10 Practical Strategies & Tips for Handling Difficult Customer Conversations Image

10 Practical Strategies & Tips for Handling Difficult Customer Conversations

10 strategies for developing a mindset to help you better navigate challenging customer interactions.

If you’re being honest with yourself, you know that at one point in time you’ve been that customer. You know – the tough customer who didn’t hold back on the choice language and let the person on the other end of the phone know exactly what you thought of them and their company.

It probably wasn’t easy for them to keep their cool, speak kindly to you, and calmly help you solve the problem – but hopefully, they did.

And now, roles reverse – you’re on the other end as a customer support rep, a customer success manager, an account manager – having to field those difficult calls. Where do those skills come from (aside from lots of practice)? It starts with preparation, of course, but it also takes some practical strategies and mindset shifts to respond to a challenging customer calmly, professionally, and effectively.

I can’t promise that at the end of reading this, you’ll be pumped for your next tough conversation, but you will at least be prepared with some tools to help you respond when it comes.

Where Do Difficult Customer Conversations Come From?

It helps to start by realizing that a touchy customer conversation or what feels like a personal attack doesn’t come out of the blue. Generally, a situation, real or perceived, leads to an emotion – which then comes out at you via email, chat, text, in-person, or on the phone.


  • Miscommunication
  • Something breaks
  • Misaligned expectations
  • Confusion
  • Something involving money

Leads to an emotion…

  • Anger
  • Frustration
  • Embarrassment
  • Fear
  • Anxiety
  • Surprise

6 Mindset Shifts to Prepare You for Challenging Customer Conversations

Understand where the customer’s frustration might be coming from, and you’ll be closer to the first mindset shift: stepping into your customer’s shoes.

1. Step into their shoes

When an angry customer comes to you, that’s most likely not the beginning of the story. Maybe their boss was giving them a hard time about the issue and yelled at them – so they’re yelling at you. To show more customer empathy, it helps to think about it from their perspective and remember they may have their own battles they’re fighting.

Even though this is easier said than done, keep in mind that they’re probably not angry at you. This can help you not take it personally, even if it feels personal.

Keep in mind that the customer doesn’t know what your day has been like, either – so it’s important to walk into each interaction with the same patience you started the day with.

On the other hand, while it’s important to display customer empathy, this shouldn’t mean you allow them to harass you or curse at you. Learn how to disengage professionally – and with hope, this will earn respect from those difficult customers.

As you try to diffuse the situation, use phrases to convey customer empathy and humanize their customer experience. For example, try saying something like, “This sounds like a really frustrating situation. I’m sorry you’ve had to go through this! Let’s see what we can do for you.”

2. Think about it like a puzzle

When you’re interacting with a difficult customer, another helpful mindset shift is to view it like a puzzle. Like we talked about above, this customer didn’t go from speed zero to sixty all at once. Put on your problem-solving hat and try to analyze the root cause.

If you have an online customer community that integrates with your ticketing system or customer success platform, the customer may have started or added onto a discussion thread outlining the original problem. This can be a great way to get some more background and add some color to the problem they’re bringing to you.

If you can unpack the real issue behind the issue, you may even be able to support and serve them better in the long run by solving more than the surface issue. Having a growth-oriented and problem-solving mindset helps you help your customers succeed – even the difficult ones.

3. Focus on rebuilding the relationship

Instead of calling it a day on the customer relationship, take the difficult conversation as a chance to rebuild. You’ve heard it said, and you’ve maybe even experienced it, but a tough customer who feels heard and helped may become a great advocate.

Here are a couple ways to focus on rebuilding the relationship:

  • Listen to their needs. They may not be upset because something is broken or they can’t figure it out – there may be a deeper issue. Ask questions to help them express this. Remember to help them feel like their frustration is valid and that you’re here to be a partner in the solution.
  • Build in some space. Take some deep breaths and pauses while you’re speaking to help deescalate tension.
  • Focus on solving the root issue. Like we discussed above, focusing on solving the deeper problem or even hearing the deeper problem can go a long way toward improving the customer relationship.

4. Prioritize clear and confident answers

When helping a customer solve a problem, try to avoid giving an answer you’re unsure about. Even if it means they’ll have to wait for a bit, giving a clearer and more certain answer when you finally do resolve the issue is a better option than saying something that may not be correct.

But remember, always communicate expectations. Give and meet clear expectations for when the customer can expect to give an update from you.

Try this powerful phrase: “I’m not 100% sure. Please let me do some more research and get back to you with the answer by .”

And don’t be afraid to update them even if the issue hasn’t been resolved. It’s better to meet expectations than to leave them uncertain about what’s going on.

5. Lead with accountability and a desire to help

“The customer is always right” isn’t always true. But even if they’re not right, they’ve come to you to help them solve a problem, and you’re the representative of the company to help them do that. Take ownership of the situation and what happened. It may not have been your fault, but the onus is on you to make sure they get an answer. Leading with accountability can earn you respect in the eyes of your customer.

6. Remember that you’ll learn and grow from hard experiences

It’s not easy to have this perspective in the moment, but often, your hardest customer experiences become your greatest lessons. If you can treat each difficult customer experience as an opportunity to learn, grow, shine, and make a difference, you’ll be better equipped to learn from each situation and successfully navigate the next challenging customer experience that you encounter.

4 Practical Tips to Apply in Your Next Customer Conversation

Aside from the mindset shifts, which may take more practice to learn, having something practical to do can help you become more customer-focused right away.

  1. Opt for a call rather than an email. It’s much easier to sort out problems via phone or Zoom – and easier for you to show empathy.
  2. After you ask a question, put yourself on mute. This creates a window for the customer to answer. It’s easy to over-talk in stressful situations. When you go to unmute yourself, it gives the customer an extra 2-3 seconds where they might start telling you something they otherwise wouldn’t have said if you responded right away. Plus, venting can be cathartic and a positive step toward moving the conversation into a constructive dialogue.
  3. When you help the customer fix a problem, show them how you fixed it so that they feel empowered if it happens again.
  4. Rely on your team for support and take time to encourage your coworkers after difficult conversations.

Keep in mind that we’re all only one situation away from becoming a tough customer for somebody. If you can shift your mindset to view difficult customer calls as an opportunity, you’ll be well on your way to becoming more customer-focused, delivering a better customer experience, and improving net dollar retention for your business.

Guest Author: Rick Black
Rick is the Director of Global Customer Support for Higher Logic. He’s been passionate about building and scaling world-class customer service organizations for the past decade. Before coming to Higher Logic in August 2020, he spent 5 years with Snagajob, leading the evolution of their customer support functions for applicant tracking and onboarding software.