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Gen Y Leaders, Boomer Coach

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[This article was originally published in The International Journal of Coaching in Organizations, 2008, Issue #3. It is reprinted here with the kind permission of John Lazar, co-founder and editor of IJCO. The complete third issue of IJCO in 2008 can be found by clicking on the Download button below.]

Sandy Smith explores the impact of generational differences on the coaching process, offering insight into the challenges and developmental opportunities for the coach. In this paper, Smith offers insight into a new style of work environment and how a unique generation of new leaders is challenging executive coaches to re-examine their beliefs, expectations and basic coaching paradigms. Aligning with the developmental focus of this journal issue, Smith concentrates on the devel- opment of these leaders within the context of developing companies. Smith identifies the opportunities she has experienced regarding her own development that she believes may have wider applicability for coaches working in this domain.

I am a 50-something executive coach with thirty years experience working with technology companies, fifteen of those years as an executive coach. Today, I work with senior leaders in a variety of organizational contexts and industries. It has been my observation that the maturity of the organization and the experience of the leader impact virtually every aspect of the coaching engagement. Companies with longer histories are more predictable and slower to change.

The more seasoned leader can also be more resistant to change. Many times a mature leader will attribute success to certain behaviors and may be more reluctant to try new things. Marshall Goldsmith (2007) addresses this issue, encouraging the leader to determine whether a leader was successful because of, or in spite of, a given behavior. Younger leaders have fewer solidified leadership patterns because they have less experience.

Usually the top leader has the most influence on the company. The Gen Y CEOs are the founders who have been able to negotiate that role during start-up funding and are therefore able to form the company to their own ideals. These Gen Y CEOs differ greatly from their older and more established counterparts – the Boomers and even Gen X’ers. They take risks, are more optimistic innovators and are comfortable in what others might experience as chaos. They are hiring their contemporaries, trans- forming the workplace and achieving success by doing it their way.


The early stage company is distinctly different when compared with a mature company. The first task of a startup is proof of concept and later proof of viability (as a business model). This is typically an iterative process with many factors being tested in parallel and lots of false starts. It can seem quite chaotic. Through this repetitive process, successful tactics get reinforced and those that fail to produce results are abandoned.

Today’s Internet companies, termed Web 2.0 companies, use an experimental model where features are launched and user reaction determines their fate (Tapscott, 2008; Lacey, 2008). This model capitalizes on the young leaders’ comfort with change and, because it continues throughout the company’s evolution, it may extend the young leader’s viability as the company grows. Kurtzman (2005) observes, that while startups are not as complex as established companies with multiple business units, divisional structures, and hundreds or even thousands of employees, they are often more complicated to run because large companies adjust their strategy annually and structure every other year, the startup is a work in progress with every element of the company in play on a real-time basis.

He further notes that the leadership skills necessary in a startup differ quite dramatically from those needed in a mature company—given that speed, not perfection, is the hallmark of the startup. It is these characteristics which make the startup an ideal environment for Gen Y’ers.

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