Ask.com almost got its goodbye message right.
Updated: Aug 18
There was warmth in it. Wit, even. A callback to Jeeves, the cartoon butler who made an entire generation feel like the internet was answering them, personally.
And then the first sentence buried all of it.
"As IAC continues to sharpen its focus, we have made the decision to discontinue our search business."
That sentence wasn't written for the people reading it. It was written for the people who nod along in a boardroom when someone says "sharpen its focus." And it had no business opening a goodbye.
I see this constantly with every B2B company writing every hard announcement. A goodbye message: product sunset. A pricing change. A contract ending. The instinct is always the same: lead with the logic. Justify the call. Present it the way you'd present it to your board.
"After careful evaluation of our go-forward priorities..." "In order to better serve our core enterprise segment..." "As part of our continued investment in strategic focus areas..."
We've all read them. Every one of those sentences answers a question nobody on the receiving end asked. Because the customer never wanted to know why. They wanted to know that you understood what this means for them.
And that's the whole thing. That's the one idea underneath everything I write about: Yes, the rationale belongs to you and your boardroom, but the goodbye belongs to them.
Why leading with logic backfires
There's a well-documented pattern in persuasion research — when people feel unacknowledged, they get resistant, even to information that would genuinely help them. So all that carefully structured business rationale you worked so hard on doesn't land the way you hoped. Because you signalled in sentence one that you weren't really talking to the reader. You were talking past them.
Leading with the human moment isn't a soft skill or a nice-to-have. It's a trust mechanism. It tells the reader: we know this affects you, and that's where we're starting.
Ask.com's notice had the right instincts — a tribute to the engineers who built the product, a closing line that understood the emotional weight of the moment, a headline that got it. The bones were good. But they buried it behind one boardroom sentence in the opening which was enough to undo all of it, because tone is hard to recover once it's broken that early.
[OPEN WITH THE DECISION, FRAMED AS STRATEGY] Lead immediately with why this is good news for the company. Use words that mean nothing to the reader.
"As part of our ongoing commitment to [strategic priorities / delivering value / sharpening our focus], we have made the decision to [sunset / wind down / pivot away from] [product] effective [date]."
[JUSTIFY THE DECISION WITH BUSINESS LOGIC] Explain what the company is moving toward. Make it sound exciting. Do not acknowledge that the reader might be affected.
"This decision reflects our continued investment in [core platform / next-generation solutions / the future of X] and our focus on delivering [best-in-class / industry-leading / scalable] outcomes for our customers."
[ONE VAGUE SENTENCE ACKNOWLEDGING DISRUPTION] Technically address the impact, but keep it brief and passive. Do not say sorry.
"We understand this may require some adjustments on your end."
[THE PRACTICAL INFORMATION, BURIED IN THE THIRD PARAGRAPH] Put the dates, migration steps,
[Product] will be available until [date]
Customers should [action] before [date]
Please refer to [link to documentation no one will read]
Contact your account manager for assistance
[CLOSE WITH OPTIMISM ABOUT THE RELATIONSHIP] End by making it about the future, not the loss. Thank them for nothing specific.
"We remain committed to your success and look forward to continuing to support you on your journey. Thank you for your partnership."
[SIGN OFF FROM SOMEONE SENIOR ENOUGH TO SEEM IMPORTANT, NOT SENIOR ENOUGH TO BE ACCOUNTABLE] VP of Customer Experience / Chief Customer Officer / Head of Strategic Partnerships
What this template ticks:
Legal sign-off ✓
Board alignment ✓
Plausible deniability ✓
Not being quoted out of context ✓
The reader understands what's happening ✗
The reader is treated like a human ✗
What Ask.com goodbye message should have opened with — it was there all along
I see this with clients constantly: the closing lines of their draft say almost everything the opening needs to say. All they have to do is move it.
"To the millions who asked. After 25 years, Ask.com is officially closing on May 1. We are deeply grateful to the brilliant engineers, designers, and teams who built and supported Ask over the decades. And to you — the millions of users who turned to us for answers in a rapidly changing world — thank you for your endless curiosity, your loyalty, and your trust. Jeeves' spirit endures."
It's specific, it's warm, and it says the news plainly. And says it in the right order.
The Template That Works
The structure below works whether you're sunsetting a product, ending a contract, changing pricing, or communicating a service disruption. The sequencing is the same every time.
[OPENING — Lead with the human moment, not the decision]
Open on a shared experience, or a recognition of what's at stake. One to three sentences. No corporate language. Use your audience's words, not yours.
Acknowledge what this thing meant to the users - the real people affected.
"To everyone who built their workflow around this..."
"You trusted us with something important."
"To those who we kept warm"
"For X years, [product/service] has been how [audience] [did the thing that mattered to them]."
[THE NEWS — Say it plainly, in one sentence] Concrete, plain, unambiguous. Don't soften it with passive voice. Don't bury it.
"[Product] will be discontinued on [date]."
Nothing more.
"[Product] will be discontinued on [date]."
"On [date], we're closing/ending/discontinuing [product]."
[WHAT HAPPENS NEXT — The practical stuff, no jargon] What does the affected person actually need to know and do? Lead with their action, not yours.
What stops working, and when
What they need to do (export data, migrate, cancel)
What you're doing to make it easier
Who to contact if they need help
[THE WHY — Here's where the logic goes] Not at the top. Here. Once you've acknowledged the person and told them what they need to know, you've earned the right to explain the decision.
"This wasn't an easy call. Here's the honest reason: [one clear sentence]. [One sentence on what this means for where the company is going — but only if it's genuinely relevant to the reader, not just reassuring to the board.]"
[THE CLOSE — End like a human, not a press release] Not "thank you for your support." Thank them for the real thing.
"Thank you for [the specific thing: the questions you asked, the trust you put in us, the years you spent here]. It mattered."
End on something the reader can hold onto. A next step, a commitment, a quiet grace note."We're here to help you through the transition."
The business logic is never the lede. It never is. "Strategic priorities," "evolving landscape," "sharpen our focus" — these aren't explanations, they're placeholders for one, and readers can tell the difference instantly. If legal needs a sentence in there, it goes at the bottom, not the top. And before you send anything, read it as the person receiving it. If the first sentence would make you feel like an account number, that's the sentence to fix.
Why this is worth getting right
The way a company communicates an ending tells customers more about its character than the way it communicates a win. Anyone can write a good launch announcement. Almost nobody writes a good goodbye — which is exactly why it's worth learning how.
When someone receives hard news and feels genuinely seen in it, they don't just tolerate the message. They remember it. They repeat it. They become the kind of customer who tells other people you handled it well.
And that difference almost always comes down to one question, asked before you write a single word of the announcement:
Did we write this for us, or for them?
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Messaging designed to survive the rooms you’re not in
I'm Vivien, I help global B2B communication leaders and teams design corporate communications that make your CEO look good.
If you have an announcement you're wrestling with? I work with communications teams on exactly these high-risk multi-audience messaging moments.
