I've been thinking about this the past two or three weeks as I really just started training my voice.
Practicing in the car to and from work seems to be helping a ton, but I've also taken it upon myself to interject what I've been learning into my male voice- slowly but surely- so people don't really notice a huge shift all at once. I do want everything to be gradual as to avoid any potential awkwardness or uncomfortableness from people that knew me before as male (everyone).
My friends have taken notice (in a positive way) as far as my speech patterns and pitch, and I'd like to think it's part of the reason why they've been nailing the pronouns recently- even though 98% of the time I am still in mega andro boy mode

If voice comes up in conversation (so far only from me asking if they've noticed), most of them think it's just the hormones until I tell them it all comes from practice. Sometimes I say something a certain way and shock myself! The girl inside is taking over and I love it!
I don't have much experience to really help you for sure because I just started, but perhaps you could try slowly feminizing your male voice? My goal is to do it slowly enough that they get used to it naturally, and hopefully they won't be weirded out at any point.