I got to experience the culture of three very different CEOs at Microsoft.

In 1993, my very first project was to modernize our IT systems off our legacy DEC VAX and IBM AS400 environment. We picked SAP as the software package to implement on a Windows Server environment. In those days, a project of this magnitude had to be approved by Bill Gates directly.

The approval meeting only lasted a few minutes because Bill looked ahead in the deck we passed out, and before we’d really begun the meeting he said, “Wait a minute. Millions of dollars to implement a software package? Are you serious?”

His exact words were more colorful, but he killed the project. Fortunately, we were empowered to rethink our strategy, allowing us to implement SAP in smaller projects that paid for themselves as we went, and to go faster than a big bang effort. Lessons like this started to change how I approached IT, but change was slow.

With Steve Ballmer as CEO the company continued to grow, but the culture changed and became more siloed since all major decisions did not have to go through Bill. I remember a customer experience meeting we had with Steve, where he was visibly frustrated that he couldn’t immediately solve cross product customer issues we raised. He wanted to, but he would have needed to override the priorities he’d set for separate product teams.

I watched Satya Nadella learn from the different cultures under Bill and Steve. When he took the reins as CEO, he took the best of both and added his own magic to inspire everyone to want to work together.

I realized from watching how Satya drove his company-wide transformation, that I was also fighting culture. Historic thinking about IT, both inside my organization and how we interacted with the rest of the company, was bogging down the change I was pushing.

In addition to the mindset change, we needed to strengthen some people skills. We had tried learning how to collaborate better as a company, and I was struggling with this in my own organization. As we tried to transform the old Microsoft traits into new, there were a lot of people who liked the sounds of what Satya was evangelizing: changing from knowers to learners, from trying to prove that you are the smartest, to trying to understand what our customers need and to be curious about diverse perspectives. But it wasn’t easy and there were missteps as people learned.

Some people would call you out for not collaborating if you didn’t agree with them. Or on the other extreme, people became so respectful that they avoided difficult discussions. I learned that collaboration requires both working respectfully and achieving a positive outcome together. To make progress quickly we could never avoid the discussions that needed to be resolved, but how they were addressed was important. These were skills we needed to improve, but the culture had to support the change, and no longer value the old ways. Without the purposeful drive to change culture, we could have never made as much progress.

When I was asked to be CIO at Microsoft in 2013, I knew I had a daunting task ahead of me. A CEO transition to Satya Nadella and acquisitions of Nokia and LinkedIn were just the tip of the iceberg. Historic IT mindsets were slowing us down at a time we needed speed. Legacy systems and processes seemed to have a mind of their own. I asked my team for help in accelerating everything we were trying to do -- some people embraced the opportunity, and others resisted. We broke some things, made mistakes, but we learned. After eventually making considerable progress including transforming how we worked and migrating almost everything we ran to a public cloud, I found myself looking back at everything we figured out and wishing I could take all the lessons and start over. We could go so much faster with far fewer missteps, and be further along on the journey with less churn. Since I couldn’t actually start over, I decided I could at least write down some of the biggest lessons for others, which led to me writing a book.

I determined that if I was going to write about the journey to fast and modern, I couldn’t use one of the old-fashioned publishing companies. One publisher that reached out to me had a very modern appeal. Pacelli Publishing offers the normal services an author expects around editing, cover art, and publicity, but also offers what you should expect in a digitally transformed world. When someone orders my book online, it prints on-demand and ships in the same amount of time we’ve all come to expect in ordering from Amazon. This Print on-Demand model means we don’t need to pay for and hold a large inventory of books. Pacelli can do this because they built their business model on top of the Amazon self-publishing service. I suspect this service from Amazon is simple, but they took care of everything for me to make it a seamless experience.

Another reason I picked Pacelli Publishing was the brand and IP they built around a series called Six-Word Lessons. It was a good format for documenting the lessons I wanted to share. They have already published more than 30 books in the series and it fit with the book I wanted to write. The Six-Word Lessons brand focuses on the importance (and difficulty) of being concise rather than wordy. In their template, every lesson needed to be exactly 6 words, accompanied by less than a page in large font to explain the lesson. It forced me, in a good way, to refine the lessons down to the real meat.

I discovered through the process of working with this modern publisher that there is a lot more in what they are doing that I think will be disruptive to the old school print publishing industry. They were open to new ideas, and we worked on them iteratively together. They were very agile with changes, and provide a better margin to authors through the efficiency and low overhead they can provide on top of the Amazon service. Their update process is also amazing.

A couple of weeks ago while presenting at an MIT event for their Center for Information Systems Research, I was talking to one of their professors who was also writing a book. We were planning to finish writing our books about the same time. He said his book was scheduled to come out early next spring, and was surprised when I said my book would be out in a couple of weeks. He then acknowledged frustration with the current publishing industry especially as I explained our process to make updates. With Pacelli Publishing and Amazon not only can I take advantage of the Print on-Demand capability with Amazon’s CreateSpace, but the process to make an update is simple. While the professor told me it was almost an act of God for him to get an update made after release, all I have to do with Pacelli Publishing is make the change and have them upload a new master. Every book after that is fixed. This is real digital transformation in action.

My book is available on Amazon now, although we are still finalizing wording for endorsements that will go in the white space on www.6wordlessons.com/jim over the next several days.

I’ll add a link to the MIT study on data driven cultures I was presenting with MIT principal research scientist Barbara Wixom as soon as it is available.

Jim DuBois is the former CIO of Microsoft and a highly sought speaker and advisor to the world's largest companies.  He is the author of Six-Word Lessons to Think Like a Modern-Day CIO.

About the Six-Word Lessons Series
 Legend has it that Ernest Hemingway was challenged to write a story using only six words. He responded with the story, “For sale: baby shoes, never worn.” The story tickles the imagination. Why were the shoes never worn? The answers are left up to the reader’s imagination.

This style of writing has a number of aliases: postcard fiction, flash fiction, and micro fiction. Lonnie Pacelli was introduced to this concept in 2009 by a friend, and started thinking about how this extreme brevity could apply to today’s communication culture of text messages, tweets and Facebook posts. He wrote the first book, Six-Word Lessons for Project Managers, then started helping other authors write and publish their own books in the series.

The books all have six-word chapters with six-word lesson titles, each followed by a one-page description. They can be written by entrepreneurs who want to promote their businesses, or anyone with a message to share.
 
See the entire Six-Word Lessons Series at 6wordlessons.com

Excerpted from Six-Word Lessons to Think Like a Modern-Day CIO.

In early 2013, I was just returning to my office at the Microsoft Redmond campus, when my phone rang. It was Kevin Turner’s administrative assistant. At the time, about half the employees at Microsoft reported up to Kevin, and it was not normal to get time with him.

I heard, “Jim, can you come to Kevin’s office right now?”

I answered, “Of course,” like I could have answered differently, but then I added, “Can you tell me why?”

A pause inspired a thrill of panic in me, “He will tell you when you get here.” I won’t try to explain all that went through my head on the way over to Kevin’s office.

I soon discovered that our CIO, Tony Scott, had decided to leave the company to take care of a family situation. Kevin told me that he wanted me to play the interim CIO while they conducted a search for the best person for the job.

Suddenly, my peers worked for me. Kind of. Temporarily. Scarily. Fortunately, I didn’t want the job. My next career goal was to go back into the product groups. So, I pulled my peers together and asked their permission to play the role. I said we couldn’t afford to lose the momentum we’d started. The company couldn’t afford for us to pause while they found us a new leader. We determined to accelerate our progress, so we could better set up our new leader when that someone was found. We drove a new mantra, “Create tomorrow, deliver today,” recognizing it had to be both simultaneously. I got to evangelize a new narrative to the organization, starting with many beliefs that had to change.

Seven months later, after exhausting other options and seeing our material progress, I was asked to take on the official CIO title without the word “interim.” I was too invested to say no, and could now start making bigger changes, giving the team permission to break some more old norms.

Jim DuBois is the former CIO of Microsoft and a highly sought speaker and advisor to the world's largest companies.  He is the author of Six-Word Lessons to Think Like a Modern-Day CIO.