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?


Five Years Ago…

Five years ago, I started this blog. I launched it in May 2014 while I was visiting the Kloster Arenberg, a convent outside of Frankfurt, Germany. I was then—and continue to be—a junkie for solitary, spiritual retreats. At the time, nothing sounded better than a quiet weekend amongst nuns. Between walks in the woods, visits to the stations of the cross, and trips to the sauna, I managed to write my first post—all 518 words of it.

In that first entry, “The Courage to Begin,” I expressed anxiety that my writing would not be good enough, and that posts shared on the web would be hauntingly permanent. But more than either of those fears, I feared the judgment of others. I wrote, “There’s vulnerability in expressing myself authentically… What if you think I’m silly, stupid, or too much of a hippie? What if you think I’m too pragmatic, too intellectual, or not intuitive enough?” While I was theoretically bought in on authenticity, I dreaded its ramifications both online and in real life.

Yet, over the last five years and seventy-five posts, I continued to put myself out there. With each post, I learned more about myself. With each post, I came to care less about the opinions of others. Just as important, with each post, I came to understand more about what mattered to me. As I moved away from worrying about approval, I focused more and more on my mission: to give a clearer view to life and how to live it meaningfully. Now, I have the courage not only to publish my work online, but also to share the collective wisdom of The Intentional in my second book, The Intentional Life: Reflections from Conscious Living, which publishes later this week.

intentional-life-ebook_frontThe element of The Intentional Life that I’m most proud of is its authenticity. While the topic of the book is living intentionally, the content could not be more personal. It includes reflections on major life events (e.g., engagement, marriage, childbirth) and mundane, everyday life (e.g., parenting, cooking, working). It shows my weaknesses, fears, and failings. And, if it has been successful, it gives a better view into what it looks like to live intentionally and calls you to reflect more on your own life.

So happy birthday, The Intentional. I am meaningfully different than I was five years ago when we started this journey. Thank you for providing an incredible platform for my on-going development – and the inspiration for my next big turn as an author.

The Intentional Life is live this week!
Order the paperback here.
Order the Kindle version here.
And, if you prefer to hear my voice while you’re out and about, wait for the audiobook release shortly!


Love It And Let It Go

book stackSince holding the first printed copies of my book, Indispensable, in my hand, the idea that it is published has become increasingly real. Surprisingly, it also became temporarily disconcerting.

My first reaction to receiving my book was amusement. It existed in so many electronic versions over time, and the publication process was so long. Suddenly, I thought, all that effort came down to this little book? That’s all? I mean, I liked the cover, but wasn’t it a little thin?

Nonetheless, it was fun to hold and even more enjoyable to see others turn it over in their hands, feel the cover, and casually flip through the pages (like one does with a real book). We chatted about the design, the paper stock, and all the other little superficialities of it.

But then, I saw for the first time in my life, someone actually sit down to read it. She sat across my office just out of shouting distance. This first witnessed reader started by flipping through casually, but then paused as something caught her eye. Oh dear God, I thought, someone is actually reading my book! Instead of feeling excited, I was suddenly horrified. Though I knew it all along, it was as if I didn’t realize until that point: People are actually going to read this thing.

I wanted to sit by her side. I wanted to answer her questions and clear up where things were ambiguous. I wanted to understand her feedback and make changes where things were insufficient. In short, I wanted to have a conversation about the ideas and their evolution.

But that’s not what books are meant to do.

Books put your thoughts out into the world through monologue, not dialogue. There is no back-and-forth. You can’t defend your thinking. You can’t learn from others’ experiences and evolve what you originally wrote.

For so long, the book was a singular manuscript in my hands. I had complete control over it. I could change words, phrases, or sentences. I could rearrange or rewrite entire concepts. The book was mine.

Indispensable_FrontBut now, there are hundreds of published copies owned by others instead of that one manuscript controlled by me. Beyond what I originally put on the page, I have no ability to inform the reader’s experience. Though in retrospect, the release of control happened incrementally through the course of copy edits, proofreads, and publication, it felt to me like it happened all at once.

And so, this is my chance to let go of the book. It’s not mine anymore; it’s yours. My writer friend, Jess, reminded me that this is common in the process of writing — and even explicit in the process of some writers’ groups: you are not allowed to speak about your own piece.

Like so many things in life, I love it and let it go. Thank you all for receiving it.


Indispensable: How to Succeed at Your First Job and Beyond 
is available for purchases here on Amazon.

What I Learned In The Ten Years It Took To Publish My First Book

I wrote my first version of Indispensable nearly ten years ago, over the early part of 2008.  Later that year, as the publishing industry struggled with the birth of eBooks, the economy collapsed, and my life moved forward, the goal of publishing it shifted into the background.  I largely put the manuscript down and didn’t touch it for years.

Now, it’s ten years later and my book is due to be published on June 26th.  The process of resurrecting, revisiting, and revising the book has been insightful.  More than anything else, the manuscript has served as a point of reflection of who I was then and who I am now.  As I set to work on revisions, I found myself having visceral reactions to the content. The tone of some sections made me cringe.  How could I be so rude, so flippant, or so ignorant?  On the other hand, some sections felt like old friends briefly forgotten.  How wise I used to be!  If I had only remembered that advice and applied it myself since writing it!  Over the past decade, I’ve learned and grown.  And the world has evolved around me.  My manuscript – from its previous incarnation and its current revisions – has been a lens through which to see all that change more clearly.

On the whole, I’ve noticed two major dimensions along which I’ve changed the most.  First, my understanding of diversity, inclusion, and privilege has expanded significantly.  In the revisions, I rotate the gender of the managers and employees chapter by chapter.  Similarly, I intentionally included a wide variety of names to be ethnically-inclusive; it’s no longer just a book about Bobs and Rachels.  But, perhaps most notably, I rewrote the entire segment on dressing at work to be comprehensive of a more fluid range of gender expressions – and to acknowledge how precious physical expression can be to people.  The passages that used to read as “just quiet down and wear whatever you need to wear to fit in” have a more nuanced tone, one suggesting that you make a conscious choice about what you wear and own the repercussions of how others may interpret that as reflective of your professional competence.

That brings me to the second shift in my approach; not just in the realm of physical presentation, but more broadly, my overarching approach became much less proscriptive and more fungible. I wrote the initial book as the essential advice you need to succeed in your first job and beyond.  The tone conveyed that this this advice was important and that the reader should carefully listen, learn, and apply each suggestion.  I positioned it as a universal formula for success.  Now, I’ve softened that approach.  I’m wise enough to know that even if some abstracted advice is broadly useful, people and situations are different. I present the book as full of useful strategies, but ones which should be considered, adapted, and applied with judgment. I focus more on the journey, the learning, and the development into your authentic self at work. Ultimately, I put the reader more in the position of power and conscious choice over their path rather than in the position of receiving wisdom from on high.

Now, Indispensable is in the final rounds of copy editing and proofreading.  From a content perspective, this book, which was ten years in the making, is suddenly out of my hands.  And I find myself looking both backwards and forwards.  Looking forward, if I am living well, won’t I learn as much over the next decade as I did over the last?  It is scary to think that the manuscript is fixed and I won’t be able to evolve it over time – as I and the world evolve in parallel. I have to believe that I’ll look back on Indispensable in another ten years and think “Wow, I missed so much.”

And so, I’m publishing something which feels not like a universal decree, but instead, a stake in the ground. But maybe that’s okay.  Maybe, since this version of the book will be fixed, it will provide a similar view into my psychology today – and I’ll be able to see the differences between now and then – and the growth that has occurred – all the more clearly.

For more on the book, buy on Amazon.

ten years graphic