Monsieur & Madame: A Field Guide to Hiring Freelancers

There are certain things from childhood that never really leave you.

For me, one of those things is a series of small, colorful French books I remember encountering at a very young age while visiting family in France. I had started learning French in first grade and continued for more than a decade, so these books left an early impression.

The characters were simple shapes with exaggerated personalities. Each one embodied a single trait taken to its extreme. They were funny, memorable, and surprisingly accurate reflections of real people.

The series was called Monsieur Madame, known in English as Mr. Men & Little Miss.

Years later, as I moved into my career and spent time inside multiple digital agencies, those characters started popping back into my head in an unexpected place.

Not in bookstores, but in proposal threads, kickoff calls, Slack messages, and projects that slowly unraveled. The freelancers I was hiring were each their own Monsieur or Madame!

Before starting Maguire Web Solutions, I co-founded a digital agency where I was responsible for operations and for building and maintaining a large network of freelancers across design, development, marketing, and operations. Before that, I worked as a project manager at another agency, keeping projects on track and translating between clients and technical teams.

Over time, clear patterns emerged.

When I speak with potential clients today, I hear the same frustrations I saw back then. Different industries, different budgets, same stories.

So in the spirit of those childhood books, here is my unofficial field guide to the most common freelancer “characters” I have encountered over the years.

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Monsieur Maladroît (The Bad Fit)

This is usually the first real pain point.

You do your diligence. Strong ratings. Solid portfolio. Maybe even a test project. On paper, everything looks right.

Then the work begins.

The results never quite land. Instructions need constant clarification. You feel like you are pushing uphill just to get to something acceptable.

Often, this is not about effort or intent. It is simply a mismatch. The freelancer may be capable, but not for what you actually need.

The real cost here is time. This is the scenario I hear about most often when someone reaches out and says, “We need to start over.”

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Madame Fantôme de Vérité (The Deceptive One)

This one does the most damage.

Communication sounds polished. Confidence is high. The portfolio looks great.

Then inconsistencies start to appear.

Quality fluctuates. Answers feel vague. Progress feels disconnected from effort. In some cases, Upwork itself steps in with warnings about suspicious behavior.

Eventually, it becomes clear that the person you hired is not actually doing the work.

Managing a team is not the issue when it is transparent. Some excellent outcomes come from agency-style setups where roles are clear and communication is open.

The problem here is dishonesty.

When you believe you are hiring an individual contributor but are unknowingly dealing with a middleman taking a cut, trust erodes quickly.

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Monsieur Disparu (The Ghost)

Monsieur Disparu usually shows up after a fixed-price project wraps up successfully. You decide to keep the relationship going and transition into an ongoing, hourly arrangement so you can tap into them periodically as needs arise.

This freelancer may still be active, still logging time, and still technically “working with you.” But communication fades. Response times stretch. Your requests quietly slide down the priority list.

On platforms like Upwork, freelancers naturally focus on their newest clients. First impressions matter. New contracts feel urgent. Older relationships, especially ongoing ones, slowly get pushed to the back of the line.

It is not always malicious. It is often human nature.

But from the client’s perspective, it feels like being quietly deprioritized while still paying for access. You are left wondering whether to speak up, wait it out, or move on.

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Monsieur Correct (The “Fine” One)

Monsieur Correct lives in the gray area.

The work gets done. Deadlines are mostly met. Nothing is catastrophically wrong.

But you are doing a lot of cleanup. A lot of rework. A lot of mental overhead.

Usually the tradeoff is speed and price in exchange for quality that is just acceptable.

Sometimes this works for a season. Sometimes the devil you know really is better than the one you do not. But over time, this dynamic can quietly drain energy and slow progress.

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Monsieur Fiable (The One You Keep)

Thankfully, this character does exist.

In my experience, roughly one out of every three freelance hires turns into a genuine win.

Monsieur Fiable communicates clearly. Timelines are realistic. Pricing feels fair. The quality ranges from solid to excellent. He asks thoughtful questions and does not oversell.

These are the freelancers you return to again and again.

This is also where Upwork shines compared to more transactional platforms like Fiverr. When it works, it feels less like buying a one-off service and more like working with someone who understands your business, your context, and your long-term goals.

That continuity is powerful, and it is hard to replicate in purely transactional marketplaces.

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Closing Thoughts

Up to this point, I’ve been talking about freelancers I hired earlier in my career and the patterns I saw repeat themselves over and over again. Those experiences directly shaped how I show up today as an active freelancer on Upwork.

After seeing what works, what builds trust, and what quietly derails projects, a few lessons became very clear to me.

New business opportunities will always arise, and they almost always come with excitement. But not every opportunity is the right one. Over time, I learned that saying no is often best for both parties.

If the budget isn’t there, excitement fades. If the skillset isn’t quite right, frustration builds. If timelines feel unrealistic, corners get cut. Those problems tend to surface eventually, whether you acknowledge them upfront or not.

I also believe strongly in trusting your gut, on both sides of the relationship. I insist on meeting clients before working together, and I encourage clients to do the same when hiring. The vibes matter. Communication matters. You cannot fake those things long-term.

I’ve made plenty of mistakes over the years, both hiring and being hired. Those lessons are exactly why I take fit, honesty, and clear expectations seriously now.

When I take on work through Upwork, my goal is simple: be Monsieur Fiable. And judging by my 100 percent Job Success rating, that approach seems to resonate.

If you’re navigating the freelance world and feeling burned, confused, or unsure who to trust, you’re not alone. Sometimes, just recognizing which “character” you’re dealing with can save weeks of frustration.