How to Hire a Freelancer | 8 Lessons from Common Mistakes

Hiring a freelancer should make things easier – not harder.

Without a clear process, it’s easy to fall into traps that cost time, budget, and momentum.

This listicle breaks down 8 common freelancer hiring pitfalls – all taken straight out of real-life stories of our business partners and clients.

If you’re about to hire a freelancer, this is a good place to start.

Read, learn, and prepare in advance for the stumbling blocks that sooner or later befall every ambitious CEO or Founder.

Mistake No. 1: Hiring Too Fast, With Too Little Info

A few months back, one of our newest clients (in the MedTech industry) was gearing up for a product launch.

They had strict timelines, investor pressure, and a regulatory review on the horizon. Then, their backend developer quit just three weeks before go-live. Hiring a freelancer quickly at that point seemed like a good idea.

The founder was in a rush. He posted an offer on LinkedIn, got a quick reply, glanced at a portfolio, and said sacramental:

“Looks solid – let’s go.”

A new team member got hired within hours.

At first, things seemed fine. But within days, it was clear the new hire wasn’t familiar with the tech stack. A key deadline was missed. As you can already imagine, investors weren’t happy about it.

All of this wouldn’t happen if there were a written scope or a basic reference check.

In the end, the founder asked us to jump in, rebuild parts of the backend, and clean up the mess.

1st lesson of this article?

Don’t hire without a strong hiring process.

On average, one-pager scope + paid trial + async comms test should do the job, but if you’re interested in a detailed view, click here to read about hiring process >

Mistake No. 2: Confusing Price with Value

This story goes back to the pre-COVID era, but it still hits today. One of our business partners hired a UX/UI freelancer for $25/hour.

On paper, it seemed like a smart call.

Many founders think:

“I just need this done – I can’t afford to overpay right now.”

But three months later, after constant back-and-forth and no real results, it was clear the hire wasn’t worth the savings. There were endless revisions, slow delivery, and lots of polished slides – but no usable output.

That’s the trap: thinking rate equals value. It doesn’t.

A more experienced person might cost $75/hour but needs a third of the time – and deliver work that sticks. Solid research and concepts only matter if they lead to working designs.

If the budget’s tight, don’t go cheap. Scope down.

Focus on what matters most. Get it done right, then build from there.

Click here to read more about Budgeting and Costs >

Mistake no. 3: Assuming They Understand the “Why”

Ever handed off a task thinking,

“It’s obvious that this or that needs to be done”?

That’s where things often go wrong.

Most freelancers will do exactly what you ask. But without the full picture, the results might miss the mark – off-brand, off-track, or not solve the real problem.

Why?

Because there wasn’t enough context. Trust us, this happens more often than you think.

When freelancers don’t understand the “why” behind a task, they can’t make smart decisions. They stick to the surface, leaving you or your team with disconnected pieces that still need rework later.

Remember, you don’t need a long brief. Just explain the goal.

• Who is it for?
• What does success look like?

That small bit of clarity saves hours later.

Mistake no. 4: No Communication Structure

Too busy to dive into details like communication channels or feedback loops?

Unfortunately, we hear that a lot.

If your kickoff plan is “we’ll figure it out as we go,” expect things to drift – fast. No shared doc, no regular check-ins, no clear deliverables? You’re setting yourself up for ghosting, rework, or both.

Async work with freelancers needs rhythm.

Here is an example of such a process:

• Clear goals on Monday.
• Check in midweek.
• Demo or update by Friday.

One shared doc or board is enough to stay aligned.

Lesson nr. 4?

A little structure now avoids a lot of cleanups later.

Mistake No. 5: Scope Creep Without Boundaries

Here’s a story we’ve collected during one of our initial calls with a client:

“It started with one small tweak. Then another. “Just a quick change”, he said. “Should only take a minute. Damn… by the end of the project, we were three weeks late and $4K over the budget!”

Sounds familiar?

Yes, scope creep always feels harmless at first. But if you don’t draw the line early, it builds up fast.

The solution is to set boundaries from day one. When hiring a freelancer, always try to be clear about what’s included, what’s not, and how many rounds of feedback are allowed.

Lesson No. 5: Clear scope = smooth project. Keep it simple – and stick to it.

Interested in the bigger picture?

Click here to read our guide: Hiring a Freelancer | Guide >

Mistake No. 6: Hoping It’ll Work Itself Out

“Let’s give it one more week…”
That’s how timelines die.

We once supported a client who brought in a freelancer for a critical feature.

A few weeks in, things already felt off – missed deadlines, unclear status, vague answers. But instead of resetting or cutting ties, they waited.

“Maybe they just need time to adjust.” – he said.

A week has passed. Then another. Still no progress.

In the end, we were asked to step in, rebuild the feature from scratch, and meet a tighter deadline than before.

The problem wasn’t just the freelancer – it was the delay in dealing with the warning signs.

Hope is not a strategy.

If communication is poor, deadlines slip, or the person avoids feedback, don’t wait and wish. Act.

You can always ask direct questions like:

• What’s blocking you right now?
• What do you need to deliver X by [date]?
• Can you walk me through your current progress?
• What’s your plan for the next 3 days?

Haven’t helped?

Set a short checkpoint or two. 2–3 days to course correct should be enough for usual tasks. Make it clear: if this doesn’t move forward with clarity and results, you’ll need to part ways.

Lesson no. 6:

When things go quiet or unclear, don’t wait. Rebrief clearly. Set a line. Then decide quickly.

Mistake No. 7: Skipping the Paid Test

Let’s say your candidate looks great on paper. Strong CV, smooth interview. It’s tempting to say at this point:

“Let’s skip the paid test. We need to move, not generate extra costs.”

We had a client once who made this mistake before reaching us for help. It turned out, the freelancer couldn’t handle the pace.

Even a small paid test could’ve caught that within two or 3 days.

We always recommend that founders to give a 3–5 hour paid task tied to real deliverables. It will show you how the candidates work, how they communicate, and how they handle feedback.

Think of it as insurance – cheap now, saves you later.

Here is a paid test example:

Mistake No. 8: Hiring Based on Buzzwords or Stacked CVs

Robust CV, impressive portfolio, great communication skills… all of this is great until it turns out that the front-end dev you just hired also works three other jobs in the meantime.

We’ve made this mistake before, and we’re not planning to repeat that.

This role needed someone who could do the work, explain their thinking, and keep things simple. Not someone who looked good in theory but couldn’t back it up in practice.

Since then, we’ve made it a rule: skip the hype and put them on probationary period.

Remember: Real work beats big words.

You don’t need a “10x AI-enhanced React guru.”

You need someone who ships clean code, communicates clearly, and gives realistic timelines.

Already made a few of these mistakes?

That’s normal.

We’ve all hired the “perfect” freelancer who disappeared mid-sprint. What matters is how you reset.

Freelancers can be a startup’s secret weapon – or its biggest blind spot of your company. The difference isn’t just who you hire, but how you manage the hiring process.

Tired of constantly bouncing the ball with freelancers? Let’s talk.

Click here to book a 30 min call with us >