Innovation and the Digital Enterprise DragonSpears

OKRs are easy to set up badly. Christine Sandman Stone, CEO and founder of Deliver at Scale, focuses on this key element for success based on her years leading agile transformations. Beginning with her journey, Christine shares her path to leadership and the critical lessons she’s learned—and shared—along the way.
In this episode, Christine provides a glimpse into her world guiding teams to hone in on their goals. First, she offers her perspective on setting the objective and determining the quantitative measurement of that goal. Then, Christine shares the critical element of measurement periods (90 days!) and how to maintain the right outlook on pursuing these goals. 
Christine offers key lessons from her book The Parent Track: Work-Life Balance Hacks to Elevate Your Career and Raise Good Humans on how to continue advancing your career during parenthood. She offers tips (ex. the word “conflict” is your friend) and her experiences that led her to share those lessons. Christine dives into her most recent book that set out to provide tangible resources for new managers: The Modern Management Mentor: Next-Level Tools for New Managers, inspired by the questions she fielded during her own daughter’s promotion. 
Later in the conversation, Christine discusses the state of leadership and management training. She endorses the advancement of individual contributors that does not necessarily require managing people and discusses a multi-track approach. 
(01:38) – Introducing Christine Sandman Stone(06:18) – OKRs(09:35) – Narrowing in on the objective(13:14) – 90-day measurements(17:45) – The Parent Track(23:20) – The Modern Management Mentor(27:04) – Leadership development(33:31) – Individual contributor growth opportunities
Christine Sandman Stone is the CEO and founder of Deliver at Scale and former Global Head of Product & Engineering, Operations & Strategy at Groupon. She has previously worked with Dell, McDonald’s, and Volkswagen. Christine is the author of The Parent Track and The Modern Management Mentor. She earned her bachelor’s degree in philosophy from Miami University and a master’s in management and organizational behavior from Benedictine University.
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Podcast episode production by Dante32.

Should we look beyond technology organizations to learn essential lessons on how to innovate and run successful, complex technology organizations? Gene Kim believes so and contains unbridled curiosity for transformation across industries, as seen in his most recent book Wiring the Winning Organization. Gene Kim returns to share new lessons in change-making for leaders and companies tackling an array of challenges. 
Gene Kim is a bestselling author of several books on technology innovation, DevOps, and organizational strategy. He founded and served as CTO of Tripwire for thirteen years, an enterprise security software company, and is the founder of IT Revolution. Gene offers an engineering perspective with an executive-eye view. 
In this episode, Gene discusses being inspired by Toyota and his goal to lead great organizations toward the most effective, liberated problem-solving capabilities. He shares how coordination is the layer that is the difference-maker in a successful company and offers several case studies across industries. Gene highlights three key factors in a cohesive organization: 1) independence of action, 2) time (for practice and planning, and experimentation and implementation), and 3) actionable feedback that reaches the right people at the right time. 
Gene offers a metaphor from his book—moving a couch—that exemplifies his experience in communication and coordination. With this simple metaphor, Gene shares how small, cross-functional teams with the right number of collaborators are a great tool for success.  
Join Gene in Las Vegas from August 20 to 22, 2024, at the Enterprise Technology Leadership Summit (formerly DevOps Enterprise Summit). 
(01:40) – Gene Kim returns(04:22) – Layer three as difference-maker(09:22) – Healthcare case studies(11:55) – Three mechanisms for a cohesion(15:04) – The CheckBox Project(20:29) – “Slowification”(26:55) – “Great in the large, great in the small”(29:03) – Specialization of roles and coordination(34:34) – The technology leader’s boss
Gene Kim is an author, researcher, and technology leader studying high-performing technology organizations since 1999. Gene founded and served as Chief Technology Officer of Tripwire, Inc. for thirteen years, an enterprise security software company. He is the WSJ bestselling author of Wiring the Winning Organization, The Unicorn Project, and co-author of The Phoenix Project, The DevOps Handbook, and the Shingo Publication Award-winning Accelerate. Since 2014, he has organized the Enterprise Technology Leadership Summit (formerly DevOps Enterprise Summit), studying the technology transformations of large, complex organizations.
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We had a great conversation with David Heinemeier Hansson in 2023 and are excited to reshare it in our “Best Of” series.
Originally published 11/2/23.
Profound innovation has occurred across web-based communication technologies in the last decade, and truly accelerated in the years since the start of the pandemic. But David Heinemeier Hansson recognized a massively neglected arena, one we all use, every day: email. Bringing his experience as co-owner and Chief Technology Officer at 37signals (Basecamp, Ruby on Rails, and more), David launched HEY, an innovative approach to email that provides a modernized, user-first service. In this episode of Innovation and the Digital Enterprise, David articulates a dedication to forging new paths in software and entrepreneurship.
He shares important lessons in approaching remote work, including the essential pillar of embracing asynchronicity. He dives into how he structures his day for success and offers a counterpoint to the American workplace culture of bragging about busyness and 80+ hour weeks. Finally, David provides insight into the current state of cloud technology and his company’s recent—successful and swift—migration off the cloud. 
(01:48) – 37signals(03:27) – HEY(09:54) – Advantages(17:32) – Detecting spy pixels(19:45) – The pandemic’s impact(23:42) – Embracing asynchronicity for success(29:07) – An American culture of busyness(34:31) – Importance of sleep(38:52) – Cloud technology(46:55) – Bringing applications home
David Heinemeier Hansson is co-owner and Chief Technology Officer of 37signals (Basecamp & HEY), creator of Ruby on Rails, and best-selling author, including REWORK, It Doesn’t Have to be Crazy at Work, and Remote: Office Not Required. David is a Le Mans class-winning racing driver, photographer, antitrust advocate, and investor.
If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.
Podcast episode production by Dante32.

Today we're sharing another insightful presentation from our most recent Innovative Executives League Summit, where Leon Chism, the Vice President of Engineering at Evolve, delivered a powerful lesson on collecting critical metrics for organization-wide success. As an experienced technologist and executive, Leon leads teams in unparalleled growth and innovation. In this presentation, Leon dives into how the collection of metrics examining speed and quality paired with human-driven evaluation and consistent reporting are the keys to success. 
In this episode, Leon first dives into DORA metrics and the significance of collecting and reporting those figures of speed and quality. He overviews the additional customization of the data he collects; in one example, he looks closely at aging reports to determine where processes are sticking and gains a live perspective on getting those tasks unstuck by allocating more resources. As the last place to observe metrics, Leon offers a compelling outlook on examining team balance and individual metrics. ("You want to measure the process and not the people.") In further support of optimizing processes and not people, Leon shares his perspective on leaderboards, comparison, and other human-oriented metric frameworks of note. 
In the final segment, Leon answers audience questions ranging from setting WIP limits (never too low), developer satisfaction, and key aspects of the communication around metrics to create a shared understanding and identify the value beyond the data. 
(02:16) – DORA metrics(07:39) – Aging Report(10:15) – Balance and individual metrics(12:22) – Metrics in the boardroom(13:35) – SPACE Framework(15:45) – Manual metric collection(17:19) – Developer satisfaction(18:48) – Gaming the metrics(20:26) – WIP limits(21:45) – Shared metrics and collaboration(26:00) – Hardware, software, firmware(27:05) – Communicating the metrics(28:26) – Value beyond the data
Leon Chism is the Vice President of Engineering at Evolve. As an experienced technologist and executive, he has led innovation and technology at Jellyvision, DialogTech, Rewards Network, Analyte Health, PowerReviews, and ORBITZ. He earned a bachelor’s degree from the Gies College of Business at the University of Illinois Urbana-Campaign.
If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in a...

Today we’re sharing another insightful presentation from our most recent Innovative Executives League Summit, where Tanya Hannah discusses the roadmap to navigate the ever-evolving tech landscape. As a seasoned transformational business executive, Tanya offers the pillars needed to survive major shifts and thrive in the opportunities presented by them. 
In this episode, Tanya shares how critical a shared vision and strategy is in preparation. Teams cannot operate only with yesterday’s logic; they must look forward in anticipation of a pivot. Tanya offers how technologists can operate at the key intersection of short-term performance and long-term planning. She stresses the importance of a business perspective having a place in tech conversations and leaning into a skillset that embraces both.
As an award-winning technology leader, Tanya sees a path forward that focuses on data, talent, and vision. Tanya describes how data provides the competitive advantage businesses are looking for and how the ability to manipulate and understand the data is essential for the entire team. In focusing on the team itself, Tanya addresses how people are the key factor in remaining nimble (embracing in-house talent) and how the current shift in the labor environment points to the direction companies must anticipate. As remote and hybrid work continue, Tanya dives further into how focusing on talent is not only essential but teams and individuals must have a common understanding of the shared vision and strategy for success. While acknowledging the evolving technology and the often disruptive forces that shape the world today, Tanya Hannah offers a foundation to prepare for the future with tech and talent. 
(01:17) – A room of disruptors(02:36) – Adaptation(04:33) – Acting with yesterday’s logic(08:40) – Preparing to pivot(10:35) – Driving business with tech(13:02) – The win-win(14:26) – Understanding data is a must(16:10) – Focusing on people(21:55) – How are we planning?
Tanya Hannah has held executive and senior roles at Aon, Amazon, CSC, and King County, Washington. Tanya is a three-time CIO 100 Award winner and a 2021 National CIO of the Year. She’s a graduate of the University of Maryland.
If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.
Podcast episode production by Dante32.

Today we’re sharing another insightful presentation from our most recent Innovative Executives League Summit, where Desiree Vargas Wrigley, Chief Innovation Officer of P33 Chicago and Executive Director of TechRise by P33, delivered a lesson in stakeholder-centric design. Desiree overviews the challenges Chicago’s underrepresented tech founders face and the process of developing TechRise’s initiatives. Highlighting the impact of TechRise and P33, Desiree presents a galvanizing picture of Chicago-based innovation that utilizes local money to generate a cycle of loyalty, growth, and investment that leans into Chicago’s advantages. 
In this episode, Desiree asks: “Who succeeds when you succeed?” As an enthusiastic believer in Chicago’s potential as an innovation hub, Desiree is also unafraid to point out its shortcomings, such as the lack of popularity in social ventures and lack of recycled capital. Demonstrating a stakeholder-centric design process with the case study of TechRise, Desiree shows how focusing on the key question of identifying all the stakeholders and all the solutions that benefit them drives success. She discusses sifting through bias for actual data and the extensive discovery process that went into developing the initiatives of TechRise. Desiree articulates how re-imagining pitch competitions (frequency, environment, etc.) has opened doors for founders by acknowledging the obstacles that women founders and founders of color often face. Desiree shares her interest in conscious capitalism and asks, “What else is possible?”
(1:15) – P33 Chicago(3:42) – Thinking about success(4:53) – A foundation for providing support and resources(6:57) – Stakeholder-centric design in four steps(9:36) – Funding women and founders of color(12:49) – TechRise(15:20) – Identifying solutions(16:35) – Weekly pitching(19:12) – Looking at impact(21:16) – What else is possible?
Desiree Vargas Wrigley is a serial entrepreneur with a track record of empowering women and people of color in the world of investing. Desiree is the Chief Innovation Officer of P33 Chicago and Executive Director of TechRise. She is a founding partner of The Josephine Collective and previously co-founded GiveForward. Desiree earned a bachelor’s degree in Latin American Studies from Yale University.
If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in a...