The transition from solo freelancer to team leader often happens faster than expected. One day you’re managing everything in your inbox and a few spreadsheets, and the next you’ve brought on two contractors and suddenly realize your system is held together with digital duct tape.
Emma Clark, founder of Clark Content Co, asked us exactly this question: What systems or tools should she implement first to keep projects, communication, and payments organized as she scales? With plans to hire more people, she wanted to know what would work long-term without creating unnecessary complexity.
This is one of the most critical questions growing freelancers face, because getting it wrong can actually slow you down rather than speed you up.
Key Takeaways from this Episode:
– Define clear roles and responsibilities before implementing any tools—the human part must be figured out first
– Use Slack as your central nervous system with strict guidelines: a channel for every purpose, mandatory threading, and disciplined use of pins and bookmarks
– Agility beats complexity every time—choose one tool and go deep rather than spreading across multiple complicated systems
The Human Part Comes First
Christine Olivas, founder of No Single Individual, learned this lesson during her decade working in high-growth startups. While everyone around her was moving fast and breaking things, she noticed something important: tools only help when roles and responsibilities are crystal clear.
This might sound counterintuitive for freelancers. After all, many of us left traditional jobs specifically to escape rigid job descriptions and organizational charts. But as Christine explains, fast-moving projects actually benefit enormously from clear definition of who does what.
Her solution is elegant: every team member gets assigned a specific role at the outset of each project. These aren’t vague titles—they’re well-defined positions with clear responsibilities documented and included in statements of work.
For example, on a marketing plan project for an agency client, one person might be assigned as the Agency Lead. Their role focuses less on executing work and more on relationship management, guiding the overall direction, and serving as the liaison between teams. Another person might be designated as Head Researcher, with a completely different set of responsibilities.
This upfront clarity prevents the chaos that happens when everyone is “just helping.” Group projects fall apart without clear ownership, and the same is true for freelance teams.
Why Slack Wins for Agile Teams
After defining roles comes the question of tools. And here’s where things get interesting: both Preston and Christine have tried nearly every project management system out there, from Jira to ClickUp to Trello. They’ve worked in corporations that mandated complex tools and tracked every minute of productivity.
And they both keep coming back to Slack.
Not because it’s the most feature-rich or the most sophisticated, but because it’s a communication tool first. And frequent, clear, quality communication consistently trumps elaborate task management systems.
Christine’s team of 24-28 people runs almost entirely on Slack, paired with Google Drive for file storage. They use ClickUp only for time tracking when required and for confidential financial forecasting—but day-to-day work happens in Slack.
The key is that they don’t use it loosely. Christine has three strict rules that make Slack work at scale:
**A channel for every purpose.** They create a dedicated Slack channel for every single workstream, even if multiple workstreams are part of the same client engagement. They also have clear internal channels—one for sales, one for existing clients, one for finance, one for operations, one for social media. Everyone knows exactly where to go for what.
**Mandatory use of threads.** Nothing kills Slack’s usefulness faster than people going back and forth in the main channel while others try to use threads. Christine’s team insists on threading so that entire conversations stay contained. For example, everything about a client renewal lives in one thread, making it easy to find and reference later.
**Disciplined use of native features.** They take full advantage of pins, bookmarks, and canvases—and they keep them updated. Channels don’t accumulate outdated pinned messages from events six months ago. Everything at the top of a channel is current and relevant.
Every new channel also gets a one-page kickoff document pinned at the top that outlines who the client is, what the project entails, and what role each team member plays. This creates instant clarity for anyone joining the conversation.
The Productivity Paradox of Complex Tools
Preston shared a fascinating observation from his experience: every time a company forced him to use a sophisticated project management tool, his productivity actually decreased—even though his productivity was being tracked more efficiently.
He’d spend extra time in the tool writing updates, assigning tasks, at-mentioning people, and configuring workflows. And then, inevitably, he’d still ping people in Slack to let them know he’d updated something in the other tool.
This duplication of effort is the hidden cost of over-complicated systems. You’re not actually managing projects better—you’re just spending more time managing the tool itself.
The reality is that most growing freelance businesses don’t need enterprise-level project management software. What they need is clear communication, defined ownership, and the ability to move quickly.
Adapting to Your Client’s Systems
One important nuance Christine mentioned: not every situation calls for you to impose your own systems. When working with agencies, for example, they often have their own traffic functions, resourcing managers, and project management tools already in place.
In those cases, Christine’s team plugs into what the client is already using rather than creating duplicate systems. This prevents the nightmare scenario of maintaining parallel tracking—updating your sheet and their sheet for every change.
However, they always maintain their internal Slack channels regardless of client systems. This gives them a dedicated space to discuss work away from client eyes—to hash out confusion, brainstorm ideas, and ask questions like “what did they mean when they said this?” It’s a safe space to figure things out as a team before presenting a seamless front to the outside world.
When to Use More Robust Tools
While Slack handles most day-to-day communication and coordination, there are times when additional tools make sense. For particularly complex projects that span six months or more, Christine’s team might create a separate project plan in Google Sheets or ClickUp.
The key is that these are exceptions, not the default. Most of their work moves too fast to justify the overhead of detailed project plans with individual task assignments and approval workflows.
This is especially true in their consulting model, where they’re often embedded with agency clients and projects start immediately. They don’t have time to spend days setting up elaborate systems—they need to deliver value right away.
Start Simple, Then Add Complexity Only When Needed
If you’re in Emma’s position—growing from solo to a small team—resist the urge to immediately invest in sophisticated tools. Start with the basics:
**Define roles first.** Create a simple document that outlines the different roles people on your team can play and what’s included in each role. Assign these roles explicitly on every project.
**Choose one communication tool and go deep.** Whether it’s Slack or something else, commit to it fully and create clear guidelines for how your team uses it.
**Add file storage.** Google Drive or a similar solution gives you a place to store deliverables and reference materials.
**Track what matters.** You don’t need to track every minute, but you should track leads generated, conversion rates, and revenue by channel or strategy. This data tells you what’s actually working.
Only add additional tools when you’ve identified a specific problem that can’t be solved with what you already have. Don’t add tools just because they exist or because other businesses use them.
The goal isn’t to have the most impressive tech stack. The goal is to move quickly, communicate clearly, and deliver great work to clients. Simple systems that everyone actually uses will beat sophisticated systems that create friction every single time.
As Christine wisely noted: you can have all the tools in the world, but if the human part isn’t figured out first—if people don’t know their roles, responsibilities, and how they’re supposed to work together—no tool will fix that fundamental problem.
Start with clarity on roles and expectations. Then add the simplest tools that support how your team actually works. You can always add complexity later if you truly need it. But most growing freelance businesses find that simple, well-executed systems are all they need to scale successfully.
