Six-Word Lessons to Think Like a Modern-Day CIO Read online

  Six-Word Lessons to

  THINK LIKE A MODERN-DAY CIO

  100 Lessons CIOs and Tech Leaders Must Embrace to Drive Business Velocity

  Jim DuBois

  Former Microsoft CIO

  Published by Pacelli Publishing

  Bellevue, Washington

  Published by Pacelli Publishing at kindle

  Copyright © 2017 by Jim DuBois

  kindle Edition, License Notes

  This ebook is licensed for your personal enjoyment only. This ebook may not be re-sold or given away to other people. If you would like to share this book with another person, please purchase an additional copy for each person. If you’re reading this book and did not purchase it, or it was not purchased for your use only, then please return to Amazon.com and purchase your own copy. Thank you for respecting the hard work of this author.

  Limit of Liability: While the author and the publisher have used their best efforts in preparing this book, they make no representation or warranties with respect to accuracy or completeness of the content of this book. The advice and strategies contained herein may not be suitable for your situation. Consult with a professional when appropriate.

  Cover image by Pixabay.com

  Contents

  Introduction

  Build a Culture Supportive of Change

  Build a Clear and Evolving Vision

  Empower Teams to Deliver the Vision

  Debunk the Myths Holding You Back

  Move to the Public Cloud Faster

  Modernize Legacy Practices to Simplify Acceleration

  Transformation is Measured by Business Success

  Accelerate Without Sacrificing Security and Compliance

  Optimism and Persistence are Force Multipliers

  It is All About the People

  Acknowledgements

  About the Six-Word Lessons Series

  Introduction

  When I was asked to be CIO at Microsoft in 2013, I knew I had a daunting task ahead of me, but I had no idea of the radical change that was about to hit. A CEO transition and acquisitions of Nokia and LinkedIn were just the tip of the iceberg. Historic IT mindsets were slowing us down at a time when we needed speed. Legacy systems and processes seemed to have a mind of their own. I asked my team for help in accelerating all we needed to do--some people embraced the opportunity, and others resisted. We broke some things, made mistakes, but we learned. After eventually making considerable progress over a few years, I found myself looking back at everything we figured out. I wished I could take the lessons and start over. I could go so much faster with far fewer missteps, and get further along on the journey with less churn.

  Given that starting over wasn’t realistic, I decided I could at least write down some of the biggest lessons for others, starting with this book. If the world around us was static, you would not need many of these lessons. Unfortunately, or maybe fortunately, our world today is evolving faster than ever. You can no longer work the way we were taught in school or by our predecessors. You can help others around you realize this, or wait for someone else to step up. Regardless of where you are in your organization, you can play a leadership role. We need to break some rules and change how we approach our mission to accelerate the pace and help our businesses transform. Just working smarter is not enough. We need to work differently to accomplish this while still having a good balance to our lives.

  Most of the lessons in this book are drawn from mistakes I made and had to figure out along the way. I didn’t always have the answer when we got stuck, but drove forward without giving up until we succeeded. Sometimes the answers came from reading or listening to peers who were also experimenting, and sometimes we had to make it up ourselves. Always driving forward helped us improve. I did get a lot wrong, sometimes dramatically, but we would not have made as much progress if we hadn’t tried and learned. In striving to bring more people along with me, I know there were times I didn’t make decisions fast enough. But we had to keep going.

  With the aspirations Microsoft had to scale, with the target we became for security attacks, and with the agility our business needed to innovate, we had to go beyond industry best practices and find new ways of working. We were compelled to adopt from companies born in the cloud, invent approaches that hadn’t been tried before, and apply these lessons to a very large enterprise with significant legacy systems and processes. With every step, including long before I became CIO, I had leaders who challenged me to think beyond what I believed was possible, to move faster than I thought was safe. If you are not feeling pushed, find a mentor who will push you out of your comfort zone.

  I believe that what we learned applies to any team trying to transform, whether that team is large or small, inside formal IT boundaries or within a department of an organization outside IT. I hope these lessons give you ideas, allowing you to accomplish everything you need, and accomplish it faster, in a world that demands speed to thrive.

  The Accelerating Pace of Change

  In January of 2016, the World Economic Forum announced that we were entering the 4th Industrial Revolution. I was at first confused about the difference between this 4th revolution (blurring the lines between physical and digital) and the 3rd Industrial Revolution (electronics, IT, automated production). Looking closer at the document, I discovered the highlight of two main differences: the accelerated pace of change, and the level of disruption from real transformation.

  It is barely over 10 years since the first iPhone was released and the start of the first app store. It is hard to imagine a world without smartphones now. It is also barely over 20 years since the internet became useful. Do a search for the Bill Gates Internet Tidal Wave memo from the mid-90s. He wrote to execs at Microsoft suggesting they try this new thing called the internet, that they look at sites like Yahoo where you could search for content, and look at sites that were starting to provide online views of their products, pointing to three companies that don’t even exist anymore.

  How much have our lives changed in just 10 to 20 years? If the pace of change is accelerating, shouldn’t we expect at least that much change again over the next 5 to 10 years? How can we prepare ourselves and our companies for that amount of change?

  We are already seeing the acceleration of disruption. Very few of the most valuable companies today even existed when I was born. And new companies are disrupting every day. Consider the largest hotel chain in the world today measured by the number of rooms to book: Airbnb. How long did it take them to get there? Nowhere near as long as the legacy hotel chains.

  Will we adapt and drive success, or will our companies or industries become the next to be disrupted? What do we need to do? I believe that the lessons here can help set you up to take on this challenge. Some of the lessons you have heard before, but the reminder is useful. Many other lessons were from my own learnings, reinforced from my industry peers.

  Every company today is talking about transforming. Some are really doing it. Transformation isn’t about making IT go faster. It is about real business transformation, enabled by changing how we work everywhere, including IT, so we can effectively work at the new place of change.

  How do we do that? I hope you discover ideas you can adopt in these lessons.

  Chapter One

  Build a Culture That Supports Change

  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 approv
ed 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 likely allowed us 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 he couldn’t immediately solve cross-product customer issues we raised. He wanted to, but 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 immediately added his own magic to inspire everyone to want to work together. I realized from watching how Satya set about to drive a 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 to support Satya. 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.

  1

  Culture does eat strategy for breakfast.

  I learned from Satya Nadella that culture really is more important than strategy, or vision, or any of the other things taught in business school. I intentionally start with this lesson because it is the foundation for everything else. If the culture in your organization loves the status quo and does not like making material changes quickly, the culture will fight against the changes you are trying to make and will slow everything down. Spend time on purposefully defining and building the culture and values you need.

  2

  The future belongs to the fast.

  I’ve heard this repeated often in the last few years, and determined that I did not want to be left behind. I learned to bring my team along, leveraging those who were ready, and helping the rest understand that the new faster pace is not going to slow down. Our faster pace is the new normal. Companies cannot thrive by operating like they did in the past. Team culture needs to embrace the transformation and accept the changes in order to thrive in the modern world.

  3

  Adopt startup lessons. Experiment. Fail fast.

  Speed requires working differently. Startup cultures don’t figure everything out before they begin. We can learn from them. Create a hypothesis for how you can accelerate progress. Define how to measure it. Conduct experiments, and stop quickly if the experiment isn’t helpful. Learn and adjust to make progress. Leverage the results and ideas from everyone on the team to make more progress. This is a significant culture change from yesterday’s IT.

  4

  Be fast, but don’t hurry (plan).

  If you never fail, you probably aren’t going fast enough, but you still need to plan. In fact planning might be even more important when you go fast, but plans must now be flexible to change as you learn. Fast comes with more risk, which you accept by better managing the risk. Create excellent contingency plans. Create urgency. Go fast, but make sure you can detect failure early and recover quickly. How you respond to failure will change your team’s behavior. Encourage risk-taking by celebrating the learning from any failure.

  5

  Insist your culture supports data-driven decisions.

  Create a culture where everyone expects to need data to support any decision. Take opinion, and the corresponding needless debate, out of decision-making to eliminate wasting time. If there isn’t clear data, do an experiment rather than attempt a lasting decision, but don’t wait. Appreciate collecting data even where you aren’t positive of its value yet. Teams will learn new value as they apply data to decisions and experiments. As Peter Drucker said, “You can’t improve what you can’t measure.”

  6

  Value growth mindsets over fixed mindsets.

  Everyone wanting to modernize should read Carol Dweck’s book Mindset. She explains the difference between growth mindsets (always seeking to learn and improve) over fixed mindsets (knowing the ways things have always worked). Everyone has some of both. Cultivate more of a growth mindset as critical to your new culture and future. Tear down the barriers of the past. Be curious. Accelerate your learning.

  7

  Ensure your culture supports healthy escalations.

  People should not feel like they failed if they need to escalate. Healthy environments move fast by rapidly determining when an issue won’t be resolved right away. All parties agree to escalate together to get leader input. All points of view are included in the escalation. Healthy is undermined if one side escalates alone. Success is not getting your way. Success is moving forward.

  8

  Promote communication. Build psychologically safe environments.

  Healthy escalations help cultivate safe environments where people are encouraged to speak up. To go fast, you must break down historical hierarchies and communication blockers. If employees feel safe, you will get the best ideas, questions for clarity, and criticisms that help you improve. Criticism is a gift. Don’t be defensive. Use it to improve.

  9

  Help everyone be their best selves.

  Culture change takes time, but happens faster when everyone really wants it. Make sure you advocate for a culture that people desire. A healthy culture listens for all opinions and points of view, feels inclusive and respectful, and values learning over knowing. It craves self-actualization, individuality, and inclusivity, allowing everyone to leverage their strengths to make a meaningful impact in the world.

  10

  Real culture change begins with you.

  Leaders go first. When actions of leaders do not support the culture you want, bottom-up change is hard. Leaders must model the desired culture, and help other leaders do the same. Rethink all the ways you recognize employees and make sure they reinforce the new culture. Explain the culture to the whole organization, and all stakeholders. Reinforcing old behaviors will stall the adoption of the new culture. Engage those willing to accelerate the change and those waiting to see progress will join faster.

  Chapter Two

  Build a Clear and Evolving Vision

  For my first three years as CIO, I reported to Kevin Turner. What I most valued from Kevin, even when I didn’t like it, was his ability to drive clarity around what success looked like. At times, I didn’t feel his vision for success was even possible, and in those times Kevin would ask me if I’d rather aim low and be safe. I knew the answer was no. I don’t think we would have made the same progress without people like Kevin pushing us to be better.
/>   Kevin loved defining a clear vision of success. I know he valued learning because as we transformed, his vision evolved. Kevin had a support staff, trying to optimize his more than 50,000-person organization in over 100 countries. They helped make sure the rest of us didn’t stray too far outside the lines, and did it so effectively that many people didn’t realize that Kevin completely empowered us to achieve the vision. Kevin told us that Satya was helping him learn to drive accountability with more empathy, but it didn’t diminish Kevin’s passion around driving for success. He was clear on the difference between activity and outcomes. Outcomes are steps toward the vision. Unless you are driving real learning, activities without results are only excuses. Kevin would say, “If you are justifying, you are losing.”

  If we encountered a disaster somewhere in the world, Kevin would tell us to “never waste a crisis.” Leverage it to make progress. In the face of ambiguity, he would say to “be bold, and be right.” I later understood he meant be right as much as possible, because when something didn’t work, Kevin would remind me that at our pace, it was impossible to always be right. He would tell me it was more important to recover quickly and keep making measurable progress toward the vision. When Kevin eventually decided to leave Microsoft, while it may have actually helped Satya’s transformation because having half the company report to one person was starting to slow us down, we definitely did miss Kevin’s ability to drive clarity around real success.