What kind of gear do you use? I shoot with a Canon 5D Mark III. For portrait sessions, I typically use my 50mm f/1.2 lens and for in-home family sessions I'll use a 35mm f/1.4. My go-to's for weddings are the 35mm and either an 85mm or a 135mm, depending on the space.
What if it rains on the day of our session?! Being in Seattle, the rain is a constant factor. My general rule of thumb is to touch base a day or two before the session to see what the forecast says. If there is a potential for rain, we'll be in touch on the day of to see how the other is feeling. Unless it is pouring outside, I tend to err on the side of having the session because you just never know if we'll catch a break.
If for some reason we do have to cancel or cut the session short because of weather, I'll work with you to reschedule to the next available date.
When is your favorite time to shoot? If it's sunny outside I love the golden hour - around 1.5 hours before sunset. Of course, half of the year we don't see the sunsets because it is too cloudy. Truthfully, I do love a good overcast session. If we have overcast skies I'll usually suggest a morning shoot (10ish) or early afternoon, just so we get enough light.