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About This Book
In this book, I provide detailed and prescriptive advice on how to best run an IT department. I do so with the understanding that there's more than one way to accomplish that goal. Your approach should vary based on the company's size, the company's plans, the CEO's style, and the team's strength. External factors, including the economy, the state of the market, customer demand, and advancements in technology all impact how you should lead.
Staying true to your values and beliefs is vital to being an open and honest leader. Don't read this book and then walk into the office on Monday morning a new and improved you. Continuous improvement concepts apply to our personal development as much as they do to our teams.
If your goal is to transform IT by pivoting to Agile and DevOps, you need to understand where your company is on its journey and adapt accordingly. IT leaders need to be agile with a little “a” before they can be Agile with a big “A.” You will find the Agile and Lean principles woven throughout the text. Although I am a staunch Agile advocate, this is not an Agile book.
People who know me well will be shocked to see that the word project appears in this book over 100 times. Like George Carlin's seven words you can't say on television, I have a list of words I dislike. These, in no particular order, are project, user, phase, and resource. My dislike for the word project came from my adoption of Agile and its association with Waterfall project management. However, I'm okay with the classic definition of a project: an activity with a defined start and stop. We all set out to do work, and hopefully, that work gets finished in the best way possible.
I wrote this book in plain language, making it accessible and hopefully enjoyable for non-technical readers. This book will provide insights for anyone in an IT leadership role and anyone who works closely with IT leaders. In today's digital age, that's just about everyone.
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1 Hey, What Do You Know?
When I got my first chief information officer (CIO) gig in August 2000, I had no clue what I was doing. The skills needed to get the job—charm and charisma—differed from the skills required to do the job.
Over the past 20-plus years as CIO, chief technology officer (CTO), and now chief operation officer (COO), I have learned many lessons, practices, and techniques that I have used to foster and develop three winning IT Departments. Most of these lessons didn't come easy; several came through failure, embarrassment, and trial and error.
We all know you learn terrific lessons from failure. You need to learn from your wins as well. What worked? Why did it work? Maybe you got lucky by hiring a hotshot project manager who muscled your initiative across the finish line. Perhaps you think you're winning, but you're destroying your team morale. Don't let the failure discourage you, and don't let the wins make you cocky. Remove emotions from your performance self-assessment. This isn’t personal; it’s business. You are not defined by your last project.
Build Your Skillset
An essential parenting skill is to remember when you were your kid's age. As much as the world has changed, remembering what you did, thought, and felt in middle school and high school will make you a more empathetic parent. This concept applies directly to leadership. I started as a programmer/analyst, an old term for developer. I moved my way up to senior programmer analyst, manager, senior manager, director, and then VP of applications. In each of those roles, I paid close attention to my leaders and, frankly, judged their behavior. There were some behaviors I despised, some I loved, and some I didn't understand. By remembering what it's like to be in the trenches, you'll hopefully be a better General to your troops.
If you didn't work your way up to CIO and instead came through a different path, there's still hope for you. If your path was a boarding school, Harvard, McKinsey, and now CIO (congrats, that's impressive), you must put in extra time and energy to get honest input from the rank and file. If your path to CIO was from a business function, read The Adventures of an IT Leader by Robert D. Austin.1 In that book, a functional leader complains so much about IT that the CEO puts him in charge of it. There are a lot of good insights in that book. The most important insight is understanding why the prior CIO got fired.
Technology is one part of the CIO role—albeit a small part. Five critical skills are needed to be a successful CIO:
1 People skills
2 Business expertise
3 Technical prowess
4 Project management
5 Administration
You're probably good at three or more of these, or you wouldn't have gotten the job. What's your weakest subject? Focus on rounding out your skillset in each of the areas. Put the most effort into the items you struggle with.
Grow Through Listening
As you look to improve, start by listening. Listen to your team. Listen to your peers. Seek out and listen to other CIOs. Read everything you can get your hands on. Build a network of IT leaders across your industry. Being a CIO is a lonely job. Although I use the word peers to describe the other executives in your company, they aren't peers in the sense that they can relate to your challenges. The first time I sat down and had a beer with a CIO from a similar-sized company in the same industry, I could feel the stress leave my body. I was not alone—CIOs in other companies have similar challenges. When I left retail and took a CIO role in senior living, the issues were remarkably similar.
Every company has challenges, and every CIO is struggling to balance the demands being placed on them. Seeking these conversations is not just imperative for your education; it's also good for your mental state.
I vividly remember an uncomfortable discussion with the chief supply chain officer. Let's call him Joe. Joe said to me, “Every day, we complete all of our work before we go home. If we get 10,000 orders, we stay until 10,000 orders are shipped. If we get 15,000 orders, then we work until they get shipped. IT only completes a small fraction of what I need. Imagine if we only shipped 100 orders and called it a day.” An IT Department's unique challenge is that only a tiny percentage of what is requested ever gets completed. Keeping your business partners satisfied while rarely giving them what they want is a tricky business.
A Proactive Mindset
In January 2020, mere weeks before the coronavirus pandemic utterly disrupted our world, I was promoted from CTO to COO of The Vitamin Shoppe. While I still oversee the IT Department, I am now one of its biggest customers. We're in the digital age, and all of my functions rely heavily on technology to be successful. Seeing IT from the outside changed my perspective.
As the COO, I consider every problem in our business to be my problem. When you accept that everything is your problem, you save a lot of time and energy not being defensive and pointing fingers. Can you develop this mindset without being a COO? A leader who focuses on fixing problems is a valuable asset to their organization.
We are in a changing field in changing times. A career in technology is a lifelong commitment to learning.