What I've learned from hiring freelancers over a dozen times

Here's what separates the applications that get responses from the ones that get deleted immediately.

I’ve hired freelancers over a dozen times. Designers, writers, developers, (and soon) strategists. And after doing this enough times, you start noticing patterns, not just in the good applicants, but in the ones you choose not to hire immediately.

Nobody ever really tells you what happens on the other side of the inbox. And today, that’s exactly what I’m doing.

Most applicants aren’t who they seem

Yes, this is deliberately provocative wording. But it’s true. And the amateurishness of many applicants is a problem.

A meaningful chunk of applications I receive come from people whose claimed experience doesn’t hold up to basic scrutiny. Portfolios with broken links. Profiles that list five specialisms but show evidence of none. CVs that describe something with no evidence to back it up.

When you’re hiring, you learn to read between the lines fast. Vague language is usually covering a gap. “Worked on campaigns for major brands” means very little without saying what you actually did and what happened because of it. What benefit did those brands get? I want metrics.

Be specific about what you’ve done. Even one clear example, with a real outcome, does more work than three paragraphs of general claims.

Tell me who you are, then prove it.

AI applications are easier to spot than you think

I’m not against AI as a tool, but there’s a particular genre of application that was very clearly written by a chatbot, and hiring managers clock it immediately.

It’s not just the writing style, though that is a dead giveaway. It’s also the absence of personality or original ideas. Generic enthusiasm is so, so easy to spot. And if you didn’t care enough to respond properly, I won’t care enough to consider you.

Originality is important. You don’t have to be ‘quirky’, but your application should have some spark behind it. What are your real opinions, experience and thoughts? Why do you really want this opportunity? Something specific that proves you’re human can go a long way.

The people who stood out in my hiring process weren’t necessarily the most experienced, but they did all clearly come across as human people.

Plus, when a bunch of others use AI, you all end up sounding the same. It’s not uncommon to discard 50%+ of applications in 2026 simply because they’re all obviously AI. Even if that seems unthinkable to you, it’s true.

Ease of reading is doing more work than you realise

I don’t have time to mine an essay for the one relevant fact buried in paragraph six. Nobody does!

The best applications I’ve received are short, clear, and structured around the actual problem I’m trying to solve. They don’t list every single skill the person has. They show which skills apply for this role, and why. Then share evidence of it.

Show me you’ve solved problems like mine before.

Contact details and portfolio links should be impossible to miss. I’ve passed on people I was genuinely interested in because finding their work felt like an obstacle course.

Place your links clearly. Make them click straight through. The more work I have to do to find it, the less I’m going to be interested.

Rate and availability are useful inclusions

A lot of freelancers treat their day rate like classified information. I understand the instinct, but from a hiring perspective, vague or missing rates slow everything down. If I haven’t set a rate in advance, I need to know what you want to get paid.

And if I can’t afford it, that’s my loss.

If your rate is way outside my budget, I’d rather know in the first message than after three rounds of conversation. It’s not a rejection of you as a freelancer, it’s just practicality.

Being upfront about availability works the same way. If you can’t start for six weeks, say so. I might wait if you’re a great fit. Or I might not. But at least I can plan the next steps.

Tailoring isn’t optional!

Spray-and-pray applications are always obvious. There’s usually a tell, often a company name from a previous application that didn’t get swapped out, or even a description of services that has nothing to do with what I asked for (you’d be surprised at how common this one is too).

Even one line that shows you read the brief properly separates you from the majority. Reference the actual project. Ask a specific question. Give a hint as to how you can solve my problem. Show that you’ve thought about it, not just your own credentials.

Following up is a skill most people get wrong

There’s a version of following up that works and a version that doesn’t. Chasing an application every day doesn’t make you look keen, unfortunately. It makes you look annoying.

A polite follow-up, after a reasonable gap (say a few days or a week), is fine. It’s genuinely appreciated. It shows you’re still interested and that you’re someone who sees things through. I’d follow up once more after that, then probably leave it alone.

The freelancers I’ve come back to, sometimes months later, for new projects, are the ones who were easy to deal with from the very first message. And trust me: that starts before you’re even hired.

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The application itself is a work sample

Before I see your portfolio, I get to see how you communicate. Your application tells me whether you can write a clear brief, manage expectations, and work without needing to be chased.

A muddled, generic, or copied application actively suggests what working with you might be like.

The bar for standing out probably isn’t as high as you think, though that doesn’t mean it’s easy. Much of it comes down to writing like a human, providing clarity and showing you know what I’m looking for.

Do that, and you’re already ahead of most of the crowd.