Depends on service and how broad the competition is. I pretty much respond the same way as the author to discount requests. If I feel that the service I charge $250/mo for creates $250/mo value to you, I'm under no obligation to lower the price.

Curious to hear if you really "want to settle into the service" without having used/tested the product at all?

Asking for a discount during your trial is one thing, asking for a discount before trying the product is another :)

I ask for discounts on yearly subscriptions, but I test the service first. Sometimes I need only a day to know if it's a right fit or not.

Ironically, we're happy to give discount pricing for a year deal - because in that case the customer is investing up front and we're confident once they're using the product they'll realize significant ROI and stay.

But re negotiations, I agree with Steli here - the customer who asks for a discount before they've ever tried the product will typically become a problem customer (especially for a young company trying to get the initial 10-100 customers).

That's totally different and not the use case I discuss in the post. It's fine to ask for a discount after you tried the product. Most of us do it :)

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If you haven't already gone with the competition you described in (1), then there's a reason you're considering them and asking for a discount.