Is there any problem to get F1 visa with an overstay of 25 days on H1 visa previously?

the reason for my overstay was due to the wait for H1 transfer/extension to be approved.

Now I want to get a Masters degree as a full time student. Will my overstay cause a problem? what kind of questions can I expect from the visa interviewer?

Legally you are allowed to stay for up to 240 days beyond I-94 expiration date provided you have a valid timely filed COS petition. So if you overstayed for 25 days on F-1 but had already applied for H-1 COS, then you should be fine.