How to Plan a Multi-Generational Family Photo Session: A Step-by-Step Guide for Busy Families

Getting the whole family together for portraits - grandparents, parents, kids, toddlers, and everyone in between - can feel like coordinating a small circus. There are schedules to align, outfits to coordinate, and at least one little one who has decided today is the day they want nothing to do with cameras. But here is what I know after years of working with families: a multi-generational session does not have to be perfect to be beautiful. It just has to be real. And with a little preparation and the right mindset going in, it can also be genuinely fun.

When Reliability Is Everything
A few years ago, I was hired to photograph a multi-generational family portrait session tied to something deeply meaningful - a couple's 50th wedding anniversary. This was not a casual Sunday afternoon shoot. It was a milestone that the whole family had gathered around, and the images from that day were going to matter for a long time.
The family had a regular photographer they loved, but they could not use that person for this session. The reason? That photographer had a history of not keeping scheduled appointments. For something this significant, that was not a risk the family was willing to take.

So they called me.
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I showed up on time, ready to go. That sounds like a low bar, but I want to be honest with you - for a family gathered around a once-in-a-lifetime anniversary, showing up prepared and on schedule was everything. It set the tone for the entire session. Everyone relaxed because they could see from the very first moment that the day was in good hands.

What Actually Makes These Sessions Work
The standard advice you will find everywhere talks about coordinating outfits and arriving early. Those things matter, but they are not what determines whether a session truly succeeds.

Here is what I have come to understand through experience.

1. Cover your classics first, then take a chance!
During that anniversary session, I did something I would not have attempted earlier in my career. After shooting the classic, formally posed family portraits - the ones everyone expects and the family came for - I tried some different, more unexpected poses. Ones that created eye-catching images you do not typically see in a traditional family portrait gallery.

The reason I could take that chance was simple: my bases were already covered. The classic images were done. So experimenting felt like a bonus, not a risk.

If you are planning your session, know that I will always make sure we get those timeless portraits first. Then we get to have some fun.

2. A reliable photographer is not optional for milestone sessions.
I mean this sincerely. When your family is gathering for something significant - an anniversary, a reunion, a season of life that will not come around again - you need someone who will be there, fully prepared, when they said they would be. Professionalism is not just a nice-to-have. It is the foundation that every other good thing in a session is built on.

3. The little kids do not need to be perfectly behaved.
This is the one I wish every parent knew before they arrived. I hear it all the time - parents apologizing in advance for their toddler, or worrying that their five-year-old is "too wild" or "won't cooperate." Here is what I want you to know: it is completely okay if the little ones are a little wild. It is okay if they are not thrilled about having their photo taken. I expect it, and I come prepared for it.
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My approach with kids is easy and open. I work with them, not against them. I play with them, earn their trust, and let the session breathe instead of forcing anyone into poses that feel stiff or uncomfortable. Some of the most genuine, joyful images from a family session come from moments that looked like chaos from the outside.

A Few Practical Things to Keep in Mind
​Beyond mindset, a little preparation goes a long way. Here are some simple things that help multi-generational sessions run smoothly:

• Choose a location that works for everyone. Think about mobility, shade, and ease of access - especially if older family members are part of the session. I am happy to help with location suggestions in Southeastern Wisconsin if you are not sure where to start.
• Keep outfits coordinated, not matching. Complementary colors and similar tones photograph beautifully without looking like everyone ordered from the same catalog. Aim for timeless over trendy so the images hold up for decades.
• Plan for a little buffer in your schedule. Multi-generational sessions involve more people, which naturally means more moving parts. A relaxed timeline keeps everyone comfortable and means we are not rushing the moments that matter.
• Communicate with the whole family beforehand. When everyone knows what to expect - how long the session will run, what to wear, where to meet - the day starts with far less stress.

Why These Sessions Matter More Than You Might Realize
​A 50th anniversary only happens once. A summer when all the grandkids are still young enough to pile onto grandma's lap - that window closes faster than anyone expects.

Multi-generational sessions are about more than getting a nice photo for the wall. They are about pressing pause on a moment in time that your family will look back on for the rest of your lives. Twenty years from now, the image that hangs in the hallway will carry the weight of everyone who was there, everyone who smiled, and everyone who has since been lost.

I take that seriously. It is why I show up prepared, why I give every session my full attention, and why I work hard to make sure even the most reluctant little ones feel comfortable enough to let their real selves show up in the frame.

Ready to Start Planning Your Session?
​If your family is gathering for a milestone - an anniversary, a reunion, or simply a season you do not want to let slip by undocumented - I would love to help you create portraits that you will genuinely treasure.

I serve families throughout Southeastern Wisconsin and Lake Country, including Waterford, Burlington, Racine, Union Grove, Kenosha, Lake Geneva, Hartland, Pewaukee and the surrounding areas.
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Reach out through robynadair.com to talk through your vision and find a date that works for your family. The logistics are more manageable than you think, and the result - a room full of people who love each other, captured honestly and beautifully - is worth every bit of the effort.