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
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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.
Step 2: Create easy response templates
Your team members do not need to reinvent approaches to predictable situations.
You will save many hours and resources if you utilise templates.
You have 2 options here:
Gather your top performers for a working session
Create them yourself as a leader
Either way, develop template responses for your most common scenarios.
For each, include:
Email notification (key points to include)
Call script with specific language for delivering the news
Pre-approved solution options to offer customers
This provides immediate structure while preserving your team's ability to personalise.
Step 3: Executive perspective first
Most teams jump into technical explanations as they try to fix issues quickly.
But it’s very important to address the business impact of these scenarios with customers.
Create a simple one-page reference guide for your team that reshapes how they structure difficult conversations:
Executive-Level Impact (Start Here)
"This may affect your ability to fully show ROI to your board by Q3..."
"This may slightly impact the rollout schedule your CEO announced internally..."
Practical Implications (Then Here)
User experience changes
Timeline adjustments
Resource requirements
Technical Details (Only If Asked)
Root cause explanation
System limitations
Technical alternatives
This immediately elevates conversations to the strategic level that resonates with your customers' leadership teams.
Step 4: Showcase progress
The gap between bad news and visible progress is where customer confidence dips.
Establish a rule that your team can implement today.
For example:
Within 48 hours of any difficult conversation, the customer must receive something tangible that demonstrates progress:
- A working prototype of an alternative solution
- Access to a specialist resource who can address their specific concerns
- A detailed plan with new milestones & accountabilities
This transforms abstract promises into visible progress that rebuilds confidence quickly.
Step 5: Quick internal reviews
It’s easy for busy teams to move on after difficult conversations without capturing crucial insights.
Create a simple way for your team to review a significant customer conversation.
Cover these points:
1. "What did the customer seem most concerned about beyond the technical issue itself?"
2. "What solution option resonated most strongly and why?"
3. "What one thing would you do differently in a similar conversation?"
Collate and review these responses to identify systemic issues, wins to replicate, or training opportunities.
🤓 The Analysis
The financial impact of how your team handles difficult conversations reverberates directly through your key metrics.
Your product solution creates a baseline value proposition, but the secret retention sauce is in how your team communicates through challenges.
Difficult conversations will happen. Don’t leave the outcome to chance.
What to expect by making these changes:
Improvement in executive sponsor satisfaction
Reduction in resources spent firefighting
Stronger long term advocacy & revenue opportunities
