Somehow we’ve convinced our leaders that they need to have all the answers. We’ve elevated company leadership to an almost mythological state of knowing everything and never making mistakes. The reality is that all leaders, including product and website design leaders, are just as confused as everyone else. They make mistakes. They screw up. They make things up along the way. They forget lessons and lose direction. In surveys for this book, almost 50% of design leaders said they are merely “reasonable leaders and still have tons to learn,” and only 13% consider themselves to be “very good” leaders. Considering that these are the people in charge of the top design companies in North America, it’s confirmation that even the smartest and most experienced leaders struggle with the challenges of leadership.
This book was written partly out of personal frustration and partly because there’s a lot of misunderstanding about what design leadership means. Leading a successful digital design organization is confusing and challenging. There’s no definitive manual or guidebook. The unhealthy perception that leaders have all the answers makes leaders less likely to ask for help. That’s a perception that can only lead to disappointment for both the leaders and those who look to them for direction. Design leaders need better guidance and insight. This book aims to provide some of that knowledge.
I’m one of those confused design leaders. I’ve been an entrepreneur in the tech and digital design space for most of my adult life. That’s about 20 years, in case you’re wondering. In that time, I’ve learned the hard way that nobody has all the answers. I’ve also learned that as a leader, you can either find the answers through trial and error or you can go directly to the source. I prefer going to the source. If you want to know how to be a great design leader, go directly to the best design leaders. When I started my own design firm, Fresh Tilled Soil, 10 years ago, there were lots of questions. Questions with no obvious answers. For a while I believed I was supposed to learn the answers the hard way, through trial and error. Over time I learned that this was inefficient and expensive. I endeavored to read about how other leaders had solved these problems but the published answers seemed a little too generic. The real breakthroughs came when I had the opportunity to talk directly to other design leaders who were more experienced and smarter than me. These conversations inspired me to create a successful strategy for myself, which allowed me to grow a multimillion-dollar design company from the ground up with no debt and outside investors. These conversations were so helpful that I made a regular habit of calling design leaders that were way ahead of me on their personal and business journeys and asking for their advice.
I noticed that I wasn’t the only one who was asking questions. These topics came up frequently during conferences, industry meetings, and casual conversations. It started to make sense to capture these conversations and gather all these perspectives and answers into a book. I imagined that what was useful to me could also be useful to other design leaders. So, to that end, this book was born.
This book is both for established design leaders and for those on the path to leadership. The book will also be useful to people who work for design leaders and want to understand them better. Ultimately, the book is for anyone who leads a design team, owns an emerging design company, or works closely with design leaders. Whether you’re starting out or are decades deep into your adventure, this book will guide you through topics like hiring the best talent, building a strong culture, finding personal balance, growing your leadership skills, designing the optimal workspace, and creating healthy sales pipelines.
We interviewed leaders from emerging and established companies. In the cases where the design firm was independently owned and run by the design leader, we focused on companies in the 5 to 100 employees range. There were some exceptions, but our goal was to talk to leaders dealing with typical growing pains. Although we did speak to leaders from larger corporations like ESPN and Fidelity Investments, we gave most of our attention to small- and mid-sized design teams. About 60% of the companies interviewed had between 5 and 15 employees, while almost 40% of the companies had 20 or more employees. Several had upwards of 75 team members. The cultural differences between these companies is enormous and it would be hard to quantify those differences. Instead we’ve captured the individual stories, universal insights, and strategic approaches to making design groups more productive, creative, and focused.
This book is not a textbook or a paint-by-numbers workbook. This book is a conversation. It is a collection of conversations teased out of hundreds of interviews that I did with the help of my colleague and friend, Dan Allard. Dan was one of the first employees at Fresh Tilled Soil and is just as curious about design leadership as I am. While I conducted the interviews, Dan lugged around the heavy video and audio equipment to dozens of cities across North America. We recorded almost a hundred design leader interviews, ranging from small companies like Haught Codeworks in Boulder, CO, to massive corporations like ESPN with its 120-acre campus in Bristol, CT. From late-2013 until mid-2015, we captured the perspectives, insights, anecdotes, and personal stories of some of the top digital design leaders in North America. Many of these original interviews are available on YouTube in their raw and unedited form. Just search for “digital design leader” and you’ll find dozens of one-on-one interviews to inspire you. Over the last two years, some of this footage has found its way into podcasts and articles, but this book will be the first time all the interviews are collected into a single publication.
I hope you enjoy reading this book as much as I’ve enjoyed creating it. I’ve learned so much from my interactions with these leaders and I hope you will, too. Getting to know them so intimately has also led to some great friendships and even a few partnerships. With the help of my editors, reviewers, and publishers, I tried to make the writing clear and engaging. We deliberately avoided making this a prescriptive manual for running a design organization. Instead, we curated the “best of breed” approaches and presented them in a way that allows you to decide what works best for your team. Our goal was to cover the subject matter comprehensively but not in such detail that it puts you to sleep. No matter what your design leadership position or aspirations are, we are quite sure you will find something valuable in this book.
We’d also like to continue this conversation with our readers and contributors on social media and in person. As I’ve said before, design leaders don’t have all the answers, and we know there’s loads more to explore and learn. Let’s work together to get smarter and spread the knowledge so we can all benefit. A rising tide raises all boats. The more informed we are as design leaders, the sooner our organizations will see results. The more we share, the more we’ll see highly engaged teams, happy clients, and positive financial returns.
Thank you for buying and reading this book. It’s been a real pleasure writing it and sharing it with so many other design leaders.
As the investor Jonathan Beare once said to me, “Every company has its own brand of culture and politics. You have to figure out which culture and politics are most interesting to you.” This chapter explores the way design leaders create and nurture the culture in their successful organizations. We’ll hear from design studio owners and executives about the links between culture, attracting talent, productivity, and purpose.
People are the cornerstone of all organizations. Great people make great organizations. Finding these people and keeping them engaged and happy is one of the primary responsibilities of design leaders. We’ll explore the innovative ways these leaders attract and nurture talent in their organizations.
Today’s workspace looks nothing like your dad’s office did 20 years ago. Walls are coming down and creative workers are more remote than ever. In this chapter we ask top design leaders what makes their design studios deliver on the promise of being productive spaces for team members and clients. We also ask them how they manage the increasing numbers of remote workers while maintaining strong cultural bonds between team members.
Design leaders are always learning, growing, and struggling with finding balance in their lives. We learned how these top performers find time to stay on top of their daily demands while not losing sight of what’s really important—family, friends, and personal growth. There is no one-size-fits-all approach either. We find out how different personalities solve this universal problem with their own brand of intuition and creativity.
The ambiguity of running a design studio or team is becoming increasingly hard. Quickly changing tech trends demand agility and flexibility from leaders. Planning for a future that seems to change by the minute requires leadership skills that are both strategic and tactical. Our design leaders describe how they are laying plans for the future while consistently delivering on today’s demands.
Each person we interviewed brings their own flavor and style to the art of leadership. No two styles are the same, but there are patterns that are consistent with successful leaders. We discuss how these styles connect leaders to their business visions and company cultures. Over time, design leaders adapt their styles to changing environments and new challenges.
Every design business needs a pipeline of work. This topic is foremost on the design leaders’ minds as they work through the challenges of attracting new clients and retaining existing clients. Our interviews gave us insight into companies big and small, and provided us with a wide range of techniques and approaches.
Making mistakes is inevitable. Unfortunately, learning from them is not. We delve into the mistakes that these great design leaders have made and what they did to bounce back from them. In these stories, you’ll learn that making mistakes isn’t something to be avoided; rather, having mechanisms to grow and improve as a result of mistakes is what makes design leaders great.
America’s Test Kitchen
The Working Group
Fresh Tilled Soil
Digital of Bureau
This book would not be possible without the tireless efforts of Dan Allard. As we crisscrossed North America interviewing design leaders, Dan was the cameraman, soundman, and general Sherpa of all the equipment. I’d also like to thank the entire Fresh Tilled Soil team for holding down the fort while I researched and wrote this book. I’d also like to recognize the Bureau of Digital founders, Greg Hoy and Carl Smith, who host the amazing Owner Camp retreats. Meeting them and the fellow campers was a tipping point in getting access to several of the design leaders interviewed here. Finally, I’d like to thank Nick Lombardi, Angela Rufino, and the rest of the amazing team at O’Reilly whose attention to detail and dedication make writing a book so much more enjoyable.
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