How to Hire a Freelancer | Management

In 2024, around 70% of small business owners hired a freelancer at one time or another.

Why?
In most cases, bringing in a freelancer costs less than hiring a full-time employee, especially when your need is short-term or highly focused.

But saving money doesn’t mean skipping effort. Freelancers still need a clear job description, defined job requirements, and regular check-ins to hit their goals.

Remember – when you want to hire freelancers, reliable freelancers, without a structured recruitment process, you risk vague expectations, no ownership, and slow progress. Deadlines slip. Job performance suffers. And teams stall.

If you’re hiring to move faster, make sure your process doesn’t slow things down.

The moment potential candidates apply, your team should be ready. Start with an initial screening call or a short phone interview to qualify the fit. Then move to the interview stage to assess both specialized skills and soft skills.

Set up a basic applicant tracking system – even a shared doc works – to keep things organized. That gives your recruitment team a way to track progress, compare options, and align on the best fit. Especially when you're looking for freelancers worldwide.

Even without a full HR department, you still need clarity. That means:

• Who’s leading the hiring decision?
• What are the hiring criteria?
• How do we know when a candidate accepts and is ready for the onboarding process?

Without answers, your project gets stuck before it starts.

Solid Hiring Team is A Key

In 2025, smaller companies and startups will increasingly rely on freelancers, remote contributors, and even artificial intelligence to fill roles. But no matter how advanced the tools or platforms, hiring the right candidate still depends on people making smart decisions.

A well-structured internal hiring team ensures that every job is aligned with your business goals, that each job description provides a clear picture of what’s expected, and that the hiring process moves smoothly – from phone screen to offer letter.

Using a standardized set of steps helps maintain consistency across roles, especially when reviewing work samples, assessing culture fit, or comparing candidates for similar positions.

When the team is aligned on roles, timing, and responsibilities, the result isn’t just filled roles – it’s a positive experience for both sides and a stronger pipeline of quality work from long-term contributors.

This structure increases your chances of turning an initial offer into a successful, lasting hire.

How to Find the Right Hiring Manager?

The hiring manager is the bridge between strategy and execution. They shape the job description, lead the interview process, and guide new hires through the onboarding process.

A great hiring manager:

• Understands the job’s daily work
• Can spot both technical and soft skills
• Has time to lead the entire recruitment process
• Knows how to adjust the brief to attract the best candidates

If the hiring manager is overextended or unclear, the process falls apart. Roles stay open. Qualified candidates walk. And your hiring decision gets delayed.

Build a Reliable Internal Hiring Team

If you’re constantly filling job openings or bringing in freelancers, a lean but focused recruitment team is a must.

They should:

• Own and update job posts across key job boards
• Write accurate, clear job descriptions
• Lead resume screening
• Conduct structured reference checks
• Follow up with potential candidates and drive toward a clear job offer

Having clear hiring criteria also removes bias, shortens timelines, and improves overall fit.

Need help streamlining this?

Click here to read more about the Hiring Process >

At Milo Solutions, we’ve seen it again and again: once the final decision is made and the job offer is accepted, that’s when the real work begins.

Bringing in the top talent – whether a full-time role or freelance – only pays off if the process is clear from day one. Before onboarding a new hire or contractor, make sure there’s a clear understanding of the job scope and expectations.

That includes:

• Defining what the job covers: deliverables, pay terms, tools, and timelines
• Setting communication guidelines: tools used, check-in frequency, and feedback loops

Whether you found your top candidate through a platform or social media, your success now depends on structure, not guesswork.

Here’s a battle-tested workflow we use to keep things moving across teams:

Set the Ground Rules Early

Before you start, define:

• What tools will you use (Slack, Notion, GitHub)?
• How often will updates happen?
• Who owns reviews and approvals?
• What hours or time zones matter?

Pro tip: Document it once. Share a single link. Keep everyone aligned.

Use a Lightweight Management Stack

You don’t need Jira to manage freelancers. Try this stack:

• Slack or Telegram → async check-ins
• Trello, Notion, or ClickUp → task tracking
• Loom → fast, async feedback
• GitHub → version control, team code review

Pro tip: Run weekly cycles with small, testable deliverables.

Get Clear on What “Done” Means

Every task should include:

• What’s being delivered?
• How it’s reviewed?
• What makes it done (tested? live? approved?)

Pro tip: Use Figma, screenshots, or checklists – don’t rely on assumptions.

Create Feedback Loops That Work

The most common mistake? Total silence or micromanagement.

Try:

• One midweek check-in
• A Friday review
• Async messages for blockers or updates
• A quick Slack nudge every 2 days

Freelancers work better when feedback is fast and consistent. And yes, it's true – sometimes you still have to be your dedicated account manager.

Treat Freelancers Like Humans, Not Tools

• Share business context: what problem are they solving?
• Ask how they prefer to work
• Respect their schedule – they’re not on 9–5

When freelancers feel valued, they deliver like partners.

When Performance Slips, Act Fast

Set non-negotiables:

• Missed deadlines
• No communication
• No testing or sloppy delivery

If these show up, don’t wait. It’s better to act early than to drag a bad fit through your roadmap.

Protect Yourself With Smart Offboarding

Before work begins:

• Who owns the output?
• Where is the code or copy stored?
• What’s the process if they leave mid-project?

Pro tip: Keep everything on your company’s GitHub. Ask for documentation weekly – not at the end.

Knowing how to hire a freelancer is just the start. Managing them well is what separates founders who scale from those who stall.

If you’re juggling 2–3 freelancers and still missing deadlines, the issue isn’t the people – it’s the process.

Want to know when it’s time to stop managing and start scaling? Let’s talk.
Click here to book a call with us >