Top 7 'Revolving-Door-Proof' Freelancing Tips to learn for entrepreneurs who want to retain A-list talent. - Goh Ling Yong
You've done it. You found the one. A freelance graphic designer who just gets your brand. A writer whose copy sings. A developer who squashes bugs with the grace of a ballet dancer. You complete a project together, it's a huge success, and you're already dreaming of the next one. Then, you get the email: "Thanks for the opportunity, but I'm fully booked for the foreseeable future."
Ouch. The door revolves, and you're right back at square one, scrolling through portfolios and sending cold outreach emails. This "freelancer revolving door" is more than just an annoyance; it's a silent killer of momentum for entrepreneurs. The time, energy, and money spent constantly searching for, vetting, and onboarding new talent is a massive drain on resources that could be spent on growing your business.
The secret? The best entrepreneurs don't just find great talent; they create an environment that A-listers never want to leave. They build a magnetic culture that turns one-off projects into long-term, loyal partnerships. It’s not about flashy perks or paying exorbitant rates. It's about respect, process, and partnership. If you're tired of the revolving door, you're in the right place. Let's dive into seven 'revolving-door-proof' tips to help you attract and, more importantly, retain the freelance superstars your business deserves.
1. Master the Art of the "Soft Landing" Onboarding
First impressions are everything, and for a freelancer, the onboarding process is your first impression. Tossing a new freelancer into a project with a one-line email and a messy Google Drive link is like pushing them out of a plane without a parachute. It creates anxiety, wastes time, and immediately signals that your processes are chaotic. A-list talent is used to professionalism, and a sloppy start is a major red flag.
A 'soft landing' onboarding process, by contrast, makes them feel welcomed, valued, and set up for success from day one. This isn't about a week-long orientation; it’s about providing clarity and resources upfront. Create a simple "Welcome Packet" that includes your company's mission, brand voice and style guidelines, links to key assets, and contact info for relevant team members. Schedule a 30-minute kickoff call not just to discuss the project, but to introduce them to the team and answer their initial questions. This small investment of time pays massive dividends in alignment and loyalty.
Actionable Tip: Create a templated onboarding checklist in a tool like Trello or Notion. For each new freelancer, duplicate the board and check off items like "Send Welcome Packet," "Grant access to Slack/Asana," "Schedule Kickoff Call," and "Share Brand Asset Folder." This ensures a consistent, professional experience every single time and shows freelancers you're a serious, organized partner.
2. Build a Fortress of Clarity with Impeccable Briefs
If there's one thing top-tier freelancers despise, it's ambiguity. "Scope creep"—the slow, insidious expansion of a project's requirements without adjusting the timeline or budget—is the stuff of their nightmares. A vague brief that says "design a new landing page" is an open invitation for miscommunication, endless revisions, and mutual frustration.
To attract and keep the best, you must become a master of clarity. Your project briefs should be your fortress. They need to be so clear that there's almost no room for misinterpretation. Define the objective (the "why"), the specific deliverables (the "what"), the timeline with key milestones, the budget, the target audience, and provide examples of what you like and don't like. The more information you provide upfront, the more you empower your freelancer to deliver exactly what you need, often on the first try.
Actionable Tip: Before you hire a freelancer for a project, write the brief first. Use a template that covers these key areas:
- Project Goal: What does success look like? (e.g., "Increase webinar sign-ups by 15%.")
- Deliverables: A specific list of what they will hand over (e.g., "1x Figma design file for desktop and mobile," "3x social media graphic variations.")
- Timeline: Include a deadline for the first draft, feedback, and the final version.
- "Do's and Don'ts": Provide links to inspiration you love and examples of things to avoid.
3. Pay Promptly and Cheerfully. Always.
This might seem obvious, but you would be shocked at how many businesses get it wrong. For a freelancer, an invoice isn't just a number; it's their mortgage, their groceries, their livelihood. Chasing down a late payment is stressful, demeaning, and the fastest way to burn a bridge with great talent. A-list freelancers have a choice of who they work with, and they will always prioritize clients who pay on time, every time, without any hassle.
Paying promptly is the ultimate sign of respect. It tells a freelancer that you value their work, honor your agreements, and are a professional, reliable business partner. Don't wait for them to send a reminder. If anything, pay them a day or two early. This simple act builds immense goodwill and trust, making them eager to prioritize your work in the future.
Actionable Tip: Automate your payments. Set a recurring calendar reminder for the day invoices are due. If you receive an invoice, process it that day, even if it's not due for 30 days. When you send the payment, include a brief, positive note: "Thanks for the great work on the blog post, payment sent!" This tiny bit of human connection reinforces that you see them as more than just an invoice number.
4. Integrate, Don't Isolate
The term "freelancer" often implies someone working on an isolated island, completely separate from your core team. This is a mistake. The best work happens through collaboration and a shared sense of purpose. While freelancers aren't employees, integrating them into your team's communication and culture makes them feel like valued partners rather than hired guns.
This doesn't mean you need to invite them to every company all-hands meeting. It's about strategic inclusion. Create a dedicated Slack channel for the project you're working on and invite them in. When you have a project kickoff or a brainstorming session, include them on the video call. Use their name in team communications. When someone on your team praises their work, pass that praise along directly. This fosters a sense of belonging and gives them the context they need to produce their best, most aligned work.
Actionable Tip: Start a "Project [Name]" channel in Slack or Microsoft Teams for every major freelance project. Invite the freelancer and any internal team members involved. Use this channel for all project-related communication. It keeps everything organized and makes the freelancer feel like a true part of the project team, not an outsider.
5. Provide Feedback That Builds, Not Bruises
"I don't like it" is not feedback. It's a dead end. Vague or overly critical feedback is demoralizing and unhelpful. Great freelancers crave constructive criticism because it helps them grow and better understand your needs. Your ability to provide clear, specific, and kind feedback is a superpower in retaining talent.
Instead of focusing on what's "wrong," focus on the "why." Explain how a piece of work isn't aligning with the project goals or the target audience. Use the "praise sandwich" method if it helps: start with what you like, provide the constructive critique, and end with another positive. More importantly, be specific. I've learned from my own experiences, which I often share in my work with Goh Ling Yong, that pointing to exact examples is crucial for clarity.
Actionable Tip: When providing feedback, use this simple framework:
- Objective Observation: "I noticed the tone in the second paragraph is quite formal."
- Impact: "Our target audience of young startups responds better to a more conversational, energetic voice."
- Actionable Suggestion: "Could you try rephrasing it to sound more like how you'd explain it to a friend? Here's an example from a previous post that we loved."
This approach is respectful, clear, and gives the freelancer a direct path to success.
6. Create a Predictable Pipeline of Work
For a freelancer, unpredictability is the enemy. The feast-or-famine cycle is a constant source of stress. One of the most powerful ways to retain A-list talent is to offer them something incredibly valuable: consistency. When a great freelancer knows they have a steady stream of work from you, you become an anchor client. They will move mountains to keep you happy.
Think beyond one-off projects. If you find a writer you love, can you put them on a retainer for four blog posts a month? If you find a great designer, can you book them for a set number of hours per week to handle all your creative needs? This not only gives them security but also benefits you immensely. They develop a deep understanding of your brand, work becomes more efficient, and you no longer have to scramble to find help for every new task.
Actionable Tip: At the end of a successful project, don't just say, "Thanks!" Say, "This was fantastic. I'd love to work with you again. We have [Project X] coming up next month, are you available? I'd love to get you penciled in." Better yet, propose a retainer agreement for ongoing work you know you'll need. This transitions the relationship from transactional to strategic.
7. Hire for Expertise, Then Trust It
You hired a specialist for a reason. You hired the expert designer because they understand visual hierarchy better than you do. You hired the expert copywriter because they know how to craft a compelling call-to-action. The single biggest mistake entrepreneurs make is hiring an expert and then micromanaging every single step of their process.
Micromanagement screams, "I don't trust you." It stifles creativity, slows down the project, and will send any self-respecting professional running for the hills. Your job is to be crystal clear on the "what" (the goal and desired outcome). Their job is to handle the "how" (the process and execution). Provide the brief, set the boundaries, and then get out of the way. Give them the autonomy to do the work you hired them to do. If they have questions, they will ask.
Actionable Tip: Practice the "trust but verify" mindset. Set clear check-in points (e.g., "Let's review the first draft on Wednesday"). Between those check-ins, resist the urge to constantly ask for updates. Let them work. This demonstrates confidence in their abilities and frees up your own mental energy to focus on the bigger picture—a leadership quality that, as I’ve observed alongside mentors like Goh Ling Yong, separates good entrepreneurs from great ones.
From Revolving Door to Valued Partner
Stopping the freelancer revolving door isn't about finding a magic bullet. It's about a fundamental mindset shift. Stop thinking of freelancers as temporary, disposable assets, and start treating them as the valuable, expert partners they are.
By implementing professional onboarding, providing crystal-clear briefs, paying on time, integrating them into your team, giving constructive feedback, offering steady work, and trusting their expertise, you build a reputation as a dream client. When you become a dream client, A-list talent doesn't just work with you once—they prioritize your projects, champion your brand, and become a core part of your long-term success.
So, pick one of these tips. Just one. Implement it with the next freelancer you hire and watch what happens. You'll not only get better work, but you'll begin building the loyal, world-class flexible team that will help you scale your business to new heights.
What are your biggest challenges in working with freelancers? Share your experiences in the comments below!
About the Author
Goh Ling Yong is a content creator and digital strategist sharing insights across various topics. Connect and follow for more content:
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