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The mistakes and misconceptions fall into 4 categories:

  • Timing

          Not starting early enough to identify and groom successors

          Not allowing sufficient time for overlap and transfer of responsibilities

  • Role behavior analysis

         Looking for a clone

         Not involving younger generations in creating a vision

         Considering the biggest business generators to be the best leadership material

         Undervaluing interpersonal skills and coaching for new leaders and successors

         Lack of transparency

  • Client involvement

        When the role is a client/customer-facing role:

          Not soliciting client views on what makes good leaders and managers

          Not asking what the client wants most in a relationship

          Not involving the client in the transitioning process

  • Not being inclusive

          Not inviting input from all generations of stakeholders

          Not making criteria known

          Undervaluing diversity in all its aspects

©  Phyllis Weiss Haserot  2007.  Revised 2015.

    pwhaserot@pdcounsel.com    www.pdcounsel.com 

SLICING AND DICING THE BOOMER GENERATION and the workplace implications




Here’s an illustration of what we mean when we say the generational cohorts are defined by “formational Influences.” And we need to look beyond “convenient” Census Bureau definitions by birth year.

Humorist P.J. O’Rourke turned to his Boomer generation (he’s an older cohort Boomer born in 1947) for a book, The Baby Boom: How It Got that Way (And It Wasn’t My Fault). In an article for AARP magazine he drew on interviews with Late Boomers and other observations to distinguish between the ends of the Boomer generation. The older half he calls the “loudest” generation. Many of he younger segment are quieter, more conservative, have no memory of Woodstock, and have considerably different formative (political, social, economic and cultural) influences according to Pew Research Center findings. They constitute one-quarter of the Boomer population. 

O’Rourke claims to have lived all the stereotypically wild, “let it all hang out” experiences of Boomers and wrote “These youngsters turning 50 are a mystery to me.”

While he took a light-hearted approach, his examination of the subject reinforces the significant point that the typical definition of the Boomers needs to be sliced and diced for a more accurate view of their general attributes (true also of Gen X and Gen Y). And even members of a typically defined generation need the insights gained through cross-generational conversation - within their own generation! 

In some ways the late Boomers more resemble the older Gen Xers: more individualistic and transformed from a (likely misinformed) slacker reputation to become very serious. O’Rourke wrote that the late Boomers are “like the quiet youngest child in a big family of older siblings. They grew up in the baby boom universe and take it for granted. They may not know there was ever another cosmos.” The older Boomers were born into the world of what we now consider “inappropriate behavior and wrongheaded social norms (as portrayed in “Mad Men”). And the older Boomers destroyed it utterly,” wrote O’Rourke.

So what does this mid-generation transformation mean for workplace succession planning? What kinds of conversations need to take place between older and younger Boomers?

  • Will the Late Boomers and Early Xers feel for urgency to go beyond vocal expression of beliefs and act tenaciously on them?
  • Will they make significant strides to change work cultures and policies to sufficiently satisfy Gen Y/Millennilals before the latter succeed in pushing them out of their way?
  • Who will initiate meaningful and ongoing cross—generational conversation?

Phyllis Weiss Haserot   www.pdcounsel.com


To achieve long-term success, it is extremely important to align succession planning with the strategic focus of the organization. Too often firms are not clear on their strategic focus, succession planning or both. Further, when these are undertaken, many important stakeholders are left out of the process. Organizations need to think in terms of both generational and other diversity challenges – two of the most difficult challenges in business continuity because both are totally human challenges.  These types of internal issues may also relate to client needs and preferences, so they can’t be ignored.

A Role for Younger Generations

The crucial alignment of the generations with organizational objectives will require a greater focus on people at all levels, a greater representation of all ages and types of diversity, and a greater effort to harness the wisdom and institutional memory of the senior professionals and executives – all this while capturing the hearts and imagination of the best mid-level and junior-level people that the firm has.

Most people think that succession planning is a top-down activity involving management and seasoned professionals. I strongly suggest that it is better to involve the younger generations as well so they can help create a vision for what the organization aspires to and for what it is looking for in long-term leadership – looking forward, not backward to a world that no longer exists. In order to retain the most talented young people, they must have a voice.

If you think of succession planning as a continual process, one way to involve the younger generations in the firm is to hold at least periodic meetings with junior employees (professionals and staff), invite them to ask questions, and encourage their input. By tapping into the collective wisdom at all levels they will learn a lot about what can make their firms more successful and what professional attributes and skills the organization needs to continue developing.

The younger personnel have a longer future ahead of them, and they see and experience the world in different ways. By engaging them in this ongoing dialogue, the firm will be more likely to retain the best talent.

At the same time, management should also be looking for leadership qualities among the younger generations. They need to encourage and allow junior people a chance to volunteer and take on responsibility for significant internal projects. In that way, they can prove themselves beyond mere technical competency. That initiative must be recognized in a way that is meaningful to both junior and senior personnel.

 Phyllis Weiss Haserot   www.pdcounsel.com

Note: This article contains excerpts from Chapter 34 of The Rainmaking Machine by Phyllis Weiss Haserot (Thomson Reuters, 2014 edition.)



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I am frequently asked about the potential for conflict between older and younger people in the workplace “Why won’t those Boomers realize it’s time to go?” some of them think.

Boomers are sticking around for two credible reasons: 1) they like the fulfillment, feeling of making a contribution, challenge and social opportunities work brings; and 2) they may very well need the money. In some cases there is a third reason as well: uncertainty that successors are well prepared to shoulder their greater responsibilities.

Economic reality meets career desires. The Great Recession had given many organizations a breather from brain-drain threats. At the same time, many Boomers would like to keep on working for a long time more, even if they can afford to retire. Surveys in 2004 and 2005 when the economy was robust and retirement funds were healthy revealed that about 80% of Boomers wanted to keep working after age 65 in some capacity – reinventing retirement.

While personal priorities will dominate each individual’s decisions, there’s a bigger picture need for restructuring. Even if we should see a booming economy, things won’t go back to what they were 20 years ago because the generational cohorts have different worldviews and expectations for their careers and work lives. And, significantly, they don’t understand each other’s perspectives and influences very well. When that understanding is achieved and accepted on an emotional level, we can move to greater cross-generational respect and collaboration.


Achieve role shifts and transitioning that benefits clients/customers and the organization as a whole. I am not in favor of involuntarily removing productive people, who do not wish to retire. Yet for the sake of providing opportunities to the generation waiting in line, senior professionals’ and executives roles and responsibilities need to shift at some point.

Shifted roles must come with respect attached. The transitioning process requires employers to rethink value and compensation for functions that were assumed to be provided gratis in the context of professional roles. Too often financial rewards come only from performing other functions that leave little time for knowledge transfer, mentoring, training and coaching. Financial disincentives need to be eliminated to reduce conflict.

And oh by the way – a word to Boomers and senior professionals: Gen Y/Millennials have discovered and seek out role shifts and lateral/lattice moves that keep them learning and doing new things. It energizes, engages and provides more choices and marketability for the long term. So why not take a lesson from them and explore that avenue to extend a career while giving those experienced and waiting a chance to move up? Consider it an opportunity.

The trick is to capitalize on Boomer knowledge and experience without alienating the bottlenecked Gen Xers and later, Millennials. One answer is to pay Boomers still in place now to transition their valuable acquired wisdom, contacts and skills before they up and leave with these precious assets or fail to pass on the baton and client bonds. That will prepare Gen Xers to thrive when the bottleneck opens as Boomers transition out over time.

If knowledge transfer and coaching is not built into transitioning roles which are made attractive by according them respect and providing work/life flexibility and engaging challenges, how will the next generation of leaders and managers get prepared to succeed? Willingness to prepare the next generation and shift roles through gradual transition can avoid generational conflict as both generations reap the benefits.

The real enduring challenge is building sustainably strong organizations that engage and retain the most productive talent of every generation. It will take frequent dialogue, listening, mutual mentoring and empathy. Organizations have to assess and re-think the connections between attitudes and expectations and the policies and financial and non-financial incentives that foster attitudes in order to prevent tensions among the generations and provide continuing opportunities for all to make meaningful contributions.

Phyllis Weiss Haserot    www.pdcounsel.com




Earlier this summer I was interviewed for a research project and master’s thesis by an EY (rebranded from Ernest & Young) Fellow in Ireland. For one of the questions, I generated a long list that provides an overview of challenges in the current multi-generational workplace. I am happy to share this with you.

Q. What do you feel are key issues affecting the multi-generational workplace at present?

A.  I easily named over a dozen issues, challenges and frustrations:

  • Senior management/decision-makers not “getting” the significant direct impact of generational challenges on the bottom line on their business.
  • Making mutigenerational teams better appreciate each member and work more effectively together.
  • Sharing and transferring knowledge – owing to compensation systems, lack of know-how and/or cultural resistance
  • Attracting and retaining clients/customers of different generations – and not taking different approaches
  • Attracting and retaining employees of different generations  - not using different approaches to meet their needs and expectations
  • Knowing when facetime is necessary and when not
  • Different generational perceptions of what teamwork is and what’s in it for them
  • Doing an effective job of orienting new employees, conveying the big picture vision and setting elear expectations
  • Comfort level with feedback and how to do it right – both giving and receiving
  • Avoiding turnover of valuable employees
  • Communicating messages that are received as intended by each generation
  • Excluding younger generation voices on leadership from succession planning
  • Tensions when older workers report to younger managers

No doubt this is a long list with much to tackle. Of course, not all of these are present in all firms/organizations or to the same degreee.

Which issues – or others – are occurring in your workplace or do you see elsewhere?

Please comment about which of these challenges and solutions to them you’d like to know more about to pwhaserot@pdcounsel.com or the Cross-Generational Conversation group on LinkedIn.

Let’s begin cross-generational conversation about these issues toward making more workplaces “best places to work.”

Phyllis Weiss Haserot    www.pdcounsel.com


HAS THE MISSING PIECE ELUDED YOU? – Find the Inter-Generational Solution

Generational differences in attitudes inform and influence attitudes and behaviors toward all the other types of diversity and individuals’ worldviews. They are integral, “joined at the hip,” so to speak.

  • If you are approaching attracting and retaining clients of different generations all the same way
  • If you are approaching attracting and retaining employees of different generations all the same way
  • If you are pitching your fundraising, member drives and engaging alumni of different generations all the same way
  • If you think the members of multi-generational teams all have similar wants and expectations
  • If knowledge transfer among generations has more speed bumps than fast lanes

then you are missing the piece that makes the ultimate difference to your long-term success rate. 

Most firms treat different types of diversity as separate silos and approach their programs as if one solution fits all and will make the crucial emotional connection that is necessary for attitude and behavior change and cultural transformation.

In the last several years, many organizations have realized that something different is going on and not going away, and their personnel need to learn about generational differences. Usually they bring in a speaker (sometimes that’s me) for an hour or so to explain the basics– and then check off the box that they addressed the issues.

It’s a good first step…but for real change to occur deepening understanding, repetition and practice is necessary. Savvy organizations are undertaking yearlong or longer initiatives and community building to address inter-generational challenges locally or globally, as relevant. That type of dedicated effort will earn them an advantage in recruiting and retaining both engaged employees and loyal clients/customers.

IBM and American Express have realized how central inter-generational initiatives are to productivity in their core businesses. IBM is leveraging learning resources and building employee communities in person and online in many countries to strengthen collaboration. With surveys and other means, IBM is assessing what different generations need and is providing recommendations to business units globally on attracting, developing and retaining talent of different generations. American Express, realizing that its shift in business strategy away from travel to financial services and other technology-oriented businesses required younger demographics, also has been focusing on inter-generational challenges.

Educational institutions are getting sensitive to the large demographic changes as at least a third of their faculty and administrative staff heads toward retirement age. For example, Cornell University’s Alumni Affairs & Development department, having done some generational programming in the past, is starting on a yearlong generational focus as one of its diversity initiatives required of all colleges and administrative units by the University.

Some of the strategies to include in your cross-generational diversity initiatives are:

  • Small facilitated group discussions
  • Educational materials and interactive courses appropriate to different markets
  • Mutual and reverse mentoring and mentoring circles
  • Significant roles for senior management as advocates and participants
  • Knowledge transfer and succession strategies

As firms, other organizations and institutions develop affinity or employee resource groups (ERGs) or business resource groups (BRGs) and other internal and cross-cultural communities, they need to be sure to cross-pollinate them. Just as gender diversity groups focused on furthering women’s careers and as leaders greatly benefit from bringing men into the conversation, diversity and inclusion initiatives for each specific focus need to bring all the generations into the conversation. Cross-generational conversations will facilitate understanding of all the views and attitudes that must be part of the solution and the pursuit of harmonious change.

Instead of “siloing,” make the cross-generational perspective the foundation piece.


Please comment and share your thoughts. Do you see this as a business imperative?

 Phyllis Weiss Haserot   www.pdcounsel.com


Does your organization have multi-level succession plans in place?

My recent workshop on the human side of succession planning and knowledge transfer got me thinking about it in relation to inter-generational relations and innovation.

If you recognize that you need to keep the big picture in mind and what's coming down the road in two or three years, since change happens ever faster, innovation and succession planning - both future-oriented functions - go hand-in-hand. A future -oriented management style understands and encourages taking reasonable and educated risks to come up with novel solutions. It fosters an organization-wide environment of innovation. According to Judy Estrin, former chief technology officer at Cisco Systems, five core values need to be instilled in the organizational mindset: questioning, risk-taking, openness, patience and trust.

And the company should not just create silos of innovation by designating an innovation group - the 'big-thinkers." What if any of those big-thinkers leaves or gets laid off?

Here's where we circle back to succession planning. It must be future-oriented rather than a search for clones of even very successful leaders, managers or vital technicians. It must include encouraging new ideas from younger generations and their view of the world and the marketplace. What do they think are attributes and skills needed by future leaders? What do they think the business challenges will be when they are moving into the current managers' shoes? What will the market, composed in large measure of their peers, need and demand in products and services? What do they need to learn to be ready?

Succession planning should be a continual process at any time. People in critical positions can be lost at any time for good or bad, happy or sad reasons. In down economies and times of crisis, the need to have succession plans in place in advance is even more crucial because there is less time to identify the best leaders for the circumstances and gear up to meet the challenges. You can’t rely on going outside, quickly finding the right people and immediately bring them up to speed.

Phyllis Weiss Haserot    www.pdcounsel.com



For some time I have been following the philanthropic and legacy efforts of Generations X and Y and how they differ from Traditionalists and Boomer generations in general. Also I’ve been advising on conflicting approaches within families that financial advisors and planners often need to address with their clients. So the report “Next Gen Donors: Respecting Legacy, Revolutionizing Philanthropy” by 21/64 and the Johnson Center for Philanthropy caught my interest. I found the conclusions align pretty much with my more limited research and my experiences working with inter-generational workplace issues.

The examples of what twenty-somethings are doing are quite enlightening. As always they want to do it their own new way, not only in their use of technology, but also in making it about connecting with other people. Though some of the young people I worked or spoke with had substantial wealth, most others were finding ways to donate very limited assets and make them add up to become very meaningful contributions.

Here are the typical elements I noticed concerning this philanthropic activities.

  • The younger generations are looking for an “experience.”
  • They prefer ongoing involvement rather than an annual event.
  • What really juices many of them is to be able to connect directly to the recipient of their contribution
  • They use e-mail blasts to urge everyone they have ever come in contact with to join in. They are very open in their connections and it’s all about connecting.
  • They like voting for “the person who contributes the most…” and cash awards and recognition.
  • They are drawn to compete in contests; they like competitions and prizes.

According to Sharna Goldseker, Managing Director of 21/64, consultants on strategic philanthropy and the generations, beneath the surface of much of the under 35-year-old involvement in philanthropic projects is a search for their own identity.

Keep in mind that the Gen Y way is another search for community much as Gen X did, but perhaps for different reasons and with a desire for individual attention. Gen X originally sought community at work because it was missing for them outside of work. Gen Y has been educated in a more collaborative environment and it is their modus operandi.

I definitely see the desire to be hands on and to produce measurable change with their giving. Interestingly, this has been characteristic of the Boomer generation of women donors and something I personally very much relate to. All my professional life I have observed that women donors don’t simply want to write checks.

As for the under 35 year olds in families with foundations desiring to maintain family bonds as philanthropists, that is not surprising. Gen X and Yers are typically quite family-centric. The tension comes.from wanting to have a strong voice and their own style of philanthropy while maintaining family harmony

Millennials don’t think they have to wait to be older and richer. They think they can make meaningful contributions right away, and they do it creatively with new methods and tools.

Phyllis Weiss Haserot     www.pdcounsel.com.


It’s not a secret that the majority of organizations are not doing succession planning and certainly not doing it below the highest levels though they give a lot of lip service as to how important it is. Many of those that do some sort of succession planning hold the process and the chosen successors close to the vest.

Why do organizations closely guard their succession plans? Several surveys cited in an article on Human Resources Executive Online indicate that the reasons are often based on internal forces as much as external ones.

So the reasoning behind the lack of succession planning is complicated. An article from HRE Online discusses a variety of rationales, including lack of transparency. These exist in companies of all sizes and at all levels, not just the C-Suite. The “secrecy” may be attributed to:

  • Business competition and not wanting external competitors to know their plans.
  • There may not be an actual succession plan.
  • They fear those not on the list of candidates may become disengaged and disgruntled.
  • Fear that another division in the company may poach the designated successor for its team.
  • Circumstances may change affecting strategy and who is best to implement it.
  • Top leaders may want to retain the flexibility to change the list of candidates.

Organizations grapple with not only whether or not to make the process transparent, but also if they should let the high potential candidates know they are being considered. The risk of telling them is they may get to feel entitled and others may feel disenfranchised and that they are not getting development attention. Whether or not the candidates are told of their status, the criteria for choosing successors should be specific, performance-based and widely communicated throughout the organization.

Phyllis Weiss Haserot     www.pdcounsel.com



Good news for the younger generation? Does this explain high salaries large firms pay to inexperienced law school grads?

As reported by the Wall Street Journal (7.25.12) a study by Stanford and Harvard scholars that consisted of 8 experiments with people in a wide variety of settings found they get more excited about individuals with promise and potential than they do about those with an actual proven performance record. Further, people are more willing to hire and pay more for the individuals with high potential.

The researchers could only speculate as to why this is so, but the findings were consistent.

Is uncertainty more appealing, the gamble that the high potential individual will achieve greatness? What do you think?


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