Telling a client their favorite app has to go
Every client has one. The line-of-business app the owner had built fifteen years ago, still running on a server that stopped getting security updates long ago, because the app won't run on anything newer.
You've raised it at three quarterly reviews and the client nods every time, then moves to the next agenda item. Nothing happens, because it always sounds like a technical problem with an expensive answer. It needs to sound like a business decision with a date on it.
Gather first: the app's role in the business, the server details and any vendor upgrade path.
The prompt:
A client runs their business on a line-of-business app that sits on an unsupported server, and they nod at every quarterly review and change nothing. Help me turn this into a decision with a date on it.
What experienced account managers know:
Owners act on business consequences, not version numbers. "If this server fails on a Monday, invoicing stops until we rebuild it" moves people. "Windows Server 2012 is end of life" does not.
One expensive recommendation gets deferred. Three options with different costs and disruption get a decision.
Doing nothing is also an option, and naming its risk out loud is what makes the other options real.
The app and what the business uses it for: [details]
The server, its operating system and support status: [details]
What we have already raised and when: [details]
Any vendor upgrade path we know about: [details]
Do this:
Describe in plain words what happens to daily operations if the server fails or is compromised, written so the owner recognizes their own business.
Lay out four options with rough effort, cost range and disruption: do nothing, isolate and protect the server, move the app to a supported platform, replace the app.
Draft a short email proposing a decision meeting within 30 days, with one line on what we will do to reduce the risk in the meantime.
Where you need a cost or a vendor fact you do not have, mark it as a gap for me to fill instead of estimating.