Freelancer project management: How to best manage external resources and deliverables

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Hiring top-tier freelance talent can help you scale your agency quickly, so it’s no surprise the freelance market is booming

But hiring freelancers is so much more than assigning deadlines and expecting results. Freelance project management can be time-consuming and complicated, not to mention risky.

If you want your freelancers to deliver consistent work that exceeds your clients’ expectations, you need to put your freelancer project management process under the microscope.

In this guide, we’ll highlight the best practices of managing freelancers as an agency to ensure they deliver the best work.

Why agencies need to master freelancer project management ASAP

Maybe you’re new to hiring freelancers. Perhaps you’ve been burned by them in the past. If you’re skeptical of why freelancer relationships matter so much, we get it. 

Let’s look at a quick breakdown of the pros and cons:

The pros of managing freelancers

  • High-quality work at a lower cost. No-brainer here. Hiring freelancers as needed is a cost-friendly alternative to a full-time hire. This rings true even for “premium” freelancers that charge higher rates.

  • Freedom and flexibility. Lose a retainer client and need to scale back? Ramping things up because you can’t handle your current workload? Either way, no problem. When you have an ad-hoc team of freelancers on deck, your business is more dynamic by default. You can handle highs and lows alike.

  • Access specialized skills on-demand. Especially for major one-off campaigns (think: rebrands), you may need some serious expertise that doesn’t exist in-house. Again, this is where freelancers can save the day.

The cons of managing freelancers

  • Time commitment. Tasks such as onboarding, educating, and providing feedback to freelancers can eat into your schedule. If a freelancer doesn’t stick around long-term, committing to all of the above can feel like a massive time-suck. 

  • Uncertainty. You and your clients may stick to a rigid schedule, but the same doesn’t always ring true for your freelancers. Your favorite freelancer could theoretically take on a new role and limit their availability tomorrow, well before you have a chance to change course. Also, some (not all!) freelancers can be flaky when it comes to deadlines or following specific instructions.

  • Lack of control. If a freelancer ghosts you or you realize halfway through a project that you’ve hired the wrong person, guess what? There’s not much you can do about it. 

The reality, though? The pros overwhelmingly outweigh the cons.

This is especially true for up-and-coming agencies looking to grow. Freelancers may very well be the lifeblood of your business. There’s only so much you can do in-house with your budget.

And besides, the most common problems associated with subcontractors can be avoided outright through more proactive freelancer project management.

It’s also important to consider some of the most common reasons why freelancers sometimes don’t work out.

  • Micromanagers with poor boundaries, (e.g. they get contacted at all hours of the day and are expected to reply right away)

  • Vague instructions, which set them up to deliver something that misses the mark 

  • No feedback, so they don’t know what (if anything) to tweak for next time  

  • Scope creep, where they’re constantly asked to work beyond the scope of the original agreement 

Listen: the goal of freelance project management is to empower your contracted talent to do their best work by making their lives easier. And through the steps below, you can create a process to do exactly that.

11-step framework to foolproof your freelancer project management 

Here’s the only project management framework you’ll ever need for your freelancers. Throughout these steps, you’ll learn:

  • How to template and streamline your freelancer onboarding process

  • The best way to communicate with freelancers (hint: not endless emails and Slack check-ins)

  • How to highlight expectations and monitor your freelancers’ progress to avoid bottlenecks and keep clients in the loop

Oh, and we’ll also teach you how to use project management software (like Teamwork!) to implement all of the above.

With that, let’s dive in!

Prior to the project: Considerations, expectations, and crucial conversations

The best way to avoid freelancer headaches?

Talk things out and discuss how you plan to work together. 

Below are some key points to consider during the planning phase, well before you’ve officially signed off on a project.

1. Be clear about your expectations (and set criteria for meeting them)

Vetting freelancers is much easier when you know what you’re looking for.

Whether you have someone in mind, you’re hiring for the first time, or are picking from an existing pool of freelancers, consider:

  • What’s their specific area of expertise (think: SEO, ecommerce, content marketing)?

  • What does their portfolio look like? Do they have proof of their past work and performance?

  • Do you plan on hiring for a one-off project or ongoing work?

For example, if you’re hiring an SEO expert you’d expect them to have a track record of metrics, KPIs, and a documented history of helping clients rank. If they don’t, that’s cause for concern.

Assessing the points above will help you narrow down your choices and likewise give you some peace of mind when choosing the best fit for a project.

2. Define your deliverables and be upfront about your budget

In short, don’t waffle on what you want.

Let’s say you’re hiring a freelance blogger. Setting the right expectations means being specific in terms of what they’ll deliver and what their work will look like. For example, you’ll need to agree upon:

  • How many posts they’ll write (two per month, one per week, etc.)

  • Word count for each post (1,000 or 2,000?)

  • Are they expected to write an outline?

  • How many revisions are included

  • Timeframe for delivery

  • Details provided to the blogger (think: images, quotes, content briefs)

And so on. 

Having these details ready beforehand means that any given freelancer will be crystal clear on what you want. This makes it more likely that they’ll knock out your project. 

It’s also important to be upfront about your budget at the outset. You should have your exact budget (or at the very least a project cost estimation) ready to go prior to approaching freelancers.

This way, you’ll know whether or not someone’s in your price range prior to talking. And the freelancer will also know whether your budget aligns with their fees.

Most freelancers work on a fixed-fee structure (think: pay-per-project). Granted you stick to the scope of work, this usually is a win-win for agencies and freelancers alike. That’s because you don’t have to worry about blowing out your budget and your freelancers can negotiate a rate that they’re comfortable with. 

3. When in doubt, start with fewer freelancers and scale later

Despite popular belief, freelancer project management doesn’t mean dealing with dozens of different people.

Or at least it doesn't have to.

Trying to onboard a handful of freelancers at once is tricky. Doing so makes it more difficult to form meaningful relationships with your workers as you’re juggling new names and faces.

You also don’t want to run into a situation where you overpromise opportunities to your freelancers. This again speaks to the importance of in-depth project planning.

Right before the rollout: How to prep freelancers for a new project

Let’s say your stakeholders have signed off and your freelancers are ready to rock’n’roll. 


Before kicking off your project, make sure you’ve done the following:

4. Establish a uniform onboarding process

This typically involves inviting your freelance team into your project management software of choice. Once active, provide access to a list of action items or some quick onboarding resources. This might include:

  • Style guides

  • Client instructions

  • Brand guidelines

  • How-to videos

  • Project examples and samples

These materials can serve as your freelancers’ go-to resources during the project and likewise provide some additional context. But many agency leads don't want to give freelancers unlimited access to everything.

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At the same time, it's simple to set permissions and roles so freelancers get what they need and everyone on your team can tell who is working on the project. With Teamwork, you can even add further details like billable and cost rates to understand how much you're spending on freelancers.

5. Build out your project schedule (including deadlines, milestones, and deliverables)

A project schedule should be a top priority for any project.

This includes not only your own completion deadline but also key project milestones.

For example,content project management might involve milestones for outlines, drafts, revisions, and final review. This should all be front-and-center in a calendar for your freelancers to reference throughout the project lifecycle.  

Here’s an example of a project scope template that provides participants with a transparent schedule and action items. Transparency creates accountability and helps freelancers understand what needs to be done (and when) to avoid bottlenecks.

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If possible, build some breathing room into your schedule. Doing so can cut down on “surprise” or “emergency” revisions. Even the best project managers can’t predict a freelancer disappearing or an unexpected instruction from a client.

6. Consolidate communication with your freelance team

Avoid getting lost in email chains by putting an internal communications strategy into action. These are the rules and expectations for communication during a project. This includes:

  • How often you’ll check in with your freelancers (and vice-versa)

  • Where you’ll go back and forth (think: team chat, kanban boards)

  • The best way to get in touch with other stakeholders if necessary

No two teams’ approach is exactly the same. This is where a project management platform like Teamwork comes in handy. Our platform allows agencies and freelancers to communicate on their own terms, all in one place.

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For example, Teamwork can consolidate your calendar, team chat, meetings, and project boards so you don’t have to bounce between multiple tools.

Unless you’re heavily involved in a project alongside your freelancers, chances are you won’t be checking in on a day-to-day basis. In short, don’t expect contractors to be available around the clock in your company Slack channel.

Project in progress: managing freelancers and keeping things under control

We’re well past the planning phase and your project has officially started. 

Awesome! Where do you go from here?

7.  Assign your freelancers their tasks (and make sure those tasks are acknowledged)

First thing’s first: make sure your freelancers know what they should be doing and when it’s due. This circles back to the project deliverables (step 2) and schedule (step 5) you and your freelancers agreed on.

Food for thought: 58% of content marketers rate communication as one of their top challenges. A great way to keep everybody on the same page and assign tasks is through a project checklist or Kanban board view

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With a Kanban board, you can keep all of your project instructions, resources, updates, and deliverables in one place. Separated into different stages based on the state of the project (e.g. first draft, revisions, final draft), everybody can easily see the content project’s journey from beginning to end.

8. Monitor your freelancers’ progress (without being a micromanager)

Like it or not, you have to give your freelancers autonomy. Besides, the world isn’t going to end if they don’t check in with you every day. 

A digital tap on the shoulder via a project management @tag is fair game. But even then, do so sparingly unless a deadline is approaching with no recent updates. When in doubt, give your freelancers a business day or so to reply to any given issue.

And if someone does go silent, you have every right to try and touch base. Of course, you’re also on the hook to provide guidance and feedback as needed.

If you want to keep track of how they're delivering, it might help to use a resource allocation tool. This helps team leads see all of the available resources (freelancers) and how much work they're taking on.

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If one freelancer is overwhelmed on a project, resource management features let you pivot and reassign things to someone who could potentially take on the project.

Make sure to watch for @tags from your freelancers to avoid creating your own bottlenecks.

9. Stick to the scope of your project (translation: avoid scope creep at all costs)

Listen: excessive scope creep is a surefire way to deflate a freelancer and make them never want to work with you again. The rule here is simple: stick to the deliverables and expectations you outlined before (step 2) and don’t try to push it.

If there is a situation that arises requiring something beyond your scope of work, touch base with the freelancer and talk about it. Be prepared to compensate them accordingly.

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And when projects keep missing deadlines or can't stick to the overall timeline, using a Gantt chart to track and manage tasks can really help. This visual into the project timelines will be essential to planning new work and avoiding scope.

Post-project: Reflections, follow-ups, and how to (hopefully) move forward

Just because a project’s over doesn’t mean that a PM’s job is done. To wrap things up, here are the final steps of our framework.

10. Provide meaningful feedback to your freelancers

Saying “nice job” is easy enough.

But providing meaningful feedback that encourages better work and makes an impact on your freelancers is a delicate balancing act. 

You may be tempted to focus on potential improvements and criticism. These points should be communicated, but not before providing positive feedback. That’s because:

  • Feedback and positive recognition are among the biggest motivators for employees (and the same rings true for freelancers)

  • Constructive feedback can help highlight changes to be made for future projects, cutting down on revisions and questions the next time around

  • If nothing else, it highlights your attention to detail and makes you more pleasant to work with

For content project management, you might provide clarification on your clients’ product or features but rave about how your freelance writer totally nailed the tone and topic.

Ask yourself: Are you happy? Is your client happy? If so, spread the joy and let your freelancers know.

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11. Assess if you want to continue together (based on expectation and outcomes)

Piggybacking on the point above, the end of one project typically means the start of another.

As you wrap things up, consider which of your freelancers you want to continue to work with or have on-standby for as-needed projects. Specifically, reflect on the following:

  • Did they meet (or exceed) your expectations?

  • Were they able to consistently hit deadlines?

  • Did they communicate effectively throughout the project? 

  • Was your client happy with the deliverables?

  • Were they receptive to instructions and feedback?

  • Do they think their rate is justified based on the work delivered?

If the answers to the questions above are most a resounding “yes,” chances are your freelancers are keepers.

And if things didn’t go well, consider it a learning experience.

For example, you may realize in retrospect that your expectations were unclear or maybe your onboarding process took too long. Managing freelancers, especially early on in your agency career, can be eye-opening in terms of understanding how to become a better team leader.

A final word on freelance project management

Agencies and freelancers need each other.

On that note, don’t forget perhaps that freelancers are people. The importance of empathy and understanding can’t be overstated. To build a positive freelancer project management culture do the following:

  • Set reasonable deadlines that won’t stress your freelancers out

  • Don’t hover and micromanage: let your freelancers work on their terms and respect their schedules

  • Strive to be a resource and advocate for your freelancers (hint: not just a boss)

  • Provide meaningful feedback to give them a stake in your projects

The best way to tick the boxes above? Use a tailor-made project management platform like Teamwork to streamline communication, stay organized, and keep stakeholders happy.

Want to see how Teamwork can help you better manage your freelancers? Get a free 30-day trial and see why so many agencies use Teamwork to connect everyone together internally and externally.

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