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Despite the acknowledgement by leaders and human resource chiefs that succession planning is a top concern and business imperative, much too little is being done about it, especially now as more Baby Boomers inch toward potential retirement and the recovering economy leads to more mobility of talent. There are several reasons, including inertia and wishful thinking that defections to other employers, deaths or illnesses, early retirements or dissatisfaction won’t happen – at least without sufficient notice. Another reason is fear of rocking the boat and the internal politics likely to arise as the succession planning process proceeds. This can be uncomfortable, disruptive and demoralizing to key players if a carefully considered process isn’t instituted.

From our experience, the important obstacles talked about less frequently are lack of confidence in the potential leaders coming up behind the incumbents – as well as leaders, particularly founders, who are too reluctant to “let go.” This article focuses on finding and preparing successors internally.

Based on our observations with clients and coaching assignments, the roots of expressed lack of confidence in naturally assumed successors may have a number of explanations, often distinct from insufficient professional competence including:

  • Personal chemistry between incumbent and potential successor, despite clients or other stakeholder’s satisfaction.
  • Work style or philosophy – Incumbent only feeling comfortable with a clone (often not the best choice).
  • Incumbent wanting to keep the potential successor with clipped wings to continue in a support role to him or her.

Factors around “like” and “trust” as well as discomfort with loss of authority and professional identity are often roadblocks. Here are some approaches to use if the potential successor needs more seasoning or the primary obstacle is an incumbent's inflexible mindset or largely emotional issues.

5 Steps to Address Lack of Confidence in Potential Successors

1 -             Surface what the actual issues are, avoiding stereotyping. Consider conducting workshops and individual coaching on understanding, bridging, and capitalizing on generational differences. Focus not only on the attributes but rather what’s behind them, implications and how to use related strengths.

2 -            Use training in personal behavioral style to bridge gaps (using assessment tools such as DiSC or MBTI). Find commonalities and how to resolve differences 

3 -            Reward leaders and managers for training, coaching and mentoring, and if needed, teach them how to perform in these roles so the professional development that will instill more confidence will occur. Adjust the reward system to a results and merit basis rather than just time expended.

4 -            Give younger professionals, managers and supervisors their own particular responsibilities (their own piece of the action) to prove themselves, have their own niche and the opportunity to shine as they develop their careers.

5 -            Identify those in power that just won’t “let go” and devise strategies to deal with them. In these circumstances, it’s not about the successor.

©  Phyllis Weiss Haserot     www.pdcounsel.com

 Please send your thoughts to pwhaserot@pdcounsel.com or comment on the Cross-Generational Conversation group on LinkedIn.



DON’T FOCUS ON ONE GENERATION: The Business Case for Multi-GENgagement

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I’ll be blunt: Building your talent strategy primarily around one generation is a big mistake!

As the new and “radical” kids on the block, the large Gen Y/Millennial cohort has captured the attention of the ever-growing contingent of media, both social and traditional. Much of the coverage is misleading. One of the aims in my work is to provide context and perspective to the generational mix we have today and going forward and emphasize the necessity for more cross-generational conversation and collaboration by making the business case for doing so.

It is a mistake to go overboard focusing on Millennials (also known as Gen Ys) and ignore the needs and contributions of the still vital Boomers and Gen Xers. And beginning to learn about the Gen Zers soon to fill the pipeline for future planning is also very important. We already have evidence that they are different from the Millennials in significant ways. Laser-focusing resources and work processes on what Millennials want and need will leave you unprepared for other generations’ different views and behaviors and how to use them together to competitive advantage.

So, firms need to take a cross-generational approach – a multi-generational initiative that proves they have the flexibility to shift with agility as warranted to new perspectives and approaches without causing inter-generational resentments and exits from the organization.

Why? To avoid lurching from one direction to another and create an integrated, sustainable culture and business model.

Once explained, the business case for cross-generational strategy and collaboration is clear and compelling. It’s all about producing a continuous flow of revenue, avoiding loss of clients and turnover costs by maximizing the firm’s ability to:

  • Attract and retain clients and business alliances of different generations;
  • Attract and retain new talent of different generations to minimize undesirable turnover and its considerable dollar and time costs;
  • Transfer knowledge among the generations so skills and relationships stay at the firm;
  • Achieve effective succession planning for all critical roles to sustain client relationships; and
  • Avoid discrimination litigation and damage to reputation.

The challenge is to get members of all the generations in an organization into the same room with open minds. Let them get to know and understand each other and commit to ongoing dialogue. A 5% increase in employee engagement will generate an increase of 3% in revenue growth in the following year, according to a recent Aon Hewitt study. Isn’t that well worth the time and effort?

 pwhaserot@pdcounsel.com      www.pdcounsel.com




Most of us would like to feel we have made a difference.

Working on a client engagement that included the challenges of transitioning planning for partners in their early 60s, I developed a series of “legacy exercises” focused on work legacy. Ideally everyone by age 50 should be thinking about legacy. 

Starting earlier is even better, as it helps to create a career vision of meaningful work. Perhaps sadly, often busy people tend not to think about legacy till later when they must try to make up for lost time. Legacy is about more than end of life and who to leave money to. It is about work, family, friends, causes, mentoring – what one passes on to the next generations and peers in as broad a sense as you would like to think about it. Primarily it is about values and about continual learning for you and others.

Here are some questions you might start thinking about as an individual or a team.

  • What do you want to be remembered for wherever you are working now? By your clients? by your colleagues? In the context or your role or roles in the organization?
  • What do you want to be remembered for in your community?
  • What would you like to pass on to the next generations – people you work with or know in other capacities?
  • What do you want to be remembered for in general as a person?
  • What can you start to do now or change now to be able to achieve that legacy?

Building legacy can be one of the most fulfilling things you can do in your life. And not only that, it outlives you and, in a way, keeps you present when you are no longer there.

Contact me to learn about our Legacy-Makers Mastermind groups and to receive a free list of “Tips for Building a Legacy at Work.”

Phyllis Weiss Haserot   www.pdcounsel.com



I was asked why, with the coming leadership gap as Baby Boomers gradually “retire,” younger generations don’t seek top positions. Really, they don’t? Here are some thoughts.

First, several surveys in the last year have indicated that there are major gaps in what employers think they need and how they are evaluating candidates. The surveys often contradict each other, so it’s hard to know what the real deal is. Also, young workers think employers are not making use of their talents to a significant degree, and they think they could be much more valuable.

Succession planning is so challenging because few organizations have been taking serious steps to do it at various levels and consider potential leaders who are not similar to the current and former leaders. Generation X, the natural place to look for leadership now by age and experience, has been pretty much overlooked in many ways in the marketplace in favor of attention to the much larger and vocal but younger Gen Y/Millennials.


For those who were not yet working or have forgotten, when Gen Xers were the youngest generation at work, many said they didn’t want the top spots and were labeled “slackers.” Since then they have been working hard and aspire to leadership. They have been frustrated suffering with the “Prince Charles syndrome,” waiting for the Boomers to finally hand over the reins. Gen X is ready.


My experience and research suggests that Gen Y/Millennials do want to lead and occupy top positions. However, many Millennials are turned off by the cultures typically find in organizations. What they say in every survey is they want training, opportunity to advance, do meaningful work (doesn’t everyone?) and to have an impact. They also want to change the structure of how work is done to fit today’s requirements and capitalize on technological resources they feel comfortable with. If they get heard and get responsibility to make change, like their Boomer parents, they will stay and step up to the plate to lead. Otherwise they are motivated to move on.

Meanwhile the leadership gap in the near future will be ably filled by Gen Xers with the support of Baby Boomers, if both of those generations are treated respectfully and made to feel continually valued for what they can contribute. It’s not so complicated. If anyone of any generation is disrespected, made to feel needlessly obsolete and not fitting a preconceived mold, they are likely to be disengaged or uncooperative or less productive than either they or the employer wants them to be. 

Phyllis Weiss Haserot     www.pdcounsel.com




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

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