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How to Spot & Successfully Manage a Difficult Freelance Client

  • November 25, 2020

It wasn’t his fault, but the team at the magazine wouldn’t listen.
When a client asked Peter Geisheker, a freelance marketer and strategist, to create and place an ad for his company in a magazine, Geisheker didn’t know what he was in for.
“He refused to pay for the ad after it ran, even though he approved the ad, and the magazine came after me for payment. That led to months of going back and forth with the magazine to prove that it was my client who placed the ad and that he was responsible for paying for it—not me,” recounts Geisheker.
He’s not alone. Most freelancers have had to deal with difficult clients, keeping in mind the term “difficult” doesn’t necessarily equate to “bad.” Steal these tips for strengthening relationships and side-stepping potentially negative situations before they begin.

Always set ground rules. Always.

When you sign on a new client, it’s impossible to predict how the relationship will pan out down the road. For that reason, you should always draw up a contract—no matter how small the engagement might be—that closely details what your work entails and agreed-upon payment terms.
Need some help getting started? Use The Freelance Contract, a customizable template we developed in partnership with The Freelancers Union. It’s ridiculously easy to use.
Having a tight contract mitigates the risks involved with working independently for clients you know practically nothing about. At present, New York City is the only major city to pass legislation that grants freelancers the ability to level formal complaints against companies who routinely pay late (or not at all).
“When I was younger, I foolishly agreed to play gigs without signing written contracts,” says Eric Salazar, a freelance musician with more than eight years of experience. “This made it so I didn’t get paid once or twice. Unfortunately, those clients were just taking advantage of me, my music, and my services. Ever since those mishaps I always draft a written contract.”
It always helps to think of all possible scenarios and utilize a template contract that you can replicate for all your new projects. For instance, did you think of including a cancellation policy in your contract? Salazar came by that thought the hard way.
When Salazar was a young music teacher, he often let his private students get away with not showing up for their lessons or worse—cancelling their lesson 15 minutes beforehand, by which time Salazar would have already driven to the agreed upon location.
He thought being lenient would make them like him, but ended up losing their respect instead—they kept not showing up. This was when he went ahead and drafted and enforced a 24-hour cancellation policy.
“Things happen every once in a while, but if you are a freelancer with a client who has neglected to show up twice in a row or several times a month without a darn good excuse, then you need to have a written document that outlines a cancellation policy. If they are going to waste your time, make them pay for it,” he advises.

Types of difficult clients

A contract is good, but not foolproof. You will have to handle your share of difficult clients anyways, so it makes sense to learn to identify them and decide how you will reach closure that doesn’t leave you frustrated at the end of the assignment.
The types below are not exhaustive, but cover the most common groups of difficult clients. It’s also important to reiterate that difficult does not always mean bad. The reality is that as an independent professional, you’ll need to adapt to a wide and ever-changing range of personality types. And, as a freelancer, the “getting to know each other” window tends to be very short.
“Professionalism is king when dealing with difficult clients,” advises Chris Baylon, a freelance music producer and recording engineer. “You will be tested, but if you remain calm and collected you will be able to work in the most difficult situations. The thing to avoid is burning bridges or making a bad name for yourself. The project is a reflection of you. “
Here are some common types of hard-to-handle clients and how to manage them:

The Demanders

These clients are tough because they expect a lot from you—but as a hustler, you know that these types of clients push you to be better and more efficient. Brisk and business-like in nature, the Demanders can be hard to read.
Demanders don’t shy away from pointing out mistakes and efficiencies. After all, they hired you so they expect the best. The biggest concern with Demanders is their propensity to push a project beyond scope. While expecting great work in a timely fashion is reasonable, pushing more on your plate than was agreed upon in the contract (there’s that word again!) is not acceptable.
How to handle Demanders: You’ll likely spot a client like this from a mile away. You might even be one part inspired by them and one part terrified. The key to dealing with strong personality types is to stand your ground and come to meetings prepared to make things happen. Time-tracking, in particular, is critically important with this crowd, as they will put more on your plate as long as you accept it.

The Reluctants

“I’ve hired freelancers before, but they just didn’t work out.” When a potential client says something like this in your first meeting, your ears should perk. Reluctant clients are difficult because they can make you feel like you must constantly prove yourself to them. In extreme scenarios, the time and effort that goes into reassuring clients that you’re worth the money can take away from the work itself. Not good!
How to handle the Reluctants: Managing expectations is key to working with “reluctant” clients who aren’t entirely sold on hiring a freelancer. Put the client at ease from Day 1 by over-preparing in initial meetings. Take the time to establish a detailed roadmap with milestones, and spell out the deliverables they can expect and when. Schedule regular check ins so your client can be up to date on your progress, without checking in with you every step of the way.
“My best advice for negative clients are to show first and ask later,” suggest Salazar. “Although it may take more time, and is risky because your ideas may still get shut down, it may be best to throw out an idea by showing the result to the client first.”
In other words, invest in trust-building activities early on to save your sanity further into the engagement.

The Micromanagers

Micromanagers want to control every minute detail. Everything you decide to do has to have their okay. These types of clients are especially difficult for creative freelancers (designers, musicians, writers and the like). Without room to exercise your creativity, the project can get very confining and draining.
Alex Foster, a freelance illustrator, finds clients who want to take complete control the ones most difficult to handle. “It is a problem if they want to dictate every little thing to you,” he says. “As an illustrator I’m hired for my expertise and what I’m trained to do, so if the person commissioning wants to micromanage every tiny detail it makes you feel like your brain is useless and they just want to tell you how to draw.”
How to handle the Micromanagers: Setting expectations at the start is important when  it comes to micromanagers. As Foster notes, “The best way to protect yourself is for both parties to know what they are getting into and what they expect of each other.”
These expectations can be set in the initial contract, with clear specifics around feedback rounds and anticipated revision cycles. Have the talk early, and micromanagers will have less room to change course later on.

The MIAs

Ever had a client go incommunicado a few days into the project? You send emails after emails, follow up with calls, but you just can’t reach them. And you find yourself stuck, with no feedback, no idea on how to proceed further, and no payments reaching your bank account. You don’t know if you should proceed with the project or just halt it, both of which have risks involved.
How to handle MIAs: It’s important to know where your MIA client is coming from. MIAs could go missing because they have too much going on (you’re not their No. 1 priority), or because they started the project for a reason, but no longer see that much value in it. They could also just be a weak communicator who doesn’t understand how to effectively manager a remote or temporary resource.
For MIAs, transparency is always a good idea. Scheduled check-ins reinforce accountability between both parties. You might even found weekly progress updates, delivered via email, to be effective when it comes to staying on the radar. Our best advice: When you feel a client slipping, have a quick conversation to get back on solid ground.

The Unreliables

Unreliable clients are the one category of difficult we would classify as “bad.” These are the partners who make a habit out of paying late, or not at all. While one of gambles you take as a self-employed person is chasing down new business and making ends meet in unconventional ways, you should never accept a client who refuses to pair you your fair shake as established in a signed agreement.
How to handle the Unreliables: This is where the importance of a pre-signed contract comes into play yet again. Freelancers who initiate projects by establishing a well-thought out SOW, that is in line with client expectations, are less likely to lose out on earned income due to flaky payers. Operating with an agreement that’s too vague, or worse—no agreement at all—are at a higher risk.
When it comes to getting paid, freelancers need to be tough as nails. Unless you live in New York City, no else will fight for your dues. As a fail-safe, independent workers should have an attorney in mind that they can call up for a certified letter at a reasonable rate. You can also hire a commercial collection agency to contact the client for payment.


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