Phil Gwoke Generational Expert | Strategist of Recruiting and Retaining Millennial Employees | Mentor and Consultant for Young Entrepreneurs

For financial, legal, and insurance professionals, client engagement is evolving at an unprecedented pace. Today’s consumers expect personalized, seamless, and trustworthy experiences—but what that looks like varies dramatically across generations. Baby Boomers may seek in-depth conversations and long-term relationships, while Millennials and Gen Z prioritize digital convenience, transparency, and instant access to information. And let’s not forget Generation X—often the bridge between tradition and transformation—who value efficiency, expertise, and a mix of both personal connection and digital accessibility.

"From Handshake to Hashtag: Generational Insights for Professional Services" provides a strategic framework for professionals in financial services, law, and insurance to effectively connect with clients of all ages. This session explores how generational values, communication preferences, and decision-making styles influence client relationships—and how firms can adapt their approach to meet evolving expectations.

Key Takeaways:

• How generational shifts are reshaping client expectations in financial, legal, and insurance services, including the balancing act Gen X plays between traditional and modern engagement styles
• Best practices for engaging and retaining clients across generations, from high-touch personal service to digital-first experiences
• Actionable strategies to build trust, enhance communication, and create long-term client relationships

By recognizing the distinct preferences of each generation, firms can develop more inclusive, adaptable strategies to serve their clients effectively in today’s dynamic professional landscape.

Four distinct generations collaborate side by side, each bringing a unique set of attitudes, values, and work styles to the table. Strengthening your team requires a deep understanding of these inherent generational dynamics. Identifying what motivates each generation and how they communicate is crucial for breaking down barriers and harnessing collective strengths. Unlocking the power and perspective of each generation fosters an environment where everyone feels empowered, valued, and understood. But do you have the tools to transform this diversity from a challenge into an opportunity?

This session delves into the identity of each generation, explores the reasons behind their differences, dispels stereotypes that may cloud judgment, and provides actionable solutions to effectively engage every generation.

In today’s fast-changing workplace—whether in the office, at a distance, or navigating hybrid models—four generations are working side by side, each shaped by defining moments, cultural shifts, and technological advancements. Add the rapid evolution of AI and new ways of working, and the need for cross-generational understanding has never been greater.

But not all employees think alike. While Millennials and Gen Z are often grouped together, they bring distinct perspectives, priorities, and workplace expectations. Millennials, now stepping into key leadership roles, are uniquely positioned—managing up, down, and across—bridging the needs of senior leaders while mentoring and engaging younger colleagues. All generations can benefit from understanding the ‘why’ behind each generation’s approach to work, communication, and leadership.

This insight-packed, fast-moving session breaks down generational myths and helps participants:

• Recognize and leverage generational strengths to build more dynamic, productive teams
• Understand key differences between Millennials and Gen Z, and how these distinctions shape leadership, communication, and collaboration
• Navigate today’s workplace evolution—from in-office to remote to hybrid—while embracing AI and technology shifts
• Apply actionable strategies immediately to enhance teamwork and engagement across generations

As people managers take on leadership roles, the complexity of managing up, down, and across generations becomes increasingly evident. "Leading Across Generations" offers valuable tools and insights to empower managers in effectively navigating these diverse leadership responsibilities.

This session places a strong emphasis on establishing trust among employees, recognizing their individual approaches to formality, motivation, and encouragement. It delves into the crucial aspect of facilitating generational understanding, exploring the events and conditions that have shaped each generation and how these experiences manifest in the workplace.

Key Focus Areas:

• Creating an experience that inspires employees to consistently show up as their most productive selves
• Highlighting the distinctive challenges faced by emerging professionals today in comparison to when leaders began their careers
• Building trust, driving engagement, and enhancing retention
• Understanding how each generation prefers to be managed

This session equips leaders with actionable insights that will elevate their leadership capabilities across the diverse landscape of generational dynamics.

In April 2021, a historic 4 million individuals resigned from their jobs, marking the onset of what is now known as 'The Great Resignation'—or more aptly, the 'Great Re-Expectation.' This transformative period is reshaping the landscape for employers of all sizes. The ever-evolving expectations from each generation in the workplace present a significant challenge for people leaders, compelling them to rethink how they mentor and coach their team members—whether returning to the office or continuing to work remotely.

In the face of this dynamic shift, 47% of HR professionals have identified retention as their top talent management challenge. Employee turnover exacts a toll both in terms of expense and time. When employees fail to find the flexibility or workplace culture they seek, they are inclined to move to organizations that better align with their needs.

This session delivers strategies for retaining top talent across generations, offering insights and actionable approaches to address the evolving needs of a diverse workforce.

The goal of this training is to equip individuals with an advanced set of skills that are proven to increase employee engagement with the teams they interact with while also building their confidence to work with diverse populations. Inclusive Leadership is demonstrated through a person’s cultural competencies to effectively engage people of diverse backgrounds, bring them together and build collaborative excellence, and innovative productivity. This session is designed to help individuals in the following ways:

• Develop a fundamental understanding of why and how to leverage the unique strengths that are represented throughout their workforce.
• Consider effective strategies to create an environment where individuals feel confident to ask questions and learn from their mistakes as well as their success.
• Be empowered with relationship building exercises that equip individuals to communicate better as mentors, coaches, and/or collaborative partners.

We aim to use our generational insights to set young talent on the path to success as well as connect managers with Gen Z and young Millennials. The generational conversation is a two-way street, so the NextGen Series consists of two workshops that can function either paired or independently. Whatever route you feel is best for your team, we will help facilitate generational understanding through engaging activities, in-depth discussions, and actionable takeaways.

Workshop for young talent: preparing the next generation for your workplace.

The multigenerational workplace is a labyrinth of communication and working styles—confounding for everyone, but most especially for young talent new to the workforce. With this workshop, we seek to ease those pains and help the next generation understand you. As Gen Zers and young Millennials enter your world, we work to prepare them for the complexities of a multigenerational workplace, your unique expectations, and how to navigate and succeed. We brief them on the strengths and backgrounds of each generation, review common clashes and how to overcome them, and hold an open conversation on how to integrate and grow within your organization.

A new generation is emerging in the workforce—new expectations, work preferences, and all—so now is the time to develop a sense for who they are and what they bring to the table. This workshop will teach you everything you need to know about Gen Z and young Millennial employees. We will focus exclusively on the young talent joining your ranks, present their unique background and traits, and discuss what you can expect when working with them. Prepare to walk away with a better understanding of next-gen communication preferences and motivators as well as actionable tips and strategies for how to get the most out of them.

A new generation is blossoming from their teens years into a unique flock of young professionals, and everyone is wondering: who are they and how will they affect the workplace? Generation Z is poised to be the most competitive generation to date. Raised by hyper-realistic Gen X parents, they're forgoing participation awards and focusing on real results. Diverse, driven, resilient, and hyper-connected, Gen Z will be instrumental in shaping our professional world. Those who look to the future now will hold the keys to building an effective, inclusive environment that attracts and retains the next generation of top talent.

Takeaways include:

• Gen Z traits and values, and how they impact the workplace
• Forecasting of future trends that will change the way we work
• Actionable strategies for overcoming generational ClashPoints
• Tools to craft the ideal environment for the workforce of the future

Love them or hate them, Millennials now make up a majority of the workforce—yet somehow managers are still puzzling over how to best recruit, retain, and engage this confounding generation. In this program, we'll demystify the Millennial management challenge and explore how to streamline communication and collaboration among Boomers, Xers, Millennials, and even the next generation. Best practices and proven strategies from Google, Netflix, LinkedIn, and other top employers provide real-world case studies of successful Millennial engagement. This comprehensive look at Millennial management strategies gives leaders the awareness, tools, and tactics to unlock Millennials' full potential.

Takeaways include:

• Management practices to bring out the best in your Millennial employees
• Debunking of harmful Millennial stereotypes that can get in the way of the manager-employee relationship
• A roadmap to groom high potential Millennials for leadership positions
• Tips for adapting Millennial-friendly feedback, communication, and work styles
  
  

The art of selling has undergone a massive shift. Traditionalists and Baby Boomers recall a time when salespeople were the experts that customers and clients turned to for information and advice. Now, with technological advancements and ubiquitous access to information, the rules of the sales game have changed. Gen Xers and Millennials are more familiar with a world where buying decisions are made after extensive research of customer reviews, ratings, and consumer reports. Baby Boomers still value an expert salesperson who knows how to build a strong relationship. This program gives implementable tactics to ensure that sales and service professionals can appeal to each generation of customer’s unique traits and preferences. Sellers will learn to avoid costly mistakes that result in lost sales, and instead wield their generational savvy to land the deal.

Takeaways include:

• How to pinpoint sales triggers for Baby Boomers, Gen Xers, Millennials and Gen Zers
• Techniques to help build stronger, more effective relationships with clients and customers
• An overview of how each step in the sales process, from introduction to follow-up, should be adapted for different generations of customers
• Actionable strategies that help position products or services in a way that resonates with each generation

 BridgeWorks has been dedicated bridging the generational divide for nearly two decades. All of their generational experts deliver presentations that are witty, smart, relatable, well-researched, and – most importantly – customized for ever room they’re in front of. Strong believers that every generational voice matters, they steer clear of stereotyping and focus on the truth.