How Life Experiences Make You a Better Leader


Life Experiences and Leadership
Your life experiences make you a better leader.

One of my favorite training sessions this past year was called “Why Should Anyone Be Led By You?”

One of our exercises was to figure out our unique differentiators by looking at our life experiences.

In other words, what unique skills or experiences do we bring to the table, that are relevant for this particular situation?

Everybody Has a Story

Everybody has a story–hopes, dreams, wins, losses, and lessons learned.  We write our stories a page at a time.

Ultimately, it’s not how the stories end, but what we carry forward that matters.

To Be a Better Leader, Find Your Unique Skills and Experiences

By looking to the past, you can find your unique skills in the present.  We used the following categories to identify and reflect on experiences:

  • Accomplishments and Disappointments
  • Activities / Sports
  • Career / Personal Life
  • Education / Schooling
  • Family
  • Friendships
  • Volunteer

By looking back and reflecting on stories, we gained insight into why we lead the way we do and what really shaped us.

The big idea was that to inspire, arouse, excite, or motivate people, you need to show them who you are, what you stand for, what you can and cannot do.  It’s about sharing yourself with skill.

To Be a Better Leader, Share Stories to Share Yourself with Skill

While I have some interesting experiences in the “Activities / Sports” bucket,  such as Kickboxing and Bulgarian workout routines, I shared some of my “Career” experiences:

  • Writing books.  Something unique that I do at Microsoft is writing books.  Given that I’ve written several books, you might say it’s more like “book building.”  I really  think of it as information engineering.  These aren’t just ordinary technical books.  These books change how people do things and think about things in the software space.  They also get used for anything from competitive assessments to changing products and tools.  Working on the books led to filing 8 patents in the security and performance space.  It also led to influencing analysts and presenting at a variety of conferences and giving talks over the years.  Most significantly, my approach to building books is similar to building software.  In fact, I call it “Agile Guidance.”   One of my favorite practices is using Test-Driven Design (TDD) for writing prescriptive guidance.  Prescriptive guidance is our pet name for the guides we write on our patterns & practices team.
  • Leading project teams.  The unique experience I have here is pitching projects, building teams from scratch and driving projects from cradle to grave.  I’ve had the experience of running distributed teams (US, India, Argentina, UK … etc.), managing million dollar budgets, working with some of the best folks in the industry, and changing the game for some big challenges.  I’ve regularly spun teams up and down over the past several years.  I’ve used Agile and Scrum long before they came into fashion.

I chose these particular examples because they differentiate me inside of Microsoft.  People write books, but not as part of their day job and not using software engineering techniques.

People lead project teams all the time, but not  usually the same scope or same budget or same project context.  Context and approach are the real distinctions.

Light Up Your Stories with Relevant Details

Once you have the heart of your stories, you can decorate them with detail.  Now, it’s one thing to say you have project management experience.

It’s another to light it up with a story.

The point is that the better you are at sharing relevant experiences that make you stand out, the more successful you will be as a leader.

People need to trust that you’re the right person for the job.  They also want to know you are human, flaws and all.  It’s your unique experiences that become your calling card when people are looking for someone to lead them.

Lead Yourself First

Whether you lead teams or lead others in some way shape or form, the key is to remember that you lead yourself first.

By looking at your own stories and experience you gain self-knowledge.

If you don’t like the way you lead yourself, start rewriting your stories today and be the self-leader you’d like yourself to be, one day at a time.

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Photo by lumaxart.


  1. Two books you have engineered have completely changed my professional life. The third recent one just keeps the trend taking me even higher. And I am just only one out of the huge crowd that appreciates your work. That is quite an accomplishment for you.

    I like the categories, I actually love such kind of guided self tests. Here it is.

    – Keeping 40 hours work week and hitting the numbers is a huge accomplishment for me.
    – Education system. From primary school all the way to the universities. It seems to me more for learning to cope with odds than learning academic stuff, which is viable skill too BTW. 🙂
    Activities / Sports
    – When I was doing judo as a teenager i met my first [and it seems like the only one until recently] mentor. My trainer was like a god for me. A symbol of fitness for body and soul.
    Career / Personal Life
    – I was combating MS HR so many times and failed, until I hit the sweet spot and got hired.
    Education / Schooling
    – “Never mix education w/your schooling” – who said that? ;). It strikes me how right he was by saying it!
    – ;). Time zone and ten thousand miles can never come between good friends…
    – Does publishing quality content on blog counts for volunteerism? On my professional blog i have published more than 200 posts and received over 50 private emails most of which are asks for tech help for most of which i had and answer followed by “thank you for your help!”. Does it count?

  2. Hi
    I liked how you suggested we find our unique skills and experiences
    by looking to the past…and then you shared some good ideas on how to categorize our life experiences.
    This is great! Thank you. 🙂
    Giovanna Garcia
    Imperfect Action is better than no Action

  3. Hi JD,

    Wow I didn’t know you were a published author. That’s so cool, especially while you have a full-time job. I like your way of differentiating yourself in the company.

    Telling stories does make a point come alive, and something I tell myself to do more often. Great post!

  4. When you use your strengths it makes work more fun and productive. We can all be good leaders when we apply our strengths to help the people in our lives. It takes a lot of practice, but like any skill the more we use it the better we get.

    I never knew you have published books. You should talk more about them. Can you buy them on Amazon or are they only for Microsoft?

  5. That is such a cool picture!

    I think if you’re going to lead a group of people you should also try never to show them any sign of fear. 😉

  6. @ Positively Present

    Thank you. You have a gift with stories and I bet you have a lot of interesting stories to share.

    @ Don Willits

    Thank you.

    @ Alik Levin

    Thank you. You have a lot of wins under your belt and many more ahead of you. You have the ability to see patterns and that will take you a long way in the architecture space. You also know the trade-offs of security and performance from first-hand experience and countless customers. That’s a major trump card.

    @ Giovanna

    Thank you. It really seems like hindsight is a great tool for foresight.

    @ Daphne

    Thank you.

    Ironically, my first book was actually to prove to my new group that I could do it.

    @ Karl

    Leading with your strengths is the key.

    Most of my books are on Amazon. I listed some in my About page. I don’t talk much about them because they’re technical guides, whereas this blog is more about life skills. I’ll have books on the non-tech side soon (at least I’m testing the path 😉

    What I might do though is share some of the book building and writing lessons that have helped me learn and organize complex information faster. It might be worth actually walking through a project from cradle-to-grave since it really is a unique process.

    @ Louisa

    There’s a lot to be said for confidence and vulnerability.

  7. Bulgarian workouts, eh? Sounds like they could be pretty intense? Abs and everything of steel??

    I like the confidence and vulnerability way of looking at things, I can certanly relate to that on stage.


    “Ultimately, it’s not how the stories end, but what we carry forward that matters.” I’m so glad you said that. Its really is all about the process, isn’t it?

    And a bit off topic, but not too far off because it has to do with business, risk and going for your best… have you watched that new reality show with Billy Mays? “Pitchmen?” I really recommend it!

  8. @ Jannie

    Yes, it’s all about the process. And it’s all about improving our process a little at a time, over the long run.

    I haven’t checked it out yet, but it sounds neat.

  9. Thanks for the great read, JD. I like the point about leading yuorself first. I am giving some thought as to how the sports and things I like to do translate over to leadership at work. The thing I love about leading in the mountains, for example, is that people’s “true personalities” come out — not always the case at work.

    Thanks for sparking my mind!

  10. @ Rick

    Thank you. I think you bring excellence and passion to work because of sports. It shows up. You make stuff happen and you hold yourself to a higher bar and I think that’s great.

  11. J.D., you mentioned a training session called “Why Should Anyone Be Lead By You?”. Was that a Microsoft internal course, or is it available publicly? One of my hats is “Trainer” and it sounds like an interesting approach, so I’d like to find out more.

    I definitely agree with you on the importance of story, and sharing yourself that way. For several years I taught a prep course for Microsoft Train the Trainer certification, and that was one of the key concepts I presented to the learners.

    “Start re-writing your stories today… one day at a time” is excellent advice.

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