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I work for a smaller business (50 employees) and am the only one handling a fairly large project for a client. This project involves upgrading software on their server.

They are consistently pressuring me for an "upgrade date", but I can't give it to them. There is a lot of prep work that needs completed by myself and other people at their company. If I set a date and the prep work isn't done, the upgrade can't happen. It's also hard to estimate when the prep work will be done because we keep running into issues.

Neither myself or the other people at the clients company were around when the last upgrade took place. A lot of it is trial and error. So far I have just been trying to explain the situation and why a firm date can't be set. Their response is just that the "old server is being discontinued (by their company) so it needs upgraded immediately".

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    Time to get learning about project management and guesstimating
    – M_dk
    Commented Jan 17, 2020 at 19:41
  • Obviously when you make an estimate, it must be based on your best estimate, and not on wishful thinking. And even good estimates can go wrong, and customers and managers often don't understand that an estimate is not a promise or a definitive date or a deadline, so better to add some time to be on the safe side. Better to have a long estimate and deliver earlier than the other way round.
    – gnasher729
    Commented Jan 17, 2020 at 20:04

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Don't discuss dates with the client, discuss milestones. Explicitly define all of the prep work that needs to be done before the upgrade can be attempted. Break it down into individual tasks and make sure that you indicate who is responsible for each task. If some tasks are dependent on prior tasks being completed then you need to make sure that the client understands. You should also let the client know which steps can be worked on concurrently. For each task include an estimated time for completion. This should give them a better idea of the scope of the upgrade and a realistic time frame assuming that the estimates were accurate and no issues arise during any step.

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    You should highlight Risks, Assumptions, Issues and Dependencies to your client. They shouldn't ever get a Big Surprise
    – Dave Gremlin
    Commented Jan 19, 2020 at 11:41
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Professional way to handle pressure for delivery date from client?

If you have already tried several things, I suggest you consult your manager on how to handle this.

You manager should be able to give you a definite answer you can give them, or take any action necessary to ease the pressure they have on your upgrades.

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