Bridging the 401(k) Gap: How to Engage Every Generation of Investors

The other day, I was organizing a panel discussion.

  • One panelist, I called.

  • Another, I texted.

  • The third, I emailed.

It wasn’t a deliberate strategy, it just happened. But afterward, I realized something interesting: the panelists were each from a different generation. One was a Baby Boomer. One was Gen X. And the third? A Millennial.

And that’s when it hit me: I had instinctively communicated with each person the way they preferred. And not surprisingly, each one responded quickly and clearly on their own terms, different 401(k) panel communication strategies.

As a retirement plan advisor, you're having these same micro-moments every day. You’re talking to plan sponsors who want to drive engagement, helping participants understand their benefits, and trying to build stronger connections that lead to better outcomes. But if you’re using the same message across four very different generations, you’re probably not getting the traction you could.

With Baby Boomers, Gen X, Millennials, and Gen Z all in the workplace, tailoring your communication strategy isn’t optional—it’s essential. When you meet each generation where they are, your message lands. Participation increases. And you show your value in a way that’s not only smart but strategic.

Let’s walk through each generation and explore how you can craft 401(k) messages that actually resonate.

Baby Boomers (born 1946–1964): Focus on security and simplicity

What they value:

Boomers are preparing for retirement or already drawing income. They want stability, clarity, and a sense of reassurance that they’re making smart decisions. And yes—they still appreciate a printed handout now and then.

How you can reach them:

  • Pick up the phone or offer in-person reviews.

  • Share printed checklists, timelines, or FAQs.

  • Explain RMDs, catch-up contributions, and income strategies in clear, jargon-free language.

  • Avoid overcomplicating. Guide them step by step.

Messaging tip:

“Let’s create a plan so you can retire confidently on your terms.”

Gen X (born 1965–1980): Focus on control and financial independence

What they value:

This group is in their peak earning years, but they’re stretched thin. Between career demands, aging parents, and college tuition, they want solutions that save time and give them control over their financial future.

How you can reach them:

Use concise, value-packed emails with links to tools or calculators.

  • Offer on-demand webinars and retirement modeling.

  • Highlight long-term tax advantages and growth opportunities.

  • Keep it efficient. They don’t want fluff, they want facts.

Messaging tip:

“Take control of your financial future. Small steps today can lead to long-term freedom.”

Millennials (born 1981–1996): Focus on values and empowerment

What they value:

Millennials want to understand how retirement saving aligns with their life goals. They value transparency, purpose, and tech. They’re open to financial education as long as it feels authentic and judgment-free.

How you can reach them:

  • Make your content mobile-friendly and visual.

  • Frame your message around real-life goals like homeownership, flexibility, or travel.

  • Emphasize financial wellness and student loan solutions.

  • Don’t just send info. Tell a story that makes the benefit feel personal.

Messaging tip:

“Your future is yours to design. Let your 401(k) help fund the life you want.”

Gen Z (born 1997–2012): Focus on tech and trust

What they value:

New to the workforce and hungry for financial independence, Gen Z wants fast, digital answers. But they also want to feel safe asking questions even when they don’t know what to ask yet.

How you can reach them:

  • Use short-form video, swipe-through stories, or GIFs—yes, really.

  • Focus on education basics: What’s a 401(k)? Why does it matter now?

  • Be approachable and transparent. Build trust, not pressure.

  • Automate good behaviors (talk with plan sponsors about auto-enroll and auto-escalate).

Messaging tip:

“Start small, start early! Your future self will thank you.”

A unified strategy: personalization at scale

Customizing your communication doesn’t mean creating four campaigns from scratch. It means being strategic about how you segment your outreach and deliver the right message to the right audience.

Here’s how you can scale that personalization:

  • Segment your email list by age or tenure.

  • Build a resource library organized by life stage or savings goal.

  • Host webinars tailored to each generation.

  • Ask participants how they prefer to receive information. Then deliver it that way.

The bottom line

You’re in a unique position to guide people toward retirement success. But success starts with connection—and connection starts with communication that feels personal, relevant, and relatable.

When you speak their language, you stand out as an advisor who truly understands what people need, not just financially, but human-to-human. And that’s what makes you invaluable.

Related: The New Rules of 401(k) Committees: Is Your Strategy Keeping Up?