I wish it wasn’t the case, but we often have to deliver bad news to customers in the onboarding phase.
Have you been there?
Something was promised that we can’t deliver.
They were told the product could do something it can’t.
They want impossible deadlines met.
The list goes on!
Given that we know this is likely to happen at some point, we should prep ourselves to handle it professionally to continue to deliver world-class experiences.
The steps below should give you a starting point.
You have 2 weeks to put them into action before the next newsletter. ↓
🧪 The Project: Bridge Builder
Let's start a repeatable system for delivering bad news that maintains hope and strengthens relationships.
Step 1: Map the impact first
Before the conversation, spend time understanding the ripple effects.
Write down:
What they expected to achieve with the missing feature/timeline
Which team members this affects
Their likely emotional response
Preparation will make you more confident in the conversation.
Plus, you can't build a bridge if you don't know how wide the gap is. 🤷♀️
Step 2: Nail your opening line
Start with acknowledgement, not apology.
Your opening sets the tone for everything that follows. It truly separates the professional experts from the newbies.
Instead of: "I'm sorry, but we have bad news..."
Try: "I've discovered something important about your implementation that we need to discuss and solve together."
Just reading those, I’m sure you had a sense of how they differ.
This positions you as a partner, not a bearer of doom!
NOTE: Please always deliver bad news in person, NOT over email. Tone makes a huge difference and you can learn so much from their real time reactions.
Step 3: Reality, Empathy, Action
This is an easy way to structure your delivery in three clear parts:
Reality: State the facts clearly in one sentence. Absolutely no waffling!
"The API integration you were expecting isn't available in our current product roadmap."
Empathy: Show you understand the impact.
"I know this affects your Q4 automation plans, and that's frustrating when you've built timelines around this capability."
Action: Immediately pivot to possibilities.
"Here's what we can do instead: [specific alternative]. Plus, I've already started documenting a workaround that gets you 80% of the functionality."
If I heard that from an onboarding manager, I would feel instantly supported.
Step 4: Processing space
After delivering the news in the step above, use this specific question:
"What concerns you most about this change?"
Then actually wait.
Count to five in your head if you must.
Their first response often isn't their real concern, it's their initial reaction.
The real conversation starts with their second or third comment. Dig deeper.
I’ll always continue to bring up the 5 Whys, because it’s so useful. Need a reminder on how to use it? ↓
Step 5: The path forward
End every difficult conversation by summarising three things in writing:
1. What we discussed today
2. What we're doing about it
3. When we're talking next
Send this within 30 minutes whilst the conversation is fresh.
This is proof you're taking ownership, that you have it covered, and the partnership remains strong.
It also provides a valuable paper trail for everyone involved.
Step 6: 48-hour follow through
Set a reminder to connect within 48 hours with progress on whatever alternative you promised.
Even if it's just to say "Still working on it, here's where we are."
This follow through is what transforms a bad news conversation from a relationship risk into a trust accelerator.
Don’t leave them hanging, wondering, and worrying about progress.
Give them the progress updates before they have to ask.
Another relevant topic to read about is The Peak End Rule that Disney use at their theme parks. ↓
🤓 The Analysis
You are a trusted advisor in customer onboarding. This comes with delivering both good and bad news.
This project is a repeatable process that you can have at the ready that turns difficult moments into demonstrations of partnership.
Sometimes, we overcomplicate the human aspects of relationships.
Customer’s don’t expect perfection. They expect honesty, empathy, and action.
What to expect by making these changes:
Faster issue recovery times
Increased trust scores
Reduced escalations
Stronger advocacy
