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How to Handle Difficult Customer Conversations to Build Trust & Drive Revenue Opportunities
Revenue can be lost through lack of process for handling difficult conversations in a strategic way.
Clare Knight
May 22, 2025 • Estimated Reading Time: 7 minutes
IN PARTNERSHIP WITH
Have you noticed that your team members deliver bad news differently?
Top performers likely emerge from these discussions with stronger client relationships.
Others leave behind frustrated stakeholders and escalation emails waiting in your inbox. 😅
These moments are operational challenges.
They're also direct threats to your retention metrics and expansion opportunities.
How your team handles unwelcome truths isn't just a valuable soft skill, it's a core revenue competency.
So, is it possible to transform your team's approach to difficult conversations without implementing yet another time-consuming program? Yes! ↓
TOGETHER WITH ASCENDR
Before we get into that
You know I love consistent 1% improvements in customer onboarding!
So I want to tell you about something cool.
What if you could see how your onboarding stacks up against industry standards?
Here is a free tool that’s quick to use & gives you a score per customer as well as suggestions for improvement. ↓
🧪 The Project: Best of Bad News
This project is distilled into five leadership actions that you can implement today to improve how your team handles difficult conversations.
Step 1: Plan when to escalate
Decision paralysis about when to escalate issues to customers slows response times and erodes trust.
You eliminate this uncertainty when you define when escalation is needed.
Set clear escalation triggers, here are some examples:
- Delays affecting the customer's go-live date must be communicated within 24 hours
- Scope limitations impacting primary use cases require VP notification & customer communication within 1 business day
- Product usability issues requires communication to VP and to customer within 1 business day
The goal is to remove the "should I tell them?" debate that causes costly delays.
This process creates a standard operating procedure for all team members improving the customer experience.
Top performers may intuitively know when to escalate and have difficult conversations with customers.
Clear triggers quickly levels up your entire team.