Ask A Contractor

Ask A Contractor: Dealing with Difficult Clients

Dear Selena, 

I’m working with a difficult client, and I don’t know how to handle it. What started as a great relationship had devolved quickly, to the point I dread working on the client’s project at all. What can I do to salvage this? 

Drawing of an ogre with a unicorn horn, labeled "ogrecorn" in block letters.

Dear Fellow Contractor,

First, I am completely sympathetic. Not all clients are unicorns. Not all clients are ogres, either. Most of them fall on a spectrum between the two, and sometimes one client can be a mix of both. An ogrecorn, if you will. Each new client is a mystery box, and often you won’t really get to know them until well into a project. We all put on our best faces until we’re comfortable with each other, and we’re all a little less shiny under our best faces.

That being said, there can be a lot of good reasons for a client becoming prickly. Before you write them off (and certainly before you procrastinate yourself into a corner), it’s worth making the effort to at least attempt to mend the rift between you. The following are some all-purpose solutions to try.

1. Give your client the benefit of the doubt. 

Disclaimer: Sometimes a client doesn’t need the benefit of the doubt. If they behave inappropriately, if they are excessively rude, or if they try to stiff you on your invoice, all bets are off. If this isn’t the behavior you’re seeing, it’s worth remembering that clients are human, too. Sometimes stress and life events get the best of all of us, and we can all have an off day. Stay polite and positive, and see if the client’s mood blows over.

2. Revisit the client’s expectations. 

Is there a chance you’ve missed an important detail or task your client wanted and didn’t get? Are you having difficulty nailing down what exactly the client needs? Take a moment to chat with your client and make sure you’re on the same page.

3. Establish and defend boundaries. 

This is a trap I fall into, even after doing this for many years. I try to be the Big Damn Hero and save the day, and then clients expect me to always be able to work miracles. I also tend to answer emails well into the dark of night, which means some clients have expected an all-access pass, 24 hours a day. Much like teaching, it’s easier to start firm and soften up as time goes on than it is to start out a softie and toughen up. Let your client know when you’ll be available, and stick to those office hours.

4. Change up how you communicate.

If you’re used to talking to your client in email or text messages, try having a phone conversation, or the other way around. Sometimes the change of venue can help refocus everyone’s energy on getting the job done.

5. Remember what you are not. 

You are not the client’s friend. (Unless you were their friend before). You are not the client’s genie. You are not the Scotty to the client’s Kirk. You’re a business, and your business is providing a service to your client’s business. Many clients understand that before they ever begin working with you, but some do not. For those clients, it’s up to the contractor to set the tone. This isn’t easy, and it’s something I still struggle with from time to time.

This is a place where it can be easy, especially as women, to fall into the “nice” trap. There’s no room for nice in freelancing. Be kind, be generous, be gentle of spirit and sharp of mind, but don’t be nice.

6. It’s okay if it doesn’t work out. 

You’re not going to click with every client, and if you both decide it’s time to part ways, there’s absolutely no shame in that. There are other clients who you’ll get along with swimmingly, and other contractors who may be just what your client was looking for. If you can’t fix it, it’s okay to politely bid each other good day. Make sure you’ve been fairly compensated for your time, and refund any advance payments for milestones you didn’t hit. Be fair and honest with your soon-to-be former client, and expect and accept the same from them.

7. Apply what you’ve learned. 

After it’s all said and done, and you’ve either made your client happy or parted on the best terms possible, give the project an objective, critical eye. What went right? What didn’t go right? Was it possible to avoid the things that didn’t go right?

Working with lots of different clients can mean working with lots of different personalities. For me, that’s one of the best parts. I’ve met scads of interesting and enterprising people from all over the world, and even the most difficult clients had plenty of positives. One client who I swore would never say a kind word about me in their life has gone on to become a regular, well-respected job source and mentor.


Selena MacIntosh has been a freelance education and technical writer and WordPress fixer-for-hire since the economy fell apart. She would be delighted to answer your questions if you drop them in the Ask Us! form. She will also totally stop talking about herself in the third person if you submit a good one. 

By [E] Selena MacIntosh*

Selena MacIntosh is the owner and editor of Persephone Magazine. She also fixes it when it breaks. She is fueled by Diet Coke, coffee with a lot of cream in it, and cat hair.

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