How to Handle Difficult Conversations with Customers

If you fail to respond properly to a customer concern, you could lose business. Challenging conversations are inevitable: Knowing this, you’ll want to prepare to face whatever comes your way. Here are some effective ways to have those difficult conversations with a customer.

Estimated read time: 4 minutes

Learning how to handle difficult conversations is an essential skill for any businessperson. Failure to respond to a complaint can cost you future opportunities.

Most business books agree that each disgruntled customer will share their dissatisfaction with 12 potential customers. In a worst-case scenario, you could face a lawsuit if you leave issues unresolved. With these tips from Caterpillar on how to handle sticky situations, you’ll have a better chance of keeping customers.



Customer complaints come in two forms: short-term emergencies and long-term problems that may take several meetings and the participation of different teams to resolve successfully.

Let’s look at emergencies first.

First steps:

Do call the customer and acknowledge the problem. Even if the complaint comes in the form of an email or text, pick up the phone first. A phone call or a voicemail is the quickest way to let them know you’re on it and lower the customer’s blood pressure.

Do try to reach a foreman, supervisor or technician for clarification and additional details if the person who lodged the complaint is not available. 

Do listen empathetically. Nobody is right or wrong at this stage. Absorb what your customer is saying. Understand the problem from their point of view. 

Don’t waste time researching answers before you call unless you have a simple solution you can offer immediately. You’ll often need details and clarity that can only come after a conversation and questions. 

Don’t wait even if the call comes late. The customer’s hours are your hours.

Don’t strategize. Apologize first, whether you feel the customer is right or wrong, and then start working on a solution.



After you have contacted the customer and assessed the problem, it’s time to find a solution. Unless the problem has a quick fix, you need to do your due diligence.

Action #1: Investigate

  • Talk to your crew members, shop foreman, technicians, estimators or admins for input.

  • Ask another veteran in your company what they think. 

  • If the problem is equipment related, talk to your dealer.

Action #2: Follow up

In a week or two, follow up with a quick phone call, text or email to make sure the client is satisfied. A month or two later, check again. On this second follow-up call ask the client if they have any suggestions for better problem-solving processes in the future. Your extra effort sets the stage for an even better relationship.

Action #3: Share what you’ve learned

Take time to create what’s called an “after-action report.” This is simply a detailed summary of:

  • The problem or challenge 

  • The recommendations made

  • The results of the application of these solutions

You may not need a written after-action report for every problem. But keep notes, nonetheless. Brief everybody involved in the outcome and thank them for helping to resolve the issue.


Not all difficult conversations with customers can be solved with phone calls and emails. Some of the most challenging conversations come when a customer asks for a sit down or review. The process to resolve these situations is much the same.

  • Do your research and ask good questions without offering a solution.

  • Discuss concerns with all the relevant people in your company. 

  • Develop a strategy and contingencies.

  • Involve relevant people from your organization. Invite the customer’s key people as well.  

  • Make sure the people who represent your organization are experienced hands, good listeners and solutions oriented.

If it turns out you can’t come to an agreement, so be it. Help your customer understand that your organization must make money, just as theirs does. In most cases they’ll respect your honesty.

And likewise, follow up. Their conditions or needs will change. They may switch to a new contractor and not like the experience. And prices, availability and technology offered by your company may change and improve the chances of you working with the customer again. A difficult conversation, even if it doesn’t get resolved, should never be your final conversation with a customer. 

Asking effective questions — and then actively listening — is essential to positive customer relations. Check out our tips for active listening and asking better questions.


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