When There Is No Perfect Choice — The Courage to Exercise Judgement
Originally published on Digoshen in August–September 2026, as part of the Beyond the Old Playbook podcast and reflection series.
Leadership often involves making decisions when information is incomplete, priorities compete and no available option offers a perfect outcome. In an increasingly uncertain world, the challenge is not simply to find the right answer, but to exercise sound judgement when several answers may be possible, each carrying its own consequences.
This reflection draws on a Beyond the Old Playbook podcast conversation with Rolf Pfeiffer, exploring how leaders and boards can navigate difficult choices without relying on established formulas or the illusion of certainty. It considers the importance of perspective, values, experience and human judgement in situations where analysis alone cannot determine the way forward.
Reflections
We often approach difficult decisions by seeking more information, comparing alternatives and hoping that further analysis will reveal an obvious answer. Yet some of the most consequential leadership choices involve genuine dilemmas rather than problems that can be solved.
In these situations, competing priorities cannot always be reconciled. Short-term performance may conflict with long-term investment, efficiency with resilience, and individual interests with collective responsibilities. Waiting for certainty can become a decision in itself, sometimes with consequences greater than those of taking action.
Good judgement requires more than analytical capability. It calls for the ability to recognise different perspectives, understand underlying values, engage in constructive dialogue and accept responsibility for choices made under imperfect conditions.
As AI increasingly supports analysis and decision-making, these distinctly human capabilities may become even more important. Technology can help us explore alternatives and anticipate consequences, but it cannot relieve leaders and boards of the responsibility to decide what matters most.
The Message
Leadership is not about always making the perfect choice, but about exercising thoughtful judgement when no perfect choice exists.
The courage to decide, the humility to recognise uncertainty and the willingness to learn from consequences are essential capabilities for leaders and boards navigating a changing world.
Sometimes progress begins not when we find the perfect answer, but when we accept the responsibility to choose and move forward.
When faced with competing priorities and no obvious right answer, what helps you exercise good judgement?
Read the full reflection here
When There Is No Perfect Choice — Digoshen
About Liselotte Engstam, Digoshen & Novisali
Liselotte Engstam is an explorer of perspectives, an adventurer of ideas, a pathfinder of meaning, and a guide of timeless transitions. She bridges the worlds of board leadership and art, helping organizations and individuals navigate disruption while nurturing creativity and reflection.
As founder of Digoshen, she works with boards and leaders to expand future insights and reduce digital and sustainability blindspots. Through research, networks, and executive programs, Digoshen supports responsible value creation in the digital and sustainable age, contributing thought leadership via books, articles, events, Digoshen Exploring Leaders podcast, and blogs.
She also serves as Chair of the Boards Impact Forum in collaboration with the World Economic Forum and the Climate Governance. The Forum convenes board members, thought leaders, and experts in dialogues, webinars, and collaborative events, accelerating action on climate, AI, and sustainability.
Through her artistic practice as Novisali, Liselotte explores creativity and meaning. Her watercolors, digitally reimagined, invite reflection and renewal, offering perspectives that connect head, heart, and hand, and complementing her work with leaders and boards.
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