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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.





Currently overall about 70% of leaders and managers are male - mostly Baby Boomers and the older half of Gen X. The agitating about Millennials within organizations and in the media attracts a lot of attention, and most of the focus is on ways to 'fix' them or appease them rather than reconsider work practices, succession planning and knowledge transfer and the influence of compensation plans.

A Board Briefing from Richard Chaplin of Managing Partner in the UK on gender parity inspired me to create a checklist of recommended practices for an equally important and challenging issue: to guide decision-makers at all levels toward inclusiveness of all generations and development of younger leaders for a more profitable and stable workforce and a sustainable future.

Current and aspiring leaders have a pivotal role in implementing changes to achieve a more engaged and profitable work environment. Best practices involve the following changed approaches and positive actions:

  1. Monitor meetings closely for potential generational bias. Think about ways to ensure that people of all generations are being heard. Be aware and open to the likelihood that they might express themselves differently.
  2. Mentor and sponsor younger generations not only by providing advice but also by encouraging them to undertake developmental assignments.
  3. Make sure that you showcase young talent for their expertise and leadership skills.
  4. Watch your language! Monitor how you and others speak about and to all generations. Check which metaphors and adjectives are used and consider alternative language.
  5. Concerning hiring and promotion decisions, keep in mind that assumptions are not always correct - check yours and alert others to check theirs.
  6. Demonstrate support for associates, for instance, by attending group meetings, and taking responsibility for multi-generational inclusion.
  7. Talk about commitments from outside your work and how they will affect your work as well as how you handle time management. They seek guidance on balancing their work lives and finding opportunities to network and contribute to the greater good. This will be just as important to the next generation coming up.

Reserve a few minutes every day to reflect on the impact of intergenerational relations. Did you or others experience or notice any tension? What went well? What would you have done differently? How can you change things for the better for your firm and individual careers?  Please send your thoughts my way.

Phyllis Weiss Haserot   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






In the month of Love (Valentines Day) and Leadership (Presidents Day), I am making a pitch for breaking down silos and creating a coalition on inclusion and true opportunity.

A primary reason dealing with intergenerational challenges at work is so crucial is that not only do they directly affect bottom line revenues, but also they intersect with other diversity factors such as gender, race/ethnicity, sexual orientation (and much more) that organizations already admit have an impact on their market position, workforce hiring, retention and productivity. 

The big data folks and the politicians know this is true, and realize it is complex. And they are better at crunching the numbers and exhorting than marshalling coalitions to work constructively and productively for change.

I will continue my writing and speaking about breaking down the affinity silos and creating coalitions for inclusion and changing workplace structures in the future. I welcome anyone who is interested to come on board with me (pwhaserot@pdcounsel.com). We can achieve much more progress together.

Stay tuned, send your thoughts and comment here.

Phyllis Weiss Haserot    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


Today (July 4th) I watched the full, original, uncut version (3 hours long) of the 1972 film “1776” - a serious and funny musical film I have always loved. This time I found it more mesmerizing and powerful than ever. I was moved to tears in parts and so drawn into the wonderful dialogue that captured in a very astute and entertaining way the full array of characters who comprised the Congress that debated, attacked and insulted each other, displayed their humanity and in the end compromised to create and approve the Declaration of Independence.

Serious history and seriously entertaining and powerful on this day 

 P.S.  The age range of the representatives in the Congress was 32 to well into the 80s. (Jefferson was second to youngest, and Franklin was the oldest.) Talk about cross-generational conversation and diversity of thought!



For the last three years I have suggested topics on inter-generational relations at work for my externs and interns to write about, and I have published a selection of them on this blog. My extern in January 2014 was Danielle Kronenfeld, a junior at the Cornell University Industrial and Labor Relations School. One of the topics she chose to write about is what her generation desires in leaders. Below are my questions and Danielle’s responses.

 Phyllis:  What attributes are you and other Gen Y/Millennials looking for in leaders?

 Danielle: I think that Gen Yers are looking for our leaders to act as mentors. We are extremely eager to learn, so we want leaders who are willing to teach us and help us grow. More specifically, we want our leaders to be intelligent and to have respect for us.

 We are incredibly driven, more educated than previous generations, and probably a little bit too arrogant. This makes us believe that we have all of the solutions, despite our lack of real world experience. Of course, we do realize that we do not literally know how to solve every problem. However, our overall confidence makes it that much more important to us that our leaders have faith in our ideas and are willing to listen.

While conducting my summer internship search over the past semester, I spoke to many previous interns and recent graduates who had just started working full time. When I asked them about their favorite experience during their internship or since they started working, most of them told stories of when a senior manager invited them into his or her office to answer their questions or give them advice. Gen Yers are happiest when our leaders are willing to give us that kind of time and attention.

Phyllis: Do you think business leaders will be younger than in the past?

Danielle: Despite the fact that we like business leaders who are more experienced, I think that leaders will be younger than in the past. With the recent and continuingly rapid growth in technology, younger people are more knowledgeable and able to adapt to the most current trends.

Phyllis: What skills other than technological savvy will they have and/or need?

I think that adaptability is one of the most valuable qualities that a leader can have in today’s workplace, and one of the most distinguishing qualities that Gen Yers have mastered. Studies show that because we grew up during this time of rapid advancements, our generation is much less loyal than previous generations.

Whether it’s to our current routine in school or at work, our favorite shampoo brand, or our significant others, Millennials feels less attached to the status quo are more likely to switch to a different practice. Gen Yers are always looking for the best possible option, and are usually not afraid to leave something behind when a superior alternative comes along.

Phyllis:   To our readers: Please give us your comments. Agree or disagree? What attributes do you think leaders in a Gen Y-prevalent work world will have?  Will be needed?

Thanks for joining the conversation.

 Phyllis Weiss Haserot    www.pdcounsel.com


A recent DDI study, Driving Workplace Performance through High-Quality Conversations, found both front-line and senior leaders lack fundamental interaction skills and behaviors required to be effective leaders. The study report concludes that what’s missing “is the ability to facilitate effective conversations, something that should be mastered by every business leader as part of a core set of interaction skills in order to build relationships and get work done.” This is at least as true of senior leaders as those with less experience according to the study.

The need to learn the skill of conversation is a challenge to the fast-paced, just get it done, data-driven world we are living in. Even some technology thought leaders are sounding the alarm. We have been champions of cross-generational conversation as necessary for business productivity and profitability since it is essential for knowledge transfer, attracting and retaining both clients and employees and enabling work teams to achieve high performance.

 Organizations need to recognize that the skill of conversation is not typically part of business education, and they must require or provide training, especially as all generations increasingly communicate electronically and often neglect context.

 Please comment and share information on any organizations you know are providing this training in-house. If you would like to learn about Cross-Generational Conversation Day, contact us (pwhaserot@pdcounsel.com).

 Phyllis Weiss Haserot    www.pdcounsel.com


Part two follows a previous post about stories of some CEOs who were faced with the upside down reporting relationships early in their careers and happened upon a formula that became one of the pillars of their considerable business success.

In anticipation of the younger manager/older staff challenges, over the last five years I have written articles, done videos and webinars and conducted workshops and delivered talks on this topic as a component of professionalism, succession planning and cross-generational conversation.


Here are 7 more learnings we can take away from the two young manager success stories:

  • Senior managers were willing to take risks on these young new managers and thought they could do the job.
  • “Sink or swim” is a tough initiation for a leader or manager but a great learning experience and can build confidence and resilience.
  • Include. Don’t try to boss.
  • Build relationships through inclusion.
  • You aren’t expected to have all the answers. It’s better not to think you know better or you know everything.
  • Be confident enough to show some vulnerability. People will help you.
  • Respect breeds mutual respect.

Reminder to the older members of the team who might feel discomfort:

  • Keep focused on the common objective and the external or internal client or customer.
  • Collaboration will benefit all long-term.
  • Your mentoring and coaching can also be your reward.

Phyllis Weiss Haserot    www.pdcounsel.com

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