Freelancing 101

10 Effective Ways to Win Retainers from Difficult Clients

Team Pepper
Posted on 30/01/226 min read
10 Effective Ways to Win Retainers from Difficult Clients

Table of Contents

  • Introduction
  • How to Win Clients?
  • How to Retain Clients in Business?
  • How to Deal with Difficult clients?
  • 10 Effective Ways to Win Retainers from Difficult Clients
  • Key Takeaways
  • Conclusion
  • FAQs

Getting clients on board can be challenging, but dealing with them regularly is a different ball game altogether. Every client is different, and their expectations are also different. Some clients are so easy to work with. They respect you and value you for the services you offer, and you look forward to working with them. However, there are a few clients with whom you just have to clench your teeth and work through. They are rude, critical about everything, and really difficult to communicate with.

How to Win Clients?

Winning new clients is time-consuming and expensive, but if done the right way, it is easy. The trick is to focus on building relationships with people rather than just networking because most clients can be won through referrals and old connections. Once the client is on board, you cannot relax. In fact, the real hustle starts once the client is on board.

Living up to the clients’ expectations and retaining them can be arduous. 


How to Retain Your Clients?

Wondering how to retain clients in business? Here are five ways:

  1. Pro-tip: Don’t just win clients; win their hearts
  2. Ensure a smooth onboarding process
  3. Provide personalized and value-added services to make them feel valued
  4. Speak their language; understand their requirements without them having to say
  5. Consistency is the key. Keep them informed and provide excellent client service from day one

How to Deal With Difficult Clients?

Clients are of all sorts. Figuring out which strategy works best for which client is the duty of a client service executive. Clients can become difficult when they are unhappy with the services being offered.

However, a few are difficult to handle and hard to please in general. No matter how perfect you are at your job, you cannot satisfy them. They are difficult clients who are like ticking bombs. They make things difficult for the business and drain the resources and energy of the people involved.

Everything is an emergency for them. They will not think twice before bothering you late at night and on weekends to discuss trivial matters. They have a habit of haggling over budget, paying late, providing unclear briefs, constantly scrutinizing work, and having unreasonable expectations.

Knowing how to deal with difficult clients is an art. Put in that extra ounce of effort, and you will be able to retain the difficult ones as well because they bring in revenue for the business.

10 Effective Ways to Win Retainers from Difficult Clients

1. Have a curious approach

Dive deeper into understanding the client and be curious to determine the actual cause of client dissatisfaction. There is nothing that open communication cannot fix. Talk to the client, understand his perspective, address his queries, and the last thing to do is try to be defensive.

2. What’s the elephant in the room

Have a straightforward approach and do not beat around the bush. If you feel a situation is wrong or sense that the agency and the client are not on the same page, address it immediately. Do not wait for the client to initiate the conversation because they probably never will and just keep sulking. The goal is to understand the issue and nip it in the bud.


3. Address the real issue at hand

Most of the time, you might be just seeing the tip of the iceberg while the problem can be very deep-rooted. Clients will not tell you directly but will expect you to understand yourself. Rather than assuming, ask the client for clarity. If the client is still reluctant to cooperate to make the work easy, it is best to bid them goodbye.

4. Set relationship rules in the contract

Some clients can be really rude, and there is a limit to enduring. Do not let them devalue and constantly discourage you. When making the contract and onboarding the client, highlight the standard operating procedures and relationship rules so that both parties can communicate and work in harmony with each other.

5. It’s pure business, nothing personal

Keep your emotions balanced, and do not take things personally. Some clients feel that they have the right to express their dissatisfaction because they are paying the business. Sometimes they aren’t very cordial in their approach and hurt the client service executives. The best thing to do is to remind yourself of the reason why you were hired, solve their problem and not take it personally.

6. Give them a reality check

Clients can sometimes be unreasonable with their expectations, and giving them a reality check is important. It is okay to not always agree with what the client is saying because they can be wrong at times. As an agency, you know what is better for the client. Set healthy boundaries, clear expectations, and communicate with respect.

7. Be a patient listener

The golden rule to deal with a difficult client is listening more and talking less. Acknowledge their problems and make sure they feel heard. If you talk more, they might feel that you are trying to defend yourself, which might make them angrier. Remember, clients love to be heard and not vice-versa.

8. Apply a specific client model

Businesses should have a well-defined Vision, Mission, and Core Purpose. Apart from that, they should also have a specific client model in place. This model will help the business gauge if the client’s values align with the business’s values. If they don’t fit in the model, the idea of getting into a partnership dies there.

9. Start with a purpose-driven outcome

Having a purpose-driven approach saves time and ensures a smooth work in progress. It is best to keep challenging clients informed. When both parties are clear about the expectations and deliveries right from the start, there is no room for confusion. Also, have a crisis management plan ready to deal with uncertainties.

10. Have a positive approach

The battle is half won if the situation is handled positively. Even difficult clients are humans, and you never know why they are so temperamental. They might be fighting their own issues, which at times might reflect on the way they conduct themselves. It is best not to judge them immediately and make them feel heard and understood.

Key Takeaways

  • Every client is different, and their expectations are also different. Tailor your approach to serving each client.  
  • Winning new clients is time-consuming and weighs heavy on the pocket. To save on time and money, businesses should retain the existing clients.
  • Businesses should focus on winning the client mandate and building lasting relations.
  • Difficult clients are like ticking bombs. They are unpredictable, and you will never know when they might explode.
  • Hold each client in high regard and be unbiased even if the client gives you a hard time.
  • No matter how much revenue a client brings, do not hesitate to let him go if he does not fit in your client model.
  • Less talking, more listening to make difficult clients feel heard and valued.
  • Do not be a people pleaser and shy away from setting healthy boundaries.


Running a business is not a child’s play. In the professional world, you will come across people with different personalities: some good, some rude. You cannot expect everyone to suit your expectations and be easygoing. Mastering the art to deal with all sorts of people is what will shape you into a strong business owner.


1. Why is it important to ensure a smooth onboarding process for clients?

The first impression is the last. A hassle-free onboarding experience will leave a lasting positive impact on the client’s minds, ensuring them that their account is in safe hands.

2. Why is open communication important to solve problems?

Not communicating clearly only adds up to the problems. Two-way communication helps the client service executives understand the client’s perspective, the reason behind their dissatisfaction, if any, and the issues can then be addressed accordingly.

3. What is the importance of keeping difficult clients well informed?

It is best to bring clients up to speed on the workings of their accounts and keep them informed right from the beginning to avoid unnecessary confusion later on.

4. Why should businesses set healthy boundaries?

Just because the client is the source of revenue for the business, it does not give him the right to devalue someone. To prevent clients from crossing the line, setting clear boundaries is important.

5. What are the types of difficult clients?

Mr. Know It All
Perpetual Complainer
The Rude One
Indecisive Forever