Navigating Generational Differences: Tips for Connecting with Younger Co-workers

Developing self-regulation as a leader takes time and effort, but it’s well worth it. By practicing mindfulness, setting clear boundaries, developing self-awareness, and building a support network, you can become a more effective and successful leader. Today’s episode we have our special guest, Jessica Cabeen who shares some of her practical tips for developing self-regulation as a leader. Tune in to the full episode and enjoy!

In this episode you’ll learn: 

• What Is Reverse Mentoring and it’s concept? 
• Having authentic humility is so important.
• Tips and importance on developing self-regulation.
• Humility and vulnerability in the workplace are going to make things just better.
• Tips for Connecting with Younger Co-workers
• How Jessica balances her work-life and fulfills both areas.
• Principal in Balance: Leading at Work and Living a Life by by Jessica M. Cabeen — Why she wrote this book. 
• Having a Bandwidth and Boundaries, Guardrails and Guide post, what you need to know.

Key Takeaways from the Episode

1. Embracing Non-Traditional Leadership

Jessica has redefined leadership by focusing on relationships, relevance, and vulnerability:

• Meet your team where they are: Jessica connects with students and staff by embracing popular culture and learning their language, from TikTok trends to youth slang.
• Show genuine curiosity: Building trust starts with showing a willingness to learn from others, even when it means stepping outside of your comfort zone.
• Balance high expectations with relationship-building: By pairing accountability with authentic relationships, Jessica creates an environment where students and staff feel valued.

2. Reverse Mentoring and Learning Across Generations

Jessica shares how reverse mentoring—seeking to learn from younger generations—has strengthened her leadership:

• Be open to learning: Approach others with humility and a genuine desire to understand their perspectives.
• Ask thoughtful questions: Simple conversations can lead to powerful insights about what motivates and engages others.
• Leverage the power of social media: Jessica uses platforms like TikTok and Twitter to stay relevant and build connections.

3. Finding Balance Between Work and Life

As a high-performing leader, Jessica emphasizes the importance of setting boundaries and prioritizing self-care:

• Start your day with intention: Jessica’s 5:15 AM morning routine, inspired by the Miracle Morning framework, includes journaling, exercise, and quiet reflection.
• Plan your ideal week: Structure your calendar to include deep work time, meetings, and flexibility for unexpected challenges.
• Recognize the need for recalibration: When life gets overwhelming, reassess your priorities and set boundaries to restore balance.

Leadership Lessons from Education for Corporate Leaders

Jessica highlights the overlap between education and corporate leadership:

• Model vulnerability and humility: Leaders who show their human side foster stronger connections and collaboration.
• Be intentional about building culture: Regularly incorporate activities that promote connection and teamwork.
• Encourage feedback and revision: Great outcomes often emerge through iteration and collaboration, not perfection at the start.

About Jessica Cabeen

Jessica is the Principal of Alternative Education Programs in Austin, Minnesota. Previously, she was the principal of Ellis Middle School in Austin, Minnesota, and the principal of the “Happiest Place in Southeastern Minnesota,” the Woodson Kindergarten Center. She has been an assistant middle school principal, a special education assistant director, and special education teacher.

Jessica was named the 2021 ED Dive National Principal of the year, 2017 Minnesota National Distinguished Principal of the Year, and was awarded the NAESP/VINCI Digital Leader of Early Learning Award in 2016. She is a NAESP Middle Level Fellow and a Future Ready Principal. Jessica is the author of Hacking Early Learning and co-author of Balance Like a Pirate, Unconventional Leadership, Lead with Grace: Leaning into the Soft Skills of Leadership and Principal in Balance: Leading at Work and Living a Life.

She is a sought-after speaker and trainer and enjoys getting to learn and lead with other educators across the nation. Jessica enjoys connecting and growing her Professional Learning Network (PLN) on social media. She can be found on Instagram, Facebook, and Twitter @JessicaCabeen.

Find out more about Jessica here: https://www.jessicacabeen.com/