How to Manage Challenging Customer Conversations

The web hosting market is highly competitive and I’m a firm believer that expert support and a personal touch to customer service is a big part of what makes a service stand out.

Most customer interactions are pleasant: a quick question, clear answer and a satisfied customer.  

However, challenging conversations are inevitable and how we handle them matters – not just for resolving the issue, but for maintaining trust, for the customer’s experience, and supporting the wellbeing of the support team. 

Here’s how I have learned to approach these situations in my time as member of the support team, and more recently, Technical Support Manager at 20i.   

Understand the problem and be empathetic! 

In the heat of the moment, it might not always seem like it, but customers aren’t trying to be difficult.  

When a message comes across as tense, abrupt, or even angry, there’s usually an underlying cause: frustration, confusion, or pressure. 

Maybe their website is down, or they’re up against a tight deadline, or perhaps they feel like they’ve tried everything and nothing’s worked. 

 Recognising the root of their frustration allows us to respond with empathy.  

That perspective often helps deescalate tension and guide the conversation toward a more positive, productive outcome 

When conversations take a turn 

Sometimes, a line gets crossed. Particularly if the language used becomes increasingly tense or hostile. When that happens, it’s okay to step back a bit. 

In those moments, we may say something like, “I really want to help get this sorted, but I’d appreciate it if we could keep the conversation respectful so I can focus on resolving the issue for you.”  

Here’s some other things you could say:  

• “I understand this is frustrating, I’m here to help to ensure we get this sorted quickly.” 

• “I’m committed to finding a solution. I just ask that we keep the conversation respectful so we can stay focused.” 

• “I hear your concerns, and I want to help. Let’s keep things constructive so I can do that effectively.” 

• “I know this situation isn’t ideal, but I’m on your side and ready to sort it out.” 

It’s not about shutting someone down, we are setting the tone for a better conversation. Most of the time, that’s enough to bring things back on track. After all, we both just want to get the problem resolved! 

Learn from past mistakes 

At 20i, we see every complaint or frustration as a signal and an opportunity to improve. 

When the same issues arise repeatedly, whether it’s UI responses that could be improved, common user errors, unclear billing or missing documentation, it’s a clear sign that something needs attention. 

We log these trends and feed them back to the relevant teams. Fixing the root cause often means fewer difficult conversations in the future.  

It’s a win-win for everyone. 

Put yourself in their shoes 

It’s easy to see a complaint and instantly label it as someone being difficult, especially when you’re  busy, but it helps to take a step back and think “how would I feel if I were in their situation?” 

A little empathy goes a long way. 

That shift in perspective from “this person is being difficult” to “this person is dealing with a problem and needs help” makes a meaningful difference.  

It not only improves the interaction, but also helps you approach the conversation with clarity, patience, and purpose. 

Conclusion

 In summary, difficult conversations are part of support, it’s just the nature of the job. However, when handled with the right approach, they don’t have to become a major issue.  

Stay calm, stay clear and try to see where the other person’s coming from. Most of the time it’s just a case of helping someone through a frustrating moment and when we learn from those moments, the whole experience gets better – for us and for the customer. 

Key takeaways for handling difficult conversations: 

• Stay Calm: Don’t let emotions escalate the situation. 

• Lead with Empathy: Understand where the customer is coming from. 

• Set Boundaries When Needed: Politely guide the conversation back on track if the tone turns hostile. 

• Learn and Improve: Use every complaint as a chance to improve systems and processes.