Learn, Adapt, Repeat

“Those at the top of an organization typically used to say that the answer lay in a sound plan. . . The reason for this is the underlying conceit that we can both know the future and master it. That has always been a dubious claim, but in today’s uncertain environment it is patently ridiculous. Rigid plans can only court escalating commitments, despite the evidence of change in the world around our organizations, and ultimate disaster.” – What Philosophy Can Teach You About Being a Better Leader

As a child, I recall my father philosophizing about shampoo. His theory was that a bar of soap was more than adequate to wash your hair. He frequently reminded me that “lather, rinse, repeat” was a clever marketing ploy to necessitate more frequent shampoo purchases. Although I never bought into the idea of bar soap as a replacement for shampoo, I’ve never included the “repeat” step in my routine.

While reading What Philosophy Can Teach You About Being a Better Leader, I was reminded that “repeat” is an essential step to learning. None of us genuinely learn how to do something if we only do it once. And although many leaders proudly profess that their agencies are ‘learning organizations,’ learning is hard work that doesn’t happen because you’ve simply decreed that it should.


I’ve written about learning as a goal, capability, and organizational asset. My mantra has been to extract at least one memorable lesson from everything I read, from everyone I encounter, and from my experiences every day. Receptivity to learning is the fertile ground where lessons take root. To be receptive, however, I must silence my ‘teach and tell’ mode. However, the NRMC team has learned that it’s often common for leaders to get stuck in ‘tell’ mode, and there is an inherent danger to this practice. The authors of What Philosophy Can Teach You About Being a Better Leader remind us that when we are focused on a transmit-receive model of communication that tells others what to do and when to do it, it creates a “consume (as opposed to create) reaction.”  Essentially, team members may feel inclined to ‘wait for further instructions’ instead of forging ahead, inspired by the information their leader has shared.

‘Teach and tell’ mode is appealing to many leaders because its results are predictable; there’s no risk of a surprise or the potential to look underprepared. However, the job of leadership isn’t to look good. The authors remind us that it’s to “create an environment in which passionate, curious, risk-taking people can flourish, develop themselves, make a positive difference and infect others with their enthusiasm.” To do this, be sure to temper your ‘teach and tell’ tendency and leave enough room to listen and learn.


In recent weeks, agility has emerged as an essential, indispensable organizational capability. Yet many organizations continue to double-down on detailed plans built on fragile assumptions. Contingency planning is a valuable exercise, but not for the obvious reason. The real benefit of having a set of contingency plans isn’t the ability to easily select Option B or C when the disruption arrives. It’s the process of contingency planning that is so valuable to a nonprofit team: the time spent discussing possible impacts of interruptions and activities to leverage the upsides and cope with the downside impacts. But there’s a decided downside of trying to work out too many contingency options.

The authors of What Philosophy Can Teach You About Being a Better Leader write, “Legislating for all possibilities makes your organization less adaptable. The complexity and disruption of the uncertain world in which we live creates so many threats and opportunities, unforeseen circumstances, and novel experiences that there is no set of delegated authorities that can legislate for all permutations. Worse still, by thinking we can legislate in this way and expecting everyone to behave accordingly, we simply make our organizations less adaptable.”


Here are a few tips for working ‘repeat’ mode into your risk management routine.

  • Make experimentation habitual: A powerful message in the book is that experimentation is essential for learning. Every skill you currently possess grew out of trying something for the first time. From riding a bicycle to learning a new language, your skills and confidence grew as you made repeated attempts, fell or failed, and tried again. To maximize learning when you experiment, identify the theory you’re trying to prove or disprove before getting underway.
  • Relish being wrong: As risk leaders, we must model a commitment to embrace rather than avoid errors. Speaking up to say, “I was wrong!” sends a powerful message to your team about the potency of failure and humility. When was the last time you broadcast an inadvertent error or a rash decision to your team?
  • Seek unique practices, not best practices: Clamoring for ‘best practices’ is a sure path to ill-fitting approaches. Will a risk committee improve the quality and value of your risk management function? It’s hard to say! Maybe. Maybe not. Meaningful results in risk management come from pursuing unique practices, not best practices.
  • Strive for relation, not agreement: Staying in learning mode with colleagues is preferable to achieving consensus. Being in relation with others means that everyone accepts that they could be wrong, “that others could be right and we could all be wrong.” Humans are fallible! To test that theory, what have you been absolutely wrong about since the first of the year? Since the first day your team began working from home?

Learn to Fail, or Fail to Learn

In addition to picking up some neat trivia about philosophers and philosophy, reading What Philosophy Can Teach You About Being a Better Leader has motivated me to re-examine my leadership traits as well as the risk leadership advice we deliver to our extraordinarily diverse consulting clients. And I’m feeling incredibly inspired by one of the central messages in the book: “The core competence of an organization is thus best expressed as the speed at which it is discovering new knowledge, based upon its skill in asking potent questions, formulating hypothetical answers, conducting decisive experiments and refining the theories in use.”

Melanie Lockwood Herman is Executive Director of the Nonprofit Risk Management Center. She welcomes your comments and theories on the interplay between philosophy and risk management, and your questions about NRMC products and services. Melanie can be reached at 703.777.3504 or Melanie@nonprofitrisk.org.