How To Handle Difficult Clients: 10 Practical Strategies

How To Handle Difficult Clients: 10 Practical Strategies

As a business owner (yes, if you’re a freelancer you are, in fact, a business owner), challenging clients or difficult customers are part of the deal. It’s an aspect of doing business you may not love, but learning how to manage and maintain business relationships will certainly make you a stronger business owner.

Of course, there are different types of difficult clients. Some situations may be easier to resolve, while others may add more stress to your business (and life) than you’re willing to accommodate.

This guide discusses effective strategies to help you tackle demanding client challenges like a pro. We’ll help you set boundaries, resolve conflicts, tackle miscommunication, find solutions, know when to let go, and, most importantly, learn from your experiences.

10 tips to help you manage challenging clients:

  1. Set clear boundaries and expectations
  2. Use effective communication techniques
  3. Maintain professionalism at all times
  4. Seek solutions and compromises
  5. Keep thorough documentation and records
  6. Know when to let go
  7. Learn from experience
  8. Utilize support networks and resources
  9. Implement feedback loops
  10. Foster a positive mindset

Plus: How to turn bad experiences into opportunities

1. Set clear boundaries and expectations

Some problems can be solved before they happen. One of the best ways to be more proactive with client problem-solving is to set clear boundaries and expectations upfront. Some things you should set expectations for from the very beginning:

If you’re working on a platform like Upwork, many of the details of your agreement will be highlighted within your freelance contract. Make sure to communicate with the client via Upwork Messages to establish any other expectations.

If you’re new to freelancing, anticipating potential issues may not come intuitively just yet. You don’t have to know it all. Do your research and learn from more experienced freelancers — the Upwork Community is a great place to start. This guide and others will help you figure out which boundaries to be firm on to avoid future difficult situations.

2. Use effective communication techniques

The success of every relationship hinges on open and honest communication. Business is no different. Good communication can come to your rescue even before you’re dealing with an upset or angry customer. In fact, it may help you avoid the negative situation altogether.

Sometimes, clients are inexperienced with working with freelancers. They may be dealing with projects they're not familiar with and don’t understand the freelancer's time and skill requirements. Clients who micromanage may also have excessive communication.

Whatever the situation, if you set clear expectations about client communication and actively work to meet those expectations during your working relationship, you may find it easier to mitigate unpleasant customer situations.

Before you start working together

As discussed, set client expectations about communication and how it will happen from the very outset. Before you start working together, outline, preferably in writing:

  • Your working hours, availability, and usual time to respond
  • Preferred communication methods — email, phone, messaging apps, etc
  • How often you’ll check in and provide project updates

Sometimes, you have to teach clients how to work with you. Let them know what you need and what to expect before accepting an offer to see if you agree.

During the project

The most successful freelancers focus on building relationships with their clients. This includes consistent and regular project updates. It also means building connections. The more you can connect with your client personally, the stronger your relationship will be.

Creating a shared connection with them will make your client feel understood and appreciated. Understanding who you're working with allows you to put yourself in their shoes and empathize with them.

Throughout your working relationship:

  • Schedule regular update calls with clients per your agreement
  • Be friendly and approachable, and make room for a bit of chit-chat in your calls
  • Have a pre-planned agenda for your meetings, and don’t waste the client’s time or yours by being unprepared
  • Respond to communication promptly (based on your agreement)
  • Send a recap of your meetings to serve as a record for reference (should it be needed)
  • Proactively ask questions and invite the client’s input throughout the project

Note: Excessive communication can hinder productivity and interrupt workflow. Clients constantly sending messages and asking for updates can signal a lack of trust. Clients who are new to working with independent professionals may be unsure how to navigate this relationship. Once again, being upfront and giving your clients communication guidelines helps set the relationship up for success. If they start overstepping, you can gently remind them of your process.

After the project wraps up

There are millions of freelancers around the world. But if you’re reliable and communicate well, clients will often treat you like they’ve found a unicorn. Clients love and appreciate a proactive, independent professional who takes an interest in their business.

  • Provide an end-of-project status report
  • Ask for feedback
  • Check in after the project has ended to make sure things are going well
  • Follow up in a few weeks (or later) to see if the client needs any further help

As you finish your first project, your communication skills will be vital to extending that relationship and continuing to work together in the future. Proactive, professional communication can help you build trust with your clients and keep them coming back.

3. Maintain professionalism at all times

If things are turning sour with a client, don’t let your emotions get in the way. If your client tries to make you angry, don’t give in. Maintain your cool and stay on the topic of business. Don’t resort to personal attacks.

Stay polite and respectful. If you feel yourself getting emotional and think you might be getting close to lashing out disrespectfully, step away. Take yourself out of the situation so that you have time to cool off and gain control of your emotions.

Hear out the client’s issue and look for a solution. However, if it seems impossible to continue working together, you’re better off ending your contract and moving on. Always stay calm and professional even if the client escalates the situation. If it’s a client on Upwork, keep the communication on the platform and contact Upwork Support if you need further assistance.

4. Seek solutions and compromises

Unhappy customers are a part of doing business. However, it doesn’t mean it’s all over. Sometimes, great conflict resolution and communication skills can help turn a situation around and turn a previously unhappy customer into a happy one.

Instead of email, try to have a face-to-face (virtual or in-person) conversation with your client. Don’t be on the defensive and assume they’re wrong; keep an open mind about the client’s concerns.

Go into the situation with a plan to find a resolution and a way to continue working together. Perhaps there was a miscommunication. Client expectations can sometimes be misaligned with the freelancer’s. Practice active listening, be empathetic, and really try to figure out what went wrong.

If necessary, take responsibility, apologize, and offer a specific solution to the problem. However, sometimes it may not be anyone’s fault; simply being empathetic with your client may help to de-escalate the situation. Work with the client to reach a compromise without necessarily sacrificing your values or quality of work.

5. Keep thorough documentation and records

As you can probably tell by now, you can mitigate many a challenging client situation by starting off on the right foot with them in the first place. This can mean avoiding miscommunication or misunderstandings by keeping thorough records, including:

  • Put a contract in place
  • Get all project details in writing
  • Email meeting recaps after a video call to have a record of what you agreed on
  • If and when clients veer away from the original project scope or goal, get the request in writing
  • Keep track of the hours you work to make sure you get paid for the work you do (Upwork’s Hourly Contracts can help with this)

6. Know when to let go

Everyone has different workstyles and personalities, and not every client will be the right fit. As a freelancer, you own your business. Part of this ownership is knowing when to keep trying with a client and when to walk away.

If a client constantly pushes your boundaries, has unreasonable demands, is disrespectful, or doesn’t pay on time, it may be time to cut your losses and let them go. Clients may sometimes have unrealistic expectations, making delivering a great customer experience arduous. These clients may also want results that are different from the original agreement, and they may try to spin the situation as poor performance on your end.

Decide whether you’ll have the discussion over email or a call. Stay calm, rational, and polite, and explain you’re terminating the relationship. Learning to say no can take some time and practice, especially if you're a newer freelancer, but in the long run it can protect your business and personal well-being.

7. Learn from experience

A difficult situation with a client can also be an opportunity to learn and use the experience to avoid similar situations in the future. It could be as simple as setting up better contracts, changing your workflow and processes, or simply learning to communicate better.

In my early days of freelancing, I had a client in a US time zone who requested a few meetings at around 11 pm my time (Australia). Eager to please, I said yes. Then, the client started requesting more meetings at odd hours, sometimes in the middle of the night!

After I refused to attend a meeting at 3 am, he was upset and said I wasn’t committed enough to the project. That hurt! But I decided then to let go of the client — there were plenty of other red flags as well. Since then, I’ve set expectations from the beginning of any working relationship and learned to establish my availability for calls and meetings very clearly in my calendar.

8. Utilize support networks and resources

When you’re dealing with a challenging client management situation, separating your feelings from what you’re dealing with can be hard. You’re only human and definitely not alone in feeling that way. Remember to stay professional. Don’t take it out on the client or your team members (if you have any). Instead:

  • Rant to a friend or family member
  • Vent to other freelancers who will most likely be able to relate and can offer support and perhaps advice as well
  • Turn to your mentor for support if you have one
  • If you feel the situation is affecting your mental health, don’t be afraid to seek professional help

9. Implement feedback loops

This one is important for all freelancers, especially if you’re new to this. As you finish up projects, invite clients to leave you feedback. Positive testimonials are great, but you should also actively seek feedback on the client’s experience working with you.

You can do this with an exit call at the end of your agreement and ask the client a few key questions. Alternatively, you could set up simple feedback forms for clients to fill out. Ask questions that encourage constructive criticism (if necessary), and don’t take it personally. Client feedback can help you learn a lot about where you can improve.

10. Foster a positive mindset

Negative experiences with clients can sometimes leave you with a bad taste in your mouth. As a new freelancer, it can be upsetting and hard not to take personally. But don’t let it take the joy out of freelancing.

Negative thinking zaps your energy and can destroy your business enthusiasm. Don’t let it get you down and affect your business. As cliche as it may sound, work on developing a positive mindset toward your clients — existing and potential, easy or difficult.

However, just saying “stay positive” may come across as trite without actually offering any practical advice on how to do it when you experience setbacks with clients. Instead of that, some practical tips include:

  • Approach each new client interaction with an open, non-judgmental attitude
  • When things feel hard, stay focused on the things that are in your control
  • Remind yourself why you started freelancing in the first place
  • Reframe the negative experiences as learning opportunities
  • Maintain an adaptable and flexible attitude to your clients, their businesses, and how they work
  • Focus on a growth mindset so you start to see possibilities rather than hurdles
  • When all else fails, take a deep breath, step away from the situation, and come back to it when you’re feeling calmer

Turn bad experiences into opportunities

As I mentioned at the beginning, as a freelancer you’re also a solopreneur — i.e., a solo small business owner. While you may already be great at the work you do, learning how to manage client relationships may take some getting used to.

Demanding clients are a rite of passage for freelancers. We’re all going to have that experience at some point. Be prepared by having a plan for dealing with challenging situations. Communicate and set clear expectations with new clients. If things start to escalate with an unhappy client, put your conflict resolution tactics into place and be ready to have some difficult conversations if necessary.

The more you put these strategies into practice, the better you’ll get at them. You’ll learn to remove your emotions from the situation — at least most of the time. You’ll also get to know yourself and your business better. You’ll learn the red flags to look out for that tell you a client may not be the right fit.

Dealing with challenging client situations can be stressful, frustrating, and, let’s be real, emotional. But with time and more experience, you’ll learn to look at your difficult client interactions as learning opportunities. Each bad experience can teach you what not to do, accept, or expect in the future.

Find quality clients on Upwork

While difficult clients may be par for the course, so are wonderful clients who respect your work, boundaries, and skillset. If you’re in the midst of a tough client situation, finding a great client can start to feel like searching for a unicorn. I promise you that’s not the case! They’re out there, and these clients are the ones who make freelancing oh-so-worth-it. They genuinely want to work collaboratively with you to achieve positive outcomes for their project and business.

First, take a deep breath. Then, let go of that negative energy and focus on attracting good clients for your business and creating great customer relationships with them. Sign up for Upwork and find quality clients for your freelancing business today.

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Author Spotlight

How To Handle Difficult Clients: 10 Practical Strategies
Radhika Basuthakur
Content Writer

Radhika is a self-confessed word nerd and content expert with over 15 years of experience writing content for businesses around the world. She is a cheerleader for flexible work, a passionate world traveler, and spends her free time alternating between a good book and a good hike.

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