How quickly do you need the photos?
Do you want to use the photos in your save-the-date next month, or is this just for fun? If you have more flexibility with deadlines, you have more time to create an e-session that perfectly represents the two of you.
Is there a favorite season?
Long engagement? Choose an e-session date in your favorite season. If you love the changing colors of autumn, stage your e-session to highlight the oranges and browns while you wear your favorite cozy sweaters. All about summer? Head out to the local beach or park to soak up the rays with a lively, warm-weather background.
Styled or straightforward?
We've all seen the sessions that are heavily styled with loads of props and themed clothing. They are lots of fun and can be a very dynamic way to share your personalities. But if you just want shots of the two of you, that's great, too. Keep in mind that if you are inspired by the styled shoots you see on Pinterest, that it is harder than it looks to keep a chic vintage picnic from looking like a random yard sale in a field. Less is more.
Favorite place or just the best light?
Some couples are very specific about the location for their e-session. Others aren't terribly destination-oriented. But all couples want these photos to turn out amazing. Communicate with your photographer about what you want in the background, whether it is the bookstore you both love or simply something "woodsy". Your photographer can also talk to you about the right time of day to shoot in that location to have the best possible light.
Normal attire or "Sunday Best"?
Decide before your session what type of clothing you should both wear. It doesn't matter if you go formal or casual, that's up to you. However, you should make sure to dress similarly. There's always something obviously stilted about an e-session with a glamorous, fashionable bride paired with a groom in a wrinkled tee shirt and bedhead. And yes, this happens. All. The. Time.
Are these just for the two of you, or to send out to family?
If these photos are going to the grandparents, make sure that you aren't making out in every photo. Some engagement sessions can definitely stray towards the sexy and passionate, and if that's what you want, more power to you. But if some of these photos will be sent to relatives, take a couple classic shots as well.
Do you want multiple location and/or outfit changes?
These things take time, and time is money. Talk to your photographer about the number of outfit changes and locations you are interested in. They can give you an accurate estimate of the cost involved, as well as how long of an appointment you will need to book. If you need to narrow it down to one location, but you want a variety of settings, choose a location with lots of different backgrounds such as your hometown's historic library, a local farmers' market, or a lively carnival.
What mood do you want to convey?
Some of my favorite sessions are those that really emphasize the personality of a couple. And that doesn't have to be complicated. If you are a couple of class clowns, don't be afraid to be yourselves goofy faces and all. Are you two the ultimate introverts? Not every shot has to be full of wide smiles and vibrant expressions. Take a few being a little pensive. We'll still love you.
Do you want to include someone else, like a child or pet?
Again, make sure to tell your photographer up front about children and pets. Much like in show business, working with little ones and animals is a tricky, time-sucking game. Especially if the child is younger, have a friend or relative on hand to help you while the tike is off camera.
Do you want your e-session to "herald" your wedding theme?
Especially if this photo will be the centerpiece of your save-the-date, it can be an interesting way to incorporate your wedding theme. Geektastic celebration? Take a few shots of the two of you playing board games or building with Legos. Chic garden party? The two of you should look more than a little fabulous all dressed up in an orchard.