How I Became the Unicorn of Microsoft

“To be yourself in a world that is constantly trying to make you something else is the greatest accomplishment.” — Ralph Waldo Emerson

I was never called a unicorn so many times in one year, based on my achievements, my accomplishments, and work experience at Microsoft.

I’ve been called a force of nature at Microsoft before.

And a unicorn, too.

But this past year, I was called a unicorn enough times to make me reflect on my journey at Microsoft.

What did I do or what did I learn that was different?

What gave me some unique experiences at Microsoft?

My philosophy going into Microsoft was to become like a “special forces agent” or like a Ninja in the technical and business arenas, and learn all I can, as fast as I can.

I wanted the ability to be dropped into any situation and frame the challenge, frame the opportunity, envision a solution, and mobilize a great change, and scale the impact.

You might say the key lessons I learned at Microsoft is “scaling impact”.   Once you achieve “impact at scale”, you know what it means to truly “change the world”.

Ultimately, I used Microsoft as “my ultimate dojo of personal growth” as well as a place to connect with some of the smartest, high achievers on the planet.

The tribe of Microsoft is smart people that want to change the world in an inclusive and diverse way.

Here is my look back on some of the more interesting aspects of my 25 year journey at Microsoft and what unique experiences contributed to my unicorn status.

Give Your Best Where You Have Your Best to Give in the Service of Others

Before we dive into my unicorn experiences, I want to share the guiding question I used to chart my 25 year journey at Microsoft:

“How can you give your best where you have your best to give in the service of others?”

It looks simple, but there is a lot to that simple question.

It means asking and answering who you really are, why do you do what you do, what are your strengths, and who do you enjoy serving.

I was lucky to have a lot of great mentors early on and I read a lot of the right books,  that helped me get really clear on my mission.

Jobs come and go, but missions have staying power, especially when you connect them to your values and your purpose.

Visions evolve, but they flow from your values and your mission.   For me, the reason I stayed so long at Microsoft is because it’s in my DNA to empower people to realize their full potential.

What I learned at Microsoft is that I genuinely and enjoy and come alive over helping people realize their potential in business and in life.

This simple statement of purpose actually helped me realize more of my potential and use all of my skills across the board.

The best kind of challenge is the one where you make progress and you grow by who you become along the way.

12 Themes of Experiences at Microsoft

I think of my unicorn building experiences in 12 broad themes…

1. Agility in work and life.   I learned how to apply Agile to software, to business, and to life.   The most important thing I learned though is how to develop the Agile Mindset, which simply means “embracing change.”  And that’s the key to pivoting to the future.
2. Startups at Microsoft.   I learned how to start things better through bigger, bolder visions and ambitions.   While I am a strong finisher, I found it’s far better to find people that live for that, so that I could help leaders drive Zero-to-One initiatives.   Because I’m a patterns guy, I think in systems (and ecosystems), and can pull together a lot of pieces of the puzzle into the big picture (and simplify), my strength is really in creating new businesses.
3. Shaping the Future.   I learned how to use stories, scenarios, trends, and insights to help business leaders reimagine the future, explore the art of the possible, and evolve how they create and capture value.
4. Learning faster.   I learned how to learn faster.   I’ve worked in complex software, complex business transformation, and industry transformation.  It’s especially unusual to work across so many domains.  I’ve worked in security, performance, application architecture, and Cloud.  And I’ve worked in automotive, banking, education, health, manufacturing, media, retail, telco, the future of cities, the future of sports and more.  And I’ve gone deep in sustainability, innovation, and high performance.
5. Sharing and Scaling Expertise through Patterns, Frameworks, and Methods.   I learned that the greatest force multiplier in any business or organization, is the ability to share and scale knowledge well.  I learned that so much of the best knowledge in the world is locked up in threads and heads, and the best thing I can do is find ways to unlock it and unleash it at scale.   A handful of thought leaders can change the world better, faster, and easier, if they scale their know how.  The better I got at building Centers of Excellence and Learning Groups, the better I got at realizing human and business potential at scale.  I really learned to value the power of mental models, frameworks, and patterns for enlightening at light speed.
6. Portfolios, Programs, and Projects.   I learned how to ship.   I learned how to ship well (I was on time, on budget, high impact for over a decade).  I learned if you want to make something happen, make it a project.   I also learned to think in terms of Portfolios, programs, and projects.   I’ve created so many “programs of change” to translate business initiatives into a set of related projects to implement the change.  I have a “portfolio mindset”now,  I can’t help but to think in terms of organizing opportunities into a portfolio to evaluate what’s worth doing and how it all fits together.  Winning portfolios win the long game.
7. Scaling Business Innovation.   I learned a lot as head coach for Satya Nadella’s innovation team.  I learned how to focus on business innovation and how to really treat innovation like a team sport.  I learned how to set the stage for innovation and how to learn ideas and innovative scenarios from the edge.  It’s one thing to be an innovator.  It’s another to be an “innovator at scale” where you empower and enable others to apply their creativity and imagination to solve problems and create new value.
8. End-to-End Change and Transformation.  I learned how to transform businesses by using scenarios and capability change along the value chain.   “All change is people change”, as my mentor puts it.   This is really how I learned more about driving culture change.  And it’s where I finally internalized why and how “culture eats strategy for breakfast.”
9. Building Better Software.   By starting off in Microsoft Developer Support, I learned a lot about software based on how customer’s used it and abused it and bent it in all sorts of ways in real-world scenarios.   That gave me a very different perspective than simply trying to design great software in a vacuum or an ivory tower.  And by working in a group focused on scaling better software practices, I learned a lot about the software cycle and how to improve it.   And by working with early Agile leaders, leaders in Lean Software, and working with great designers, I learned to really integrate business perspectives, technical perspectives, and user experience perspectives more consistently.   And by focusing on the extremes of software in terms of security, performance, and architecture, and by doing high stakes competitive assessments and reviews, I really learned how to bake quality into software and how to build things that are more supportable.  And of course, I ultimately learned how to “design for change”.
10. Quality Attributes.     I learned how to evaluate quality attributes such as security, performance, reliability, manageability, maintainability, etc. end-to-end in terms of architecture and design, implementation and deployment.  As a wise mentor put it, “If you’re thinking about trade-offs and concerns, you’re an architect.”  What drove me though was how to bake the experience of experts into the software development process, and how to transform how software gets built.
11. Dream Teams and High Performance Innovation Teams.   Work happens in teams.  And not all teams are created equal.   I learned how to create “Dream Teams” that change the world.   I was pushed early on to find “the best in the world” at what they do.   This forced me to become an extreme talent scout.   Once I realize that the game of results is really a challenge in building high performing teams, I learned all I could about team process improvement, and dealing with conflict.   I learned with diversity comes conflict, and if you can lead and manage through conflict, the team operates at a high level and can take on bigger and better challenges.
12. Super Productivity.    I learned a lot about high performance and productivity as an individual contributor, team leader, and coach for large teams and organizations.   Productivity on teams can be like a chain—you are as productive as your weakest link.  So I focused a lot on helping individuals realize their productivity potential by focusing on strengths and flow.   When you bring out each person’s best, you bring out the best in the team.  (Hat tip to the late, great basketball coach, John Wooden.)

Looking back, my experiences helped me become a futurist, a strategist, an analyst, an innovator, business architect, and an entrepreneur… aside from a “CEO Whisperer.”

Firsts at Microsoft

I had the chance to be a part of many firsts at Microsoft.  Here are some example…

• I was the first pilot for the first “webinar” at Microsoft.  It was an experiment long ago to reach more customers in a 1-to-many way.  It was awkward for me.  I didn’t know what to expect.  I was used to giving talks to people in a room.   I remember sitting down at a desk and the director said just give your talk into the camera.   It wasn’t interactive, and I couldn’t see anybody.  I wondered where the customers were.  It was weird just talking into a camera wondering who was watching the session.
• I led the first “How To” effort at Microsoft.  It was an exercise in creating a library of How Tos to provide customers with step by step instructions.  It was an experiment to see if we could use How Tos as a strategic content type to
• I was part of the first Blue Books at Microsoft.   A friend of mine had done a very great thing at Microsoft.  He paved the way for “guides” on the platform.   I created an early set of guides that Eric Rudder, former Tech Assistant to Bill Gates, referred to as “Blue Books” at Microsoft.  He thought they were similar to IBM’s Red Books in that we were providing guidance on real-world scenarios learned with our customers and field.
• I was part of the first “Life-Cycle Service” at Microsoft.   This was a pilot to wrap “life-cycle” services around the customer’s journey to the O365 Cloud.   The big idea here was to help customers from the beginning of their journey, through deployment, through adoption, and through the evolution of their Cloud service.  Really, the goal was to answer the question: “How do we support customers using a Microsoft Cloud service in an ongoing way?”
• I was the first Digital Business Transformation role at Microsoft.   I was early on this because of my unique role in Digital Advisory Services and because I was specifically focused on business transformation.

Startups at Microsoft

I spent the bulk of my journey at Microsoft doing startups…

• Microsoft patterns & practices.   I was part of this startup at Microsoft to help developers and solutions architects put the Legos of Microsoft together, better, against real-world scenarios.  The first version of the group was called PAG, which stood for Prescriptive Architecture Guidance, and conveniently could also be Platform Architecture Guidance.   Inside Microsoft people used us like a verb… “Could you PAG that?”, and also like a noun, “Is there a PAG for that?”   I got to learn a lot about software patterns and pattern languages.   This is also where I spent 10 years of “deliberate practice” in sharing and scaling expertise.   My second book was downloaded 2,000,000 times in less than 6 months, so it was my first taste of using books to scale impact.  I created several frameworks for security, performance, architecture, team development and more.
• Microsoft Enterprise Strategy.    I was part of the startup at Microsoft to help businesses realize the full potential of their Microsoft investments.   This including connecting business and IT (Information Technology), and driving end-to-end enterprise change and transformation.   Here I learned deep strategy skills, value engineering, adoption & change, and more, working with former Gartner, McKinsey, Accenture, Deloitte, Booz Allen, as well as some of Microsoft’s best and brightest enterprise architects.
• Microsoft Cloud Vantage.   This startup at Microsoft was all about selling, deploying, implementing, and operating O365 in the Enterprise.    I learned a lot about designing better offers and driving productivity with the field.  I ended up building a lot of frameworks and scenarios.
• Digital Advisory Services.    I was part of the original startup for the Digital Advisory Services at Microsoft.    Just like there was a “digital” group and focus at McKinsey and other large consulting firms, we created one, too, at Microsoft.   This is where I learned and applied even more about Digital Transformation and driving innovation and shaping the future.
• Sustainability at Microsoft.   Actually, this counts as multiple startups, since I spanned multiple sustainability startups and efforts that were coming together.   I learned a lot about making sustainability actionable and how to anchor it in the customer’s journey end-to-end.   I created, curated, and shared stories, scenarios, trends and insights across thought leaders and doers around the world.   I feel like I got to the see the future of every industry, and it’s a reminder that the future is already here – it’s just not evenly distributed.

The big things I learned from startups are how to be a change leader vs. a change agent (and why that matters), and how to grow from a small, kernel of idea, into a far reaching and game changing success.

I also learned and internalized that all things are created twice, first in the mind, then in the market.

My Most Interesting, Friendly Titles at Microsoft

You know what you’re doing is working when somebody gives you a special title at Microsoft.

Aside from unicorn at Microsoft, here are a few of my more interesting titles from over the years..

1. The “Blockbuster” PM.   I solved very big problems that required outstanding orchestration and execution.  I was known in the group for leading epic projects and shipping things that changed the world.    I learned to dream big by leading dream teams that changed the world.   And the results spoke volumes to what happens when you inspire achievers with big ambitious goals.  The feelings of impact are contagious.
2. The Abilities PM.    I earned this because of my focus on quality attributes like security and performance.  I baked them into the software life cycle end-to-end.   Working across multiple quality attributes gave me a multi-perspective view of the world.
3. Chief Clarity Officer.  One of our Microsoft CVPs actually made business cards for me with the title, Chief Clarity Officer.  He would always say that among the world of chaos and complexity, I could always simplify down to actionable insight and a clear mental model.  He liked the way I framed things and the simple stories I could tell to share big ideas and vision.   And whenever there were conflicting ideas about what was going on the system, he would ask for my point of view.
4. King of Dreams.  I earned this title because of shipping the Book of Dreams for years.    I was in a unique and unicorn position to see all the patterns of how big businesses and organizations were dreaming up the future in every industry.
5. Secret Squirrel.   I earned this title because my manager recognized my ability to learn what was happening throughout the organization through my networks and find out things long before the rest of the organization knew what was coming.

27 Managers at Microsoft

I had 27 managers at Microsoft over 25 years.  What did I learn?  Enough to write several books.

Having such a wide variety of managers contributed to my unicorn status at Microsoft.

While some people have had more managers than me, the surprise is how many manager changes I had in short periods of time (for example, 7 managers in 3 years), and how I had some managers for such long periods of time (1 manager for almost a decade).

Here are my key takeaways:

• Management philosophy varies wildly.   I got exposed to a wide variety of management styles and philosophies.  This helped me understand and appreciate more styles of leadership.  It also helped me better understand how different management philosophies could really create big differences in team life style, clarity, energy, and results.
• Hierarchy and command-and-control versus empowerment and influence without authority.   I learned that some leaders like to use positional power, while others focus more on empowering the team.  They focus on pushing as many decisions from the trunk of the tree, out to the branches and the leaves of the tree.   Some leaders learned, the more power they give away, the more leadership trust they gain.   Experiencing a wide range of approaches and influence helped me see very big differences in team satisfaction that have informed my leadership style over the years.
• Vision, mission, and values are the backbone of the team.    I learned to fully appreciate how much  the vision, mission, and values matter at a team or organization level.  I carried the best lessons forward from team to team.   Along these lines, I got exposed to so many different styles of planning, organizing, and executing work that this contributed to my flexibility in style and massively grew my toolbox over time.
• Agility varies.    Some managers put their faith in plans.  Some managers put their faith in the process.  Some managers put their faith in the people.  And I learned the best managers know how to leverage all three, and how to adapt when something isn’t working.   I found that “learn-it-all” managers tend to embrace agility by focusing on learning by shipping and building better customer feedback loops.  And the really skilled managers use Agility as a way to balance workload by building better backlogs, chunking big things down into chunks of change, and flowing continuous value.   Experiencing different level of agility helped me grow my agile leadership skills far better than if I only ever saw a few styles in action.
• Diversity & Inclusion.  I got to experience a wide range and continuum of diversity & inclusion.  I learned how some managers are very good at appreciating cognitive diversity.   I got to see how some managers are very good at creating a culture of inclusion.   I got to see how some managers were very good at combing the uniqueness of individuals into a high performing team with vulnerability-based trust and psychological safety.  Without this, I wouldn’t be half the unicorn I am today.
• Who you serve is a strategic choice.    I got to see and feel first-hand what happens when you change who you serve.  For example, a developer audience is very different than a consumer is very different than the C-Suite.   I also got to feel what it’s like when a group is far removed from customers versus when a group is customer-obsessed.   By serving  a wide-range of personas in various groups, I earned a balcony view of business and IT and how to connect them.
• Forming, storming, norming, and performing is a thing.   When you’re the new kid on the block, I found it helps to know the basic flow of gelling on a team.  From a Unicorn standpoint, I had to do this so frequently that I learned how to bend in more mysterious ways.
• People vs. Things.   Most people tend to have a “thing-orientation” or a “people-orientation”.     For example, one person might be fascinated with the Tesla, while another is fascinated with the makers of the Tesla.  I’ve had managers that were exemplars of the extremes of both.   From this, I got to add another lens to my toolbox in terms of how differently people can see the world.
• Precision vs. Accuracy.   As a mentor put it, “precision is filtering out everything that’s not relevant.”  I picture precision as hitting the bullseye, while accuracy is hitting the right target.    I noticed that some managers were very good with precision.  Some were very good with accuracy.   And some were good at both.   I learned a lot from these unicorns.
• Filters and priorities.   This is one of the best lessons a mentor gave me long ago.   Every manager has filters (the language they use to see and explain their world) and priorities (the short set of critical things on their mind).   If you don’t use the same language as your manager, it can create conflict even when you violently agree.  It’s easy to talk past each other.   And when it comes to staying connected and relevant, the key is to focus on that short list of priorities.   I learned to think Ii n terms of “labels vs. concepts”.   So, for example, if my manager called a “daisy” a “rose”, I’d focus on the concept of “flower”, and recognize that their label, or handle they are using for that concept is “rose”.
• Thinking differently.    Some managers surround themselves with people that think differently.   Some managers surround themselves with people that think the same.   I learned to appreciate the managers that value diversity and embrace different thinking styles.  I became fascinated with cognitive diversity and conflict management.
• Ideas vs. Shipping.  Some managers put a high value on ideas.   They realize that without ideas, there isn’t really anything to build a future around.    And while ideas might seem a dime a dozen, some managers recognize that not all ideas are created equal, and they realize that “business” ideas are a high value asset for the business.    But some managers stare at their precious diamond looking at the facets, too long.   Other managers, put an extreme focus on shipping.    And this works well, when there are ideas worth shipping.     Some managers balance this by getting better at using customer feedback to improve.   The best managers I’ve seen create a strong balance of exploring ideas and executing results.   And the best of the best are able to do this at both the organization level, and within projects and systems.  The learn how to bake innovation and learning into their processes large and small.
• The “Goose” vs. the “Golden Eggs”.   Some managers squeeze the goose for the golden eggs.   Others, really value the goose and protect the goose, because they know their future depends on their ability to create new value.

Overall, by getting exposed to a wide-angle lens of management styles, I really appreciate the fact that for any management idea or principle I bump into, I have experiences to draw from to support and validate, or to challenge from a place of curiosity.

Sometimes well-intended ideas are just out of context, and if you can figure out when, where and how to apply them, they make a lot more sense.

Microsoft Program Manager, On Time, On Budget for 10+ Years

This achievement is something of a Unicorn level, not just at Microsoft, but in the wide world of project management.  I can say the early years were the roughest years.

The early years were heroic effort and at extreme costs to work-life balance and wellness.

Luckily, I had some incredible mentors that showed me specific solutions for each of my big challenges and collectively changed the game of program management for me.

The key things I learned here that helped me change my game come down to:

• I learned how to fix time, flex scope.   The pattern I observed in myself and other high achievers at Microsoft is that when you want to change the world, you tend to be scope driven.  When you are scope-driven, scope creep happens.   By creating a cadence of shipping at a regular rhythm, it forces you to figure out smaller chunks of value.   It’s easier and healthier to manage planning, designing, implementing, shipping, and learning easier when you wrap the team around incremental value versus big bang.
• I learned how to apply axiomatic design to solutions and shipping.    One of the challenges of shipping smaller things is interdependencies.   I had to learn how to implement loose coupling and high cohesion across a set of deliverables.   My mentor explained axiomatic design this way:  “If you have a faucet, the classic, and coupled design is that the each knob controls temperature and flow.   A better design is to have one knob for temperature, and another for flow.  This way you can work on each variable independently.”  This helped me manage quality better, while dealing with moving parts.  I learned how to visualize inter-dependencies for the team better, so we could factor better.
• I learned to separate the project cycle from the development cycle.    I remember the first time I saw a whiteboard with a timeline of milestones at the top, and then a bunch of swirling development cycles underneath it.   It was suddenly so clear how it was easier to communicate a simple timeline of milestones to key stakeholders, and not expose our development churn to uninterested parties.   And at the same time, it helped me create space within our development cycle to experiment with different engineering methodologies to ship better, faster, easier, while sticking to a clear timeline of outputs.
• I learned how to build high performing teams.    I found there are really 3 keys to high performing teams: 1) cognitive diversity, 2) conflict management, and 3) vulnerability-based trust.   Complex challenges need diverse thinking to solve them.   Diversity in thinking creates conflict.   But if you can manage through the conflict, you set the stage for vulnerability-based trust.   It’s when people on the team got your back.  And when the team’s got your back, you can go out on a limb and give your all.
• I learned how to bring out the best in the team, by bringing out the best in individuals.     Not only was this good for everybody, it was great for the team.    The best way to get great results from any team, is to bring out the best in everyone on the team.  I learned how to appreciate and embrace different learning styles, different thinking styles, different energy styles, different productivity philosophies and more.  I learned to always ask, what’s are you passionate about?
• I learned how to create more sustainable teams.    I was an early adopter of the 40 Hour Work Week in agile, that was later renamed to Sustainable Pace.   But the big idea was to learn how to better manage scope and expectations,, while creating a well-oiled shipping machine.   I found that even little changes, such as shipping on Wednesdays instead of Fridays, helped people win their weekend back.   I found that by creating a backlog of high value items, it was easier to create a flow of continuous value without heroic effort.   And I found that just giving people a chance to demo their good work and get positive feedback from the team goes a long way.
• I learned how to factor exploration from execution to reduce risk.    This is one of the most important things I did, especially when working on really complex, big audacious goals.   I leveraged experts to help identify the high risk areas early and experiment against them.    I was never worried about figuring out everything up front.  Instead, I was worried about finding big surprises when were ran out of runway.   By exploring the high risks that impacted big decisions around architecture, I simplified and de-risked project execution.

Overall, I learned how to embrace chunking, changing, and recalibrating.   And no amount of process and planning came make up for a lack of vision or a solution concept that is fundamentally flawed.

The Book of Dreams Framework at Microsoft

This just might be the most unicorn aspect of them all—who would expect something like a Book of Dreams framework at Microsoft?

Peter Fisk wrote about the Book of Dreams some years ago describing it like so:

“Microsoft’s Book of Dreams helps business leaders to understand the growth opportunities of digital-enabled transformation.”

I created the Book of Dreams framework ultimately as a catalyst for Digital Transformation and innovation and ultimately industry transformation.

The way I described the Book of Dreams to business leaders was like this:

“The Book of Dreams is an innovation framework to help leaders reimagine how to create and capture value for the digital era.”

Aside from creating a movement at Microsoft to rally around Digital Transformation, the bigger deal was how the framework helped to rapidly learn, share, and scale ideas around the world.

Otherwise, everybody is forced to recreate the wheel and struggle relearning what other people already figured out.   The Book of Dreams helped bring fire from one village to another.
I ended up working with the world’s best experts in automotive, banking, education, health, manufacturing, marketing, media, retail, telco, the future of cities, the future of sports and more, in the US, Europe, Asia, and more.

The experience of working across so many industries and GEOs gave me a very unique balcony view of the future of innovation and digital transformation.

Here are a few of the highlights from that journey…

• Human Desirability + Tech Feasibility + Economic Viability.    I learned that this trinity is what turned innovation from science projects into real-world value.   Building anything that didn’t have human desirability always failed in the market.
• Business because of technology.   I learned the highest value contribution was to show how technology could enable a business to do something that it couldn’t do before.   Sometimes it took a village to birth a Book of Dreams.   That’s because it was an extreme challenge to know how to fully explore and exploit new business capabilities that technology enables.
• Exploring the art of the possible.  The Book of Dreams was both a framework for Digital Transformation as well as a series of playbooks that helped customers explore and exploit the art of the possible.
• Swarming on customer challenges to create the future.   I learned how to build better virtual teams around the world that could swarm on customer challenges by industry or topic.
• Reusable knowledge changes the game.      I was amazed by how many people around the world stepped up to the plate and surprised me with their amazing stories.   By building a library of trends, stories, scenarios, and business value, it creates a snowball effect where more people were empowered to advance the space they were working in.    This library also created a breading ground for cross-pollinating ideas.   For example, when we figtured out how to build “raving fans” for sports teams, suddenly all our retail banking leaders wanted to know how to build a tribe of “raving fans” for their banks.   And that’s how breakthroughs and disruptions happen.
• Stories, Scenarios, and Solutions.  I learned how by focusing on stories, scenarios, and solutions within each industry and within 3 primary GEOs (US, Europe, and Asia), I could learn how to change the industry in the large.   It’s this combo and this pivot that reveals better and bigger business breakthroughs.   It’s a way to actually see how future value will be creates, and how current value will be destroyed.
• Trends & Insights.   I really learned how to better organize trends and insights to discover and curate innovate scenarios.      It’s easy to get lost in a sea of trends & insights.   But with a simple framework, it’s easy to translate those trends into new business models and patterns of business value.

Overall, I would say the most important lesson I learned is how to empower an entire organization or multiple organizations to change the world through a well-designed framework.

This experience gave me the confidence and clarity to be able to change a sales organization or marketing organization or even an engineering organization at multiple levels and to win in the market.

The power of dreams is what I can say with confidence is what created some of the most compelling business advances and breakthroughs in every industry.

It’s such a consistent reminder that all things are created twice – first in the mind, then in the market.

And it’s a race to the bottom when leaders and their employees forget how to dream big to change the world.

Imagination is a limitless source of value creation.

Head Coach for Microsoft CEO Satya Nadella’s Innovation Team

My role here was to create a more systematic way to drive business innovation with customers.

The unicorn aspect of it was being the one to empower and improve our ability to innovate across all industries around the world.

That education was priceless and something I could never buy from a school…I could only learn it from the school of hard knocks.

This is where I had to really grow up fast in terms of leading and driving Digital Transformation and innovation.

• Business Innovation Framework.   The game of the group was to help a short set of customers make the market in each industry, while we learned how to innovate better at scale.  But to up-level our game, I had to turn innovation into a team sport.  To turn innovation into a team sport, I created a simple framework of canvases for sharing and scaling business innovation.
• Trends & Insights, Stories, Scenarios, and Solutions.  Soon I realized that the key to better business innovation was the ability to share and scale trends & insights, stories, scenarios, and solutions, within each industry.   By learning from around the world, we could come up with ideas better, faster, and easier, while improving our ability to discover and create new business models.   Stories brought scenarios to life and gave context for human desirability and business value.
• Business Model Innovation.    The best thing Satya did was constantly say, “Bring me new business models”.   That little mantra helped remind people that the highest value of our innovation efforts is to bring back new business models to help shape and ship our future.

The most important thing I learned is that I needed to think of myself as a coach versus the one who is the innovator.

While I could certainly drive innovation, this was more of a “team of teams” scenario, where the best thing I could do was to enable more teams to innovate better around the world.

So that’s exactly what I focused on.

What surprised me in the end was how so many business models boil down to common patterns that actually work.

The key, of course, is to know when to use them.

Digital Transformation Trends & Insights for Satya

Satya liked the approach and results and asked me to directly send him and his chief of staff my insights on digital transformation.

So periodically, I would send Satya a distilled set of lessons learned and key insights in the form of stories, scenarios, and patterns.

Looking back it was a reminder how everyone is a leader and how you never know just how valuable what you are learning might turn out to be.

I learned how to translate a lot of noise in the news into meaningful insights that could help us find a way forward and to be the beacon of value for the future.

I metaphor I use in my mind is that I am creating a constellation in the sky and lighting up the highest value stars.

Bringing this back to customers, imagine if you had the map of the constellation of future value for the organization and could easily see high value clusters.

The unicorn experience for me here was that not only did I learn how to source insight from around the world, I had to distill it into useful, actionable insight that I could easily share.

I think looking at Digital Transformation through the lens of multiple industries and changes around the world was a very unique vantage point for the future.

If nothing else, I got to see a lot of anti-patterns how businesses didn’t change fast enough or didn’t change their culture deep enough to thrive, let alone survive.

For more on this, see How I Created Trends and Insights for Satya Nadella at Microsoft.

Storyteller at Microsoft

Becoming a storyteller, grew out of necessity.   I needed a better way to relay trends & insights on Digital Transformation for Satya, as well as for different pockets of Microsoft.

So much amazing work was happening around the world, but if nobody was able to share the story, great work went unrecognized, and risked getting cut.

I found that the people doing great work, weren’t always good at telling and selling their story.

I learned how to bring more amazing stories of innovation from around the world to the halls of Microsoft just by telling stories of the amazing people on the ground doing amazing things.

The more stories I told of amazing things happening around the world, the more I realize how many untold stories there are.

Every single day, somebody around the world is doing something amazing with a customer somewhere.

And yet, very few people get to learn about these amazing stories, unless they happen to know the person living it.

When our CVP asked me for a short-list of recommendations to improve our Digital Transformation approach, the first thing I suggested he do is invest in journalists.

I said if we had a handful of journalists that could capture and share the stories that are unfolding in every industry, the momentum, insight, and inspiration we would generate would be unfathomable.

Some of the stories I learned to this day that people still don’t know about continue to inspire me to what we can do for the future.

CEO Whisperer

I spent a few Summers as a CEO Whisperer to practice my skills of business change at the top.

I didn’t formalize it, in fact, I kept it informal, as part of my agreement to meet with  various business leaders.

When somebody brought a CEO to me to connect with, I only had a handful of rules:

1. It’s informal.   Think a jeans and t-shirt conversation over coffee, not a suited affair (yet sometimes, they will still show up with a small entourage of suited support).
2. I’ll share some fish, but I’ll mostly focus on how to fish.   While I could share how some key trends might be a source of disruption and new value creation, I was more interested in setting up a sustainable business that knows how to win the future in a resilient and repeatable way.   Mostly, this comes down to becoming a learning organization that’s customer focused, empowers its employees, and set up sustainable innovation that’s connected to new value drivers in the market.
3. It’s fun.   We’ll laugh, we’ll learn, and we’ll enjoy the process.   I remember one of my least enjoyable sessions  was supposed to just be an informal 1:1 conversation.  But it turned into an all day session where I was asked to help align all the leaders around a common approach for the future.  I did it successful, luckily, which was a surprise for everyone, since they fought for months.  I simply walked them through a common framework that was inclusive of all perspectives.  But I didn’t enjoy it.   It easily could have been a game of politics.  So after that, I made a stronger commitment to myself to keep it fun and fruitful and insist on 1:1 sessions where the CEO could speak freely, and me, too.

I ended up getting exposed to a lot of very interesting challenges and perspectives, even ones far outside my wheelhouse.

My favorite experience was actually a conversation around the future of healthcare.

I simply shared an end-to-end view of the customer care journey that resonated with the CEO and made it possible to explore challenges and ideas in a simple way.

When I led by framing his business challenge for the future, he was surprised.  I struck him like a unicorn.

He was used to, and expected a pitch on Azure, so he said I was the first person to actually start by framing the business challenge.

Here was a CEO that had been pitched to and sold for years by Microsoft, but I was the first person from Microsoft he said to actually practice, “Business before technology.”

This experience helped remind me how much more effective it is to frame any big change against business challenges, business priorities, and desired business results.

I’ll share more on what I learned as a CEO Whisperer in the future because I think it will help business leaders be more effective in terms of business change.

Leading and Growing Business Innovation at Microsoft

There is a lot of focus on technology innovation at Microsoft, so having the chance to really dive deep into the world of business innovation was a unicorn creating experience.

It’s an amazing thing when you create new business capabilities with technology, or as we used to say on the team:

“Business because of technology.”

The experience of innovating in every industry was probably the best use of all of my combined skills.   It really stretched my strategy and business development skills.

And it was a great way to apply all my experience in end-to-end value engineering.

The biggest challenge was that there was a gap in terms of business innovation evangelism at Microsoft.

I remember the day I realized we had an entire developer evangelism organization, but we didn’t have a corresponding organization for business innovation evangelism.

The way I see gaps is that they are opportunities if you act on them.

One of the best things I did here, aside from creating the Book of Dreams Framework, is I created a Vision Memo to crystalize and catalyze the idea of business innovation evangelism at Microsoft.

To see how I framed out the opportunity for business innovation evangelism at Microsoft, here is my Vision Memo:

Example Vision Memo—The Rise of the Business Evangelist at Microsoft.

To set expectations, I wrote it in an hour, and kept it raw and real to bake a bit of fire and passion into it.   So it’s more like a draft, but it still went viral.

In this case, I took a page out of Amazon’s playbook and recognize that it’s a powerful thing to write down an idea in narrative form and share it with the world.

I remind people how Bill Gates was able to learn from around the company, around the world through Think Week papers.

And I remind people how Jeff Bezos was able to inspire and win over Wall Street by sharing his vision as a narrative memo.

Jeff’s narrative structure was basically, here’s how I see the world, here’s how I see the world changing, here’s what I see as the opportunities, and here’s how I see Amazon can play a role in the future.

This is how he was able to get people to stop thinking quarter by quarter and instead take a balcony view and look to the big changes that might be 5-7 years out.

Talk about an inspiring approach to visionary leadership.

I would argue that one of the best example we have at Microsoft, is when Microsoft CEO Satya Nadella wrote his epic email to employee’s about the mission and strategy.

I think in today’s “always on” world, we just don’t see enough of these kind of “framing memos” and “vision memos” that help us gain better perspective and see unfolding opportunities before us.

Again, this is a gap that I would challenge any leader to step up and do more of.  It builds amazing visionary leadership skills and is a fairly unique muscle to flex.

Innovation Offices, Innovation Centers of Excellence, and Innovation Hubs

I remember the day our general manager asked me to create an Innovation Office for customers.

The room looked at me, as if to reinforce, of course JD should be the one to do it.

I like the validation, but I was also wondering how in the world would I rally all of Microsoft to stand behind a model for customer innovation?

Well, I’ve taken on bigger challenges before, so this was just another job for innovation.

Little did I know how complex this challenge would be, even with legions of smart people that had been doing it with customers around the world for years.

In fact, the best thing I did was setup individual interviews with more than 40 of our most seasoned leaders in the field that were driving innovation with customers.

I learned more in a span of a couple months than I had learned in a year, and I was already a speed learner.

But the sheer volume of exposure to all the ways we were helping customers leap frog into the future was beyond mind blowing.

I ended up with yet a whole new network of innovators around Microsoft and around the world, and every day my biggest challenge was how to absorb everything I was learning at lightspeed.

The good news is that I was able to share and scale what I learned through several channels at Microsoft and I was able to help organize innovation for a fairly large group at Microsoft that compounded it’s benefits through better innovation management.

I think that’s really what I learned more deeply here is how to structure innovation management in a way to both “run the business” and “change the business” in parallel.

It’s one thing to read all about it in articles and books.  It’s another thing to apply it at Microsoft and with customers around the world.

Building Better Knowledge Bases for the World

When you build a knowledge-base for a world-wide audience, it grows you.   This one experience alone is a maker of unicorns.

Imagine if you are the architect of a solution where you can leverage the smartest people in the world to create such a “just-in-time” learning system where users always have the answers they need.

This job requires deep empathy for customer pains, needs, and desired outcomes, and it requires experience with real-world scenarios.

And it absolutely demands hard-core experience and expertise of the domain from a problem and solution perspective.

The better you can map out and frame the problems, the better you can solve them in a scalable way.

Here are a few highlight of what I learned from building world-class knowledge bases:

• Questions, task, and concepts.   You can break any domain down into questions, tasks, and concepts.  It sounds simple, but this is the fastest way to learn and master a space.
• Your knowledge base advances the space. Your knowledge base is an enabler for the world to advance the space and to help everybody “stand on the shoulders of giants”.
• Scale your best experts through content.    The big mistakes most groups make is they have people that don’t have experience, write about the topic.   It’s like a deep fake. It looks good on paper.  And then when somebody tries to use it, something is off, even if they can’t put their finger on it.   In my experience, the teams that win here always have their best experts sharing and scaling their knowledge.  It’s good for users and good for experts. It helps experts move on to higher order problems versus play the broken record answering the same things over and over.
• Managed vs. unmanaged vs. community.  It helps to separate content by source so that it’s clear that one body of content is from the creators, and another body of content is from the community (aside from process differences, this signals values, quality control, etc.)   You can also take the community seriously and seed it with experts and recognize and reward the high value contributors.   None of us is as smart as all of us and it’s the power of community that can exponentially advance a space.
• Getting started, core, common and niche.  The catalog becomes more useful when you organize it into 4 broad categories:  Getting Started, Common Scenarios, Core Scenarios, Niche.
• Planned vs. Ad-hoc content plans.   A big thing that I learned is that it helps to create two parallel tracks when it comes to content creation.  One track is focused on executing a plan of content around the major topics in terms of Getting Started, Core, Common, and Niche.   The other track is focused on addressing what you missed and hot topics that come up as you go.    It’s this dual strategy that helps the user base forge ahead better, faster, easier.
• Periodic reviews and cleanup (“sweeps”).    Content can decay pretty fast, even when you attempt to create evergreen content.  It helps to separate “volatile” from “stable” content, but there will still be some erosion and change, as knowledge and know-how in the space advances.   The best solution I’ve experienced is to periodically review and “sweep” the content to keep it fresh and useful.  I find it helps to batch process and to set up a regular rhythm such as quarterly “sweeps”.

Fore a deeper dive into my experience here, see What I Learned Building Knowledge Bases at Microsoft.

Create the Security Information Model and Organize All of Microsoft’s Security Content

This was an incredibly unique experience and unicorn worthy.

The challenge I was given was to basically created an organized catalog of all of Microsoft’ security content across support, product development, marketing, MSDN, Technet, GotDotNet, and anyplace where we had a public security portal.

As you can imagine, this was a major undertaking and I learned so many surprising things about organizing such a massive catalog of content of thousands of pages.

To create an organizing model, I basically worked through dozens of the major websites outside of the technical arena, to learn different perspectives and organizing constructs.

Here’s a distillation of some of my key insights:

• Information models are extreme competitive advantages.   The breadth and depth of your information model can help you easily understand strengths, weaknesses, and opportunities.  You can easily build a library of use cases against your information model and assess in terms of criteria such as “first-time experience”, “complexity”, “compliance with best practices”, etc.  Imagine a consumer reports style report that shows you your red, yellow, green.
• Your information model helps users navigate all of your value.  Making your information model. for your content explicit helps users understand the map and your catalog.  Your content catalog signals to your user base how good a job you did (or didn’t) do in a very simple way
• It all comes down to topics and types. You can organize all the world’s content down into topics and types (content types).

Building World-Class Frameworks and Methods

This is where I got some of my best bruises and battle scars in the halls of Microsoft.  This made me a much stronger unicorn.

As my Mom always said, whatever doesn’t kill you makes you stronger.

Trying to build world class frameworks and methodologies takes a lot out of you, so it’s really a job of purpose and passion and dedication.

It takes a village to raise a framework.   After all, when you build a framework you are attempting to synthesize the best knowledge into a repeatable approach.

If you do this well, the rewards are rich…you basically enable and elevate the users of your framework to a higher level of productivity and proficiency.

But building frameworks not for everyone.  it takes a

Here are some examples of the kinds of frameworks I either created, evolved, shaped or influence in some way:

• Agile Security Engineering Framework.   I created this to address the intersection of hard-core security engineering with the emerging world of Agile software practices.   I wanted to “bake security into the lifecycle”.
• Agile Performance Engineering Framework. Similar to security, I created this to address the intersection of hard-core performance engineering with the emerging world of Agile software practices.   I wanted to “bake performance into the lifecycle”.
• Application Architecture Framework.   I wanted to create a framework that would help make it easier to collaborate on strategic architecture choices and quality attributes for common types of business applications.  Architecture is already tough, but what I wanted to achieve here was to create “a language for architecture” that would help get everybody in the game and make it easier to swarm on the tough architecture challenges.
• Digital Transformation Framework.    I needed to make it easier for smart business leaders and smart tech leaders and smart user experience leaders to swarm around customer challenges and business opportunities to create breakthroughs and better businesses for the future.   This created a movement at Microsoft where it rippled around the world and empowered our field in the large to advance and innovate in every industry using a common framework and approach.
• Innovation Acceleration Framework.   Similar to creating a Digital Transformation framework, but here I went deeper on the innovation side and baked in all I had learned as head coach for Satya’s innovation team and from building a model for Innovation Offices, Innovation Centers of Excellences, and Innovation Hubs.
• Lifecycle Practices.   This turned out to be more of a stealth effort, but I ended up creating a deep catalog of software development methods and techniques to improve software quality end-to-end.  For example, taking all I learned from doing security architecture and design reviews, security inspections, security code reviews, and security deployment reviews, as well as similar work for performance and other quality attributes, how could advance how we build better software?   This is where I evaluated the effectiveness of different techniques and methodology on building better software faster, easier, and higher quality as a team sport.  I learned more here than I ever go to share because I ended up in a phase of reorgs.
• Lifecycle Service Framework.   This was really about creating a glide path for customers to adopt the Cloud.   The idea was to map out in detail the key steps and changes in a journey going from early decisions to implementation to adoption to run state.
• Value Realization Framework.   This was some of the best buried treasure and lost gold ever created at Microsoft.  The purpose of the framework was to help customers realize the full potential of their Microsoft investment.  I didn’t created this framework, but I got the chance to work on it, evolve it, and even lead the team.   I also created some spin off frameworks to apply the framework to different industries and domains.   I will say that working on this framework seriously grew my ability to stretch far and wide across Microsoft, and to look left and right further, and up an down, and drill deep as best I could.   This was like early training before creating the Book of Dreams framework.

Learning from Around the World

This is another unicorn building experience, and one that I think gave me the biggest insight into our future.

My colleagues often wondered how I kept learning about the amazing stories from around the world.

Easy.  It was my network.

But also, it was email.   That might sound silly and yet, email was my ultimate hack for learning from everybody around the world.

I could only meet with so many people in person or in video calls.

But with email, I could connect with anybody who could read and write.  In fact, many people were much better when they could write on their own time with great depth and detail.

So, for example, I might wonder how the pandemic was changing the world.  I would individual email my network around the world to people that would represent an industry, like retail or manufacturing, and representing a particular region like the US or Europe or Asia.   So the next day, I might have 40+  emails from thoughtful individuals who are living very different realities, sharing with me all they were seeing, experience, and learning.

And very often, they would volunteer a follow up call, if I wanted more information, or they might even recommend more people to check with and learn from.

Imagine doing that a few days each week.  Multiply that by several years.  Imagine the network that creates and imagine how much new information and insight that creates.

It was yet another reason I had to become better at sharing and scaling expertise, and all of experiences on the Microsoft patterns & practices team, and working on Microsoft’s knowledge bases helped me compound this knowledge into learning frameworks across the company.

Super Connector and Boundary Spanner

I had been called a Super Connector before, but I had never heard the term Boundary Spanner until a colleague in HR said I need to understand the value I create for the company.

He said it was a special term and one that HR was starting to realize was one of the most important kinds of people in the company – and definitely a unicorn builder.

Think of it as the ones who can bring fire from one village to another, or who can help bring people together to invent the wheel, or who can learn from around the world across business boundaries.

HBR takes Super Connectors and Boundary Spanners, very seriously.   So much so, that HBR published an article called:

The People Who Make Organizations Go—or Stop

Here are a few of my favorite parts:

“It is entirely possible to develop informal networks systematically.

In fact, our research suggests that if senior managers focus their attention on a handful of key role-players in the group, the effectiveness of any informal network can be enhanced.

After analyzing informal networks at more than 50 large organizations over the past five years, we’ve identified four common role-players whose performance is critical to the productivity of any organization.”

Here are the common role-players according to HBR:

1. Central connectors.  The central connectors link most people in an informal network with one another. They aren’t usually the formal leaders within a unit or department, but they know who can provide critical information or expertise that the entire network draws on to get work done.
2. Boundary spanners.  The boundary spanners connect an informal network with other parts of the company or with similar networks in other organizations. They take the time to consult with and advise individuals from many different departments—marketing, production, or R&D, for instance—regardless of their own affiliations. Information brokers keep the different subgroups in an informal network together. If they didn’t communicate across the subgroups, the network as a whole would splinter into smaller, less-effective segments.
3. Peripheral specialists.  Peripheral specialists are anyone in an informal network can turn to for specialized expertise.

As you can imagine, because I was on so many different teams and worked on so many cross-company projects, and by being a “go-to” person, it was only natural for me to play the role of Super Connector and Boundary Spanner.

It was born out of necessity of the jobs that I was in, and it was earned over years of deep work and deep connections, and it was something I learned to embrace as just part of my journey at Microsoft.

But looking back, one thing I will say is that I believe becoming a Super Connector, helps you achieve productivity and impact at a scale you could never achieve alone.

The secret of modern productivity is… it’s the network.

Changing the World Through Dreams, Teams, and Streams

The key role of a Super Connector is not to know everything.  It’s to help the network know everything and to share everything.

So one thing I learned how to do is to setup Microsoft Teams to help virtual teams learn from each other better, faster, and easier from around the world.

I call my approach Dreams, Teams, and Streams, because I used a 3-pronged approach:

1. Dreams – Have a vision for the future that is for the greater good, that brings everybody together, and inspires their best work.  Plus, pragmatically show how by working together, everybody will advance, and nobody will feel out on their own or left behind.  Not every leader is good at sharing a creative vision, but that’s what the separates the best from the rest.   This is all about generating energy and a groundswell or movement.  I always found that the better I could describe how the world will be better when we’re done, the easier it was to inspire people to join forces.  Microsoft is a tribe of smart people that want to change the world.  All I was doing was channeling that into worthy outcomes where every person could realize their potential while scaling their impact.
2. Teams – I overloaded this a bit because the main idea was to first and foremost establish a team.  A virtual team.  A coalition of the willing to change the world.  A pragmatic side of this is that I implemented a knowledge sharing platform for the team at large using Microsoft Teams.  I would sometimes describe it as a file share with social support.  I was making a couple points here.  One is that there is high value in a well organized library.  But just having a library of good information is not enough. It’s the people that bring it to life, evolve it, and use it.   And they help each other find stuff, otherwise, it’s needles in a haystack.  Without a well-organized library of reusable knowledge nuggets, the wheels on the bus go round and round, and people burn out.
3. Streams – I am a fan of sharing knowledge through videos.  I setup shows to go with our teams, and I used Microsoft Streams to do it.  Imagine having a deep library of videos where practitioners walkthrough how they actually drove digital transformation or innovation or sustainability with a customer.   The surprise is how many amazing adventures happen everyday around the world that nobody knows about, except the lone team living it.   What I tried to do here was empower the community at large to record and share videos in a simple way.   I wanted a friction free experience like TikTok, but this was a pretty good start.   Plus, it’s more about culture change to open sharing than it is about the technology.   After all, culture is the values, actions, and norms you reward.

The best thing is that I learned how to build rapid learning platforms to go into any space and advance it.

This is a skill I highly value, and it was only a few years ago when Bill Gates validated it as an approach for life.

High Performance Innovation Teams

This is my sweet spot.   Even in my earliest years at Microsoft, I focused on building high performance teams.

I didn’t focus on innovation for change sake.  I focused on innovation for goodness sake.

Any time I took on a big challenge, I first examined and explored what was not working and why.

I would then make sure that I didn’t repeat the problem, as the definition of insanity is doing the same thing and expecting different results.

First and foremost I focused on building vulnerability-based trust.  That’s the backbone of high performing teams.

Nobody goes out on a limb when somebody is busy sawing the limb off.

But I also focused on learning all different processes for building solutions as teams.

And I learned all I could about conflict management and building better teams.

Building high performance innovation teams is tough stuff, but there are amazing leaders to learn from, incredible practices, and even some amazing software know.

I’ll share a lot more on this topic in the future as I believe it’s key to the future for everyone.

Getting Results at Microsoft

Another unicorn aspect at Microsoft, was coaching colleagues to realize their potential the Agile Way.

Because I am a best-selling author and a seasoned Softie, I was often asked to present and coach teams based on my book, Getting Results the Agile Way.

In the early days, this was a lot of smaller teams of 30 or so, because of logistics.

I remember the first time I was asked to present to a group of 70 in a room, and I was asked to make it interactive.   Luckily, I had a great facilitator who helped me go around the room during exercises.

Fast forward, and just in the past couple months, I presented virtually to a group of 400+, another group of 300+, and another group of 200+.

In the past year, I’ve definitely had a lot more asks to share how Agile Results can be used for mindfulness, wellness, and mental health.

I’ve been also asked to do a lot of variations of my talk to focus on things like career growth.

So many individuals have circled back over the years to tell me how Agile Results has changed their life.

And I love learning how different individuals and teams have implemented Agile Results.

Never Stop Learning!

If you want to lead a life of wonder and amazement, then never stop learning.  When you stop learning, you start dying.

The key is to keep your fire burning strong, and to surround yourself with the people that help light you on fire.

If your light goes out, you are often just a person, book, quote, thought, video, idea away from flipping the switch back on.

And one of the best kinds of people in this lifetime… are the ones who help us shine brighter, no matter what comes our way.

Learn from everyone you know and share it with your world.

Call to Action

1. Explore the continuous career challenge–How can you give your best where you have your best to give in the service of others?
2. Pick one idea from here to explore more fully and to see how you might tap into your inner unicorn and use that to create amazing adventures for the future.  This is your chance to become a strategic unicorn, by finding your voice and adding value your uniuque way.
3. Start a journal of your favorite adventures at work and turn them into little stories, first for yourself, then share them with others either to inspire, educate, or maybe someday a song.

You Might Also Like

Innovation Hub
Amazon Leadership Principles for Innovation and Impact
The Best Advice I Got from Bill Gates About How To Live Life
How I Created Trends and Insights for Satya Nadella
How To Become an Innovator
How Satya Nadella Transformed Microsoft
Satya Nadella Quotes on Culture, Innovation, and Leadership
The Agile Innovation Framework
What is Innovation?