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Ultimate Guide to Difficult
1. Introduction 2. When you don’t know the answer 3. When you have to transfer a customer to someone else 4. When a customer requests a feature or product 5. When a customer asks you for a favor that you cannot do 6. When there’s something wrong with the delivered product 7. When you close the conversation 8. When a customer is angry 9. When a customer is unwilling to pay 10. When a crisis occurs 11. When you have a frequently complaining customer 12. When customers complain on social media 13. When you have legal issues 14. When you have to deliver bad news 15. When you have an abusive customer 16. When customers cross boundaries 17. When the customer speaks a different language 18. When a customer asks a vague question 19. When customers ask when something is going to be available 20. When you or your fellow agents made a mistake 21. When a customer wants to speak with a manager 22. When you can’t resolve the issue right away 23. When you need to let a customer know that it was their mistake 24. When a customer reaches you by mistake 25. When a customer asks how your product is different from others 26. When a customer is worried about how secure your service is 27. When a customer says that they forgot their password 28. When you want to point a customer to your documentation 29. When a customer violated your terms of service 30. When a customer is not tech-savvy 31. When a customer is right, but your policy is not 32. When a customer sounds like a bigot 33. You’ve got this!
Difficult Conversations

Ultimate Guide to Difficult

published / updated
May 2, 2019 / Dec 9, 2019
also available at


Support is like a box of chocolates — you never know what you’re going to get. One day you might get a delicious bunch of caramel filled bonbons, and the next you’ll get something that’s hard, and kind of ashy and tastes vaguely like a sweetened cleaning product on the inside. It can be a bummer, but at least you’re expecting it because people who work in support know it is never going to be one of those jobs where things remain the same.

For many support people, this variety is what keeps it fun. There’s something challenging in honing your skills to the point that you can deal with any and all questions that might come up. But, it can also be difficult. People that are excellent at support are also, by their nature, incredibly empathetic and often take on the emotions of the people around them. So, in the case of an angry customer who emails back and forth with an agent for a day, it can feel like carrying a ton of weight in a sack on your back at the end of the day.

This user guide will provide support agents and other customer-facing folks with some guidelines on the best ways to respond to specific scenarios or questions that can be notoriously tricky. We’ll even toss in some common ones that might not be so tricky, but could be useful to have a response up your sleeve for. Let’s go!