Let’s be honest: engaging members used to be a lot easier.

You’d send a welcome email (or a letter if you’re still Team Print), point people toward your benefits, and boom! Loyalty for years.

Now? You’ve got five generations in your membership, each with wildly different expectations. And while that sounds like a dream for community building… it’s also a nightmare for communications.

What Gen Z wants? Not even really close to what a Baby Boomer expects.

But you can’t exactly create five separate onboarding flows, five versions of every email, and five networking strategies just to keep everyone happy.

You’d need five of you.

So here’s a better way to think about it.

Don’t Treat Everyone the Same. Don’t Treat Everyone Different, Either.

We’re all kinda tired of one-size-fits-all messaging. You know the kind: “Welcome to your membership! Here’s every resource we’ve ever made in a single email. Good luck!”

Cue the overwhelm. No one reads it. Nothing gets clicked. The end.

On the flip side, the idea of building fully custom paths for every member based on age, role, tenure, preferences, and learning style? HA! That’s a full-time job, and it’s already your job.

The truth sits somewhere in the middle. You can personalize at scale, but it doesn’t start with better segmentation.

It starts by asking a better question.

What If You Just… Asked?

Imagine this: someone joins your association. Instead of guessing what they want, you ask them: “What’s most important to you right now?”

It's simple. It's quick. It's easy to answer. And the real magic? Their answer tells you exactly what to say next. No guessing. No “millennial-friendly version” of your newsletter. Just a response that meets them where they are.

When we did this recently with an association client, more than half of new members said they were just starting out in their careers. Not something we’d have known by default. So guess what? They sent them information that actually helped with early career related things. Not governance updates. Not advocacy recaps. Not a 12-page PDF on the committee structure.

We gave them a mentor directory. A new member checklist. A quick-start guide.

And they engaged, because we didn’t waste their time.

Networking: Not Everyone Wants to Grab Coffee

Now, let’s talk about networking. Or as some members see it: That Thing You Force Me To Do Once a Year at the Annual Meeting.

We asked a group of association professionals how their members prefer to connect. Nearly half wanted both in-person and virtual options. Another quarter leaned fully digital. Some only wanted face-to-face. And a handful said, “Please just leave me alone and send me the content.”

Fair enough. The point is: you can’t make assumptions.

Just because you love conferences doesn’t mean your members do. Just because you hate online forums doesn’t mean your younger members aren’t thriving there.

Ask them what they want. Then offer options. Big conference? Great. Slack-style community? Even better. A 30-minute Zoom for people who hate Zooms? Yes. All of it. Let people self-select, and connect them to that selection. That’s where the value is.

Career Growth Means Different Things at Different Stages

Quick thought experiment: A Gen Z member, a Gen X member, and a Boomer walk into your association.

What do they need?

• The Gen Z member wants a job, a mentor, and help navigating early career chaos.
• The Gen X member wants a seat at the table. Leadership. Visibility. Next-level growth.
• The Boomer? They’re thinking about legacy. About giving back. About mentoring the next wave.

If you send all of them the same “Here are our career resources” email… who are you really helping?

Instead, ask: “What’s your top career goal right now?” Then match them with the right opportunity.

So… How Do You Do This Without Losing Your Mind?

This is the part where most people say: “Okay, sure. This all sounds great. But who’s going to do all this?”

Valid question.

You’re not a full-service personalization engine. You’re one person (or maybe a small but mighty team) trying to do a million things. But you don’t need to build five journeys. You need one smart system that adapts based on what your members tell you.

This is what we call Conversational Engagement, where you ask a question, capture the response, and act on it immediately. It works across email, your website, SMS… wherever your members are. And it doesn’t require a huge lift, just a smarter approach.

Email’s Not Dead. But It’s Not Enough.

Gen Z lives on their phones. Boomers still check email daily. Gen X is somewhere in between. If your entire engagement strategy is based on email opens and click-through rates, you’re already behind.

Here’s the play:

• Use email for longer-form updates or onboarding sequences.
• Use SMS (with consent) for fast nudges and reminders. Especially with mobile-first members.
• Use your website as an interactive space, not an info dump.

One of our favorite client examples? They added a question to their homepage: “What brings you here today?” That tiny shift turned a static site into a conversation starter. Oh, and it also generated 6 figures in revenue (seriously, you can read about it here).

No More Guessing. Just Start Asking.

TLDR? Personalization starts with listening.

Stop assuming what members want. Stop sending everyone the same thing. Stop thinking “segmenting by member type” is enough.

Ask a question. Capture the answer. Respond in a way that actually matters.

You’ll get more engagement. You’ll make your members feel seen. And you’ll finally get out of the cycle of “Well, that email worked OK, I guess?”

Want to see this in action?

👉 Watch the full webinar replay right here

🎁 Or grab our free guide: 10 Lies Associations Tell Themselves About Member Engagement

Need help making this work at your association? Let’s talk.

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