If you are looking for the video of the Collaboration and Communication: Mastering the Art of Building Successful Relationships between Clients and Freelancers seminar, head to the blog. 

This is the entire transcript for anyone who wishes to access the event in a script style format.

four people look at the camera, smiling

L to R: Carolyn Stebbing, Craig Watson, Olive Garside, Rebekah Lambert.

Rebekah MC: Welcome everyone to the Collaboration and Communication: Mastering the Art of Building Successful Relationships between Clients and Freelancers seminar.


Obviously, I’ve chosen a very succinct name for this one, so succinct I can’t even remember it myself. You are joining us today from all different places from Rounded, from the family of Little Village Creative and the Freelance Jungle, and the audience for talent podcast, Tap-on. You’re in for a bit of a treat.


I’m coming from Windang which is in the Illawarra. It’s where the First Nations people met to reconcile their differences and come together for better communication, sort out all their differences, and then go fishing and prawning to settle them. And I’d really like to bring that to our attention today. Because I think sometimes with clients and with freelancers, we get caught up in the argy bargy of the small stuff, and sometimes we need to get it out of our system so we can get on with the job and get to it. I’d like to acknowledge the traditional owners of the land of the lands that we are gathering on today and want to pay respect to anyone past, present or emerging who is an elder in their tribe. And we recognize the Wodi Wodi People of the mighty Dhawaral nation from the Illawarra. We are here for the Wurundjeri Woi Wurrung people of the Kulin Nation for people in Melbourne. And of course, Bunurong and Wadawurrung Peoples for around I think was Werribee area. We pay our respects to past, present, and emerging elders today.


We’ve got some fantastic people here for you. The Freelance Jungle has done this with the help of Rounded, for supporting this seminar and making it possible. So, thanks very much to Olly and the Rounded team for making this happen.


Every day in the Freelance Jungle, we are talking about client woes. And one thing that I’m often hearing is that people are having trouble working with marketing agencies. They don’t know how to approach recruiters and work effectively with recruiters, and startups are something that they often avoid completely, because they’re worried about how to manage things. So, I thought what a great opportunity to bring some representatives from these communities that are effectively working with freelancers to come and have a bit of a chat with them, get a big inside scoop of their brain and see how we can all work better as clients and freelancers to manage those relationships effectively. So, I’ve got here, Carolyn Stebbing, from Little Village Creative.


Hello Carolyn.



Carolyn: Hello, everybody. Thank you. Great to be here.



Rebekah: I’ve got Craig Watson. He’s from Tap-on, which is the hip new recruiting podcast.



Craig: Thanks for that Bek, great to be here.



Rebekah: And a few people should obviously recognize Olly from the many things that he does for Rounded.


Olly: Hey Bek, nice to see you.


Bek: Nice to see you, too. Okay, so I’m going to start with Carolyn. Carolyn, can you give us a little bit of an introduction about yourself with your agency, and then I’ll crack on into some questions.



Carolyn: Welcome. I’m Carolyn. I’m the founder of Little Village Creative here in Melbourne. I have been working in advertising, marketing, and creative services in a bunch of different roles for the last 17 years. I started in big agencies. I’ve worked in small agencies and have worked in-house. I have also been a freelancer. And about eight years ago, I started my own agency, Little Village Creative.



Rebekah: You’ve been the freelancer, you’re now an agency founder. How does your previous life as a freelancer inform your new life now, Carolyn?



Carolyn: So, it’s an interesting question. And I think to expand on that, I’ll just go back into a little more detail of my career history because that’ll help. As I mentioned, I’ve worked in big agencies very much at the start of my career and I came from the land of client service. That is account service, which, for anyone who is not familiar with it, you are really the voice of the client within the agency. You’re also responsible for getting great creative work out on time, managing the brief to the budget, and really pulling everybody that’s involved in the project together.


It’s really the fusing of creativity and the commercial aspects of what we need creatively to do in a marketing and advertising sense. And I really love that I’m really interested in that fusion. I think you need creativity to be commercially successful, and it’s why I started my business. Coming from that background, I really took that ethos into freelancing. I’m probably a bit of a weirdo in that I don’t mind some of the more boring aspects of freelancing. I enjoy the numbers. I quite enjoy the business side of it, not just the creative side of it, which is what I got into it before. But I really enjoy that fusion and getting those two things working together. And that’s really the ethos I’ve taken from freelance life into agency life over the past eight years.



Rebekah: Now, Carolyn, can you share some insights into how your marketing agency effectively collaborates with freelancers? What strategies and processes do you have in place? How do you get the smooth communication and the successful outcomes that you’re looking for?



Carolyn: It comes back to what you do from the outset. Obviously, there’s all the bits and pieces you do while working together. But it really comes back to the brief. It’s such an underrated part of what we do. The brief reflects the scope of work. From the outset of working together, it’s imperative to have a clear brief. And when I say the brief, I’m not just talking about the brief to freelancers, but the brief to the client, as well. Everyone needs to know what they are working on and what to expect. Getting that scope agreed on is important.


Something that we do from a process perspective is use Slack. Slack can be a real pain if you don’t manage it properly. But we’ve got a great system for it. And every time we work with a freelancer, and freelancers are such a big part of what we do at Little Village, it’s partly why we called Little Village Creative, is working together to get our little villages, our freelancers, onto a project specific Slack channel. And so, we have clear communication all the way through the project.


And we take the attitude as well that our little villages, our freelancers, are very much part of our team. We treat them like a part of our team, but we also respect their running their own business too. Making sure that we have clear communication, and not assuming that they’re working with us all the time or treating them like they do, because they’re not.



Rebekah: Trust – it is such a delicate aspect of the client-to-freelancer relationship. But it’s so necessary to be innovative, and especially creative, right? If you don’t trust people, you can’t be vulnerable enough to do your best wacky work. So, what steps do you take as an agency to build trust proactively with freelancers and maintain a positive working dynamic throughout the duration of a project?



Carolyn: Trust is really interesting. The tricky thing with trust is you can’t build it overnight. Trust takes time. The hard flip side of that is that trust can be broken in an instant, just by one little thing going wrong.


We’re all human, and it happens. But the point I’m trying to make here is that trust is built through lots of little actions, rather than one big thing. There are lots of little things that we do. There’s a brief I spoke about before, a really clear brief and clear expectation upfront of what they’re going to be doing and what that scope is. That helps.


I think another thing to think about these little micro-actions – I don’t love that word, but I’m going to use it – these little micro actions that we can take with freelancers to support them. For instance, can we pay them early? If it’s our first job together, paying them early so that they can trust us and they know that we’re going to come through with payment, and so they enjoy working with us as a result. As an agency, we look for things, giving them a heads-up if stuff is going to come through late. Communicating things are changing. The reality is with clients, things change. It doesn’t matter how good a project manager you are; the commercial reality is that things are going to change. Particularly if you’re working with a lot of startups as we do.


I think it’s on both sides of the coin. It really takes both sides to build that trust. Those are some things that really helped. But something also mentioned here too, is that in the context of the relationships, some of the really great things that freelancers have done to build trust with us, are things being really honest with us about their specialties, their time, and whether they can take on a job. We’ve got a wonderful freelancer who we work with and we’ve worked with him for a number of years now. And he’s just always clear with me. It’s either a hell yes, or it’s a no. So, if he can’t take on the project, because it’s too small for him, or it’s the timings aren’t right, he just says no. But otherwise, it’s hell yes. He’s really transparent about that. And I think those little things throughout the relationship and the communication process really, really worked to build trust.



Bek: Absolutely. It sounds like it’s all the raindrops of consistency that come together to make a happy client bucket.



Carolyn: That’s such a lovely description. That’s exactly that’s exactly it. Just little things, you know, it’s, it’s how you can, how you can perhaps delight your client, have some empathy for them, or have some empathy for the freelancer that makes their life a bit easier? Because we went from that, right.



Bek: Oh, totally. Once you’ve established and trust in this empathy, and by the way, I’m available. How do you give the autonomy within the creative work? There’s the potential for a client to feel nervous about someone spending time acumen and budget potentially on mistakes and missteps. So, how do you balance expectations with the potential for giving that freelancer the ability to explore their creativity, and the breadth they need?



Carolyn: I’m going to make a really broad assumption here.


You probably have to divide projects into sort of two buckets when we think about autonomy.


You’ve got your projects where you’re engaged to do something that’s quite simple. And it’s just about getting work done on time and on budget. I’m thinking about things like, for instance, image resizes. If you’ve been brought on board to work with a client for a day or an agency, for a day, if you’re a designer, and you’re just that’s what you’re doing, the most important thing there is just to really deliver that to the clients happy, you’re happy, you get paid, and everything’s good.


Where you need that autonomy, obviously, is on those projects that require a lot more creative thought. The big thing that I’ve learned, and I’ve learned this through making mistakes and seeing what works and what doesn’t, is that it’s important to have test projects together. That’s how I like to work as an agency. If we’re bringing on someone for the first time as a freelancer, and we think they’re going to be great at those kinds of projects, then let’s do a test run together. So, let’s maybe write up a little village blog together, or let’s do something creative for the social channels, see how that goes, get a feel for their style and their communication, they get a feel for us. And then I think we’re able to honour that autonomy. Just being really clear about how we can make that space for them during the credit process.



Rebekah: So, minimising the risk, so that it’s not an all-or-nothing style situation. Agency life is tough. It’s usually a quick or the dead situation. So how do you manage the need to pivot without endless scope creep, or the potential for overwhelming your chosen freelancer managing those client expectations and all the rest of it together?



Carolyn: Always, always a painful thing. It’s the reality of the world we’re in. And I think if I can look back over, my 16-17 years of doing this, we’re seeing pivots, more and more things are moving faster. Businesses work very differently. I mean, agile wasn’t even really a thing when I started out in advertising, back in the day makes me sound really old. But now we move quickly, to think really, we have to sort of think really fast. And I guess it becomes really tricky when you have a fixed scope of work. But there are quite a few ways we do that.


Look, I think the best thing to do really is to look at that scope of work right from the beginning, building lots of room for a bit of backward and forwards, particularly if you know the client and you know that there’s going to be a likelihood that things change, timelines are going to change. Again, I’m speaking about this from the agency perspective, but this could apply to freelancers too. Looking at that scope of work but also having in mind that things are going to change, and you can pinpoint areas where things are likely to move.


From the agency perspective, building a bit of room for that, so that the client feels really comfortable with it, but also the client knows what the boundary is. And then also communicating that to the freelancer and making sure that the freelancer is actually on board with that scope. And having a really clear agreement that, if we exceed three rounds or there’s a change of scope, we have to re-scope this. Again, it just comes back to that outset. And I think it can feel a little stressful and painful at times when these things happen. But this is just the reality of the commercial world we’re in now and giving yourself a bit of buffer and your quotes as a freelancer or agency to combat that is really important.



Rebekah: Absolutely, we’re definitely in a changeable world, if the last three years have taught us nothing else. So, your scenario is unique because you’re managing both the client and the freelancer expectations? What’s the best piece of advice for making that as stress-free as possible for all concerned?



Carolyn: Look, it really just comes back to communication, I think. There are lots of little things you can do depending on the project, but communication and expectations are key. We’ve had very few issues when the expectations have been set clearly upfront with all parties. Just keep up the communication and put yourself in the other person’s shoes. As an agency person, the best freelancers I’ve worked with will give me a heads up if they’re running behind. They’re honest, and they’re transparent about that. So, if they’re having a problem with something, they let me know. If there’s a problem with the brief, they’re in touch. The rest of my team would say the same. So just be communicative. And don’t be afraid to communicate if you’re having an issue, especially if you’re working with a good client or agency. They will understand. So lean into that fear a little bit, feel it, but communicate as early as you possibly can if you’re having an issue. That’s how you build trust too, because people know they can rely on you to flag an issue.


My two key tips would be to get your scope clear, which is a communication thing upfront with either party, and then be honest, transparent, and clear with your communication, which comes from having empathy for the other people involved in that relationship.



Rebekah: Thanks for that, Carolyn. We’re going to cross to Craig for a brief minute and open up the recruiting side of things. Craig, for everyone who hasn’t met you before, can you give us a little bit of a touchdown on who you are?



Craig: Yeah, sure Bek. I’ve been in the recruitment industry for a long time, probably 15 to 20 years. Initially, I worked in tech recruitment, then I started recruiting recruiters specifically, so I gained a better understanding of them. Most recently, I ran a platform for freelance recruiters, helping them find projects and take care of themselves in the gig environment. It’s really interesting how the industry has changed and embraced freelancers as a significant part of recruitment, both as freelancers themselves and as candidates for opportunities.



Rebekah: I remember when I first started out in 2010, if I tried to find a recruiter, they sent me for typing tests. I’m glad we don’t do that anymore. So, picking a freelancer to work with a client is more complex than it seems. It’s like being a matchmaker between the two. How do you manage that?



Craig: First of all, it’s crucial to understand why freelancers choose to freelance instead of being part of a permanent workforce or considering contingent or contracting roles. A lot of it comes down to flexibility, the ability to choose clients and projects, and finding a good fit in terms of values and culture. So as a recruiter, it’s essential to understand the freelancer because without knowing their motivations, it’s difficult to make a positive and proactive match for both parties. Many freelance engagements come through referrals from their own network or through bids on platforms they use. However, considering the significant size of the contingent workforce in recruitment, which is nearly 50%, recruiters need to have a better understanding of this market. It’s no longer heavily skewed towards permanent placements as it was five years ago when it made up around 80% of engagements via recruitment agencies. Now it’s more balanced with 50% permanent and 50% contingent or gig roles. Recruiters need to adapt to this shift.


When making a match, there are factors beyond just the financial aspect. Although the financial aspect is important, recruiters act as intermediaries between the organization willing to pay a certain amount and the freelancer looking for a specific rate. Negotiations often come into play. So, it’s a combination of factors that contribute to making a successful match. I’ve mainly focused on the freelancer’s perspective here, but it’s equally important for recruiters to understand their clients well. Good recruiters, as opposed to bad recruiters, know their clients, and understand what works well within their organization. They develop relationships over time, perhaps forming a significant portion of their workforce. They talk to incumbents and hiring managers to get a feel for the business before making any recommendations.



Rebekah: Absolutely. Okay, I don’t mean to talk you out of a job, because I know that’s how I feel every time someone mentions ChatGPT. But imagine there is no recruiter. How do we replicate that success as freelancers or an organization? How do we recruit the right people for the project at hand in that brief span of time that we’ve got?



Craig: What’s interesting about recruiters is that we can see them as a mechanism or tool that can be utilised or not. If you choose not to use a recruiter and prefer to find work on your own as a freelancer, regardless of the industry you’re in (whether it’s tech, creative, finance, etc.), you need to wear multiple hats. You become part salesperson, part marketer, part lawyer because you have to understand the engagements you’re entering. You also become a matchmaker, navigating various moving parts. Personally, I believe there is an overreliance on the recruitment industry. Many engagements can be done independently, as demonstrated by established platforms like freelancer.com, Upwork, Fiverr, expert 360, and emerging ones. However, if you choose this path, you need to possess additional skills beyond your core expertise as a freelancer. Otherwise, you may encounter difficulties, such as misunderstandings about contracts or communicating with the wrong individuals internally. Recruiters, despite the frustrations they may cause, often handle these issues behind the scenes.



Rebekah: So, we should focus on the positives of eliminating headaches, right?



Craig: Absolutely. If you find a good recruiter, your quality of life as a freelancer will significantly improve because they will do the challenging work to secure the gigs you desire for the durations you prefer. It’s incredibly frustrating, particularly in the tech market, for those working in a gig or contracting capacity, to witness the rapid changes that have occurred in the past six months. It’s a daunting and unsettling experience. This applies not only to tech but also to other evolving markets affected by factors beyond our control, such as politics and the economy. However, recruiters can help alleviate that stress and manage these uncertainties for you.



Instead of hoping it all resolves itself while feeling overwhelmed, it’s best to find a reputable recruiter with whom you have a connection. Let them handle the difficult conversations and challenges on your behalf.



Rebekah: Okay, so can you share some strategies and processes that you have for identifying and engaging in selecting the freelancers that you want to work with for various projects and positions? How do we make ourselves stand out and have that competitive edge?



Craig: It’s fascinating to see how freelancers come from diverse backgrounds and industries that now offer gig opportunities where they previously didn’t. To truly stand out, let’s face it, recruiters have their preferred places to find the right candidates for the opportunities they have. As a gig worker, if you’re seeking opportunities that recruiters may present, you need to make yourself visible. In a professional setting, having a well-curated LinkedIn profile is crucial. It should highlight your current experience and be regularly updated to reflect your latest work. It’s highly recommended to gather positive recommendations from colleagues and clients who can speak about the quality of your work. In the tech industry, platforms like GitHub or Linktree can also be relevant. Testimonials hold significant importance, especially in creative fields where platforms like TikTok can attract the attention of creative recruiters. The channels recruiters use may vary depending on the industry, but expecting to be discovered without creating your own presence is simply unrealistic. Sitting passively and wondering why opportunities aren’t coming your way or why recruiters aren’t reaching out won’t yield results. If you were active in these channels, recruiters would likely inundate you with contact.



Rebekah: So, for those actively engaging on LinkedIn, you’re doing the right thing?



Craig: Exactly. It’s important to be strategic and informed about the channels where your target audience and potential clients are present. As a freelancer, you’re essentially selling your expertise and leadership in your specific area. This means understanding where the people who can engage and hire you are looking. It’s not limited to just one channel; different industries and even roles within industries may have distinct channels recruiters rely on. It’s an exciting and sometimes overwhelming process, but if you navigate it successfully, you’ll have clients clamoring to work with you.



Rebekah: That’s fantastic. I love the perspective of self-advocacy rather than purely marketing with freelancers. So how do you suggest freelancers advocate for their skills, experience, and preferred working conditions? How can they effectively communicate whether they want to work remotely or have other specific requirements? Do you have any guidance or resources to offer?



Craig: First, let’s address the elephant in the room: imposter syndrome. Freelancers often work independently, and confidence can be a fluctuating challenge. Imposter syndrome affects many people, and it’s crucial to overcome it because self-efficacy involves highlighting your strengths and the value you bring to the businesses you engage with. Despite your personal motivations for doing the work you love; it ultimately boils down to a commercial transaction. You need the ability to advocate for yourself. While freelancers have a supportive community, they typically work on their own. So, it’s important to remember that imposter syndrome is not a solitary experience—it affects everyone. However, finding ways to move past it is essential for success as a freelancer. You must be able to promote your skills confidently.


Now, when it comes to the relationship with recruiters, transparency and trust are key, as Carolyn mentioned earlier. Let’s be honest, recruiters don’t always have the best reputation in terms of trust. There’s a fear of commissions and concerns about the recruiter’s involvement in transactions. While there are both bad and good recruiters, it’s crucial to build trust with the ones you choose to work with. Transparency has proven to be the foundation of successful interactions in my experience in the recruitment industry.


It’s crucial to address hard conversations upfront and bring attention to any red flags in a candidate’s profile or body of work. From the candidate’s perspective, recruiters deal with an unpredictable product—people. Unlike screws or furniture, we can’t predict how an individual will perform in a work environment due to various personal pressures and stresses they may have. Transparency can help mitigate some of the uncertainties, but unfortunately, it’s not always common. Freelancers often feel uncomfortable discussing personal matters that might affect their ability to take on or succeed in a project. This relationship between freelancers and recruiters is transactional and challenging. Transparency and trust aren’t typically established in the first interaction; it takes time. So, to simplify, transparency is vital.



To ensure success, it’s essential to prioritize transparency. Be open about any issues or successes that arise. If you’re missing a small requirement in a project, don’t try to hide it. Instead, be upfront and transparent about it. For example, if you lack experience in a specific CRM environment, don’t pretend otherwise. Clearly communicate that you haven’t worked with that particular CRM but highlight your ability to pick it up based on your experience with other systems. Gather recommendations from previous clients, include links to your portfolios or profile, and use QR codes for easy access to hidden information. I recently invested in a digital business card that looks like a credit card. When I hand it to someone, all my contact details are automatically stored on their phone. Making things easy and transparent increases your opportunities.



Rebekah: It sounds so sensible and reasonable when it’s put that way. Now let’s move on to Oliver. Oh, sorry, Olly. I’m not used to calling you Oliver. Can you introduce yourself and Rounded Olly for the three people in the audience that haven’t heard of you?



Oliver: Rounded is an invoicing and accounting app specifically designed for freelancers, with a focus on creative freelancers in particular.



Rebekah: Fantastic. Just a heads up, there’s a poll currently happening for freelancers on Zoom. So, if you haven’t participated yet, please take a moment to answer it. Oh, it seems everyone has already answered it. Oh well, I might get excited and launch another poll then.



Oliver: According to the results, responsiveness appears to be the most important scale for clients in a project.



Rebekah: That’s great. I love it when soft skills come out on top. Now, let’s discuss the best approach to working with freelancers when starting a startup. How do you set freelancers up for success considering the inherent risks? Startups often have limited time, budget, and resources to spare. So, how does Rounded tackle this challenge?


Oliver: Yeah, that’s a great question. To answer it, I’ll draw from my hindsight and experience. When I joined Rounded and started working with freelancers, I had limited knowledge of the freelance world. I had some experience as a hiring manager in the corporate world, but hiring for my company and finding my footing in that realm was a different story. What I’ve come to realize is that, as a business, it’s crucial to have a clear understanding of what you want. For example, if you need someone to write blog posts, knowing your audience, the frequency of posts, and the desired outcomes makes it easier to provide a concise brief to freelancers and evaluate their performance. However, there are scenarios where you identify a gap in your organization, lacking internal expertise and even the knowledge to ask the right questions about what the solution should look like. In such cases, hiring becomes more complex and requires sophisticated conversations. We’ve had success in these situations, but it involved trial and error. So, the first thing I’ve learned is the importance of self-awareness regarding your own position and effectively communicating that to potential hires.



Rebekah: Absolutely. Now, let’s discuss how freelancers and business owners can find common ground and align their goals during a project. It’s common for both parties to have their own perspectives, with freelancers focusing on their needs and business owners prioritizing their own requirements. How can they bridge this gap and establish a shared understanding?



Oliver: Certainly. When it comes to freelancers approaching a business owner, there are a few key aspects to consider. Speaking from my experience at Rounded, we have primarily hired freelancers directly without involving recruiters. Fortunately, our customer base comprises incredibly talented individuals who appreciate what we do. In fact, some of the most successful freelancers we’ve hired were initially our customers. This is advantageous because they already understand our market, our customers, and our services, providing a solid foundation of shared knowledge. From my sales and relationship background, I can say that I’m easily convinced if the approach is right. The best freelancers I’ve encountered and hired were able to identify and articulate the specific problem I was facing and demonstrate how they could swiftly solve it. This is the starting point for building trust, as Carolyn mentioned earlier. When entering a professional relationship, having an initial understanding of who I am and what I aim to achieve is like laying the first brick of trust. It assures me that my time won’t be wasted in conversations with this person. From there, trust naturally develops and progresses. Just this week, we welcomed a new team member who immediately hit the ground running. She flawlessly executed tasks, anticipated my needs, displayed initiative, and showcased outside-the-box thinking. It reached a point where she approached me saying, “I’ve completed all these tasks and just need your approval to proceed.” I was taken aback and realized that I didn’t even need to give her approval anymore because I trusted her completely.


As a business owner, reaching this level of trust is nirvana. It means that we are now operating at a higher level than ever before. I no longer have to think about the specific problem she’s solving—it has been taken off my plate. Whatever I’m paying her is worth every penny. On the other hand, in the early days, when I was less certain of what I wanted and couldn’t articulate my needs clearly, there were instances where I found myself constantly checking and rechecking the work of early hires. It was a reflection of my own shortcomings and lack of clarity. I reached a point where I thought, “I might as well do it myself because it’s not solving a problem for me; it’s costing me time and money, and I’m just as involved as before.



Rebekah: Certainly, I find this aspect quite interesting, especially considering that around 50% or even more of your workforce consists of freelancers, right?



Oliver: Yes, that’s correct.



Rebekah: So, how do you maintain a clear distinction or prevent the blurring of lines when your services or software are used by freelancers? Hiring such a large number of freelancers who also understand the product can have its benefits, but does it create any conflicts or challenges? How do you manage that?



Oliver: Well, when it comes to the freelancers we hire, we categorize them differently based on the nature of the work. Some tasks are ad hoc and relatively simple. For instance, we have a designer in Singapore who handles our social media and blog visuals, as well as designing our eBooks. Our relationship with her is primarily transactional and conducted through Slack. We also have other freelancers who essentially work full time with us. We treat them no differently because they are freelancers. We value them as integral team members and grant them access to our internal systems. They are invited to our all-hands meetings and included in our general communication channels, where we share everything from cat videos to Friday afternoon banter. In essence, we strive to create an environment where freelancers feel included and part of the team. Trust is a two-way street. I trust them to do their job better than I can, and that happens because they feel valued and respected. When they ask for something, I make a genuine effort to deliver on time, knowing that my actions affect their ability to perform their tasks effectively. When I hire someone, I focus on creating an environment where they can do their best work and be excited about working with me. Some team members even consider me their biggest client because of the long-term relationships we’ve built. Over the years, we have gradually expanded the scope of their work organically. I feel a responsibility to treat them as if they were permanent staff members. Building relationships with freelancers is similar to building relationships with recruiters or agencies. It’s not an exact science, and mistakes will be made. In fact, the key to consistently recruiting top talent is learning from past experiences, including those with less successful hires. Understanding what you want and don’t want is crucial.



Rebekah: Absolutely, it’s a good point. We often overlook the importance of empathy and transparency while striving to appear confident and business oriented. However, these qualities are essential in project management. How do you ensure a strong relationship and cultivate empathy when managing freelance relationships, especially when dealing with individuals located in different places like Melbourne and Singapore?



Oliver: Building and nurturing relationships, like any other, require effort and consideration. It’s not impossible. The key is to see people as individuals, not just by their job title or how they define themselves professionally. We make sure everyone on the team understands this perspective. Like a new employee, it takes time for freelancers to find their footing. To facilitate this, we utilise collaboration tools like Slack and Google Drive, making it easier for them to form relationships with not only me as the boss, but also with other team members. Simple steps like including them in the general communication channels, granting access to relevant information, and inviting them to all-hands meetings help foster inclusivity. It’s not about a single action, but a general approach. When I approach it, I ask myself, “How can I support these individuals in doing their best work?” When they are happy and producing their best work, it benefits both them and the company. It’s a win-win situation.



Rebekah: Absolutely, that’s precisely it. I often encounter resistance from freelancers when the term “startup” is mentioned. They worry about the unpredictable nature, constant changes, and high-pressure environment. What is the best advice you’ve received regarding working with freelancers in a startup setting? Or any advice you would give?



Oliver: I can’t recall receiving specific advice, as most of my learning has been through personal experiences and self-reflection. I take full responsibility for the mistakes I’ve made when hiring freelancers. However, if I were to offer advice to a freelancer considering working for a startup, I would emphasize the importance of getting the team as excited about the company as I am. It’s challenging, but not impossible, to inspire the same level of passion and engagement in others for a company that you helped build.



It’s a difficult task, but it’s definitely achievable. And I believe it’s the same with anything. You need to give people enough autonomy to perform their job. Personally, I prefer to lead from a position of trust. Once I’ve decided to hire someone, it means I’ve assessed their skills and believe they are capable. I allow them to demonstrate those skills without second-guessing them. Of course, if they consistently underperform, that’s a different situation, but ideally, my assessment is accurate, and we can establish a mutually beneficial relationship. My advice to freelancers, as a startup founder, is to remember that founders or company owners are also human beings. They can be difficult and may be unaware of the pressures they are facing, especially in a startup that is going through changes. However, you have to be okay with that if you want to be involved in a startup. It’s the nature of the beast. I’m not suggesting there’s leeway for not paying invoices or anything like that. From a freelancer’s perspective, if I consistently pay their invoices on time, it’s a good start in building trust. We won’t go down that route. As a freelancer, understanding what your client wants to achieve and sometimes uncovering their true objectives, even if they don’t explicitly state them, is crucial. That’s how you build trust and demonstrate the value you bring. Yes, having tangible skills as a graphic designer, copywriter, or any profession is important, but equally important are the softer skills, such as the ability to articulate how you will help the client. So, I apologize if I didn’t directly answer your question.



Rebekah: No problem. I enjoy going off on tangents and exploring more interesting topics. It’s all good. By the way, I’ve eliminated all the formal questions, so we can now open it up to the audience for their questions. Let me quickly browse through and see what we have here. Shall we display the other poll now? People can participate in it while we go through the questions. Please keep in mind, I’m checking for any questions you may have. Drop them in the chat. While we wait for some hot questions to come in and put you on the spot, let’s address a topic I frequently discuss with freelancers: how to say no. Freelancers often say yes to everything, which can lead to problems, as other presenters have mentioned. Craig, how do you say no while leaving the door open for potential future collaborations or contacts?



Craig: I believe it’s crucial to maintain transparency and clearly communicate your minimum expectations from the beginning. Whether it’s your day rate, the type of projects you’re willing to work on, or the specific industries you prefer, having open discussions with recruiters about your expectations can prevent the need to say no later on. If an offer comes your way that doesn’t align with your preferences, you can simply say, “We’ve already discussed that, and it’s not in line with my current focus.” As a freelancer, you’ve made a decision based on your own needs, and you must have the confidence to say no when necessary. It’s a short word and easy to say. It’s all about how you deliver it. You can say no in a polite and respectful manner. Some people may worry that saying no will close doors in the future, but I believe that being honest and upfront about what you can and cannot do will earn you more respect. It also prevents you from becoming overwhelmed and allows you to manage your time and commitments effectively.



Absolutely, absolutely. I see a question from Matt F. that asks, “Roughly, what percentage buffer do you recommend?” Was that question directed at Carolyn and related to her presentation? Apologies for the overlap. It appears to be intended for Carolyn.



Carolyn: Contingency? Yes, happy to discuss that. The short answer is it depends on the project. Let me give you an example. If you’re hired as a creative to come up with a campaign idea and manage it through revisions, you can plan for three rounds of amends. However, it’s wise to keep in mind that there might be a fourth round and factor that in when estimating the project. You can approach this in various ways, such as being upfront about your hours or providing a project quote based on your experience and gut feeling. Context is essential in determining the right amount of contingency. Consider allowing for an extra round of amends in your quote.



Rebekah: Now, Carolyn, many people are curious about charging day rates, hourly rates, and whether it’s possible to work part-time as a creative director at an agency. What’s the short answer to all of that?



Carolyn: Yes, this is an interesting topic. In the past, freelancers often charged by the day, especially when working at agencies for a week or two. However, nowadays, it’s more common, from our perspective, to work with a project fee. Keep in mind that when working with a fixed project fee, having a clear scope and brief is crucial. As a freelancer, be cautious if clients expect you to work with a fixed fee but provide insufficient details for quoting. It’s important for your clients to provide a clear scope of work if they want a fixed fee arrangement. If necessary, you can respectfully decline or request more information. This agreement and trust are important when working with set fees. At our agency, we prefer quoting set fees for our clients, but we also need to uphold our end of the agreement.



Rebekah: Speaking of briefing, because it comes up a lot, it’s in the chat that comes up in the Freelance Jungle. We talked a bit about having enough space to pivot and follow what the client needs. But also, you know, freelancers need certainty and the breadth of the work and all the rest of it. How do you manage the two different worlds only when you’re dealing with freelancers that you need the flexibility to pivot and change and learn as you go, but also not robbing the person by making them do 16 versions of a project for the price of two?



Oliver: Yeah, I believe that a good freelancer wouldn’t let scope creep happen. Personally, I try to be mindful of avoiding scope creep myself. With deciding whether to hire someone as a staff member or a freelancer, it depends on the role. For our customer success team based in Manila, they have been full-time employees from the start because we need their consistent presence and support for our customers. They are arguably the most important people in the company. We set clear expectations from the beginning regarding the number of hours required. We provide a minimum expectation that we will pay for, regardless of the workload. As the company grew, we increased their minimum hours to a 38-hour week contract. They receive paid holidays and certain other benefits. Although they are contractors and freelancers themselves, we treat them as employees because we need them to function as part of the team.


Regarding our relationship with Liam, our head of SEO and content, we have been working with him since before COVID. Initially, it was a matter of budget and figuring out what we could get for a certain amount. He started by writing one or two blogs per month, which was an improvement for us at the time. Over the years, as our budget allowed and as Liam demonstrated his capabilities, his retainer has increased significantly. He has taken on additional responsibilities such as email marketing, backlinks, and other tasks. These relationships have developed organically. Profitability is not necessarily the main driver when hiring people. My focus is on hiring the right individuals for the right roles, which ultimately leads to company improvement and, consequently, improved profitability. I hope that answers both yours and Matt’s questions, albeit in a roundabout way.



Craig, there’s a lot of curiosity about where to find good recruiters, like the mythical unicorns.



Craig: It’s an interesting question because many listeners and freelancers come from different sectors, seeking diverse opportunities. Personally, I would suggest approaching mid-sized companies that specialize in the contingent gig freelance space. By understanding their work in this area and forming a relationship, you may find promising options. If anyone is listening in my area and wants advice, I’d be happy to provide guidance and point them in the right direction. While I could list 150 great recruiters, that would take up a lot of time.



Rebekah: Perhaps we should dedicate a separate episode to that. We could call it “Craig’s Guide to Australia.”



Craig: Regarding the comment about recruiters being perceived as cookie cutters, it’s true that many follow a process. However, it’s crucial to consider the commercial transaction in recruitment. Ultimately, it’s the client who pays the bill and provides specific requirements. While recruiters may seem like cookie cutters, good ones go beyond that and explore additional possibilities. They engage with candidates and present the benefits of slightly deviating from the standard approach to the client. Finding a good recruiter involves transparency and identifying those who act as consultants, providing valuable insights to clients. I’m more than willing to discuss specific areas and recommend reputable companies or individuals. If anyone is interested, feel free to contact me.



Rebekah: Yeah, sure. And we can even take some of the resources into the Freelance Jungle, that’s perfectly fine. I guess the question I have for all three of you is, when you’re looking at people, what is it outside of the price point that floats your boat? Is it their attitude? Is it their adaptability? Is it their reliability? Is it a culture fit thing? Really, what’s the one thing that you always need in the mix to have a happy little farm for your project to grow on? So I’ll throw that to Carolyn first.



Carolyn: Yeah, good question. I think there are a few things that are wrapped up in my answer. It comes back to empathy, which I’ve talked about a lot. It’s one of our key values. A demonstration of empathy and the way the person is going to work with us is important. You pick up on little cues subconsciously when you’ve been doing this for a while. So, for me, it’s about effective communication and a quick acknowledgement of things, along with respect. I don’t expect everyone to get back to us quickly if they’re juggling other jobs, but an acknowledgement within a reasonable timeframe is essential. I also look for a reflection that they understand the business. It’s hard to describe without specific examples, but if a creative is briefed and they come to me suggesting that something could be done better with additional budget, that shows transparency and a genuine consideration for the project. On the flip side, red flags for me would be radio silence or not hearing back by a deadline. It’s anxiety-inducing for the client and the agency team when something gets missed. So those are the key things for me.



Rebekah: Awesome. And what about you, Olly? What are you looking for?



Olly: To me, it all comes down to the initial approach. If a freelancer can quickly explain how they can help me succeed, they’re the ones I want to hire on the spot. That’s the most concise way I can put it.



Rebekah: Nice. Concise is always good. And Craig?



Craig: From a recruiter’s perspective, it’s important that the freelancer or candidate going into an opportunity reflects the recruiter’s brand. The recruiter needs to have confidence in the person’s ability to understand and deliver on the opportunity. Communication plays a crucial role, as recruiters won’t risk their reputation with someone they are unsure of. It’s about assessing whether the freelancer can meet the desired outcome and deliver what is expected.



Rebekah: Brown raised a valid point that clients can exert pressure on freelancers, and it’s underestimated how much they can get away with. Freelancers often hesitate to address issues for fear of damaging the client relationship. It’s a common scenario in the freelance industry. So how can freelancers handle this challenge? How can they manage the fear of breaking the relationship? Olly, would you like to share your thoughts on this?



Olly: I want to acknowledge that my previous comment may have sounded a bit glib, but that wasn’t my intention. I understand that there are scenarios where freelancers like you can experience pressure from clients, and I don’t want to downplay that reality. From my perspective, I frequently work with one of my freelancers, Liam, who handles SEO. We often find ourselves dealing with shifting requirements and constantly changing timelines. I tend to get excited and propose new ideas, asking if we can implement them immediately. It comes from a place of enthusiasm and energy, without any intention to take advantage. Liam is really good at managing these situations. He would say we can do it, but it means bringing forward resources that were originally planned for next month. So, if we proceed with this new idea, there will be a gap in the following month. It becomes a decision about prioritization and understanding the trade-offs. Liam doesn’t simplify it into a binary choice but encourages me to make a prioritization decision based on what I want to achieve and comprehend the consequences of that decision. I hope this clarification helps.



Rebekah: Consequences are indeed an important point to consider. Carolyn, would you like to add anything to the discussion?



Carolyn: I just wanted to chime in and share my thoughts on this as well. I agree with the debates and the valid points that have been made. I’ve been in this situation many times, both as a freelancer and as part of an agency. I want to validate the feeling of anxiety, especially when you work for yourself. It’s easy to fall into a negative mindset where you feel obligated to take on every piece of work that comes your way. However, we’ve all been in that position. When I first started freelancing, my accountant gave me some excellent advice. He said that if you think of your time as money, it’s actually better to say no to opportunities that consume too much time and instead take a break or enjoy a day off. By doing so, you’ll have the capacity to say yes to the right opportunities. So, if you’re feeling pressured and facing changes in a project, be courageous. With practice, it becomes easier. As Ali mentioned, it’s about presenting the client or agency with choices. You can say, “It’s not a problem for me to assist you with this, but I’ll need to charge you XYZ or make certain adjustments to make it happen.” Sometimes, framing it as doing what’s in the client’s best interest while setting boundaries can be effective. It’s hard to argue with someone who approaches the situation with your interests in mind and sets the necessary boundaries to produce excellent work. I hope this empowers anyone who’s concerned about bidding on projects to have meaningful conversations. Transparency and boundaries allow you to deliver your best work, benefiting both you and your client, whether they’re an agency or a business.



Rebekah: It seems to tie back to what Craig mentioned earlier about imposter syndrome. We tend to personalize the disconnect, but it’s important to acknowledge that not all clients and freelancers are meant to have seamless collaborations. We have different values and attitudes, and sometimes the project doesn’t align with our initial expectations. And that’s okay. So, Craig, when we find ourselves in the midst of a project, how do we prevent imposter syndrome from creeping in and making the project unnecessarily challenging to complete?



Craig: I’m not sure if there’s an easy answer to that because we all go through different struggles, and there are different triggers. But from my perspective, if you’re in a freelance gig organized through a recruiter, it’s their responsibility to handle that pressure. That’s what they’re getting paid for. Pick up the phone and tell them about the changes in scope, the issues you’re facing, the agreements you’ve signed. The recruiter has to sort it out for you. They’re making money from it. Let them handle the headache if you’re using one. I understand most people don’t have that option, but I’m just pointing out one of the benefits if you are in a relationship with a recruiter. Don’t take on that stress. Impostor syndrome is a different beast and difficult to overcome because there are clients or organizations that may push boundaries or engage in scope creep. They might think, “We’ve hired this person for this specific work, but let’s just ask for a bit more without giving them extra time or compensation.” Many people find it challenging to speak up against this. I don’t have the answer. Unless you have a recruiter, you can ask them to handle it.



Rebekah: And that beach vacation is looking more and more tempting by the second. Another question to consider is how do we address the industry’s bad habits? Some people have picked up these bad habits when working with freelancers, and it creates a cycle of poor practices as everyone learns from each other. How can we disrupt this cycle and help someone improve their working relationship with us? Whether it’s on an agency level, freelancer level, or any other level you’re working at. Carolyn, do you have any specific approaches you try to implement?



Carolyn: This is a difficult question to answer, and I’ll be completely honest here. When I hire someone for my permanent team, it’s my responsibility as their boss to develop their skills. I need to take a vested interest in their career development to ensure they enjoy their work and produce their best work with us. The tricky part with freelancers is that when you bring them in, you’re relying on their experience and expertise to support your business. They’re expected to hit the ground running, and you’re paying them a freelance fee for that. So, there’s a certain level of expectation. If someone comes in and I provide them with feedback, but they don’t respond or make improvements, we will end that relationship. I may sound a bit harsh here, but what I mean is we will wrap things up, compensate them, and move on without engaging them for further work. It’s not because I don’t want to help them, but the commercial reality of running a boutique agency is that I don’t have a lot of time to train and nurture a freelancer who doesn’t already know what they’re doing. My permanent team doesn’t have much time either. So it’s important to be mindful of that. It’s not me being harsh; it’s just acknowledging the realities of being a founder who works almost seven days a week. I have to choose where I invest my time, and it will be on my team, new business clients, rather than extensively nurturing a freelancer unless it’s a mentoring relationship and completely unrelated to Little Village.



Rebekah: Absolutely. And when it’s a client that is taking advantage or being unreasonable, how do you educate them to improve their behavior?



Carolyn: That’s a really tricky situation, but I can share some advice. It goes back to what I mentioned earlier. I have implemented a screening process with clients where we have a kickoff and chemistry session before any financial transactions take place. This is to ensure that we are a good fit not just in terms of the transaction but also in terms of building a strong relationship and having open and honest conversations. If challenges arise during the relationship, it’s my responsibility as an agency leader to address them. I usually make an effort to meet the client in person, whether it’s over a beer, at their office, or inviting them to our office, to troubleshoot and find solutions. However, this investment of time is necessary even when things are going well. Tough conversations should not overshadow the overall positive relationship. It’s crucial to build a relationship beyond those difficult discussions, and this applies to freelancers as well. If there’s a difficult situation or feedback that doesn’t make sense, it’s important to have a conversation and discuss how we can work more effectively together. Most clients appreciate this open communication.



Rebekah: I see a few heads nodding. Craig, do you have any recruitment insights or strategies to share?



Craig: Well, I would say that if we’re being honest, everyone feels a little anxious when it comes to the clients who are paying the bills. It’s an extension of imposter syndrome. When you’re in a recruiting role, and the client is taking advantage of the situation, you might panic a bit. Your first instinct isn’t to assert yourself and confront them. Instead, you worry about the number of invoices you have with them and the freelancers you need to pay. It’s a mild panic that needs to be addressed, and you’ll likely go through a process. As Carolyn mentioned, it’s your responsibility as a business owner or account manager to clarify the project scope and the expectations within the relationship. It’s not easy; it can be quite scary at times.


From a freelancer’s perspective, they might also be taking advantage of the situation. In this case, your first step would be to remind them of the agreed-upon statement of work and the expectations outlined within it. If the issues persist, it’s likely a problem within the relationship. I know it may sound unemotional, but it’s essential. For those listening who have experienced the premature termination of a project due to lack of success or attitude, they should take a moment to reflect on themselves. Reputational damage as a freelancer can be detrimental, as word spreads quickly. It can lead to fewer opportunities and ultimately jeopardize their freelancing career.



The same goes for ratbag startups or companies. Their reputation becomes apparent, especially during both good and bad times. Those companies that have a negative reputation during tough times will be remembered when good times return. They will struggle to attract good people to help them.



Rebekah: Absolutely. Olly, was there anything that you wanted to add to that?



No, actually, I think that Carolyn and Craig have pretty much nailed that answer.



Carolyn: Can I add one more thing? Despite everyone’s best efforts and even if you’re a top-notch freelancer or working with model clients, sometimes things just go wrong. One important lesson I’ve learned, and we continue to learn because we’re human, is to try and depersonalize those situations. I’ve been in situations where, to be completely honest, I had checked all the boxes in terms of delivering work, being punctual, and being a great account manager. I stand by my performance. However, sometimes factors beyond your control can come into play. It could be that the client is going through a difficult time and taking it out on you. That’s not acceptable. But I want to reassure anyone who may be feeling overwhelmed by comments like “just stand up for yourself.” While I’m a strong advocate for self-advocacy, there are instances where things go wrong despite your best efforts. In those cases, give yourself credit for your hard work, take a break for a couple of days, and then pick yourself up again. It happens, and it happens to everyone.



Rebekah: Absolutely. There’s also the aspect of identity, right? It’s wonderful to be passionate about your work and find fulfillment in it. But when work becomes the sole defining aspect of your identity, it might be a good time to step back and reflect on that. If we live and die by others’ opinions of our work, which is often subjective, it can be challenging. Alright, were there any final thoughts? We’re nearing the end of our time, and I’ve enjoyed our conversation. Oh, Ali has the final point: reliability. People value reliability, and it’s a fantastic quality. Alright then, thank you all for joining us. If you joined us later, you can catch an Action Replay on the Freelance Jungle blog. And Carolyn, where can we find you if we want to get in touch?



Carolyn: Oh, you can find me on LinkedIn of course. You can also find us via the website, littlevillagecreative.com.au or via Instagram, littlevillagecreative



Rebekah: Great, Craig. If we want to check out your list or your podcast, how can we find them?



Craig: The easiest way to find me is on LinkedIn because all the other channels are listed there. It’s a convenient communication platform for me, and I respond to everyone on LinkedIn.



Rebekah: A recruiter who likes LinkedIn, shocking! And besides the Freelance Jungle where we can find your fantastic adventures as part of our freelancer appreciation month, where else can we find you, Olly?



Olly: You can visit rounded.com.au or find me on LinkedIn. Those would be the easiest ways to connect.



Rebekah: Fantastic! Folks, if you’re interested in client management, Olly and I have a survey in the freelance jungle. We value your opinions and want to gather data to present to you and your peers. Plus, there’s a bunch of swag to be won. So even if you just like shiny toys, it’s worth answering a few questions. Without further ado, I’d like to thank you all for joining us today. You’ve been a wonderful panel.

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