Kara Penn: An interview by Bob Morris

PennKara Penn is cofounder and principal consultant at Mission Spark, a management consulting firm dedicated to organizational change and improvement in complex and often resource-constrained settings. In guiding her clients’ thinking, planning, and action, Kara focuses on best practice and implementation, an approach that puts her at the front lines of practical management in varied domains. Kara has fifteen years of experience in senior leadership positions, including as founder, director, chair, coach and board member. She’s led award-winning community collaboratives; designed, managed, and evaluated multiyear social change initiatives; and provided in-depth consulting services to more than seventy social enterprises, corporations, and foundations.

Kara graduated from Colorado College, where she was a Boettcher Scholar. She completed her MPP as a Harris Fellow at the University of Chicago’s Harris School of Public Policy and her MBA at the MIT Sloan School of Management. MIT Sloan recognized Kara with the Seley Award, the highest honor given to a graduating student. Kara has also been awarded several national fellowships, including the Thomas J. Watson Fellowship, which supports independent, purposeful travel to foster fellows’ effective participation in the world community, the Coro Fellowship in Public Affairs to develop principled public leaders, and the Forté Fellowship to promote women leaders in business.

Kara co-authored Fail Better: Design Smart Mistakes and Succeed Sooner with Anjali Sastry. It was published by Harvard Business Review Press (November 2014).

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Morris: Before discussing Fail Better, a few general questions. First, who has had the greatest influence on your personal growth? How so?

Penn: The greatest influence on my personal growth stemmed not from a “who” but a “what.” When I was 22, I spent a year engaged in independent travel abroad. I grappled with loneliness, failure and taking risks. I was away from my very supportive network of family and friends, and I confronted setback after setback. After several months of grappling with what was missing, an immense sense of possibility, personal accountability and self-direction emerged that has continued to grow and guide me. I became keenly aware that I could welcome, benefit from, and create room for the unexpected. I learned to be truly alone with myself and be at ease, and I learned that at all times I could be a student of what others had to teach. The experience was immensely freeing and powerful.

Morris: The greatest impact on your professional development? How so?

Penn: I’ve often asked myself which professional development experiences I’ve had have been the most impactful. The answer always comes down to immersion experiences, when I had an opportunity to put learning into action with protected time to reflect and embed new insights. Though I’ve completed two graduate degrees through traditional learning institutions, my time as a Coro Fellow was the most influential professional development investment I’ve made.

The Coro Fellowship in Public Affairs is a national, nine-month program modeled off of a medical residency, where each fellow works in intensive six-week rotations in organizations representing different sectors of society. At the same time, fellows focus on developing leadership, public speaking, civic engagement, project management, media and other professional skills. Coro is basically a leadership and experiential learning boot camp. As a fellow, I worked on high-level projects for an airline, a union, a government agency, a hospital, and a nonprofit. I worked on a political campaign for an elected official.

Other fellows were doing the same, for different organizations within the same sector. We’d come back together after long days working to compare notes and create a snapshot of that sector, and relate it to others we had already worked within. By the end of nine months, we emerged with a much more integrated and realistic view of how things get done within complex systems. And through a process of intensive 360-degree feedback, self- reflection, creating new habits, and skill building, I developed into a more effective change agent.

Morris: Years ago, was there a turning point (if not an epiphany) that set you on the career course you continue to follow? Please explain.

Penn: I’ve always been a mission-driven person, one who cares deeply about positive social impact, and social and environmental justice. My personal life and career reflect a desire to serve and to focus on pressing social and environmental issues. Though I can remember this calling as always being a strong force in my life, the Gulf War Oil Spill in 1991, when I was 15, was one of the first periods of my life when I took on the role of activist and organizer. I can remember finding some like-minded collaborators, and together we planned an environmental education summit for our community because it was what I could think of to do at the time.

Morris: To what extent has your formal education been invaluable to what you have accomplished in life thus far?

Penn: My formal education experiences have opened up invaluable networks of colleagues and friends, and allowed intense and protected periods of time to learn, experiment and explore. My time at MIT was particularly valuable as I had opportunity to work with a multi-disciplinary group of students on effecting change within the MIT system relating to embracing principles of social, economic, and environmental sustainability. My time working with them and the results our efforts produced, are among the highlights of my educational experience.

Morris: In recent years, there has been criticism, sometimes-severe criticism of M.B.A. programs, even those offered by the most prestigious business schools. In your opinion, in which area is there the greatest need for immediate improvement? Any suggestions?

Penn: The move to providing more action learning experiences seems to be a positive direction for business school curricula, but there seems to be room for tighter feedback loops, iteration of ideas over the course of a project, and the embedding and sharing of lessons learned to help students develop and grow their professional and personal skills. In some ways, my co-author, Anjali Sastry and I developed the method that underpins Fail Better to address some of those needs. Of course, these are not challenges only MBA students face as they carry out multi-faceted projects, but MBA programs seem uniquely suited to design curricula and experiences in such a way that students have a “safe sandbox” in which to experiment, make mistakes, test assumptions, develop rigorous habits of reflection and improvement, and share what they’ve learned.

Morris: Now please shift your attention to Fail Better. When and why did you and Anjali decide to write it in collaboration?

Penn: Anjali and I began collaborating at MIT Sloan in 2005. She was a Senior Lecturer in System Dynamics. I was a new MBA student. We were both motivated to effect positive social impact and began working closely together on a variety of projects. Anjali served as a faculty advisor for a course others and I wanted to pursue to track implementation of a theory of change. At one point I was her TA for an experimental course in practicing management.

As we worked together, we became intrigued with what distinguishes those that produce breakthrough results, and those that fall short, projects that achieve or exceed their goals, and projects that fail. In applying principles of action learning in classroom and organizational environments, we began to see consistent patterns — supported by research — that underpinned the highest impact projects. We began developing tools and curricula to build in experimentation and a higher level of rigor to testing ideas, and overcoming common failure modes.

We went on to test and refine our approach over seven years — Anjali through the founding of the Global Health Lab at MIT, and I, through strategy and management consulting work provided by my company, Mission Spark. Together, we experimented with the concepts of Fail Better in more than a hundred projects. We wanted to share what we learned, through experience and research. It was our good fortune that HBR Press saw value in what we proposed, and Fail Better was born.

Morris: Were there any head-snapping revelations while writing it? Please explain.

Penn: We care deeply about implementation and practicality. This is the lens we continually returned to, to examine and improve upon the book. We continually focused on refining and simplifying ideas. And had we not been on deadline, we probably would have welcomed a round or two more, and the book would have become shorter! Anjali and I are perfectionists. It was good to apply our own method to the process of writing the book, and to test and experiment along the way with layout and content, examples and tools, trying to ensure points of feedback throughout the collaboration process.

Morris: To what extent (if any) does the book in final form differ significantly from what you originally envisioned?

Penn: One significant difference from our original concept is that we had envisioned an accompanying workbook full of guiding questions and tools. As we went through, we realized building in examples and case studies, along with enough grounding for implementation (such as the checklists at the ends of chapters 4, 5 and 6) added both illustrative and practical elements to the book while leaving room for readers to apply concepts within their own circumstances. We may still develop additional tools to support implementation – and perhaps make them available online — but eventually we decided that the book in final form achieves the practical and accessible orientation we were so eager to provide.

Morris: What does it take to start failing in a better way? What does the process behind good mistakes – mistakes that help to achieve strategic objectives — look like?

Penn: Behind the current pro-failure hype adopted in many innovation circles, there is plenty of encouragement to “fail early and fail often” but little advice on how to do that, especially when in the “trenches” of a highly competitive marketplace. Similarly, most successful individuals with a public platform describe their own life paths as those littered with failures that were critical to their eventual triumphs. While inspiring, these stories do little — beyond dramatizing the importance of resilience — to explain how to make the most of setbacks. Our book addresses this problem by offering a practical approach to embrace good failures while preventing the bad. The premise behind this approach is that the most useful failures are those that emerge from the planned exploration of unknowns.

To do this, we offer three linked steps (1) to launch every innovation project with the right groundwork so as to avoid common failure modes and set the stage for more productive surprises (this step makes salient how your actions lead to desired outcomes, takes inventory of available and needed resources and fills gaps, and builds and supports the right team for the project), (2) to build and refine ideas, products and services through experimentation—designing iterative action that elicits and uses data, tests hypotheses, and informs the next step of the project, and (3) to identify and embed the learning to succeed sooner in future efforts— by evaluating outcomes, identifying practices, skills and habits to embrace or discard, and sharing key lessons in actionable ways at the team and organizational level so others benefit from your insights.

Morris: What would we stand to gain if we were more aware of how we should act to make better mistakes?

Penn: We argue that the gains to be made are based on changed and purposeful action (as described in the Fail Better method), and that implementing this approach is best supported by two things: (1) cultivating a mindset that allows for growth, compassion, discernment and accountability, and (2) creating favorable conditions for learning from failure by setting stretch goals for teams, providing actionable and timely feedback and creating levels of freedom and safety to explore and test.

If such an approach can help with distributed change efforts that span multiple projects, it may provide a way to take on the world’s most pressing problems. Research on complex systems—not to mention human experience across a vast reach of time and space—teaches us that big problems are never solved by a single stroke of genius. Could all of us, building in more of these concepts, tackle more of society’s messy, complex challenges? The Fail Better method is, at its essence, about making every individual effort more effective, and every effort more connected to others, so as to better enable learning and improvement.

Morris: For more than 25 years, it has been my great pleasure as well as privilege to work closely with the owner/CEOs of hundreds of small companies, those with $20-million or less in annual sales. In your opinion, of all the material you provide in Fail Better, which do you think will be of greatest value to leaders in small companies? Please explain.

Penn: As an owner of a small business myself, I think the beauty of the Fail Better method is the ability to deliver on the work at hand while building in room for experimentation, smart risk-taking, illustrative mistakes, and individual and team development. In resource-constrained environments, expensive training and development programs, and large R&D investments, are often out of reach and over budget. This unique method empowers small businesses to design their work differently to reap greater insights, advance skills, and ultimately achieve better results.

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Kara cordially invites you to check out the resources at these websites:

Fail Better link

Mission Spark link

Groundwork MIT link

Facebook link

Twitter links



Fail Better

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  1. Rekha Ginde on April 8, 2015 at 1:09 pm

    Very professional interview. Kara did a great job in detailing each question with thought provoking answers. Well done, enjoying reading it.

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