Two of my favourite estimation conversations (roles are indicative, not pointing fingers).
The What Is It?
Project Manager: "How long will it take you to test our disaster recovery solution?"
Me: "What's your disaster recovery solution?"
Project Manager: "We don't have one yet, but we need to test it."
Me: "I'm not convinced that is a valid approach."
Project Manager: "Well, what shall we do then?"
Me: "Create an disaster recovery solution."
Project Manager: "Can you do that?"
Project Manager: "How long will that take to test?"
Me: "I don't know, I would be creating it, so I can't test my own work"
The Anything But...
Product Person: "Can you provide a forecast for how long these would take to implement?"
Me: "Are you asking for an estimate?"
Product Person: "Lets call it a gut feeling then. In days"
Me: "Is that different?"
Product Person: "OK, I'll settle for a quote."
Me: "We may be straying into semantics here."
Product Person: "Just try and gauge it."
Me: "You know humans are rubbish at estimating time right?"
Product Person: "I know but I'm just asking for a projection."
Me: *sighs audibly*
As a heuristic, if this rings true:
Time spent generating estimates > Time spent doing the work
Then you should seriously have a think about estimating how long it takes to come up with an estimate. Mind the magical development unicorns sprinkling star dust on your product while you do. Or talk about alternatives to estimates as a means to gather information, try what success looks like, or a definition of ready. Break the cycle.