I have to disclose I am a remote worker for JonAtkinson.
I believe set estimates are not the best way to approach this problem because how do you estimate it? If you are in new territory then what seems trivial to one person may require some research and extra understanding by another. Also when you set a deadline it becomes more of a target for the individual action and instills a time wasting mentality.
It's especially difficult when a new employer enters the company as they feel under pressure that this is the expected deadline. One of the most helpful things Jon has done to elevate this situation when it arises is allow honest conversations without any fear which come from I guess a personal understanding/experience.
I also don't believe this problem is specific to remote working, it's simply a managerial problem within the industry as I am willing to openly admit this (having a problem and not speaking up) also happened at my previous job but the openness didn't exist hence a lot of dodging and ducking was performed until the task at hand was accomplished.