Cross-Generation Communication in Your Business with Lindsey Pollak

Cross-Generation Communication in Your Business with Lindsey Pollak

podcast scale - winning team Mar 27, 2024

In the latest episode of "Keep What You Earn," Shannon sat down with Lindsey Pollak, a renowned career and workplace expert, to delve into the intricacies of cross-generational communication in the modern business environment. The nuanced discussion unpacked crucial strategies for business leaders to adapt and succeed amid a multigenerational workforce.

Multigenerational workplaces are the new normal, but leading a diverse team can be particularly challenging when it comes to communication. Lindsey emphasized the importance of understanding the ‘why’ behind different generations' communication preferences. For example, while some employees may prefer instant messaging for its speed and convenience, others might value the clarity that comes with an email or the personal touch of a phone call. Understanding these preferences goes beyond surface-level adjustments – it's about fostering a culture that values everyone's voice.

Shannon underscored Lindsey’s insights by sharing her approach within her own business. She implemented a stipend for personal development, which respects individual learning preferences and supports her team members' growth in a way that resonates with them personally. This kind of tailoring speaks volumes to employees who want to feel seen and understood in their workplace.

The conversation then shifted to a macro perspective, discussing the evolution of career paths and opportunities across generations. Lindsey illuminated the shift from traditional corporate trajectories toward a plethora of options including side gigs, entrepreneurship, and startups. She recounted how Gen Z's acute awareness of these opportunities, coupled with a growing distrust in job stability, has fueled a diversified approach to their careers. This cultural remix - as Lindsey aptly described - is crucial for business leaders to embrace in order to support the varied career aspirations in their ranks.

Furthermore, Lindsey touched on the value of internal mobility and personalized career paths. She advocated for a workplace where employees can pivot within the company to roles that fit their evolving aspirations, a practice that benefits both the individual and the organization.

The discussion also recognized the changing definition of a successful career. Gone are the days when success was solely equated with climbing the corporate ladder. Today, it encompasses a broader spectrum encompassing job satisfaction, work-life balance, and personal fulfillment. It’s vital for employers to recognize and support these wider career definitions to attract and retain the best talent.

Shannon's enthusiasm for Lindsey’s work was palpable as she highlighted Lindsay's resources, which include her book "The Remix: How to Lead and Succeed in the Multigenerational Workplace" and her website,, that offers leadership tips and learning courses. Lindsey's expertise provides invaluable tools for leaders looking to harness the strengths of a diverse workforce.

Adding a practical layer to the conversation, Lindsey advised listeners, particularly small business owners, to consider tapping into local academic institutions for internships. This practice can bring in fresh perspectives and help businesses find individuals who fit into the organizational culture while contributing to the development of the next generation of the workforce.

A poignant takeaway from the episode was the importance of clear, defined communication and understanding personal deal breakers in communication methods. Shannon and Lindsey both stressed that the ability to adapt to different communication styles isn’t just a skill – it's a communication superpower within a corporate setting.

From Shannon’s promotion of "CFO on Demand," which aims to enhance financial understanding, to Lindsay’s treasure trove of leadership resources, EP525 of "Keep What You Earn" was replete with actionable advice and thought-provoking insights. It underscored the need for leaders to not just navigate but also celebrate the complexities and opportunities presented by today’s cross-generational communication landscape.

Closing the episode, Shannon encouraged the audience to engage by leaving ratings and reviews, showcasing the symbiotic relationship between a podcast and its listeners in discovering and implementing business insights that resonate in today's market. With these tools at their disposal, entrepreneurs and business leaders are well-equipped to keep what they earn - a thriving, multi-faceted team capable of exceptional performance across the generational spectrum.

Lindsey Pollak is a New York Times bestselling author and a leading career and workplace
expert. She is passionate about helping individuals and organizations thrive in today’s ever- changing, multigenerational world of work.

She is the author of four career and workplace advice books including her latest, Recalculating: Navigate Your Career Through the Changing World of Work. Her speaking audiences and consulting clients have included more than 250 corporations, law firms,
conferences and universities.

For six years she served as an official ambassador for LinkedIn, and her advice and opinions have appeared in such media outlets as The TODAY Show, The New York Times, The Wall Street Journal, CNN and NPR.

Lindsey is a graduate of Yale University and is based in New York City.




What you'll hear in this episode:

04:02 Challenging career expectations and exploring different paths.
08:03 Generational shift in small business success strategies.
11:13 Challenges with offering non-traditional internship opportunities.
16:17 Understanding and embracing generational differences in communication.
18:50 Preferred communication methods for team members discussed.
20:57 Knowing deal breakers, expressing preferences, communication styles.
24:00 Knowing your deal breakers and adapting flexibly.
26:52 Leaders and business owners should question their "why."

If you like this episode, check out:

Mastering Recruitment: Marketing Strategies with Shannon

How My Dad's Advice Shaped My Career and Business Success

Is Hiring Your Family the Right Thing to Do?


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The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.