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- Herausgeber: John Wiley & Sons
- Kategorie: Fachliteratur
- Sprache: Englisch
Invaluable stories and lessons that will help you tackle one of the most challenging jobs in technology and business - leading transformation In Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership, Isaac Sacolick, a technology leadership expert and a former CIO and CTO, delivers a hands-on guide to help technology and business professionals at all stages of their careers acquire the skills necessary to drive transformative change. With an eye-opening collection of stories and more than 50 lessons, Sacolick gives readers a view into what goes on behind-the-scenes in leading digital transformations. From tense IT Ops conference calls to make-or-break executive meetings, Sacolick presents the challenging scenarios faced by product, technology, and data leaders and helps readers learn to lead transformations and become Digital Trailblazers. In the book you will: * Step out of your comfort zone and develop the management and leadership skills required to influence executives and win over detractors in driving technology changes * Learn how to transform experiences, lead data driven organizations, and foster high performance teams * Discover how to deliver innovation, empower agile self-organization, and evolve standard digital practices that drive culture changes in your organization A can't-miss resource for product, technology, and data leaders - from those aspiring to leadership roles through vice presidents, CIOs, CTOs, and CDOs, Digital Trailblazer delivers real-word stories and need-to-know lessons that will accelerate your technology leadership journey.
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Veröffentlichungsjahr: 2022
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Table of Contents
Cover
Praise for
Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership
Title Page
Copyright
Dedication
Preface
Acknowledgments
Chapter 1: Transitioning to Leadership: What's a Cookie?
Transformative Leadership Requires Working In and Out of the Weeds
Notes
Chapter 2: Dev: Technical Debt Is Now Your Problem
My Recipe: Creating the Perfect Bowl of Spaghetti Code
Dramatize the Mess: Getting Leadership's Buy‐In to Address Technical Debt
Bad Code in Modern Platforms: Still a Problem
Note
Chapter 3: Ops: Wearing the CEO's Diet Coke
Building an Ops Team: The Good, the Bad, and the Ugly
When a Strategic Transformation Collides with a Global Catastrophe
Chaotic World, Chaotic Leadership, and Its Organizational Impact
Notes
Chapter 4: Product Management and Architecture: Trials and Triumphs
What to Do When Asked for a Roadmap
When the Product Roadmap and Architecture Require a Hard Pivot
When You Pivot a Major Initiative, Step In and Help the Teams to Transition
How to Create a Blow‐Up Moment
Awkward Blow‐Up Moments Often Lead to Innovative Solutions
Note
Chapter 5: “That's Not Agile”: Defining Your Organization's Agile Way of Working
Bringing Agile Startup Cultures to a Large Enterprise
Not One Agile: Adapting an Agile Way of Working
Prioritizing Technical Debt—Because They Are Business Issues
Why Agile? It Connects Transformation Strategy to Execution
Notes
Chapter 6: Transforming Experiences with a Global Perspective
Why Visit India
Chapter 7: Buried in Bad Data
Avoid Bulldozing Institutional Hills as Your First Transformation
How to Find Early Data‐Driven Partners in the Marketing Department
Democratizing Data Exposes Data Quality Issues and Backbones Transformation
Notes
Chapter 8: Transformative Culture, Empathetic Teams, Diverse Leaders
Learning Team Building and Culture Without a Playbook
Fostering Empathy on Agile Teams
Developing a Digital Trailblazing Leadership Team
Notes
Chapter 9: Selling Innovation to the C‐Suite—and Reducing the Stress
Selling Innovation and Product Management Practices to the C‐Suite
Great Leaders Rally Everyone on the Vision and Acknowledge Challenges Ahead
Chapter 10: Transforming Beyond Crisis and Becoming a Digital Trailblazer
Learn Your Decision‐Making Style from Personal Transformations
Reflect on the Externally Driven Transformations That Impact Your Business
Top‐Down Business Decisions Spark Strategic Transformations
Digital Transformations Are Very Different from Strategic Transformations
Four Types of People to Influence on Your Digital Transformation Journey
Building Blocks of Digital Transformations Require One‐Page Guidelines
Successful Digital Transformations Slowly Bring More People Aboard the Journey
Notes
Epilogue
Appendix Digital Trailblazer Lessons
About the Author
Index
End User License Agreement
List of Illustrations
Chapter 4
Figure 4.1 Ronan's Roadmap Stayed on My Whiteboard for Months
Guide
Cover Page
Praise for Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership
Title Page
Copyright
Dedication
Preface
Acknowledgments
Table of Contents
Begin Reading
Epilogue
Appendix Digital Trailblazer Lessons
About the Author
Index
Wiley End User License Agreement
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Praise for Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership
“Isaac gives digital leaders a programmatic and comprehensive approach to tackling the ever‐changing challenges in digital transformation. Digital Trailblazer is the must‐go‐to playbook for not only leadership advice, but also real‐world stories on how to handle the toughest challenges in culture, process, and technology.”
—R “Ray” Wang,founder and CEO, Constellation Research, and two‐time best‐selling author, Disrupting Digital Business and Everybody Wants to Rule the World
“You'd be hard‐pressed to find another author with a closer knowledge of both IT management and the underlying technology that powers enterprises. Isaac Sacolick has been there and done that as a CIO, so his advice is hard‐bought—and thanks to his sharp writing skills, clear as a bell. Anyone involved in a transformational IT initiative would do well to read this book.”
—Eric Knorr,editor‐in‐chief, IDG
“Isaac Sacolick holds a unique vantage point in the CIO world. From individual contributor to board partner, he has seen and done it all. His latest book offers a roadmap to the opportunities and challenges of being a modern Chief Information Officer. It's a world where technology is the crucial enabler of transformation, and the CIO is a business leader first. Isaac's journey is personal, important, and offers valuable lessons to the rest of us. If you are a CIO or aspiring CIO, then read this book.”
—Michael Krigsman,publisher, CXOTalk
“Digital Trailblazer should be required reading for rising technology and business leaders. The candid stories and pragmatic lessons will help you take your career to the next level and prepare you for the many challenges you're bound to face in the future.”
—Dan Roberts,CEO, Ouellette & Associates Consulting, and Host, CIO Whisperers Podcast
“I have had the pleasure of working with Isaac for several years in his role as a leader of numerous executive‐level discussions for CIOs at the programs I run. His sessions are always the standout, must‐join piece of content at our events. His first book, Driving Digital, was a revelation, and I regularly advise my CIO clientele to treat it as a bible for digital transformation. This next installment might just be even better. Don't miss it!”
—Ross Abbott,CEO and founder, SINC USA
“If you're involved in any aspect of product development and digital transformation, you need to absorb the wide‐ranging lessons Isaac Sacolick shares in Digital Trailblazer. Having served in many leadership roles in my career—including as CEO of a fintech company—his book gave me a new understanding and appreciation for the skills it takes to effectively lead transformations.”
—Myles Suer,facilitator of Twitter #CIOChat, top CIO influencer, and eWeek Contributor
“Isaac's first book is an essential and pragmatic guide for technology leaders to drive tough, fast‐paced digital transformation; this second book is a personal journey through a decorated career that blends relatable, real‐world storytelling with that same exceptional practicality. It distills impactful lessons for everyone to adopt—from the individual contributor to the project manager all the way up to C‐level leadership. All too often in the world of business and technology, we forget about the human experience—Digital Trailblazer does an exceptional job of using human experience to teach while entertaining the reader with situations to which I'd venture to say every person in this field has had some relatable interaction.”
—Anthony Juliano,general partner and CTO, Landmark Ventures
“Isaac has found a way to share relatable experiences that are entertaining and educational. They help drive home the key skills digital transformers need to make their organizations successful.”
—Philippe Johnston,national president, CIO Association of Canada
“Isaac reveals from his own career journey the many impediments that can derail digital and data transformation initiatives, particularly within technology teams and their leaders, with the goal of offering no‐nonsense advice to drive, survive, and thrive beyond those career and project tripwires that we encounter along the way. With easy‐to‐read insights for current and future leaders, he will give you a healthy serving of advice, confidence, and lessons learned to guide your career journey to digital transformation leadership.”
—Kirk Borne,PhD, chief science officer, DataPrime
“You have in your hand (or on your screen) the most important business book you will read all year. Half memoir and half instruction manual, Digital Trailblazer is the truth you'll need to drive innovation in your workplace. I know, because I've been fortunate to have had Isaac Sacolick guide two of my teams through the digital transformation process—both with remarkable success.”
—Larry Lieberman,CEO, Mouse.org, and former COO, Charity Navigator
“It's rare to hear the real stories behind transformations. Rarely rosy—transformations almost always involve overcoming technology debt, disagreements about priorities, and other unexpected challenges that are largely impossible to plan for. Finally, someone is brave enough to show us what really goes on in executive meetings and boardrooms. Isaac Sacolick doesn't hold back in these personal stories and offers battle‐tested lessons that leaders will get great benefit from, now and in the future. This is a book I know I'll be recommending often.”
—Shelly Kramer,founding partner and lead analyst, Futurum Research
“Digital transformation is a process that will make or break a company—regardless of size or scope of that transformation. It's a scary concept for any executive or product leader starting on this journey. Isaac Sacolick takes his formidable digital transformation experience and expertise and translates that for the ‘rest of us’ who need to understand what we don't know so we can successfully lead a digital transformation of our own.”
—Kathy Greenler Sexton,CEO and publisher, Subscription Insider
“Leading digital transformations requires winning over hearts and minds. Through descriptive stories, Isaac Sacolick's Digital Trailblazer teaches emerging leaders the ins and outs of how to secure support and successfully execute new ideas—big and small. This book is a must‐read for technology and business leaders who want to encourage culture change in their organizations.”
—Jay Ferro,EVP and chief information and technology officer, Clario
“Finally, a comprehensive, 360‐degree look at what it takes to be a hugely successful transformation technologist from someone who has observed it, taught it, and done it! Digital Trailblazer provides key lessons and real outcomes that every technology leader should know to successfully drive digital transformation—everything from how to speak to a Board of Directors, when to go deep, when to listen, and when to question.”
—Adriana Karaboutis,global CIO and chief digital officer at National Grid
“As a CIO, I've long been passionate about building a talent pipeline for the next generation of transformational leaders. The honest stories and lessons in Digital Trailblazer will help rising technology and business leaders leapfrog many of the challenges they'll encounter in their careers. CIOs should assign this book to their teams to speed up their journeys and allow them to become tomorrow's leaders today.”
—Angelic Gibson,CIO, AvidXchange
“Isaac Sacolick's advice is both timely and pragmatic. His insights are not theoretical or academic but based on his years of leadership within technology and are valuable for anyone starting their career in technology or seasoned leaders looking to improve and advance their careers.”
—Jason James,CIO, Net Health
“Isaac Sacolick has a history of positive disruption. His ability to walk you through a path of breaking down barriers and driving transformation through uncompromising storytelling is as distinctive as it is informative. No matter your place on the leadership evolution, his advice through lessons and relatable content is a page turner—not just another hard‐to‐finish instructional manual—that adds actionable intelligence to anyone's toolbelt.”
—Jason T Burns Tilson,CIO
“Practical and useful advice for transformational leaders at all levels. Isaac uses stories from his many years of experience to illustrate problems and guide the reader through a series of practical learnings to help them build and develop.”
—Martin Davis,CIO and managing partner, DUNELM Associates
“What got you here isn't what'll get you there. Sacolick takes technical folks on his own leadership journey and elicits relevant lessons for making the leap from technical expert to digital leader.”
—Jonathan Feldman,CIO, coach, and columnist
“Finally, a guide to career growth from techy to top dog. Isaac's story‐led approach breaks down the imposter syndrome barrier new leaders face and imparts practical knowledge in a consumable way, saving the reader from experiencing the pain of making the same mistakes.”
—Helen Wetherley Knight,co‐founder, TechForSocialGood.ca
“Empathy is one of today's most critical leadership skills. It's a trait that can make or break any digital transformation. In Digital Trailblazer, Isaac Sacolick provides a rare, well‐rounded look into what it takes to be an empathetic leader.”
—Jo Peterson,vice president, cloud & security services, Clarify360
“Leading transformation is one of the most challenging jobs in business and technology. Isaac's book makes the journey less daunting by providing tactical advice that will be as useful in planning innovations as it is in the C‐suite. Digital Trailblazer is the mentor professionals won't know they need until they experience a similar scenario. When they inevitably do, they can recall Isaac's entertaining stories and useful lessons to deftly navigate whatever is thrown their way.”
—Robin Yeman,CTO, Catalyst Campus, and strategic board member, Project & Team
DIGITAL TRAILBLAZER
Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership
ISAAC SACOLICK
Copyright © 2022 by Isaac Sacolick. All rights reserved.
Published by John Wiley & Sons, Inc., Hoboken, New Jersey.
Published simultaneously in Canada.
No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per‐copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750‐8400, fax (978) 750‐4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748‐6011, fax (201) 748‐6008, or online at http://www.wiley.com/go/permission.
Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Further, readers should be aware that websites listed in this work may have changed or disappeared between when this work was written and when it is read. Neither the publisher nor authors shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages.
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Library of Congress Cataloging‐in‐Publication Data
Names: Sacolick, Isaac, author.
Title: Digital trailblazer : essential lessons to jumpstart transformation and accelerate your technology leadership / Isaac Sacolick.
Description: Hoboken, New Jersey : Wiley, [2022] | Includes index.
Identifiers: LCCN 2022007541 (print) | LCCN 2022007542 (ebook) | ISBN 9781119894537 (cloth) | ISBN 9781119894551 (adobe pdf) | ISBN 9781119894544 (epub)
Subjects: LCSH: Leadership. | Technological innovations.
Classification: LCC HD57.7 S226 2022 (print) | LCC HD57.7 (ebook) | DDC 658.4/092—dc23/eng/20220218
LC record available at https://lccn.loc.gov/2022007541
LC ebook record available at https://lccn.loc.gov/2022007542
Cover Design: Wiley
Cover Image: © tomertu/Shutterstock
To Michele, Ronan, Pietra, Jasper, Mom, Dad, Pam, Frank, Danny, Lisa, Allison, Langdon, Matthew, Brendan, Ilana, Jonathan, and Nova—my family's trailblazers.
In memory of Bill and Dean.
And a big thanks to all the great mentors I had during my journeys.
Preface
A storm is brewing outside, and it's a perfect metaphor for today's workshop. I'm speaking to a room filled with business leaders, technologists, and innovators who seek my outside‐in perspective on transforming their business. Some are eager to evolve their organization's digital strategies, while others are apprehensive about changing what works today.
I'm readying the group for the day's first collaborative exercise, and I need everyone's full participation. I'm on my toes, raise my hands, and shift my gaze from one leader to the next to get people's attention as I explain today’s and tomorrow's realities. Outside the conference room windows, I see the sky darken.
“I know you're working harder and faster than you've ever had to before, and your teams are out of breath,” I tell them. “You have the right instincts because the transformation initiatives you're leading are on a treadmill that must accelerate to remain competitive. What was emerging technology two years ago, for example, natural language processing, AR/VR experiences, and real‐time data processing, is becoming mainstream.
“The pace of technology change is increasing, and you must reevaluate your digital strategy and priorities. Frequently. You will always be transforming, and your organization must establish transformational practices as essential core competencies.”
I pause and look around the room. I need the message to sink in without me saying it. Today's innovations are great progress, but they will become tomorrow's legacy systems. They will need to transform again and again. The treadmill doesn't slow down, but the organization can build up the endurance to run marathons. That's why this next point is so important.
“And your business will need more transformation leaders—what I call Digital Trailblazers—who can lead teams, evolve sustainable ways of working, develop technologies as competitive differentiators, and deliver business outcomes.”
I look around the room and wait till all eyes are on me, then ask everyone a fundamental question.
“Are you ready to take on a digital transformation leadership role in your organization?”
That's the question and advice I share with product management, technology, and data leaders aspiring for greater responsibilities. You must learn to become a Digital Trailblazer. You must develop the skills to define a vision for digital transformation initiatives, lead agile teams, and evolve technology practices. I wrote this book for you to read my stories and learn the lessons that can grow your responsibilities, guide you through handling a transformation's challenges, and accelerate your career.
You've probably already had roles in digital transformations. Maybe you're a product manager and launched digital products, improved customer experiences, and delivered financial results. Perhaps you're a software developer, DevOps engineer, work in IT Ops, or are an architect who has modernized application architectures, automated workflows, or developed customer‐facing applications. You may also work in data science, DataOps, or data governance, paving your company's data‐driven journey. Or maybe you're a business leader committed to learning the more technical aspects of digital transformation.
This book serves as a guide to help you expand your skills and confidence in leading transformation initiatives. Through my collection of stories and lessons, you will see some challenging scenarios unfold without waiting for them to happen to you. In writing this book, I intend to help current and future leaders accelerate their journeys in technology leadership by giving candid accounts of how I handled transformation's challenges.
Product management, agile development, DevOps, and proactive data governance are digital transformation's building blocks. From those starting points, I hope you want to expand your skills and confidence in leading transformation initiatives that will help evolve the business model, target new markets, and deliver innovations. But it's not easy, and program managers and scrum masters must help teams collaborate, improve productivity, and deliver quality results.
I hope you are one of these high‐potential leaders—and maybe you've already experienced some of the challenges, such as addressing technical debt, getting buy‐in for data governance programs, or winning over detractors who hold on to the status quo. I'll be sharing insights around these and many other transformation leadership issues in this book.
Or maybe you're already on your leadership journey. You oversee transformation initiatives and guide multidisciplinary teams but maybe have little experience presenting to the board or the strategic leadership team. When should you create a blow‐up or shock‐and‐awe moment to help teams see opportunities from new perspectives? How do you balance innovation, self‐organizing practices, and standards to evolve your organization's way of working?
You also might be a director, a vice president, or a senior vice president and striving to one day become a CIO, CTO, or CDO (both digital and data).
When I meet people like you in any of these roles, you tell me how hard it is to just keep up with the technical skills required to be employable. And now, you're faced with new leadership challenges that are hard to learn without direct experience.
Let me share how I got here and how my journey can help you accelerate your path to becoming a Digital Trailblazer.
After studying machine learning and medical image processing in graduate school at The University of Arizona, I take a job as a software engineer at a biotechnology company where I develop algorithms to compare genetic samples. I learn the basics of developing commercial software applications, but the Wild West of building internet applications at a startup lures me to New York City, and less than two years out of graduate school, I join this media startup as their director of software development. Back then, working at an “internet company” and joining a startup is a nontraditional career path, but I have a history of taking the off‐beaten trail and just see an adventure into unchartered territory.
The founding CTO hires me to build a natural language processing engine to enable our search algorithms. We are having dinner where he tells me I won the job, then asks me if I want to hire the ex–Russian signal processing expert now cab driver sitting next to us. I do, and we go on to create the foundations of our software development lifecycle. But after a couple of years, several strategic investors come in and refinance the company. The founding CTO goes on to other opportunities, and I land the CTO job.
It's the late 1990s. I'm in my twenties and promoted to CTO of a growing and promising startup. It's still fairly uncommon to see young CTOs, but the internet is evolving from a technology tool to a disruptive business model, and it's my generation that's driving the innovation.
And now, I am the most senior technical leader in my startup and manage an office network, a colocated data center, and dozens of tech vendors. It isn't the first time I have had to figure out new technologies independently, and I am building confidence to manage the new responsibilities.
I report to the CEO and attend our board of directors meetings with highly seasoned executives. I must prove the organizational model and execute my strategy to grow the team, mature the development process, and scale the infrastructure. My responsibilities require creating multiple strategic plans and selling my strategies to colleagues, the CEO, and the board.
I'm young, cocky, and overly confident. Figuring out the technologies isn't the hard part. Managing the team has its challenges, but we're a small organization aligned to our vision. Partnering with other leaders and driving through the murky waters of growth, well, let's just say I have many hard lessons learned from the experience—and that's part of what I want to share with you.
Less than ten years later, I pivot my career and leave the world of being a CTO in startups to one leading transformation as a business unit CIO in an enterprise. Again, I am ahead of the times, a young CIO in his thirties, and entrusted to lead an organization through significant change. I go on to be a transformational CIO in three companies over the next ten years.
I had a front‐row seat to industry transformation and disruption. I watched newspapers, magazines, banks, financial service companies, nonprofits, commercial construction contractors, manufacturers, tech startups, SaaS companies, universities, and other companies struggle with transformation.
I established several best practices during this period and started blogging in 2005 to share my insights. Today, I have over 800 articles published on leading publications for IT leaders, including CIO.com, InfoWorld, The Enterpriser's Project, and my blog, Social, Agile, and Transformation.
That led to my first book, Driving Digital: The Leader's Guide to Transformation Through Technology, an Amazon bestseller. This book shares detailed best practices on agile continuous planning, product management, citizen data science, and others instrumental to the transformations I led. You might have seen me keynote, speak, or moderate panels at one of the 150 events from 2017 through 2021.
I highlight several foundational practices in my roles as a CTO in startups, a CIO in transforming businesses, and now as CEO of StarCIO, a digital transformation consulting and services company.
Many organizational leaders understand top‐down strategic planning. But transformation also requires “bottom‐up” practices, knowledge sharing, innovation, and transformation management. Businesses need the ideas, innovations, and process improvements from everyone in the company to best adjust to market changes, excel with customer experience, and digitally enable the workforce. The essential transformational practices include continuous agile planning, DevOps, product management, becoming a data‐driven organization, citizen technology capabilities, proactive data governance, hyperautomation, and culture transformation.
As I collaborate with more digital and technology leaders, it becomes apparent that as transformation grows in importance across more industries and businesses of all sizes, it is critically vital to groom new transformational leaders. My most vocal supporters are not just the CIOs, CTOs, CDOs, and product leaders but their direct reports and secondary reports. These leaders are challenged by the growing technical skill gaps, which are significant, but they also struggle with the leadership skill challenges and forming diverse leadership teams.
Let's consider how much has changed just over the last five years.
Five years ago, data scientists could get away with being data visualization experts and later learn fundamental statistics and analytics. Today, you need expertise in DataOps, predictive analytics, and machine learning. Organizations look for “full stack” software developers who can build applications from the front‐end user experience all the way through their underlying database architectures. Operational engineers must not only keep the applications, databases, and networks reliable, secure, and high performing, business leaders expect you to automate most of the infrastructure and deployment processes. Product managers can no longer just prioritize backlogs, and you must learn how to research markets, capture customer needs, develop visions, and sell business cases.
But nowhere in these expectations, development needs, and mentoring is an easy path to learn transformation leadership skills. Classroom learning isn't sufficient to help you lead diverse, agile, and innovative teams that drive transformation management and change the culture. You will encounter challenges educating colleagues on leveraging data, intuition, and listening to others when making decisions. And when detractors emerge to transformation programs, how do you sell them on the vision, quell their fears, and win over their support?
And while organizations of all sizes often offer their own leadership programs—or funding for their people to learn leadership skills through conferences and classes—there's only so much you can cover. In fact, my company, StarCIO, has workshops in digital transformation, agile planning, DevOps culture, data‐driven methods, and product management practices, and we help teams select a limited number of learning sessions to cover in any one workshop. But there are only so many stories that I can tell during a keynote, course, or workshop.
That's how the idea for this book came to me. I wanted to tell more of the stories behind my first book, Driving Digital. It's through stories that many of us learn and remember our best lessons. It is why Steve Jobs' presentations are so memorable and why TED Talks are so successful. Before we can learn from our actions, decisions, and mistakes, we learn largely through other people's experiences.
That's what I hope to do here. Each chapter is a mashup of stories from my career, and I jump back and forth in time to expose some of the key learning moments that remain relevant today. The names and characteristics have been changed, some events have been compressed, and some dialogue has been recreated. There are times when I am critical of people's behaviors and approaches—including my own. I mean no harm or disrespect to anyone and hope all will read this in the spirit of learning and improving.
Product, technology, data, and digital leadership are complex responsibilities requiring many skills, practices, and diverse perspectives. It's tough, fast, and can be unforgiving, and that's why I share some of these stories. At the end of each chapter, I conclude and share the underlying leadership lessons, and there are more than fifty transformation leadership lessons published in this book. You can also find more information about these lessons at https://www.starcio.com/digital-trailblazer/intro.
You will learn transformation leadership through your own experiences and hard lessons, but these stories and lessons will help you accelerate the journey to digital trailblazer.
Disclaimer
This book reflects the author's present recollections of experiences over time. Names and characteristics have been changed, some events have been compressed, and some dialogue has been recreated.
I'm not a frequent f‐bomber, and I don't use profanity in the course of business. But I sometimes use this language in my head when I see or feel something terribly wrong, and the younger me was more emotionally reactive to my environment. Since this book has many of my personal stories, and I share them as I felt them at the time, you'll see me use some colorful language at times.
Acknowledgments
I went outside of my comfort zone in this second book, and it's been a three‐year‐long journey. A very special thanks to Ginny Hamilton, the “Chief Feedback Officer,” editor, reader advocate, and inspiration over the last six weeks of finalizing the book. With her guidance, ten chapters of stories and lessons were transformed into the book you have today, and I hope you enjoyed and walked away with many lessons learned. Thank you, Ginny!
I want to thank the full cast of characters in Digital Trailblazer, including Adam, Alexandra, Alice, Bart, Bill, Blake, Boswell, Brian, Catherine, Charles, Clark, Craig, Daniel, Delores, Donna, Donovan, Elanor, Gracie, Henry, Hesam, Ilan, Jasper, Jerry, Johnathan, Jonah, Josh, Karina, Ken, Nagesh, Leo, Matt, Michele, Matthew, Niles, Pavel, Patrick, Phil, Pietra, Pranav, Ronan, Theresa, Warren, Wes, and Yasmine. Also thanks to many others whom I reference in the book without naming.
Thank you to everyone who contributed endorsements and quotes in the book: Ross Abbott, Kirk Borne, Jason T Burns, Martin Davis, Jonathan Feldman, Jay Ferro, Paige Francis, Angelic Gibson, Jason “JJ” James, Philippe Johnston, Anthony Juliano, Adriana Karaboutis, Helen Wetherley Knight, Eric Knorr, Shelly Kramer, Michael Krigsman, Larry Lieberman, Jo Peterson, Dan Roberts, Kathleen Greenler Sexton, Myles Suer, Kim Wales, R “Ray” Wang, and Robin Yeman.
A big thanks to several people who reviewed early versions of the book's chapters, including Michelle Fagan, Deb Gildersleeve, Roger Neal, Wendi White, and Joanna Young. Specials thanks to Sheck Cho, Leslye Davidson, Dan Roberts. Thank you to everyone at Wiley who worked on Digital Trailblazer.
I've had a great team of people to collaborate and grow with at StarCIO and want to thank Jay Cohen, Ginny Hamilton, David Morgen, Mitch Schussler Anshul Goyal, Sandy McCarron, and Liz Martinez. A very special thanks to StarCIO partners, customers, and supporters. Thank you to my friends at CIO.com, #CIOChat, Foundry, #IDGTechTalk, InfoWorld, SINC USA, nGage, CXOTalk, TechTarget, The Enterpriser's Project, DevOps.com, and Leadtail.
Thank you to all my mentors, including Adriaan Bouten, Linda Brennan, Brendan Burns, Jason T Burns, Bill Castagne, Jay Cohen, Keith Fox, Ginny Hamilton, Carter Hostelley, Sandra McCarron, Dean Kelly, Larry Lieberman, Alexa McCloughan, Mariella Montoni, and Roger Neal. Thank you to my health coaches, Brian Hollander and Nancy Regan, and to my pandemic support group, Helen Wetherley Knight and Jonathan Landon,
Most important, I also want to thank my family trailblazers: Michele, Ronan, Pietra, Jasper, Mom, Dad, Pam, Frank, Danny, Lisa, Allison, Langdon, Matthew, Brendan, Ilana, Jonathan, and Nova.
Chapter 1Transitioning to Leadership: What's a Cookie?
“Fuck.”
That's exactly how I feel today. I am the first one in the office, and getting in early before the crack of dawn is not something I do very often. The last software build failed, and I have to get it working before everyone gets here. Especially before Jessie gets in. Because once Jessie sees the problem du jour, well then, my day is freaking over.
I make a small change and start another software build. It's dark outside. Way too early to be here. I can't believe I started working on this problem before my first cup. But now, I have ten minutes to wait for this build to compile the code into runnable software. Plenty of time to fill the carafe and get a coffee drip going. Enough time to consider what music I will select to keep me inspired and moving. Maybe today it will be the new System of a Down CD because, well, I'm just in that head‐banging mood. If I was more at peace, I might put on Pavarotti. Anything to help my concentration.
I think about how the rest of this difficult day will go. There's the 10 a.m. management meeting that I loathe attending, and I ponder how to best prepare for it. What should I report to the other leaders? Should I start with the root cause of the last issue—like I really have a freaking clue what it is—or should I focus on the status of this crazy important, better‐hit‐the‐deadline, our‐business‐depends‐on‐it project that we're all working on?
What will the managers ask me this time? Probably the same things they always do. They almost always start by asking, “How's it going?” Then they get bolder. “When will the application be completed? Does it run fast enough? Do we have to buy more hardware? Did you hire another developer yet?”
I feel like the lead physician at a hospital that's in the middle of experimental surgery. No one quite understands what's going on, but they know the procedure is important. From their vantage point, if the tech works, then they can go back to their day‐to‐day business. So, the last thing I want is to make them nervous. That'll disrupt the meeting and get them solutioning. If they panic, they'll run around the office like chickens with their heads cut off, barking orders at everyone. That's the last thing I want.
This is how leadership meetings run every week, and as the coffee drips, I contemplate what happens to me during them. Why is it that everyone's eyes are always on me? And why is it that we're always talking about the underlying technology? Why aren't we talking about what we're selling, what customers we're winning, and why we're losing business? Why aren't we going over the financials to be ready for the next board meeting? What the hell are we getting out of all the money we're spending on marketing?
Most important, how do I answer questions that appease my colleagues? I can't shut down their questions, or they'll claim that I am not a team player and am being technically incomprehensible. But if I give them too much information, they'll dig deeper into the technical details. Their objective is to deflect the conversation off their areas of responsibility and onto another business area. Tech has a target on its back, and me being the youngest in the room makes that target sizeable and easy to hit.
Jessie is sure to zing me on something. She asks for twelve things. I commit to seven and deliver nine. Nope, that's not fucking good enough. She must deal with the salespeople who want the missing three that she should have said no to in the first place. She has incredible skills at navigating these meetings and sits next to the most influential leaders. She only shares the good news, and with such elaborate flare, it gets everyone raving. It's not just what she asks; it's when and how she goes about it. She picks the perfect time and gets everyone's attention. Her question missile is laser‐guided and almost always aims at me, and I stand no chance. Especially when there are operational issues.
I'm too young, inexperienced, and not very confident. The 27‐year‐old chief technology officer (CTO) working at a pre‐internet‐bubble startup is easy pickings when the business isn't moving fast enough. And when the company is doing well, and we're signing up new customers, well then I'm the last in line to get a shitty bonus. Cheers for Sales! Marketing are heroes!
And where is Tech?
Where are the high‐fives for the developers, testers, and systems engineers for a job well done? How come no one applauds the product managers for picking the right features or cheers the data analysts who quickly produced the new reporting dashboard?
I get it. The way they see it, there's always something broken, something slow, or something new that at least one executive team member expects. After a release, it always feels like we're out of the kitchen and into the fire.
And then that's when I hear that happy, whirling, swishing sound, bringing me back to the here and now.
Fabulous, the coffee is ready, and I pour myself a mug. Black. Just like in engineering school when we were studying for midterms. Some of those classes are still useful. The statistics, the physics, and the signal processing classes, but there was no way that the antenna theory class would ever be valuable. Why the hell was that a required class? Waste of my damn time. A communications, writing, or marketing class would have been far more useful.
I walk back to my desk, thinking about some of the lessons learned from my grad school days through today: the mistakes I made in pursuing overly elegant technology solutions, debating what should go into minimally viable products (MVPs), the collaboration skills needed to lead agile teams, and how to understand the business through its data. These are lessons people driving transformation need to know, learn, and adapt to their circumstances. And maybe, one day, I will share them with my teams and teach other leaders.
I look at my screen; thank goodness the build is done. Whenever I make a code change, I have to build the software to test it. It's one of those things Jessie and the others don't understand about developing software. I don't just code. I also have to deal with all the infrastructure that makes software run. It's the late 1990s, and as the internet is starting to boom, this means managing the complexities of running a data center, adding servers, and scaling networks. It requires the webserver software and the integration necessary to run the website. And on this day, it means packaging the software to integrate, deploy, and run within the server. This all takes time away from developing the bells and whistles that Jessie and others have on their mile‐long list of requirements.
Today I'm trying to debug this nasty defect. How is it that two users can log into the same account, one being the real account owner and the second one getting access illegitimately? It's not their fault, and I've already determined that this isn't someone trying to hack into our login system. This is a software defect, and I have to figure out how two different people using two separate computers and browsers can access the same account.
I think about the problem from a technical perspective. We use cookies to remember the user, and that's the first thing the application checks to match a user to their account. Cookies. Who the hell came up with that term anyway?
I'm trying to focus on the problem, but thinking of the meaning of browser cookies brings me back to another time and place.
Six months ago, I was sitting in one of my first board meetings at the Conde Nast building in New York City. It's brand‐new on 42nd Street in the heart of Manhattan, and an architectural standout, especially for Times Square. Just hours earlier, we meet Craig for breakfast in their expansive cafeteria that could live up to Gourmet magazine's high standards. Craig is an important board member and a member of “the family” that controls one of the largest media empires. I'm with our chief executive officer (CEO) previewing the primary news and decision points, and we hope Craig will help steer the discussions.
After breakfast, we ride the elevator to the top floor and start our first board meeting after the new round of investment. I'm sitting at the biggest freaking table I have ever seen. There's no way to reach across this table to shake someone's hand, and the room reminds me of the boardroom scene in the movie Gung Ho. In the movie, Michael Keaton's character asks his Japanese hosts, “Did you decorate this place yourself?” It's meant to be an ice‐breaker, but it doesn't connect with the board and winds up being a disastrous way to start the presentation. I fully expect Brian, our CEO, who is sitting a few seats over from me, to pull out his death stare if I say the wrong thing.
We're working with hundreds of media websites. They publish newspapers, and we help bring their content and data to life on the World Wide Web. It's 1999, and the boom of the internet is in high gear—with nearly 250 million people logging onto it.1 Napster is growing in popularity, eBay has gone public, and Craigslist incorporates as a for‐profit business.
Our board, owners of thousands of newspapers, are antsy but not worried. They have been around a long time and weathered many storms. This internet thing is just another phase for them. Remember Compuserve and Prodigy? Blips in technology history. People won't abandon their local newspapers and the trust built up from reading the paper daily and weekly over generations.
So they thought.
Daniel, our ad sales leader, is explaining his new product concept, describing how we're going to put ads across all the newspaper websites. Everyone on the board is looking at him like he's Marie Curie trying to explain how she discovered polonium and radium.
The obvious question should have been, “How are you going to get those ads on our websites?” But no, one of our more technical board members is one step ahead and asks, “How are you going to track impressions and click‐throughs across all of our websites?” To which Daniel replies, “Oh, we'll cookie the user.”
That draws a moment of silence, and then Craig, who is usually quiet during these meetings, lifts his head from looking at the printout of the board presentation and asks, “What's a cookie?”
Instinctively, they all know to look at me. It's the executive radar that pops up when someone talks tech jargon at a business meeting.
I should point out that if I, as the chief technology officer (CTO), had used some form of tech terminology, then their radar would have triggered a devastating verbal missile attack. No one wants the CTO to go deep into technobabble or use overly complex buzzwords that would never appear in a business magazine. If I do such a thing, Brian would wait until after the meeting and give me more than an earful for dropping jargon and making the technology sound unnecessarily complicated.
Even worse is when a board member raises the issue with the CEO about having a CTO who can't talk “the language of the business.” One missed word can launch an entire cycle of having to defend yourself from the barrage of MBA‐fired warheads who want to monopolize the jargon and make sure it's their language that dominates the conversation.
Okay, so all eyes are on me. Now, if I were a little more experienced, then I probably wouldn't have been panic‐stricken inside. My first “real” board meeting, and I'm asked an off‐script question. And not just any question, but a somewhat technical one that is hard to answer without knowing how web browsers and web servers work. Eyes begin to look in my direction as I catch a glaze from Brian sending me a clear message.
He is saying, “This one is on you. And you better not fuck it up.”
So, should I respond with the technically correct answer? “A cookie is a key value that a developer can store in the web browser's cache by utilizing the set‐cookie header and then retrieving it on subsequent page views. Since web browsers are stateless clients that interface with a web server, setting a cookie is an easy way to retain the state from one page view to another and is commonly used to store user and session identifiers. The browser is smart enough to send cookies only from the domain of the web page the user is viewing.”
Yeah, that would have been the right technical answer. In fact, I think the technology team back at the office would have been proud of how I explained a technical concept in such efficient language. But if I answered the question that way to the board of directors, I would be shown the virtual elevator down to the CTO morgue. That is where geeks with ties go when they can't explain technical concepts in simple language.
Here's how I actually answer the question: “A cookie is an identifier. We can track the ad across multiple websites by setting this identifier and having it sent back to our website even if the ad is on your newspaper's website.”
I get a look back from Craig. It probably lasts for only three seconds, but it feels like an eternity. In the corner of my eye, I can see Brian's “oh, shit” face, fearing that we're going to take the meeting off the rails. Two days earlier, when we rehearsed the presentation at the senior leadership team meeting, he kept repeating to us, “We need to get these guys on board,” and yes, the board was all men. And then he reminded us how dumbed‐down we must make everything.
Craig opens his mouth and looks like he is getting ready to fire off another question. But his head turns, and he looks back over at Daniel to ask, “How do we make money doing this?” It's the right question and why I respect Craig.
Most important, I pass my first test.
And this is how I know the coffee I'm drinking today hasn't set in. I'm moving from one thought to the next. This problem is hard enough, and I need a clue before we meet this morning.
