of other important communication needs.

Meetings in person or online – include pre-organised agenda meetings to avoid disorganisation and bloat.

Overall, I’d suggest a more proactive approach with set goals and agendas rather than a reactive approach.

Also, learn how to be a manager

There are loads of online courses and continuing education courses you can do. We’re always looking at Udemy, and Creative Live, and places like that for reasonably inexpensive online courses. But don’t be afraid to invest in management training. Don’t assume that because you’ve gotten to a certain degree of experience in your practice, that you’re going to be able to lead other people. It’s an entirely separate skill set.

And bring people together if you can. I try to bring everybody together twice a year not only for working on the actual work that they’re doing, but also to involve them in the bigger picture vision of what I’m trying to achieve. Even though they’re not employees, I still want them to be a part of that story and feel like they’ve got ownership of the vision for Creative Plus Business.

But my contractors still maintain their independence and do their own thing. And that means honest discussions about Intellectual Property (IP).

For example, I invitee everybody on my team to bring new ideas in to discuss for the possibility of turning that into something we could make money out of, but the conversation about the intellectual property happens from the first breath. If you’re not my employee, then intellectual property is a really important thing that we have to talk about.

That’s one of those areas where I can educate somebody about what that means, what I need, what they need to think about, and where those boundaries are. Because if you bring me your best possible idea, and I can think of a way to make money out of it, I probably am going to do it. And so you need to be careful that you don’t also want to use that idea for your own purposes, because then we’re going to have an issue.

Do you let clients know that you’re using freelancers and the contractors you’re managing have their own businesses?

I don’t involve the people who work for me with the intellectual property side of the conversation. That’s my job to work out with the client.

In terms of work style transparency, it depends on the client. There are some clients that I’ve had in both my current organisation and in my film production company where it hasn’t mattered. Other time, it wouldn’t have worked for the clients to know that all of those people were not an integral part of my business, and that when that project was over, they’re all going to leave and go back home.

To sum it up, it’s probably about power. How much you, as the lead person possess, how much power you have with the paying client.

I’ve had some clients that really would have treated me like I was less important if they’d known that the large group of sexy people I was working with were freelance and doing their own thing. But now with the work that I do at Creative Plus Business, it benefits my business to say with a great deal of confidence that all the consultants that work for me also run their own creative businesses. Because what we’re doing here is trying to help other people learn how to run a creative business. So the more of us who are doing it, the more legitimacy we gain.

How do you ensure your subcontractors don’t steal your clients or act underhandedly? Is it in the contract? Is it in the way you find or manage contractors?

It’s about making sure that you have a really clear idea of what your boundaries are.

If you don’t want your subcontractors to poach your clients, you need to be really clear about that.

This may take the forms of:

1.      Early conversations about engagement

2.      The contract that prohibits working with the clients directly during the project or in circumstances after it

3.      A non-compete clause that says you can’t take any of the clients that you work with here and have an external relationship with them until it’s been 12 months since you left

4.      Extending the non-compete to say you cannot work with these specified competitors (of the contracting business or potentially clients) for another three months after you leave

5.      IP protection – you can’t take any of the processes or IP that you’ve learned because of the contract.

A short contractor horror story

When I was working on a branded content series, I had a writer working on it. I brought him in to create a kind of writers’ room and we were brainstorming ideas.

As we were heading down in the lift, this guy says to my clients, “If you’re ever looking for any more film work or video work, particularly from a writing point of view, we should definitely talk.”

The clients are looking at me quite nervously. This was a job that I had a tender, so of course this wasn’t appropriate behaviour. Later, I had to smooth things over with the client. The guy was making me look bad in front of the client.

I ripped the writer a new one once we were alone and said that is completely inappropriate. To take full responsibility for what happened, though, I hadn’t been explicit with him about not poaching clients. I assumed he wouldn’t do it because he was a grownup professional. I wouldn’t do it, but you can’t predict other people’s behaviour based on what you do. It was a learning experience for me, and I think that’s why I got so strict about making sure the conversation happened earlier rather than later.

He promised me he’d never do it again. And I said no, you won’t do it again because I’m not hiring you again. And that was also the end of a friendship.

Hiring and managing contractors is different to freelancing

Most people looking to hire contractors don’t have experience in hiring others. We also have to remember that a lot of freelancers (including me when I was freelancing), have never had a job, let alone experience as somebody else’s manager. That whole job thing can be very confusing. And I think hiring out of desperation creates a huge number of problems.

How the pressing need for help influences the contractor hiring process:

·        People hire when they’re already busy and they’re already desperate to match the needs of a big client and find themselves at sea

·        They grab a bunch of people in order to be ready for that gig and/or service it in a hurry.

·        We tend to hire our friends or people that we already know. That’s not a good reason to hire someone.


I talk to clients all the time who say, “I’ve hired this person, she’s not particularly good. But she’s my friend, and she needed the money. And I needed someone to do the work.”

You wouldn’t hire people who aren’t very good normally, it’s common sense. But a big part of the reason we do is that we haven’t done our preparation.

How to avoid that:

·        Remember that a job ad differs from a job description.

·        Write up a comprehensive job description for that gig. Even if it’s just someone to help you with your admin for one hour a week, or someone to do some freelance work for you in a particular job.

·        That job description doesn’t necessarily get shared in its fullness with the person you’re going to hire. It is for you to figure out the right person to meet your needs.

In the job description, answer the following questions:

1)     What kind of person do you want?

2)     What skills do they need?

3)     What does the job involve? What’s the job scope?

4)     How do we measure successful completion of the role?

That comprehensive job description can help you in so many ways:

·        It’s going to help you work out exactly what you want and need

·        It identifies what’s important and what’s not

·        It’s a basis you can turn into an advertisement, a callout and promoting that you’re looking for people

·        It can help inform your interview questions

·        Give you the KPIs you need to measure their performance.

With inside staff, I do a performance review every six months.

Are the places that you would recommend people go to set up their relationships properly so that they don’t fall foul of legal problems or the ATO or anything like that?

Because I work exclusively in the creative industries, the one place I’ll always recommend is the Arts Law Centre of Australia. They have a vast range of content and contracts you can download, and they also have a subscription service.

If you’re a creative practitioner, you can spend a yearly fee, and gain access to legal advice and assets.

If you’re outside of the creative industries, then I would suggest cobbling together a contract made up of all the contracts that you’ve ever signed, or bits of pieces of information that you can get, pull it all together into something that you think looks good. And then fork out a fee to pay for a lawyer for an hour to go through it and tell you what you need to change to ensure its legally binding.

I’d also suggest that you look up Fair Work Australia and the Fair Work Ombudsman because that’s where you’ll get a lot of information about working for free, what makes up an intern placement, what makes you an employee versus a contractor, and that sort of stuff.

What else should we know when managing contractors from a legal point of view?

You need to investigate whether you need to be paying your contractors and freelancers superannuation. The superannuation guarantee for contractors has been around for over a decade. And yet apparently, nobody seems to know about it. If you’re not paying your freelancers superannuation and you’re supposed to be, then you can face large fines and get audited.

The Superannuation Guarantee isn’t a choice. There is an employee contractor decision tool on the ATO website that you can use to help you figure out what your super obligations are.

A big part of managing contractors is making sure you pay them on time. What sort of things do you do to make sure that you’ve got the cash flow ready to pay your contractors, no matter what the end client is doing?

I have always made it a rule to pay other people whether I’m getting paid or not. I usually pay people the day they give me their invoice, even though  we ask people to give us 14-day terms.

Everything I do works on a strategy. I will not hire you unless I know that the money is coming from somewhere. Making you wait is going to create drama where there doesn’t need to be any.

Clients come and go; jobs come and go. But if I’m going to build a business, that’s going to last even if it’s a business of me and sixty freelancers, then I’m paying everybody on time. That’s how you create loyalty.

How do you manage cashflow?

I’m not a fan of debt and I’d advise nobody to go into debt. But what I would advise is to get a pre-approved overdraft on your business account. A pre-approved overdraft will not cost you any money unless you actually have to use it. So, if you have to pay someone because they’ve invoiced you, and you need to pay them right now, for the client will not pay for a month, then okay, you’re going to have to dip into your overdraft for a month. But it’ll be worth it because that freelancer is going to be happy. That freelancer is going to love you, and they’ll always want to work for you, and do a fantastic job.

It also forces you to be more strategic in how you invoice the clients. That means invoicing clients in instalments, especially if there are many people working for you.

How do you reduce your risk when hiring contractors?

I am the only person at Creative Plus Business that is working full time. Everybody else who works here is a freelancer or a consultant, or is on staff as an employee. I expect everybody to have a creative career outside of their work here.

That is a branding and kind of expertise issue for me, because we provide advice for creative practitioners. And so everybody who works here needs to be a creative practitioner, otherwise, our clients are going to smell the bullshit from a mile away. But that means that the expectation is that they all need to have something else that they’re doing as part of their creative practice. And even the employees get time off to pursue that creative practice.

I’m also doing that for selfish reasons. Because ultimately, the only person who has to financially depend on this business is me. Because if I, if everything suddenly goes bad, and I don’t have the cash flow to keep everybody going, there’s complete financial transparency, they all know what’s going on. They’ve all got something else that they could do if I had to let them go.

I don’t want to let them go. But if I had to, they wouldn’t drown. They’d be okay. So that’s just something that I’ve done to help me manage the bigger picture issue.

It’s also very clever to teach people not to be reliant on you and putting emotional labour on you to solve their issues.

How do you check a contractor is on the level?

Do your own due diligence when managing contractors.

·        Find out what their ABN is and whether they’re working under a business name

·        Check their GST registration

·        Spend some time looking at their social media, especially LinkedIn

·        Check out their website

·        Review the projects they’ve worked on

·        Reach out to your contacts and ask about them.

I am a huge fan of a book called Thinking Fast and Slow written by Daniel Kahneman. He won the Nobel Prize in Economics for this book. And it’s about how we make decisions and how our thought processes work. He gives you all the reasons you should trust the thing you call your gut instinct. There’s an animated 10-minute version of it.

What stands out in the crowd with the good subcontractors?

I really like it when people don’t ask me for work.

I get inquiries all the time, and the inquiries where they’re just interested in themselves. I’m not interested in hiring that person. If you’re unable to empathise with my situation as the leader who’s in charge of everything, then I really don’t want you to work for me. I don’t want to be your mother.

Instead, treat me like a person:

·        Ask me how I am as a person and take an interest

·        Promote what we’re doing

·        Spruik the other people you like working with.

The ancillary benefit is that I’m probably going to give you more work as we pay it back and forward. Anything that you can do to softly reinforce my feeling that you are both loyal and ambitious in your relationship with me will continue to keep you inside the pool.

Also behave yourself:

·        Don’t poach my clients.

·        Don’t be an arsehole.

·        Don’t sexually harass people.

Care about the people, places and work we do.

You can find out more about Monica Davidson and the vital work she does with the creative industry by heading to the Creative Plus Business website



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