Comfort in the Unknown: The Truth About Building for Uncertainty

Leadership often finds itself at the intersection of truth and fallacy. For those of us in engineering or quality-focused roles, this challenge is amplified. Many organisations expect cookie-cutter solutions, plug-and-play models that apply universally without friction. But as any experienced leader will tell you, the realities of navigating complex systems, teams, and goals rarely align with such expectations.

The Fallacy of Certainty

When stepping into a leadership role, I’m often met with the same assumption: that I’ll bring a tried-and-tested “playbook” of processes, strategies, and tools that will seamlessly map onto the organisation. This assumption isn’t inherently wrong, it’s comforting. Certainty is reassuring. But fallacy lies in the idea that context can be ignored, or that agility can be achieved without iteration.

This leads to a choice:

1. Lean into the fallacy.

Present a polished but inflexible plan to gain buy-in. The cost? Retconning and course-correcting when reality inevitably misaligns with promises, or worse, delivering suboptimal value by adhering rigidly to a plan that doesn’t serve the organisation’s real needs.

2. Choose the truth.

Accept the discomfort of acknowledging unknowns upfront. Focus on building resilience to navigate uncertainty by accruing context, iterating, and appraising along the way. This is the foundation for achieving optimal, long-term value.

The second option is my compass. It’s aligned with my belief in empiricism and the importance of uncovering information, not just applying it. But truth requires courage and leadership audiences like Heads of Engineering, CXOs, and Directors need to hear why embracing the unknown is essential, even if it feels uncomfortable.

Testing as an Information-Uncovering Tool

Del Dewar’s reflections on the synergy between testing and checking offer a valuable metaphor for broader engineering strategy. Checking confirms what is already known, while testing explores and uncovers what we don’t yet know. Similarly, leadership involves balancing operational execution (checking) with strategic exploration (testing).

Read more from Del’s article, The Testing-Checking Synergy here.

When we design systems – whether technical or organisational – it’s tempting to operate within the bounds of “known knowns.” However, as Donald Rumsfeld famously noted, what truly challenges us are the known unknowns and, more critically, the unknown unknowns. Good testing and good leadership require deliberate processes to uncover these blind spots.

In practice, this means framing leadership and engineering work as an iterative exercise in information gathering. It’s about moving beyond “What are we doing today?” to “What do we need to learn?” and “What might we be missing?” Comfort in the unknown comes from creating a system that thrives on uncovering information.

Comfort and Resilience in Uncertainty

Another key influence here is the idea of psychological comfort in the unknown, informed by research into agility and resilience. When leaders create environments that embrace uncertainty, they allow teams to be more innovative, adaptable, and aligned with changing business needs. This isn’t about pretending the unknown doesn’t exist; it’s about giving teams the tools to navigate it.

This is where systems thinking comes into play: as described in discussions on iterative and evolutionary strategies. Rather than prescribing static solutions, effective leaders ensure their systems can evolve based on the feedback they gather. Iteration isn’t just a technical principle; it’s a cultural one.

From Unknown Unknowns to Strategic Insights

As a leader, my goal is to help organisations move through this Rumsfeldian hierarchy of knowledge. Start with what you know, identify what you don’t know, and build processes that uncover insights about what you didn’t even know you didn’t know. This progression isn’t linear, it’s iterative. Each cycle adds layers of understanding.

For engineering leaders and CXOs, this principle extends to decision-making. It’s not enough to chase efficiency at the expense of learning. In an increasingly complex world of distributed systems, AI-driven testing, and cross-functional dependencies, it’s critical to prioritise information flow as much as output.

Key Takeaways for Engineering Leaders

1. Certainty is a Myth: Build systems that thrive in uncertainty by prioritising iteration, information gathering, and the resilience to adapt.

2. Balance Checking and Testing: Confirm what you know while deliberately exploring what you don’t.

3. Uncover Blind Spots: Use tools and frameworks like Rumsfeld’s known/unknowns to identify gaps in your strategy or execution.

4. Create Psychological Safety: Comfort in the unknown comes from fostering an environment where teams feel empowered to experiment, fail, and learn.

5. Align Systems and Culture: Evolutionary systems require an agile culture. Empirical leadership bridges the two.

Ultimately, leadership is about guiding organisations through a shifting landscape. By choosing truth over fallacy and focusing on building comfort in the unknown, we create systems and teams that are not only resilient but also capable of delivering exceptional value in the face of uncertainty.