HR Management & Compliance

Q&A: Guiding Coaching with Generational Understanding

Part of having a successful organization requires a healthy coaching environment. There are many factors that go into creating a successful coaching program, including generational factors.


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We recently discussed the issue with Bill Bennet, CEO of InsideOut Development.

HR Daily Advisor: How scientific are your guidelines for coaching various generations? Are the results dependable and repeatable?

Bennet: These guidelines are founded in a few areas of discovery: longtime industry research, a proprietary InsideOut Development survey, and years of hands-on work with Fortune 500 companies to instill coaching practices for all employees. InsideOut Development has been studying intergenerational workplace dynamics not only to offer our customers relevant and current best practices in coaching but also for a survey we conducted early this spring on Generation Z (Gen Z) workers and their workplace expectations.

From this survey of 1,000 Gen Z workers, we learned that they expect managers to lead by coaching and would leave a company if their boss managed through fear. We also found that Gen Zs are looking for quick and regular promotions, which means managers should watch for ways to advance their Gen Z employees in responsibility and accountability—not necessarily in earnings—to help foster Gen Zs’ ambitions.

In addition, many of these guidelines have come through years of experience working with our customers and analyzing feedback. For instance, at a Fortune 500 technology company, we found that if you have a manager who struggles to coach, help by educating his or her staff on the principles of good coaching. When those staff knew what to look for in their 1:1s, we found it encouraging to see that rather than acting critically toward their manager, those employees encouraged and reminded their manager to stick to the coaching principles they had been taught. That realization expanded our thinking to account for the importance of educating not just coaches but also those being coached.

HR Daily Advisor: To what degree should someone developing a coaching program hedge their assumptions about specific needs of a generation?

Bennet: That’s a great question. For managers working with 10, 20, or even 50 people on their team, it can be overwhelming for them to hear that every coaching interaction should be catered to a specific generation. We consider the best communication approach to be one that empowers every employee at every level to use the knowledge he or she already has to perform at a higher level. We see this when a manager approaches his or her employee and asks probing questions like, “What’s working? Where are you getting stuck? What might you do differently next time?” This allows the employee to learn entirely on his or her own. These questions are cross-generational and empower anyone at any age.

However, what we’re hoping to achieve by providing these guidelines for generations is to give every worker—be that the CEO, manager, or new intern—a clearer perspective of how to effectively interact with different generations and tap into their strengths.

HR Daily Advisor: A lot of your generational base guidance is focused on Fortune 500 companies. How well does that translate into small to midsize businesses, if at all?

Bennet: Although Fortune 500 companies have established more rigorous coaching programs and management systems, they do provide an extremely large sample, which helps us to set a standard for workers’ expectations and coaching best practices. However, every company, large or small, can and should take ownership from the top down to create a culture of coaching. According to the Human Capital Institute, organizations with strong coaching cultures report revenue growth well above their industry peer group (51% compared with only 38%) and significantly higher engagement (62% compared with 50%).

We’d expect that goes the same for small to midsize businesses.

HR Daily Advisor: Is there some guidance that works well for every generation?

Bennet: es. Choose coaching over managing, which empowers and leads your workers to follow their own best advice—not yours. This applies to any generation.

What changes are the delivery and the outcome you might expect. For instance, we’ve found that Baby Boomers prefer face-to-face communication, while Gen Xers prefer e-mail, Millennials are apt to use technology (messaging apps, chat, etc.), and Gen Zs prefer a blend of selective technology and face-to-face. Choose the right communication channel when coaching each generation.

HR Daily Advisor: What is your most surprising finding?

Bennet: What I find most interesting, and what I think actually solidifies my point that coaching practices are cross-generational, is that every age group is asking for two things but in different ways: freedom and feedback.

Baby Boomers want open-ended questions that honor their solutions plus frequent follow-ups. Generation Xers expect the freedom to problem-solve and enjoy flexible schedules, along with the needed feedback to continue exploring new growth. Millennials appreciate brief but direct feedback while recognizing and supporting their desires to make a difference. And lastly, Generation Zs appreciate opportunities to be entrepreneurial and creative while still getting consistent, encouraging feedback.

HR Daily Advisor: What would be the most important coaching takeaway for each generation?

Bennet: It would be to see the value in what each generation brings to the table. Seventy-five percent of managers agree that managing different generations is difficult, but much of that struggle can be eliminated by shifting your mind-set: It doesn’t have to be difficult; it can be exciting! Working with so many cultures, backgrounds, age groups, and habits means more ways for success. When managers choose to value this diversity, address it correctly, and channel it, it’s a win-win for the coach, the coachee, and the entire workforce.

Bill’s guidelines for coaching generations:

For Baby Boomers:

  • Communicate face-to-face when possible.
  • Become friends.
  • Utilize body language.
  • Ask open-ended questions; honor their solutions.
  • Follow up but don’t micromanage.
  • Recognition = ignition.

For Generation Xers:

  • Opt for e-mail.
  • Honor flex schedules.
  • Aim to be “hands off”; let them problem-solve.
  • Offer variety and stimulation.
  • Allow them to get in, get things done, and then get moving.

For Millennials:

  • Tech rules when it comes to communication.
  • Go “hands on” for guidance.
  • Leverage the team.
  • Create unique paths for project execution.
  • Challenge their personal best.
  • Keep it brief but direct.
  • Support their desire to make a difference.

For Gen Zs:

  • Check your tech; keep it up to date.
  • Give frequent feedback.
  • Play toward their competitive spirits.
  • Motivate with positivity—never fear.
  • Enable opportunities for entrepreneurial creativity.
  • Teach them management skills.
  • Give encouragement through coaching.

Bill Bennett is a seasoned executive with more than 30 years of leadership experience, including 15 years in the training industry. As the former division president of FranklinCovey, he was responsible for all FranklinCovey operations worldwide for the Organizational Solutions Business Unit. Bennett began his career at IBM and spent 15 years with the company in a variety of management roles. He currently serves as CEO of InsideOut Development, a revolutionary coaching company that helps leaders hold the conversations that drive real results. Learn more at