You’ve been at this leadership game for a long time. You’re good at it. Some days are great, some filled with anxiety, some are spent staring out the window of the platinum member airport lounge wondering what it’s all about. What will be your mark on the world? Then you remember how you got here. All the people who depend on your leadership to keep the company lights on and the paychecks coming. Your staff hopefully admires you. That newly minted MBA thinks you’re a walking Harvard Business Review case on mastering the art of reorganization, and the Sales teams demand that your administrative assistant block time on your calendar for every prospective customer demo day. Yeah, life is good. Life was good.

Until that first-quarter strategy retreat.

Your business model has been upended. You’re going to need to become a software-driven enterprise. To get there, you’re going to lead a four-year, hundred-million-dollar “digital transformation” program to bring delight to the customer experience. And HR has been told that everyone in the organization—everyone—will learn how to code and focus on automation. Everyone is now a software engineer. This may sound strange to some, but the day of the citizen technologist is here.

You may know little to nothing about managing software engineers, software projects, software vendors, software integration, or software as a service. Even if you do and have managed the complexities of delivering and maintaining your current applications for a long time…well, those times are changing. Cloud, SaaS, disruptive business models, and changing workforce dynamics have all served to put pressure on your current business.

Take heart though, because you do know business. You know your business. It’s changing, yes, but it’s still your life’s work and no startup or webscale giant can take that away from you. You know that mediocrity can never be tolerated, and you know that inefficiencies lead to disruption. And you know yourself. And you know that you’re willing to learn.

All we ask is that you keep an open mind as we take you on our journey in digital transformation. We hope to show you the “other side of the test,” the playbook from a competitor, or at least some real-world insight from the disruptive technologist perspective.

We know software engineering. We know software engineers. We know digital transformation. Both its power and its suffocating effects. We know software can be a dirty, ugly, gut-wrenching business. But we also know that software can bring big data, agile processes, bleeding-edge technology, lights-out automation, ideation, and innovation all to life.

This book presents a new perspective on agile leadership principles, from presenting vision and authenticity to building trust and creativity and positivity geared toward: (1) a digital workforce that either grew up in a Cloud-based, crowd-sourced, work-life balancing act; (2) the traditional systems engineers who already have answers to the problems that you haven’t even posed to them; (3) the other leaders in your organization who will drag you into cross-functional KPI setting; and (4) IT consultants with pre-ordained technology solutions, abstract of any clear strategy setting.

We will then attempt to demonstrate how these agile leadership principles can be applied, particularly in how you look at making judgments, across the business, technology, and people domains. The software game is filled with imprecision, moving targets, competing interests, security threats, and the inevitable, sometimes inexplicable setbacks and failures that serve to have every decision you make ripe for scrutiny, or perhaps utter disdain. We will look at how deep thinking can mitigate organizational doubt with strong vision-setting, well-researched industry points of view, and stake-in-the-ground portfolio innovation and execution.

Putting these principles to work is the ultimate goal of this book. More than preaching theory, we hope to impart the courage to try these principles in your own organization, by describing case studies where they have been successfully applied, and also by developing potential use cases that your organization might face, in light of current digital transformation strategies and connective technologies emerging across market sectors.

Lastly, we know that good leaders need to challenge themselves, personally—to dig deep, if you will. At some point, you need to have the conviction to set and stick to your plan. To know when to challenge the dogma, resolve conflicts, and when to just let it go. And to take comfort that you’re not alone. Your friends on the golf course are all facing similar challenges—whether it’s a friend in automotive manufacturing, who needs to see a car as a hundred million lines of code on four wheels; or a retailer who needs to find a way to make shopping as rewarding as clicking; or the cable company that doesn’t understand why millennials don’t want to “subscribe” to anything.

This book will help you face the angst of digital transformation, with the courage to get out of your comfort zones. Close the laptop. Pick up a dry erase marker. Manage by walking around. Compete. Respect the weeds that find a way to survive.