How I Think About My Career Growth (Think Big, Think Broadly, Think Beyond)



“It’s not what you achieve, it’s what you overcome. That’s what defines your career.” — Carlton Fisk

A few folks have asked me how I think about career development and personal growth.

So in a 20-minute sprint, I’m going to share what I’ve learned, and how I think about career and personal growth.

Hopefully, an idea or two might inspire how you think about and shape your future.

Some people are doing their jobs, some are climbing their careers, and others are finding their callings.

To put a bow on everything, before I dive in, I think of work as the ultimate form of self-expression.

As a friend would say, the key is to do more art – whatever your art is.

And I think of Microsoft as the ultimate dojo of personal growth.  The common bond between Softies is smart people who want to build a better world.

Really, Microsoft is an empowerment company.  And I am a big advocate for realizing your full potential, the Agile way.

Think Big

I joined Microsoft years ago because of Bill Gates.  I saw a guy with all the money in the world, that still showed up every day, because he loved what he did.

What a great test and testament of a company.

I wanted to learn how to make incredible impact and I thought that Microsoft would be a platform for growth and greatness.

As a kickboxer and martial artist, I like competitive playgrounds to test myself and to take on things bigger than me.

Before Microsoft, I kept outgrowing my container.  Rather than be a big fish in a small pond, I thought I could finally become a guppy in the Ocean.

I wanted to run with fast wolf packs and learn how to use technology to hack a better world.

When people ask me why I joined Microsoft and why so long – I say because of my simple, driving mission:

“To improve the quality of life, for as many people as I can, as long as I can.”

Think Broadly

I remind them to take a look around – Microsoft is a platform of empowerment.  Everyday, there is something amazing going on around the world.

And we have astronauts, doctors writing code, best-selling authors, musicians, former Jim Henson Studios, former Marvel Comics, leaders in the military, leaders in government, leaders in education, amazing business leaders, amazing innovators… you name, it’s here (and former Apple, former Google, former Facebook, former Amazon, etc.)

There is no shortage of diversity, and if there is anybody who walks the talk of inclusion, it’s Satya Nadella, so we’re in good hands.

And Satya has a good heart.  He’s moved up Maslow’s stack, so he really does want to use public Cloud for public good and create meaningful work.

The beauty is that on any given day, you can add somebody new to your network from around the world, or learn a new skill, or a strategy, that might forever change how you see the world… or how you show up in the world.

Think Beyond

I challenge myself to bring all of Microsoft to any situation.   I want to know what’s going on with our products and platform, including the latest R&D.  I want to know real stories from around the world, such as how Microsoft is responding to Covid-19 in different markets.

And I want to know that latest innovations or innovative approaches that change how we do things or how we view things.

I like knowing the nooks and crannies across Microsoft.  And I love exploring the treasure troves of deep knowledge and insights that we have on just about any topic you can imagine.  I can go far off into the deep end of the pool with genomic research, or fly high into the sky, the cloud is no limit, with drones.

Or boldly go where no cognitive capabilities have gone before, with the promise and potential of Artificial Intelligence (AI) and Machine Learning (ML).  And if I want to really mix things up, there’s no shortage of Mixed Reality playgrounds.

In fact, that’s how a friend long ago (no CVP at Microsoft), taught me how to think about my time at Microsoft:

“Think of Microsoft as one giant technical playground.”

He said if you aren’t having fun, you aren’t learning enough.  If you are bored, it’s you.  If you aren’t making enough impact, you just haven’t found how to leverage the giant technical playground all around you.

So, to this day, I always challenge myself to look far and wide, and to look to the future:

It’s always a vision that guides me.

A vision of my future self.  A vision of the kind of world I want to live in.  A vision for the kind of company and team I want to be a part of.  A vision for the world I want to inspire, challenge, and forge for the road ahead.

Find Your Super Skill

If there’s one thing that has served me well, it was finding my super skill.  It was a blind spot for me, but a trusted friend called it out to me.  He said that my Super Skill is actually information modeling.

I thought it was a stupid super skill.  But he said, no, it’s a big deal.  It’s what architects do, it’s what analysts do.

He told me to do more of it.

I said it was silly to me, because it’s like asking Michael Jordan to do more lay ups.  It’s too easy.

He said, easy for me, not so for others.

I trusted him enough to try it.  So I focused on doing more of my Super Skill.  That year, I ended up becoming the right hand person to our General Manager(GM) and shaping our future product line.  And I ended up creating 6 patents, all related to information models (in security, performance, and application architecture).

I ended up using my Super Skill to win competitive platform assessments, building libraries of patterns, creating the Book of Dreams framework at Microsoft, and using it to map, manage, and respond to future trends, as well as helping leaders figure out how to create and capture value.

I also used that Super Skill to author 10 technical books, and a non-technical book.  My non-technical book is about applying “Agile for Life” and it’s been a best-seller in time management and productivity.  I ended up training teams inside and outside of Microsoft on the art and science of high performance, leveraging lessons from Agile and Program Management.

Do What Makes You Come Alive

I was torn between two paths.  One path promised an amazing future and lots of learning.  The other promised definite career jumps.  I was torn between the tree of knowledge and the pot of gold.

One of my best mentors asked me a very deep question long ago:

“What do you want to spend more time doing?”

I wanted to climb the tree.

Follow Your Growth

Interestingly, in one of my groups, we had a saying about how to figure out what’s next:

Follow the money.

The key was to know where the money is, so you would know where the market growth would be.  But we tempered it with a related saying:

Follow your growth.

People who follow their growth become, as Einstein would say, a person of value.

3 Paths of Happiness

Speaking of value, if you are curious about what all the science has learned about the paths of happiness, here they are in 3 levels:

  1. Happiness in the now.  Just do whatever the hell you think you want.  This path is fleeting though.  It burns people out.  They make bad choices.  It’s shallow.  Happiness in the moment, is not fulfillment in the long run.
  2. Live your values.    This is accessible to anybody.  Spend more time in your values.  If you like learning, then learn from folks around you.  If you like excellence, then master your craft.  If you value health, then advance what we know.  You can turn any chore into a chance, if you connect it with your values.  One of my values is adventure.  When I was a Program Manager, I would make every project an epic adventure for the team, and I became known as “the director of blockbusters”.
  3. Give your best, where you have your best to give – in the service of others.  It’s one thing to spend more time in your Super Skill.  But you compound and amplify your feelings when you do it in the service of others.  Tony Robbins asks us why do we communicate?  He says it’s simple:  to amplify the feelings.  A stadium of one, just never cheers the same as a crowded stadium where the benches over-floweth.

What you learn really, is that the key to YOUR happiness (not what other people think your happiness should be), is a journey of self-awareness and a deep dive into how you create value – for yourself, your team, your customers, the world… no limits.

Find a Model and a Mentor

One of the best pieces of advice I got from a seasoned mentor was this:

“Whose job do you want?”

He said you have to give people a model for the job you want, so they can help you.  They need to relate.  They need to know how big you are thinking.  They need to know what that role looks like.

He gave me an example.  He said, “Level X, Distinguished Engineer”

That instantly gave me a frame of reference.

He said, once you have the model for what you want, figure out the gap, and use a mentor.

Mentors are the ultimate short-cut.

Find the Roles that Suit You

It’s better to find a role that suits you, than to try to suit yourself for the role.

People break themselves all the time, trying to fit into roles, that aren’t great fits.  So many people that would be shining stars, get battered or beaten into a mold that was made to be broken.  (yet somebody runs around with a sharp, cookie cutter)

In fact, there is a pretty incredible book called Patterns of High Performance: Discovering the Ways People Work Best, and the author is very clear:

You already have a pattern where you naturally do your best work.  Discover it by going back through all your greatest triumphs.  Use that pattern again.  Don’t let other people break your high performance pattern.

One of my favorite roles was Principal Program Manager.  That was one of my longest roles at Microsoft.

For 10 years I was on time, on budget, leading high impact programs, while building dream teams with people inside and outside of Microsoft.

What I really liked about Program Management is shaping and shipping an idea from cradle to grave – that end-to-end aspect of forming a team, shaping a concept, and shipping value that changes the world in some way.

I love learning by shipping!

3 Inspirational Questions

If I think back to what inspired my greatest growth, it was actually three questions my GM at the time would ask:

  1. How will the world be different when you are done?
  2. Who is the dream team you need to pull this off?
  3. What is the information model?  (how will you share the “castles of the mind”)

He wanted to first create incredible clarity around the change – which was effectively – the vision.

He wanted me to be able to articulate the vision in a compelling way to inspire others.

After all, if the vision isn’t worth it, if the change is not worth it, why bother.

Life force is precious and fleeting.  Don’t’ waste yours or the people around you.

He wanted me to really know the talent in the world – not just in our own backyard.

Think in Terms of Career Growth, Professional Growth, and Personal Growth

I’m a fan of mental models and thought frameworks.  I especially like this framing around growth.

Long ago, a seasoned Softie in our group walked through how to think about your growth in terms of 3 tracks:

  1. Career Development – Become a stronger leader.
  2. Professional Development – Become a better craftsmen.
  3. Personal Development – Become a more capable person.

An effective way to think about it is:

“Are you the person, the professional, the manager, or the executive you want to be?”

When it comes to career growth, thinking in terms of 3 tracks can help you think big, think broad, and think beyond.

Find Your Why

About a few weeks after a particular leadership class at Microsoft, a peer reached out to me and asked me to be her mentor.

It was really an interesting encounter.

She wanted me to be her mentor… and her successor.

I asked her why me?  She said because she liked the questions that I ask, and how I thought.

I remember thinking I thought I didn’t say much – I try to be brief and to the point in a training session.

Anyway, I agreed to be her mentor, but it felt like she was teaching me, in some sort of reverse mentor scenario.

She offered to do my “Golden Circle”.  If you don’t know what that is, it was a $25,000 workshop for execs to figure out your Golden Circle – Your WHY, Your WHAT, and Your HOW.

She did multiple exercises with me until she figured out my ultimate WHY:

“The phrase you used most frequently in your workshop was ‘getting results’.  It’s clear that results are your personal currency, and they have more value to you when you can see and experience them as abundance or fulfillment in your life, and in the lives of others.  Since it helps to find a very simple way to relate to your Why – get a motto or quote that says something about what you believe in.”

She was right.

Maybe that’s why I called my book Getting Results the Agile Way.  It’s less a book about productivity and way more a book about realizing your full potential in all dimensions of your life: mind, body, emotions, career, finance, relationships, and fun.  It’s really a personal results system for work and life.

You Never Really Know What You Are Capable Of (until you try)

I’m still learning what I’m capable of.  I’m still exploring possibilities and my own art of the possible.

On Satya Nadella’s innovation team, a highlight for me was when Satya asked me to personally “send him insights on digital transformation.”

(He asked me to join Peggy Johnson’s monthly board, too, but I never did – at the time, I couldn’t add more meetings to my schedule)

When I launched my different blogs, I focused on learning and making impact.   I didn’t know that I would meet Tim Ferris, Tony Robbin’s son Jairek Robbins, Guy Kawasaki, Marie Forleo, and more.   I didn’t know all the radio interviews I would do, or all the other crazy opportunities it would lead to (such as a former billionaire asking me to help him land an idea for a theme park to go beyond Disneyland).

Keep Creating Serendipity and Your Journey Will Never Be Boring

At the start of each year, different folks from innovation teams fly out to interview me about innovation and trends.  Just before Covid-19 quarantine, an agent from the Department of Defense flew out to interview me about innovation.

So did heads of innovation, from a few other companies/countries (Brazil, S. Korea, China, etc.).  And I was invited to a roundtable of folks that work with the UN.   It’s likely a combo of my posts on trends, and my network.  I just never know who I’m going to meet next.

One of the smartest things I did was become a “CEO Whisperer”, a few Summers back.    I told my manager at the time, that I was bored and wanted to practice my skills.  He said CEO Whisperer would be a good approach, and then I can share whatever I learn to coach others.

I learned a lot.  I’ll share those stories another day.

*Ding* — My 20-minute timebox is up.

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