How to Host a Productive Generational Conversation

A decade ago, American organizations were largely unaware of the predicament they faced. The initial wave of Baby Boomers (many of whom occupied senior leadership roles) was set to begin a mass retirement. Many organizations were completely unprepared. Then something curious happened. The recession hit and many would-be retirees stuck around. In one somewhat morbid sense, the recession turned out to be a blessing in disguise. By now, succession planning routinely takes generational demographics into close consideration. Generational-oriented training is mainstream.

So how does your organization or team address generational dynamics from an awareness perspective? Are you at least having the conversation? Given how many employees find themselves at odds with colleagues of different generations, it’s worth thinking ahead. Here are some ways to make the conversation a productive one.

Generational Headbutt

Have the Conversation

Believe it or not, many organizations resist holding generational training discussions in the first place. HR fears someone will be offended. Finance doesn’t want to pay for “unproductive” time. It’s important to understand what’s at stake. Generational mindsets and preferences about work and leadership are extremely unique to this era, especially given the technology advances of the last few decades. Baby Boomers will continue to retire en masse. Millennials have now become the largest generational segment in the workforce and are starting to creep into senior leadership roles. (Actually in these cases it’s more of a dash). At any rate, they have significant influence. It’s a great risk to put this conversation off.

Represent & Involve Each Generation

When comparing and contrasting generational themes, don’t leave anyone out. Better yet, solicit perspectives from each. Share the floor. Generate quality interactions. Make the goal better understanding and collaboration. Don’t let one group lecture the other. Do look for ways to build stronger connections.

Bring Out the Best

Are Millennials entitled? Are Baby Boomers out of touch? If that’s the extent of the conversation, be prepared for damage control. Focus on the good. Each generation has an incredible list of traits, perspectives and preferences to contribute. No one likes a lecture. Every segment is important.

Make it Fun

If you can’t find the humor in generational differences, you’re doing it wrong! Most diversity topics are off-limits for poking fun. This one is a little different. Do it tastefully, but give it a try. Each generation has its share of quirks. If you’re nervous, try a video to get the conversation (and mood) going. (This is one I’ve used before).

Keep it Up

Once you’ve held your first event, don’t call it quits. Keep the conversation and the momentum going. Ask for input from your team. Implement some of their ideas. Be willing to adjust your style at times and ask the same of them.

At the end of the day, the team with the best talent wins. If your organization can’t attract and retain the top talent from each generation, you’ll be at a sharp competitive disadvantage. Invest the time and planning now to hold productive, meaningful and engaging generational discussions. Everyone will be better for it.

Nathan Magnuson is a leadership consultant, coach, trainer and thought leader.  Receive his ebook Trusted Leadership Advisor by subscribing to his website or   follow him on Twitter.

Nathan Magnuson is a leadership consultant, coach, facilitator and author of the book Ignite Your Leadership Expertise. Click to download Nathan's free white paper: Nine Ways to Be the Boss Everyone Wants to Work For.