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5 Questions with Inter-Generational Expert Jessica Stollings

Jessica Stollings

Jessica Stollings is no stranger to the challenges and opportunities that exist between the different generations. She’s lived them out personally as a Millennial navigating “the real world” and professionally through leadership roles in a Fortune 500 company and through her role as a nationally syndicated news reporter and producer for Focus on the Family. She turned her passion for healthy inter-generation communication into her role as President of ReGenerations, an organization that connects generations to build a better future. Jessica recently published her first book, ReGenerations: Why Connecting Generations Matters (And How To Do It). Find her online at

1. We met when we were both attending a semester at the Focus Leadership Institute at Focus on the Family. We both went on to work at Focus on the Family during our early 20s. For me, that transition had a steep learning curve. What challenges did experience as a new employee?

Like you, my transition from college to career was a bit rocky.

Despite all my planning, I quickly realized that no “to do” list could help me figure out if I should call my boss by his first or last name, or when HR said to report at 8 a.m. if that meant to show up at that time or be working by then. And then there was my first paycheck. It was missing money. What was FICA?

A few months into the job, I began to question it. I wasn’t hearing feedback and had no way to gauge my efforts. Was I a good reporter? Or — my real fear — was I bad? I needed advice and knew just who to turn to: my dad. As I started to text him, another question emerged: Am I even allowed to text at work? I couldn’t risk it, so I snuck into the bathroom to send my career-altering text. Dad’s response shocked me: “No news is good news in the working world.”

Many of today’s workplace norms are different from those our parents experienced. But as we navigate this new territory, understanding expectations, asking questions, and engaging the help of mentors can help us move forward with grace and success.

2. It’s easy to look at technology, and Millennials’ ease with navigating technology in all its various forms, as the main difference between the generations. But there’s more to it than that. What are some other differences that affect the interactions between Millennials and other generations in the workplace?

When we study generations, we explore the social and cultural influences that impact a group of people as they come of age — things such as world events, the national mood, and media. The rapid pace of change in American society (think globalism, technology, communication methods, and increasing ethnic diversity) means that each generation has grown up in a vastly different world, resulting in distinctions we don’t always recognize.

For example, many who experienced World War II were influenced by military-chain-of-command leadership styles — so, “Here’s what we’re going to do, now do it.” Fast forward several decades to a generation who was raised in the self-esteem movement and encouraged to ask questions to find their place in the world — so, “Why should we do it?” Naturally, these instinctive behaviors clash, causing one generation to feel disrespected and the other to shut down.

Ultimately, all generations have more in common than they do differences, but surface-level misunderstandings are causing conflict as reported by 60 percent of organizations in America.

3. You describe a moment when members of different generations fail to communicate because of differing generational perspectives. As an audience primarily of Millennials, how can we help prevent our messages from getting “lost in generational translation?”

At a recent training I asked the group to share the first historical moment they remember. A Baby Boomer raised her hand and said, “The moon walk.” Before she could finish, an excited Millennial responded, “The moon walk? I love that dance!” #NeilArmstrongorMichaelJackson

Words and phrases can have different meaning depending on the era we grew up in, as do the channels and styles we feel most comfortable using. As the sender of the message, it’s on us to ensure it is successfully received, so try these tips when talking with established generations:

  • Understand your audience. Who are you trying to reach? How do they prefer to communicate?
  • Ask, don’t assume. To figure out how someone wants to stay in touch, ask them.
  • Meet people where they are. When possible, adapt your style to the format the receiver of your message is familiar with.
  • Be professional. Use proper grammar and punctuation and courteous phrases such as “please” and “thank you.”
  • Clarify your intent. Share your reason for asking a question, which is usually positive: “Because I want to add value, can you please explain the ultimate vision of this project?”
  • Build on commonalities. Story is a great bridge builder. Research shows it unites the brains of the storyteller and the listener.

If all else fails, listen more than you speak and you’ll be A-OK!

4. My preferred method of communication is e-mail, while my boss, who is 15 years my senior, makes phone calls more often. But many of our newest employees prefer to text. How do we figure out when we need to adapt to something we’re not familiar or comfortable with, and when we need to challenge the expectations or the mindset of “This is how we’ve always done it?” How do we show respect, no matter what generation we are?

Among a wide array of communication channels, it can be confusing to determine which to use for what purpose or person. I don’t think there is a right or wrong answer, but rather a set of questions that should be considered:

  • What communication channel(s) work best for your team/project dynamics?
  • Should you use different channels for short updates, than you do for longer explanations?
  • What channels are relevant for your company culture and context?
  • In today’s changing world, what communication approaches should you start using, stop using, or continue using?
  • Where can you adapt personally?

Bringing an intergenerational team together to hash out these questions is a great way to find solutions. It could also provide an opportunity to host a mentoring or reverse mentoring “lunch and learn” on past and emerging communication forms.

5. For older Millennials who are beginning to step into manager roles, how can they best prepare for leadership? How can they cultivate an understanding and healthy respect for inter-generational collaboration?

With Baby Boomers retiring at a rate of 10,000 a day and Millennials set to make up half the workforce by 2020, an epic demographic shift is underway. Based on sheer numbers, it’s clear our generation will have opportunities to lead, shape the workforce of the future, and make a difference in our world. With this honor comes responsibility.

The Moses-Joshua transition offers clues for how we can prepare. Joshua didn’t just wake up one morning and become CEO. He spent decades apprenticing under Moses, taking on menial and stretching assignments, and building rapport with the people he would eventually lead into the Promised Land. His story, in modern terms, reminds us to:

  • Stay humble. Don’t just expect a leadership role. Work hard for it. Allow yourself time to mature.
  • Honor elders. Learn about the current work environment and the generations who helped shape it. Understanding and respecting their “whys” helps you lead effectively.
  • Find a mentor, and be a mentor. Who do you admire? Consider asking their lessons learned and advice for your life story. Extend gratitude by sharing what you learn to help others. Live with succession in mind.

I’m so excited for our generation’s potential to lead! As we rise, let’s enlist the guidance of those who’ve gone before and remember to be strong, and courageous, knowing that the Lord our God is with us, wherever we go (Joshua 1:9).

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