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David Stillman

David Stillman

Solving the Generational Puzzle
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Program Descriptions

Make Way for Gen Z
Bellieve it or not... There's life after the Millenial Generation.  A new generation is impacting out workplace and marketplace; yet not enough leaders are paying attention!  Are you ready for GenZ?  Don't be surprised when you find out when they are nothing like Millennials.  The time to get to know them is today.  If you treat GenZ like millenials, it will backfire.  The leading edge of GenZ is well into their 20's. 

Four distinct generations are working together shoulder to shoulder, each with a unique set of attitudes, values and work styles. It used to be that older workers were bosses and younger ones took orders. Now, roles are all over the board and rules are being rewritten. Organizations are feeling the pain of generations as they struggle to manage productivity and morale while maintaining high standards of quality and service in a challenging economy. When Generations Connect demonstrates not only why it’s important to understand what shaped the generations, but why they behave the way they do. Find out how generation gaps hit the bottom line. Learn what to do about the approaching talent gap; grasp the keys to retaining the generations you need most and discover how to convert this form of diversity from an obstacle into an opportunity.

Business is being rocked by a powerful generation that is going to comprise 75% of the global workforce by 2025. Millennials (born 1980-1995) – the first generation to rival Baby Boomers in population size – are showing up at work with their own set of attitudes, expectations and values. Tech-savvy, demanding and ambitious, they’re bringing with them an entirely new way of doing business. How prepared are Gen Xers, Baby Boomers and Traditionalists to manage them? Breaking Into the Millennial Mind offers strategies for recruiting, retaining and motivating this influential new workforce. Companies that are forewarned and forearmed will reap the rewards of the Millennial generation’s talents and their creative and pragmatic approach to the world of work. 

Each generation has left a unique footprint on the fabric of our society. Shaped by their unique generational personalities, the lasting legacies can be traced back to impactful trends that different generations have championed. This presentation will examine some of the freshest trends that have been identified by our generational junkies. From Millennials and their disruption of hierarchy that has ushered in the era of the network, to Boomers and the way they continue to rage against aging and redefine what it means to retire, Trend Talks will shed light on these fascinating trends and examine their potential influence on the workforce, marketplace, and our culture in general. 

To truly understand their customers, salespeople must think beyond income level, education, buying preferences, and spending habits. The best salespeople need a clear understanding of who the generations are in today’s marketplace, how they differ, and how their unique needs play out in the sales process. This presentation helps audiences understand which sales approaches and techniques appeal to each of the four generations by demystifying generational marketing and offering hands-on advice for marketers and salespeople who want to think in new ways about reaching these diverse demographics of customers and clients. 

Leadership today is more complicated than ever before. It is no longer necessarily determined by one’s position on an organization chart or skills and experience on a resume. With roles constantly changing, being a leader can simply mean being reliable and responsible, regardless of age or rung on the corporate ladder. From attitudes about loyalty to staying on the cutting edge, each generation brings unique leadership traits to work. While some try to figure out which generation’s way of leading is best, in reality no generation is better or worse; they’re just different. Our speaker(s) will help you identify the obstacles and opportunities for leadership within each generation and understand the potential impact everyone can make as a leader.


While many generational training sessions talk about how organizations can change their tactics to cater to the new generation entering the workforce, very few teach Millennials about the more experienced employees in their workplace and how best to work with them. This true “two-way street” mindset fosters an environment of respect, effective communication and team synergy. Millennial Boot Camp is an interactive, entertaining educational program for Millennials, taught by a Millennial expert on the BridgeWorks team. Millennials will learn first-hand from a member of their own generation about Traditionalists, Baby Boomers and Gen Xers and gain strategies on how to best communicate with each generation. 

The Millennials are here and are making their mark on the world and the workplace. But a new generation is ready to shake things up once again. Gen Edge (the generation born after 1995) is poised to be the most driven, competitive, and resourceful generation to date. They have already lived through a recession and witnessed multiple terrorist attacks on the home front and across the globe. Raised by hyper-realistic Gen X parents, they’ll be forgoing participation awards and focusing on real results. Though they’ve been immersed in a highly connected world of technology their whole lives, Gen Edgers are surprisingly adept at knowing when to unplug. The research is ongoing, but all signs point to Gen Edge being a force to be reckoned with. This presentation will give you an intro into a fascinating new generation that is proving to be incredibly sharp, down to earth, and determined to succeed.

Associations exist primarily to serve their members. But serving is tougher today as key resources are shrinking and government has taken a diminished role in funding programs. In addition to these challenges, today’s associations are made up of four diverse and outspoken generations of members. While Traditionalists and Baby Boomers have been loyal attendees for a long time, Generation Xers, and Millennials are proving tougher to attract and retain. Putting on a great conference or convention is no longer enough. 

The key is figuring out the right scale and combination of services needed to satisfy each generation of members. How do the expectations of each generation differ around engagement—working relationships, time commitments, and returns they should expect from association membership? The ability to capitalize on each generation’s energy, expertise, and leadership potential has never been more critical.

Nonprofit organizations suffer the same frustrations and face the same workplace problems as profit making companies. To be effective, nonprofits need good leadership, strong management systems, marketing savvy, and an ongoing commitment to excellence. They also need to understand what motivates four generations of staff, volunteers and donors to give their time and their money. Awareness of generational differences is crucial to organizations that must compete for well-qualified and loyal workers when resources are limited. What messages will attract skilled workers to the nonprofit world? What does it take to make connections with Traditionalists, Boomers, Generation Xers, and Millennials, so they not only donate but also keep giving? How does acknowledging donors of each generation differ? Board members, staff and hands-on service providers will learn to reach across generation gaps and build lasting bridges.

BridgeWorks works hard to customize presentations that resonate with every industry and client. Sometimes, generational issues experienced in a particular industry can be incredibly specific. In response to that, we’ve created a few presentations specific to the industries of hospitality, finance and healthcare. 


It’s no secret that each generation has a distinct generational personality, and we’re seeing more and more the impact that these personalities have on everything from the way they do business to the way they enjoy their leisure time. It’s important that leaders in the world of hospitality understand the key differences between the generations and their unique expectations. From Handshake to Hashtag will explore how generational trends are impacting the hospitality space and what leaders can do to stay ahead of the trends by:

  • Explaining who the generations are in today’s marketplace
  • Identifying key factors in how generational trends are impacting travel and hospitality
  • Exploring travel preferences for each generation
  • Emphasizing the unique perspectives of each generation
  • Presenting solutions for communication and engagement that will help attendees build stronger relationships with guests and employees of each generation

    In the finance industry, the last thing you want is for wealth to change hands and walk out the door. But what does retention look like across four generations? When Wealth Changes Hands will teach you how to speak your client’s generational language through a finance lens. Learning the position of each client’s financial outlook is a crucial part of relationship management yet we find that many times professionals use the type of communication that they prefer as opposed to the language of the client. We’ll provide some practical tips to help you alter your approach so that it suits each generation of client whether it be a Baby Boomer, Gen Xer or Millennial. 

    In the health care industry, change is happening quickly and employees are feeling the pressure – new government regulations, the exchange, the shifting relationship between patient/payer/provider – and the demand for quality care has never been higher. A shortage of healthcare professionals and the growing need for their expertise can be difficult to manage. Boomers are approaching retirement, Gen Xers are unsure if they’re properly prepared to take over leadership positions and Millennials are searching for their place in an industry built on history and structure. How do you keep each generation engaged and motivated while staying focused on patient and customer care? BridgeWorks will help you understand where the generation gaps arise in health care organizations and how you can start bridging the communication divide the next day.

    Dr. Google has changed the game of health care. With so much transparency brought by health care reform, and the always increasing access to information because of technology, companies are being forced to understand each generation of consumer – how to reach them, engage them and nurture them. Speaking the language of the patient can be incredibly difficult, especially when Boomers, Xers and Millennials all have different expectations of what that relationship looks like. We find that many times providers use the type of communication that they prefer as opposed to the language of the patient. We’ll offer actionable tips to help you understand how to navigate these different conversations.
  • Biography Read more

    As an early Gen X voice in a business world dominated by Baby Boomers, David Stillman became one of the youngest, most outspoken, and popular keynoters to hit the national circuit. His unique blend of humor, fairness, and frankness won over audiences of all generations and made him a go-to speaker for organizations that ranged from the IRS to MTV. David’s keynote speeches and workshops on bridging the generation gaps in the workplace and marketplace continue to receive rave reviews from corporations and associations nationwide.

    In addition to speaking, David co-authored the best-selling book When Generations Collide: Who They Are. Why They Clash. How to Solve the Generational Puzzle at Work (HarperBusiness). His latest book, The M-Factor: How the Millennial Generation Is Rocking the Workplace (HarperCollins) has become a business favorite. As a cultural commentator, David has appeared nationally on CNN, CNBC, and the Today show and has been featured in such prestigious publications as TIME magazine, Entrepreneur, The New York Times, and USA Today.

    Prior to launching BridgeWorks, David worked for ABC television in New York City as an intern for PrimeTime Live. Later with CBS radio, he embarked on a round-the-world trip covering such topics as the end of apartheid in South Africa and the fall of the former Soviet Union. Upon his return to the United States, David was employed as creative director for a multimedia company where he worked with clients such as 3M, American Express, and Wells Fargo. There he concluded that communication strategies that hit the hot buttons of one generation often miss the mark with another. This resulted in the creation of BridgeWorks with business partner Lynne Lancaster.

    David is a graduate of the University of Wisconsin at Madison with B.A. degrees in Communications and Sociology. He was selected as a fellow for the Michigan State University Mass Media in Britain program and studied in London with the BBC. Most recently, David received a certificate in non-profit management through the University of St. Thomas.

    David is a happily married father of three who recently took on a major role with the nonprofit organization, Free the Children, with the goal of bringing the concept of giving and volunteering to schoolchildren globally.

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