Coaching Across the Generation Gap

First published in Coaching World in October 2019, published by the International Coach Federation.


Coaching across generations can be tricky. You may wonder: Who are these Millennials?  Who is Generation Z?  What are they like and what do they care about?  It can feel like, if only we could understand them, we would be able to meet them better where they are.

Similarly, you may wonder about the methods for best engaging them:  What are the unlocking questions for today’s youth?  Would they respond more to encouragement or challenge?  Do they yearn for embodiment, balance, stability, fulfillment, authenticity, or something else entirely?

However exhaustive the descriptions or guidance for intergenerational coaching might be, it will necessarily be of limited use. Expanding your capacity to coach the next generation is not about figuring out the tips and tricks. Instead, your ability to coach across generations is determined by your own inner preparation rather than by any external knowledge you might acquire.

Inner preparation is important because the challenges we face in coaching intergenerationally are largely the limitations that we, as coaches, bring to the table.  Our societies are engrained with patterns of how we treat those older than and younger than us.  Embedded power dynamics privilege age above youth along certain dimensions (e.g., wisdom) and youth above age in others (e.g., energy). On top of these broad patterns, we have our own individual experiences of aging, authority, wisdom, youth and even death. If we have not worked through these challenges, we bring them as baggage into our coaching relationships, often impeding our ability to be of service.

So, how to approach this work?  First, set aside some time for reflection.  Consider your relationships across age—both as the junior and as the senior—and look for how they affect your coaching relationships.  Spend time unpacking your relationship with youth, aging, authority and wisdom.  What did you hate about being younger?  What do you love about being older?  Inevitably, reflecting upon age brings up the bogeymen of our own mortality; face these, too. To help you get started on this process, I’ve included an approach for structured reflection below.

Ultimately, as with all coaching, it is only by doing our own inner work that we are able to be of service to others. Generational differences across coaches and clients are a call for us to break out of our patterned ways of acting. Awareness and reflection are the first steps.

Reflection Questions

The following questions are intended to unpack your thinking about generational differences.  Focus on the handful of prompts that feel most resonant to you in the “Expand and Understand” section. You need not answer every question; three to eight questions is sufficient.  Then move on to answer each of the questions in the ”Synthesize and Apply” section.  For maximum benefit, you may want to sit down in a quiet space, avoid distractions, and write your answers out longhand with pen and paper.

Expand and Understand

  • Views of Age and Youth
    • Older people have…
    • Older people lack…
    • Younger people have…
    • Younger people lack…
  • Generational Responsibilities
    • The future generations must…
    • The future generations cannot…
    • When it’s all said and done, I think the impact of my generation on the world will have been…
  • Personal Experience of Age
    • What I love about being my age is…
    • What I loved about being younger was…
    • What I’m excited about growing older is…
    • What I hate about being my age is…
    • What I hated about being younger was…
    • What I’m dreading about growing older is…
  • Past Experience of Intergenerational Relationships
    • When you were younger, how did the older generation treat you?
    • If this was not ideal, how would you have wanted to be treated?
    • When you were younger, who “coached” you (even if this was not formal coaching)? Who mentored you or gave you advice?
    • What worked well in those situations? What worked poorly?
  • Current Experience of Intergenerational Relationships
    • What relationships do you have now that have an age gap to who you might coach?
      • Mid-level manager to young employee?
      • Grandparent to adult grandchild?
      • Parent to child?
      • Boss to employee?
    • What patterns have you developed in those relationships?
  • Your Legacy
    • What do you have to give to future generations?
    • How do you want younger people to see you? To interact with you?
  • Associations with Related Values
    • What is your relationship with authority?
    • …With wisdom?
    • …With aging?
    • …With youth?
    • …With death?
  • Fears
    • When you think about youth, what scares you?
    • When you think about aging, what scares you?

Synthesize and Apply

  • What did you learn through your reflections? What is emerging as true?  What else are you curious about?
  • Where, if at all, are these mindsets and patterns of behavior showing up in your coaching?
  • What’s the impact of those? Alternatively, what might the impact be?
  • What do you want to do about it?


Keep it Simple, Smarty

I had lunch with a colleague this week during which we talked about her near-term plans and long-term aspirations over a bowl of bi bim bap. She reflected on options ranging from graduate school to life-long ambitions, from alternative career paths to renegotiating her relationship with her childhood pastimes. At the end of the discussion, as I munched on the leftover bowls of banchan, she paused, reflected for a moment, and remarked: “You ask really good questions.”

I? Ask good questions? That’s interesting, because I wasn’t trying to ask good questions.

There was a time when I tried to ask good questions. In fact, I’ve wanted to ask good questions most of my life. As far back as elementary school, I sought to ask the interesting, non-obvious question to the teacher, less because I wanted to know the answer and more because I hoped to signal just how advanced my comprehension was. “I understand graphing real and imaginary numbers on a two-by-two, but what if you add a third dimension?” I delighted in stumping the teacher and didn’t mind taking the class completely off-track.

This inclination continued in the working world. Asking the right “high-gain question” was celebrated as a great skill. If someone was evaluating many options, I might say “It seems like there are really two approaches here: A or B. Which seems most useful?” Similarly, if someone was trying to understand a situation, I might say “In my experience, it is always a matter of X or Y. Which is at stake?” My questions were crawling with clever frameworks and embedded advice. Intentionally or incidentally, I casually showcased how brilliant I could be while simultaneously seeming helpful. While my questions presumed to help the other person find their direction, let’s be honest: they were all about me.

As I’ve started to work on my ego (only partially successful to date), I’ve tried to shift to asking questions in the service of the other instead of for my own benefit.  This has prompted me to realize two things:

The smarter you try to be, the less useful you become, and

The most powerful questions are the most simple.

Everyone has heard the perennial advice to “ask open-ended questions.”   Beyond this, I propose adding the guidance: “ask simple questions.” It’s not about providing a maze of options, a clever trade-off, or a new framing. It’s not about leading people in the direction that you see unfolding. And it’s certainly not about receiving recognition for your endlessly clever perspective.

Instead, it’s about reducing to the simplest question in service of the individual:
“What do you want?”
“What’s important about that?”
“How do you feel?”
“What’s next?”

Though I can’t always get out of my own way, I am always most useful to others when I’m not trying to be clever.  In other words, keep it simple, smarty.

So, what now?