Inculcating Curiosity

In 2009, the Ciudad Real International Airport was completed with a $1.1b investment to serve passengers flying from the greater Madrid area. With the Madrid airport becoming increasingly busy, the Ciudad was supposed to ease the load by catering to the growing demand among airlines.

In 2012, the management company filed for bankruptcy — the neighboring Madrid airport had expanded operating capacity, leaving airlines with no reason to operate out of Ciudad that was further away from the main city. The Ciudad Airport is one of many mega projects that were unsuccessful due to lapses in planning, research and feasibility assessments.

A brief study of some of these projects highlights the importance of challenging assumptions and questioning the details. For startups, some of the biggest breakthroughs come from not following conventional wisdom. For management teams, a common challenge is to inculcate a strong sense of curiosity across organizations — I frequently come across others asking if it is possible to train teammates on questioning the status quo, on seeking to understand the reasons for why we do what we do.

Organizations are typically shaped after the behaviors of the leadership team. Most businesses operate on a set of assumptions, which need to be challenged and fine-tuned with each passing quarter. I’ve found the below set of exercises to be a useful starting point in inculcating a sense of curiosity across organizations:

  • Monthly Business Reviews (MBRs) — serve as an important forum to review progress in key areas, highlight domains in which we want to develop a deeper level of understanding, and question assumptions that we may not think of in the day-to-day operating rhythm.
  • Framing the Agenda — If leaders are constantly asking questions and demonstrating awareness around the limitations of their awareness, so will others within the organization:
    • Weekly All Hands — serves as a key forum to build alignment around values and progress, and can be used to identify areas or questions in which our understanding remains limited.
    • Quarterly Off-Sites — provides a platform to disconnect from the usual operating rhythm to re-align on priorities and/or re-frame the agenda.
  • A dedicated Strategy and Planning team — In organizations operating at scale, the slightest shift in direction can have a profound impact on outcomes. With a laser focus on delivering against monthly or quarterly goals, functional teams often do not have the bandwidth to conduct in-depth diagnoses and/or analyses on key strategy questions. Having a dedicated strategy and planning team can help build deep perspectives in areas that may otherwise be ignored.
  • Championing the Naysayers — In large teams, naysayers play an important role of being the skeptics in the room that need to be convinced on a given strategy. The best teams are able to find a harmonious equilibrium between optimism and pessimism.
  • Operating at Low Levels of Detail — During my time at DoorDash, Tony Xu, the Founder/CEO, maintained a consistent emphasis on what he referred to as, “the lowest level of detail.” Oftentimes, teams settle for surface-level answers without getting to the root-cause factor of a problem or a trend. The best teams keep asking the “why” question until they’re able to get to the true root-cause factor. The “Five Why’s” framework further elaborates on this.

In the best organizations, teammates at every level are questioning the status quo, uncovering new insights and driving change through a bottoms-up process. Inculcating a sense of curiosity is typically easiest to achieve at the earliest stages of setting up an organization.

It is much easier to build culture than to change an existing one.

Posted: October, 2022