I tell them their timeline is unrealistic (when it is), detail the requirements on both sides to achieve the desired end result, and basically rehash what Renata included in her post. But, unlike your grant writing clients, who have an externally imposed hard deadline, my clients are basically pulling an "I need this by X date" out of a hat. So, if they're eager to work with me, they'll usually reframe the timeline. Another technique that I use is "if you need it by X date, then A, B, and C will have to be sacrificed" (e.g., it won't be 750 words per section, it will 500 and/or this is my rate for prioritizing your project -- or something like that).
But, again, my clients have more flexibility than yours.
I'm fairly new to upwork but I'm finding it the oposite. I agree deadlines with the clients and keep them but I don't get any feedback to meet any of the timelines we have set after the first one and they come back to me after a week or so sometimes. Work proceeds the same until the end of project. I don't mind it but as I'm used to off line from upwork to always keep to all deadlines and have feedback straight away for milestones I keep worrying rather than enjoying the less stressfull work way.
There is no reason for my clients to have hard deadlines for anything at all, other than the fact that they want articles published within a certain date. But, that doesn't stop them from setting hard deadlines. When I was just starting out as a freelancer I would just take these projects anyway, and just work around the clock until I was done.
Now, if I can see that I can make the deadline, then I accept, but if I know it can't be done with me working hours that are comfortable for me, then I just decline it. Then there are issues like the one I'm in now. I can complete within the deadline if everything is set up properly, but the client is too slow creating new milestones. So then he's not gonna get his articles before deadline. As simple as that. For long term clients I try to hurry up if they need something fast, but for new clients I don't.
Way too many clients thinks that just because I'm a freelancer I'm just sitting around all day waiting for them to send me something to do. That's not how it works in my world. That's why I prefer working without deadlines, and then they can sit around waiting for me to deliver something. Much more comfortable for me.
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