Why Every Generation Needs Leadership Coaching

The following is an executive summary for our latest white paper, Leadership Development for a Multigenerational Workforce. To download the full white paper, click here.

There are now five generations in the workforce, and a one-size-fits-all approach to leadership development simply won’t work. Each generation has its own world view, values, and preferred communication and learning styles. The pandemic, the switch to remote and hybrid work, and The Great Resignation have made their differences — and in many cases, similarities — even more evident. These unprecedented challenges have made leadership development more critical, and more complex, than ever.

Understanding the Generations

Managing different attitudes and expectations has always been challenging, but effective leadership development must now consider each of the five generation’s preferences and values. Understanding each generation provides the information talent leaders need to properly identify strengths and blindspots from which to develop leadership capabilities for today and tomorrow. 

Traditionalists (born 1928-1945) are dependable workers, straightforward, and tactful. They respect rules, authority and a hierarchical work organization. They value seniority and job titles and prefer to communicate with personal touches and handwritten notes instead of an email. They are loyal to their organizations. Not many of this generation remain in the workforce, but to retain and manage those who do, employers should provide satisfying work and offer them opportunities to contribute. 

Baby Boomers (born 1946-1964) are optimistic, hard-working, and team-oriented. They have a great sense of duty but are not afraid to challenge authority. They value flat, more democratic organizations and prefer to communicate in whatever way is most efficient, including phone calls and face-to-face meetings. They are loyal to their teams. To retain and manage this generation, employers should articulate specific goals and deadlines, place them in mentor roles, and offer leadership coaching.

Generation Xers (born 1965-1980) are independent, flexible, informal, and skeptical. They respect change and see it as an opportunity, not a threat. They value diversity and work-life balance, and prefer to communicate in whatever way is the most efficient, including phone calls and face-to-face meetings. They are loyal to their manager and their own personal-professional interests. To retain and manage this generation, employers should be open to their suggestions, respect the skills they bring to the table, and offer leadership coaching to develop their professional interests.

Millennials (born 1981-1996) seek order in their world and meaning in their work. They respect autonomy, meaningful work, and fluid work styles. They value flexibility, challenges, growth, and development and prefer to communicate through IMs, texts, and email. They are loyal to their colleagues. To retain and manage this generation, employers should provide plenty of professional development opportunities, leadership coaching, and measure performance by results, not desk time.

Generation Zers (born 1997-2012) are global, entrepreneurial, and progressive. They respect individuality and creativity. They value diversity and personalization and place lower value on salary than other generations. Their preferred communication style is face-to-face or by email and they are loyal to the work experience and their own values. To retain and manage this generation, employers should offer plenty of development opportunities, leadership coaching, and even stress management programs — but not necessarily in traditional classroom settings.

Generational Involvement in The Great Resignation

When building a leadership development strategy, it’s important to understand the generations as a whole, as well as their individual reactions to current workforce trends. When the COVID-19 pandemic closed many workplaces in March 2020, many employees began to work remotely. Now workers in all generations agree that they’re happy with this shift. In fact, a 2021 survey by software company GoodHire asked employees from each generation if they were happier because of remote work. More than a third (37 percent) of Baby Boomers said they were. Some 58 percent of Generation X workers said they were happier because of remote work, 68 percent of Millennials agreed, as did half of Generation Z. 

However, with this shift to remote work, leaders face a brand new set of challenges. Some of these include, finding new ways to replicate face-to-face feedback sessions and impromptu teachable moments, handling productivity concerns, and learning how to help employees balance work and life. But working from home isn’t the only new issue that leaders are managing as the pandemic rolls on, and it’s more important than ever to mitigate these leadership development challenges.

According to the Bureau of Labor Statistics, a record 4.5 million U.S. workers left their jobs in November 2021 — breaking records set in August (4.3 million) and July (4 million). This trend, known as The Great Resignation, is affecting workers of all ages. Survey results from software company Goodhire found that Generation X, Millennials, and Generation Z who recently left their jobs cited their boss as the top reason for their departure. This insight illuminates a critical issue that, if solved, could break a critical part in the cycle of lost talent.

Supporting development of key soft skills like self-awareness, communication, empathy, emotional intelligence, problem solving, collaboration, and conflict resolution are the foundation of effective leadership. These skills are not only eminently suited to leadership coaching, once consistently in practice they help to build greater job satisfaction for leaders and their direct reports.

Leadership Coaching Solutions that Scale

Leadership coaching enables unbiased thinking and imparts the valuable tactics needed to change behavior so that leaders at all organizational levels, in all generations, can manage their direct reports more effectively. Leadership development can also be an essential talent retention tool, especially when it is not reserved solely for senior leaders. Managers and employees of all kinds should be counted as leaders: They lead conversations, projects, schedules, and enable cross departmental collaboration. In fact, reserving leadership development only for those in management roles can lead to high potential employees joining the numbers of The Great Resignation.

The youngest generation, in particular, wants a personalization approach to their development. According to “Generation Z vs. the Workplace,” a 2021 study from HR Future, 71 percent of Generation Zers responded that when it comes to which development opportunities they value, they desire the ability to work with coaches and mentors. This is valuable information for organizations’ leadership development planning, but managing this level of 1:1 support can be a heavy administrative burden.

Leveraging technology in leadership coaching is essential to support and scale personalized development outside of the traditional, in-person classroom. In a 2021 case study on software company UserTesting, Sounding Board found that:

  • An automated coach matching model resulted in a 97 percent satisfaction rate
  • Coachees reported a 91 percent average coach satisfaction rating after their first session 
  • When asked if their coaching experience was off to a good start 93 percent of coachees agreed 
  • 91 percent of coachees agreed that their coach was a good match for them
  • 86 percent said they had a good understanding of how coaching could work for them

Tech-enabled leadership coaching does more than just engage younger generations, it provides both successful personalization in coach-matching while alleviating the administrative burdens associated with management and measurement.

Next Steps

The presence of five generations in the workplace creates real challenges for employers, but understanding where each generation comes from, their world views, work preferences, and loyalty can help employers design effective, personalized leadership development programs, including leadership coaching. It’s important to understand generational world views and build leadership development programs and experiences based on what generations have in common. 

Our latest white paper, “Leadership Development for a Multigenerational Workforce,” explores:

  • Each generation and the experiences that shaped its members’ world view. 
  • The generations’ relationships to authority, their work expectations, and work-style preferences, and how talent leaders can use this knowledge to develop leadership coaching programs to nurture leaders of all ages. 
  • How remote and hybrid workplaces have changed where and how employees from each generation prefer to work, and what this means for talent development initiatives. 
  • Who is leading The Great Resignation, and how organizations can use leadership coaching to attract, retain, and more effectively manage a multigenerational workforce.


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Lori Mazan is the Co-Founder and Chief Coaching Officer of Sounding Board, the preeminent global leadership development enterprise platform changing the face of leadership development through innovative technology for leaders at all levels of an organization. Lori is a seasoned executive coach who has guided hundreds of corporate executives through 1:1 coaching focused on business outcomes and developing critical leadership skills. Client companies advanced by Lori’s expertise include Fortune titans such as Chevron and Sprint as well as high growth and public companies like Intellikine, and Tapjoy, plus 10XGenomics, which became a public company in 2019 while top executives worked with Lori and the Sounding Board team.
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