Jenna Rogers Of Career Civility On How To Navigate The Generational Differences That Are Disrupting Workplaces

An Interview With Cynthia Corsetti

Listen!!! Don’t listen to validate your opinion, listen to be challenged and to learn something new. Think back to when you were new to your most recent job: how eager were you to learn? Tap into that curiosity and inquisitiveness throughout your career, especially when working with new people. Each individual you work with is an opportunity to practice your listening skills. Listen to their ideas, their verbal cues, and their communication style.

Today’s workplaces are a melting pot of Baby Boomers, Gen Xers, Millennials, and Gen Zers. Each generation brings its unique perspective, work ethics, communication styles, and values. While this diversity can foster innovation and creativity, it can also lead to misunderstandings, conflicts, and productivity challenges. How can businesses effectively bridge these generational gaps to create harmonious and thriving work environments? As part of this series, we had the pleasure of interviewing Jenna Rogers.

Jenna Rogers is the founder of Career Civility, a workplace communications training firm based in Chicago, dedicated to helping professionals navigate the modern workplace. With over 40,000 followers on Instagram (@careercivility), Jenna is an influential leader in this field, known for her clear and actionable personal and career-focused tips, scripts, and advice.

Driven by her personal experiences navigating communication challenges in the workplace, Jenna understands that we each have our own societal and life experiences, and unique communication styles that drive how we communicate at work. She’s on a mission to bring civility back into the workplace.

Thank you so much for joining us in this interview series. Before we dive into our discussion about succession, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

After getting my Master’s in communication from Northwestern University, I spent years in corporate America as a sales leader and unfortunately dealt with one too many toxic work environments. Everyone knows communication is the “soft skill” of the century, yet no one knows what productive communication actually looks like in practice. And that’s been even more evident in the workplace. Communication doesn’t have to be hard, and I want to help people embrace that and thrive. That’s why I founded Career Civility: to bring humanity back into the workplace by using Civil Communication as the tool to help people communicate more effectively.

What do you think makes your company stand out? Can you share a story?

Career Civility is here to help bring humanity back into business by teaching effective communication in the workplace. We can no longer “check our humanity” at the door when we clock in for work. We can no longer accept people being disrespected in the workplace only for someone to turn around and say, “It’s not personal, it’s just business.” Wrong. Business is personal.

My first experience in corporate America was an experience of conformity, bias, and discrimination all wrapped up with a bow of professionalism. I once had a manager pull a ponytail out of my hair because “I looked like I was going to play an intramural softball game.” As if my hair would diminish my intellect or the impact I had on my clients.

I felt the pressure to wear heels every day, always have on a full face of makeup, and never wear my hair in a ponytail. I was one of two biracial employees in the office. At the time, I was proud that I could fit into the mold. I fit in. I was accepted. And, at the time, that was success to me. But I quickly learned that fitting in or what I thought was “being professional” was simply adhering to a mold that didn’t give a voice to the deserving and was downright disrespectful.

Career Civility is here to provide templated communication scripts, advice and training for those in business who have been disrespected, alienated, looked over, and passed on. Because the reality is that people can be hard to work with and effective communication is the key to improving working relationships.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. Consistency: I may not be the smartest person in the room or the person who has the most resources, but I will be the person who shows up day in and day out to put in the work. Take something as insignificant as my social media strategy and following. I’ve grown my Career Civility community to 40,000 people over 4 years because I continue to show up and put in the work.
  2. Curiosity: Learning is incredibly valuable to me. Whether I am learning in a formal setting or through a networking conversation, I am always asking questions, seeking different perspectives, and curious about how to approach things differently or more effectively.
  3. A bad memory: ha! But truly, it helps to let the mistakes and failures roll off your back more easily. They say the best athletes instantly forget the errors they make because it helps them remain in the moment and out of their heads. Surprisingly, as an athlete growing up, I was always in my head and it interfered with my ability to play well. Now as a business owner, I don’t sweat the small stuff. I know that every mistake, every ‘no,’ and every failure is an opportunity to learn.

In your experience, what are the most distinct characteristics, values, and work preferences of each generation currently present in the workplace?

In today’s business world, there is a lot of negative rhetoric around generational differences. It’s important to recognize the unique strengths that each generation brings to the table based on their own lived experiences and careers.

For example, Gen X gets some serious credit for navigating the ever-changing landscape of technology throughout their careers. They are the pinwheel generation who started with a Rolodex, paper and pencil, and evolved through technological advancements like the pager, PDAs, desktop computers, and smartphones.

Meanwhile, Boomers have invaluable grit and wisdom cultivated over decades in the workforce that younger generations can learn from and build upon.

As for Millennials and Gen Z, they inherited a completely different economic and business landscape than previous generations yet used this as an opportunity for innovation to climb the ranks.

Despite these differences, recognizing the commonalities in the work that needs to get done and leveraging each generation’s strengths can foster an environment of mutual respect and success.

Can you describe a specific instance where generational differences caused a significant challenge in the workplace? How was it addressed, and what lessons were learned?

The hybrid work environment has added a new layer of miscommunication, especially across generational lines. When it comes to email communication, all generations communicate differently. Gen Z communicates with emojis, millennials have a fondness for exclamation points, Gen X is direct, and Boomers prefer in-person communication over email.

As an organization, it is important to 1) have an explicit understanding of the primary means of business communication and 2) seek to understand how each individual communicates best. Solving generational differences is not one-size-fits-all and it needs to be approached with transparency, understanding, and explicit expectations.

Technology adoption varies greatly between generations. How do you recommend companies bridge the tech-savviness gap without alienating any generational group?

Introducing new technologies can be exciting but daunting, especially for those who may not be comfortable or familiar with them. And that is okay!

In business, there will always be a learning curve with new processes, and technology is no exception. When bridging technological gaps, it’s important to adopt a change management mindset and a clear implementation process. This includes creating buy-in, designing tailored training programs, providing support, and finding a way to seamlessly implement the new technologies into the workflow of every day.

How can organizations create cross-generational mentorship programs that allow older and younger employees to learn from each other?

The simple answer is to just go for it! However, the reality is that everyone is strapped for time, bandwidth, and resources. Therefore, it is necessary to be intentional about creating mentorship programs.

Have you ever worked for an organization that had a seamless onboarding process? Where you felt completely uneasy walking into your first day of work only to be met with an already built-for-you schedule to follow, training material to digest, an onboarding buddy to shadow, and a structured curriculum that set you up for success? I would apply that same process and structure to a mentorship program. Design goals for the program, create a professional development curriculum, assign a buddy system, designate cross-functional tasks to complete, assign counterparts to collaborate with, and hand the mentees/mentors an established manual to follow.

From face-to-face conversations to instant messaging, each generation has its communication preference. How can businesses foster effective communication that caters to these diverse preferences?

Allow the diverse preferences! Establish a primary means of communication as an organization and then enable each individual and each nuclear team to communicate how they are most comfortable.

The trick here is to ASK each person on your immediate team how they prefer to communicate. Don’t assume everyone will respond to instant messaging or is comfortable picking up the phone to resolve an issue. Seek to understand how people are most comfortable communicating and then, if possible, enable that mode of communication because that will be most effective.

How should training and development programs be tailored to cater to the unique learning styles and expectations of different generations?

Start by creating your learning and development programs under the guidance of a professional who is familiar with adult learning theories. Just as we cannot teach each child the same, we cannot expect adults of different generations to be trained the same. By adding in specific lessons and activities designed to cater to different learning and communication styles, training will be more productive and successful.

Think about it like this: if you assume everyone is an extrovert and all of your team-building activities are designed for group discussions, it will deter the introverts from joining in on the conversation and you will lose valuable connections among the team members. By creating inclusive learning environments, you’ll be able to cater to different generations in the workplace more effectively.

In what ways can leaders ensure they’re being inclusive and not harboring unconscious biases towards one generation over another?

The first thing to do is recognize that we all have unconscious biases. We find safety in familiarity and, specifically in the workplace, we need to know we are doing a good job to feel secure. When we are met with opinions that differ from our own or people who have different experiences than what we are familiar with, it can feel threatening. However, dissent in the workplace is necessary to problem solve. The ironic part is that working intergenerationally is a natural form of dissent. So, despite this, what’s the best way to foster inclusive workplaces? Work to create psychologically safe work environments, invest in expert-led unconscious bias training to ensure your hiring processes and leaders are always working to foster awareness and belonging and don’t be afraid to have tough conversations.

As we look towards the future and the eventual integration of newer generations into the workforce, what strategies should businesses implement now to be prepared for even more diverse generational dynamics?

Invest in leadership development for middle managers. Middle managers have one of the toughest jobs in the workplace. They are the conduit between executive leadership and the individual contributors. As younger generations enter the workforce at the ground level, they must be met with supportive managers who will not only lead them to grow in their careers but will also be able to harness their strengths to better support the business. Younger generations have a fresh perspective that could benefit every workplace. It is up to the business (and the managers) to find a way to cultivate their team’s strengths. By giving middle managers leadership development tools, they will be able to help do just that.

What are your “Five Things Leaders Need to Know About How to Navigate the Generational Differences that are Disrupting Workplaces”?

  1. Recognize others’ lived experience and honor their expertise. The beauty of the workplace is being able to collaborate with and learn from diverse groups of people. Older generations have a wealth of knowledge that younger generations can learn from and younger generations have a fresh perspective that older generations can tap into. Harness those qualities!
  2. Listen!!! Don’t listen to validate your opinion, listen to be challenged and to learn something new. Think back to when you were new to your most recent job: how eager were you to learn? Tap into that curiosity and inquisitiveness throughout your career, especially when working with new people. Each individual you work with is an opportunity to practice your listening skills. Listen to their ideas, their verbal cues, and their communication style.
  3. Be patient. This can be a tough one in today’s business world because time is money. Everyone possesses different work styles, personalities, and communication styles. it is apparent in today’s workforce that generational understandings can be frustrating. For example, Millennials seem to work very fast and talk very fast. To older generations, this fast work style can be seen as reckless resulting in a lack of attention to detail. To younger generations, Boomers can be perceived as working too slow or take too long to articulate their thoughts. Neither working style is inherently bad, however, they are perceived as negative to the other generation based on their own lived experience and perspective. To work through those frustrations, we need to listen and be patient with one another.
  4. Seek out conversation. What better way to learn from others than by engaging in conversation with them? By actively seeking out conversations with people across different generations and backgrounds, we can work past the stereotypes and add value to our network.
  5. Get curious. Ask questions such as, “What has been your experience with…? Tell me about… What has your career path been like for you? Where do you want to go in your career? How can I help you?”

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

As a teenager, my dad always used to say, “You take the good with the bad and run with it.” That quote always stuck with me because it reminds me that with light there will always be dark. Keep moving forward. With challenging times, there will always be happy times. Good and bad can coexist, and it is on us to keep going.

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

As someone with rampant anxious thoughts, I am working on calming those inner voices that keep me awake at night and spike my cortisol levels at 2 a.m. after I’m soothing my baby back to sleep. The two main questions that I wrestle with late at night are “Am I doing enough to support my community?” and “Will my kids be okay?” Both questions force me to remind myself to keep putting one foot in front of the other to make small progress on the goals and actions needed to create positive change.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Gosh, such an important question. It’s a tie between improving the education system or the healthcare system. Health is wealth and kids are our future. Pay teachers more and improve the working conditions of healthcare providers.

How can our readers further follow you online?

To continue learning about effective communication in the workplace, you can follow me on Instagram @careercivility and to learn how to work with me you can go to

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.