A Story About Dilemmas
A Glaswegian woman, a child of World War II, grew up knowing two things for certain about the life she wanted: a highly adventurous world-traveling life and children. For most people, these two desires would be in perpetual conflict. For her, they were as inseparable as two sides of the same coin.
Her adventures would eventually take her to nearly 100 countries, and she would bring her children to most of them. She took her first child, by boat, halfway around the globe when he was just a month old, completing the circumnavigation five years later with a second child in tow. She travelled long stretches of the world’s three longest rivers and through pirate-infested waters off the coast of Somalia. She drove from Scotland to Yemen, and twice from Scotland to Jordan and back again, the first time with her two-, three-, and seven-year-old children. They passed through Syria during a civil war. They navigated the Empty Quarter of the Arabian Peninsula. They drove deep into the Hejaz region of Saudi Arabia to visit a sixth-century Christian monastery and to see rare petroglyphs in Qilwah; No roads, just maps and a compass.
This was the texture of her life: extraordinary, deliberate, and carrying genuine risk. The thread running through it all was a tension she never fully resolved. She wanted adventures for herself and her children. But how do you have those adventures while keeping your children safe? This was her lifelong dilemma. There had to be trade-offs. There had to be detailed plans and contingencies. There had to be courage because it was never entirely safe, but it was never boring.
Her willingness to navigate that tension, rather than resolving it by choosing either adventure or kids, produced moments of formation that no school or suburban childhood could replicate.
For example, when her oldest son was 14, to help him expand his horizons and improve his French, his mother checked him into a Paris youth hostel. She gave him a map of the city, a list of places to visit, sufficient cash, a train ticket to London, and the address of a friend’s house in the north of England to meet at in five days. The hostel was home to global nomads and a colourful cast of misfits from six continents, with wanderlust similar to the boys’ family. He explored the Catacombs, Versailles, and the Louvre, located the graves of Oscar Wilde and Jim Morrison, and climbed the Eiffel Tower, all items from his mother’s list. He also went ‘off-piste’ for his own adventures, such as navigating the Pigalle neighbourhood on a Saturday night, and knocking on the side door of a patisserie at 5:00 a.m. for fresh croissants.
Somehow, he made his train at Gare du Nord, arriving in London on a Sunday afternoon with no money, and so stood on the street asking strangers for the money for a train ticket to Carlisle. He finally arrived at the friends’ door that evening, having done and seen a few things not entirely ideal for a fourteen-year-old, but having had a life-enhancing experience. It led in no small part to his decision, twenty-six years later, to return to Paris to study, where he met his future business partners and formed friendships that would shape the rest of his life.
The mother told her son that leaving him alone in another country had been both one of the easiest and hardest decisions she had ever made, and that it led to one of the most anxious weeks of her life. She had no doubt he could manage on his own, but she could not sleep properly until he knocked on that door 5 days later.
She never resolved the tension between adventure and safety. She managed it. Every trip was a negotiation between those two values. Every decision was a trade-off. What she modelled, without knowing it, was the art of living with a genuine dilemma.
In every time of profound turbulence, whether driven by war, technological disruption, or political upheaval, leaders face a recurring trap. We may reach for the tools that served us well in calmer times: analytical frameworks, best practices, decisive action plans. These are the tools of problem-solving. But the defining challenges of volatile periods are rarely problems. They are dilemmas. And that distinction, misunderstood or ignored, is the root cause of many leadership failures.
This article explores the fundamental difference between problems and dilemmas, examines how this distinction plays out in two of the most pressing situations facing governments and corporations today, and offers four approaches that leaders can use to navigate genuine uncertainty without relying on the false comfort of premature resolution.
The Core Distinction: Problems vs. Dilemmas
The terms “problem” and “dilemma” are often used interchangeably. This conflation is not merely semantic; it is operationally dangerous.
Problems Are Solvable
A problem, in the strict leadership sense, is a situation with a discoverable answer. It may be complex, resource-intensive, and time-consuming, but it has a solution. A supply chain bottleneck is a problem. A product defect is a problem. A cash flow gap is a problem. These situations call for analysis, expertise, and execution.
Problems respond to “technical work”, applying existing knowledge and established methods to a challenge that is reasonably well understood.[1] Harvard professor Ronald Heifetz, who coined the term ‘adaptive leadership’, distinguishes between technical problems, for which authoritative expertise can supply a known solution, and adaptive challenges, which require innovation and changes in values, beliefs, or behaviour.[2]
Dilemmas Are Irreducible Tensions
A dilemma, by contrast, involves two or more values, goals, or imperatives in genuine tension, where advancing one necessarily constrains the other, and where no analytical solution fully resolves the conflict. Dilemmas do not have answers. They have trade-offs. They require not the mindset of the engineer but the judgment of the experienced diplomat.
Exceptional leaders can hold two opposing ideas in constructive tension and generate creative resolutions superior to either alternative in isolation, using what Roger Martin, in The Opposable Mind (2007), calls “integrative thinking.” [3] A government deciding whether to impose costs on its own economy to advance strategic interests is a dilemma. A corporation navigating between productivity gains and obligations to its people is a dilemma. These are genuine value conflicts, not information gaps.
While navigating dilemmas, you still must solve problems, but they always serve the tensions in play. For example, in the story of the mother, while planning the Saudi desert journey, deciding who should make the trip was a problem to embrace, in the service of the dilemma. She wanted four vehicles for the trip so no one would have to travel alone in an emergency. She wanted vehicle ‘interoperability’ so that they could share spare parts and tires if needed. She chose an archaeologist for his expertise. Critically, she chose someone she suspected was an MI6 officer, reasoning that if anything went wrong during the excursion, the UK government would find him and bring him home, thereby increasing the safety of the entire group, and specifically, her family. It later turned out she was correct in her suspicion.
“The most dangerous leadership error is treating a dilemma as if it were a problem, because it leads to false certainty, premature closure, and decisions that unravel under pressure.”
Why the Confusion Is So Costly
The instinct to convert dilemmas into problems is deeply human. Ambiguity is psychologically uncomfortable, particularly for leaders who are expected to project confidence. But forcing a dilemma into the frame of a problem produces failure: strategies that optimize one value at the cost of another, coalitions that fracture when trade-offs become visible, and crises that recur because the underlying tension was suppressed rather than navigated.
Conversely, treating a genuine problem as a dilemma, overthinking it, seeking endless consultation, and delaying action wastes time and erodes trust. We have all seen leaders who cannot distinguish between the two, leaving them perpetually overconfident or paralyzed. Both are fatal in times of great change.
Case Study I: The Strait of Hormuz and the Dilemma of Strategic Dependency
No geopolitical situation better illustrates the problem-dilemma distinction in 2026 than the crisis unfolding in and around the Strait of Hormuz. What is often framed as a security or logistics problem is, for most national governments, a profound structural dilemma, and leaders who have treated it as the former have found themselves acutely unprepared for the latter.
It is instructional to listen carefully to how the media and leaders describe the news from the Persian Gulf at present. Watch carefully for questions and answers that are problem-centric, not dilemma-centric.
The Strategic Stakes
The Strait of Hormuz is the world’s most critical energy chokepoint. At its narrowest, it measures just 33 kilometres across, with shipping lanes barely three kilometres wide in either direction. According to the U.S. Energy Information Administration, approximately 20 million barrels of oil transit the Strait daily, roughly 20 percent of global oil supply, and about 20% of global liquid natural gas (LNG) too. Critically, around 80 percent of that oil is destined for Asia: China, India, Japan, and South Korea combined account for nearly 70 percent of all crude passing through the strait.
The February-March 2026 conflict between the United States, Israel, and Iran has, at the time of writing, transformed a long-standing risk into an active, ongoing disruption. Following joint U.S.-Israeli airstrikes on Iran beginning on 28 February 2026, Iran’s Islamic Revolutionary Guard Corps (IRGC) declared the strait “closed” and began attacking vessels attempting to transit. Tanker traffic dropped by approximately 70 percent before falling to near zero. Oil prices, which stood at roughly $65 per barrel before hostilities commenced, broke the $100 mark within days. War-risk ship insurance premiums increased by four to six times within a single week.
The Dilemma Governments Face
For the governments most exposed to the crisis, Japan, South Korea, India, China, and the European states dependent on Gulf LNG, the Strait of Hormuz situation is not a problem awaiting a technical solution. It is a structural dilemma between two legitimate imperatives: energy security and geopolitical alignment.
Iran’s clearly planned response has been deliberately differentiated. Rather than closing the Strait universally, Tehran has signalled its willingness to grant safe passage to vessels from states not aligned with U.S.-Israeli operations, a move designed precisely to exploit the dilemma of non-aligned governments. Pakistan-flagged tankers received passage. India was granted exceptions for two LNG carriers bound for western Indian ports. Turkey secured passage for a vessel after direct diplomatic engagement. China entered negotiations to protect both crude oil flows and Qatari LNG shipments. The Malaysian Prime Minister announced on 26th March 2026 that they had “spoken to the leaders of Iran, Egypt, Turkey, and other regional leaders” and that Malaysian vessels were now being allowed to pass through the Strait of Hormuz. These exceptions were not offered on the basis of legal right; they were exchanges based on geopolitical positioning.
For Japan and South Korea, the dilemma is particularly acute. Deep alliance obligations to the United States pull in one direction. Energy security, the literal functioning of their industrial economies, pulls in another. Neither imperative can be fully satisfied without compromising the other.
For governments that had treated their energy dependency as a supply chain problem to be optimized, rather than a strategic dilemma to be managed, this moment has arrived without adequate preparation. The leaders now navigating it most effectively are those who recognized, years earlier, that dependency on a single chokepoint created not a logistical challenge but an ongoing geopolitical exposure requiring sustained, deliberate management.
The Business Downstream
For corporations, the Hormuz crisis is a downstream consequence of a failure to recognize dilemmas at the governmental level, and a stark warning to any executive who has treated geopolitical exposure as a risk to be monitored rather than a dilemma to be navigated. Companies with supply chains running through Gulf energy have found themselves at the mercy of decisions made by governments that were themselves unprepared.
The Hormuz situation is, at its core, a dilemma between two values that cannot be simultaneously maximised: the efficiency of concentrated, optimised global supply chains and the resilience of distributed, redundant alternatives. Leaders who built for efficiency found themselves exposed. Leaders who had built in resilience, at some cost to efficiency, found themselves better positioned to absorb the shock.
Case Study II: Artificial Intelligence, Productivity, and the People Dilemma
While governments navigate the Hormuz dilemma in public and in real time, corporate leaders are wrestling with a dilemma of equal consequence but less visibility: how to integrate artificial intelligence to achieve competitive productivity gains without betraying the people-centred values most organizations espouse. This is not a technology problem. It is an ethical dilemma at the heart of modern organizational leadership.
The Productivity Imperative
The productivity case for AI integration is compelling and effectively non-negotiable. McKinsey estimates that AI and automation technologies could generate up to $4.4 trillion in annual productivity gains across the global economy. J.P. Morgan’s deployment of an AI coding assistant for its software engineers reportedly increased productivity by 10 to 20 percent. Salesforce CEO Marc Benioff stated that AI agents now handle approximately 50 percent of the company’s customer interactions, enabling the firm to reduce its customer support staff from 9,000 to 5,000. The World Economic Forum’s Future of Jobs Report 2025 projects that 92 million jobs globally will be displaced by automation by 2030, while 170 million new roles will be created, a net gain of 78 million jobs, but one distributed extremely unevenly across skill levels, industries, and geographies.
The Values Contradiction
Most large organizations maintain explicit commitments in their stated values, employer branding, and ESG disclosures to treating employees as their most important asset, to investing in people, and to operating with integrity and fairness. These are not just rhetorical positions. They are the foundations of organizational trust, the implicit contract through which employees invest discretionary effort and loyalty.
The AI productivity drive places these commitments under extraordinary pressure, and the evidence from 2025 and early 2026 suggests that many organizations are failing to manage the tension honestly. According to an analysis by Challenger, Gray & Christmas, nearly 55,000 U.S. layoffs in 2025 were directly attributed to AI, out of a total 1.17 million job cuts. The pattern across major corporations has been strikingly consistent: public commitments to reskilling accompanied by actions that prioritize replacement.
Accenture eliminated approximately 11,000 roles, with CEO Julie Sweet explicitly stating that workers who “cannot be reskilled will be exited.” Amazon cut 14,000 corporate positions while CEO Andy Jassy had previously told employees that AI would mean the company would “need fewer people doing some of the jobs that are being done today”, before subsequently characterizing the decision as “not really AI-driven.” Workday reduced its workforce by 8.5 percent to “reallocate resources toward AI investments.” A Forrester analysis found that 55 percent of companies that had executed AI-driven layoffs subsequently reported regret, primarily because they had overestimated AI’s near-term capabilities and underestimated the institutional knowledge being lost.
The paradox is striking: leaders proclaim that employees are their greatest asset and that reskilling will be the key to navigating the AI era, yet their actions often tell a different story. Worker sentiment around AI is shifting as AI layoffs continue to dominate headlines. In fact, employee concerns about job loss due to AI have skyrocketed from 28% in 2024 to 40% in 2026, according to preliminary findings from consultancy firm Mercer’s Global Talent Trends 2026 report, which surveyed 12,000 people worldwide. Mercer’s research shows that 62% of employees feel leaders underestimate AI’s emotional and psychological impact.
The Dilemma Properly Framed
The AI workforce dilemma is not “Should we use AI?” That is a problem with a clear answer in most competitive industries. The genuine dilemma is the tension between two legitimate and equally important organizational values: the obligation to remain competitive and financially sustainable, which requires embracing productivity-enhancing technologies, and the obligation to the people whose labour built the organization and whose trust sustains it.
As more organizations create executive roles focused on AI, such as Chief Innovation and Transformation Officers, it is critical to appoint leaders who have the skills, ethics, and emotional intelligence to leverage the opportunities of AI adoption while managing the profound cultural and organizational changes it brings. Most stalled AI initiatives fail not because of algorithms, but because leadership systems, governance structures, and culture are unprepared.
Leaders who treat this as a pure productivity problem, optimising AI adoption for efficiency, will make decisions that are economically rational in the short term but organizationally corrosive in the longer term. Leaders who treat it as a purely ethical problem, refusing to displace workers regardless of competitive consequences, will find themselves unable to sustain the organization that employs those workers. The dilemma lies precisely in the space between these two imperatives, and it requires navigation, not resolution.
Four Strategies for Leading Through Dilemmas
If dilemmas cannot be solved, but must be navigated, this demands a different leadership posture; one oriented toward judgment, adaptability, coalition-building, and honest communication.
1. Name the Dilemma Explicitly
The first act of dilemma leadership is also the rarest: naming, clearly and publicly, what is actually in tension. Leaders who do this create the conditions for honest deliberation. Leaders who do not force their organizations into a kind of collective cognitive dissonance where everyone senses the tension, but no one is permitted to name it publicly.
Heifetz and his colleagues describe this as “giving the work back”, resisting the temptation to paper over a genuine conflict with optimistic framing, and instead returning the adaptive challenge to the people who must ultimately live with its consequences.[2] Applied to the AI workforce dilemma, this means a CEO telling employees directly: “We face a genuine tension between remaining competitive and protecting the people who built this organisation. There is no option that fully satisfies both. What we are deciding is how to weigh them, and we owe you an honest account of that weighing.”
Applied to the Hormuz dilemma, it means a government telling its public and its allies directly that energy security and alliance solidarity are in genuine, unavoidable tension, and that managing that tension requires both resilience investment and diplomatic positioning, neither of which is free.
- Frame the challenge as a tension between two legitimate values, not as a technical problem awaiting a solution.
- Identify the specific trade-offs involved; what is gained and what is sacrificed in each direction.
- Create structured forums for deliberating on values before making directional decisions.
- Involve people deep in the organization in these structured forums, as more employees are ready to address AI than many senior leadership teams expect.
Failing to engage and communicate honestly will only force people to speculate about the future based on rumours and discussions with others who are similarly in the dark. This is never productive and always corrosive.
2. Manage the Tension Rather Than Resolve It
Because dilemmas are irreducible, the goal of leadership is not resolution but management. This means developing the organizational capacity to hold multiple imperatives in productive tension simultaneously, adjusting the balance over time as circumstances evolve.
Rather than choosing between two opposing models, the integrative thinker seeks a creative synthesis that preserves what is valuable in both. In the AI workforce context, this might mean genuine investment in reskilling as a structural commitment, not a talking point, alongside honest, transparent communication about which roles are at risk and on what timescale. A Forrester analysis found that 80 percent of business leaders are now considering reskilling employees, with 51 percent identifying it as strategically important. The gap between strategic importance and operational commitment is precisely where the dilemma management work lies.
- Avoid the instinct to permanently resolve what is inherently cyclical; build learning loops and governance mechanisms for regular rebalancing.
- Invest in organizational flexibility as an explicit strategic asset, not merely an operational buffer.
- For AI integration, treat reskilling investments as measurable commitments with accountability, not as rhetorical hedges against displacement decisions.
3. Build Coalitions Around Values, Not Just Interests
In moments of great change, alliances built purely on shared interests tend to fracture because interests and circumstances shift. Coalitions built around a shared understanding of how to navigate a value conflict are far more durable.
The Hormuz crisis offers a live illustration of this principle playing out imperfectly. The U.S. call for a naval coalition to escort vessels through the strait was met with scepticism from most allies, in part because “most U.S. allies opposed this war to begin with,” making them “feel relatively less inclined to provide support to it.” [5] Coalitions assembled around a single tactical interest, in this case, opening a dangerous shipping lane, without prior alignment on the underlying values of the operation, proved difficult to constitute at speed.
For corporate leaders navigating the AI people dilemma, the lesson is the same: employees who understand that a leader is genuinely wrestling with an ethical dilemma, rather than using ethical language to dress up a predetermined financial decision, are far more likely to extend the trust and latitude required to navigate it imperfectly.
- Invest time in explaining the dilemma structure to key stakeholders, not just communicating the decision.
- Build trust capital during stable periods that can be drawn on when difficult trade-offs become necessary.
- Distinguish between stakeholders who disagree with a specific decision and those who reject the dilemma framing altogether; the latter require a different kind of engagement.
4. Cultivate Adaptive Leadership at Every Level
No single leader, however gifted, can navigate a complex dilemma landscape alone. The organizations that demonstrate genuine resilience are those that have distributed dilemma-navigation capacity throughout their leadership layers, or “adaptive leadership realized at scale”.
Amy Edmondson’s research on psychological safety provides the organizational infrastructure for this kind of distributed adaptive capacity.[4] Edmondson demonstrates that teams perform most effectively in uncertain, knowledge-intensive environments when members feel safe to speak up, share dissenting information, and admit the limits of their understanding. Without psychological safety, the signals that would identify an adaptive challenge as distinct from a technical problem are suppressed, often until they have become a crisis.
The mother in our story modelled something close to this at a family level. She did not make every decision alone. She prepared her children for the environments they would encounter, briefed them on risks, and trusted their judgment within the latitude she judged appropriate. She created the conditions for adaptive capacity in the people around her.
In the AI workforce context, this means creating cultures that reward managers who raise the ethical dimensions of AI deployment, not just those who deliver adoption metrics. It means building systems to track not only productivity gains from AI but also the human costs: displacement rates, reskilling outcomes, workforce trust levels, and the health of organizational culture under transformation pressure.
For governments managing the Hormuz dilemma, building adaptive capacity means investing in intelligence, scenario planning, and diplomatic infrastructure that enable decision-makers at every level to identify dilemma structures early, before a crisis converts a navigable tension into an acute emergency. The nations best positioned in the current crisis are those whose energy and foreign policy institutions have invested in exactly this capacity over decades, and ‘listen to learn’ from the organization.
- Redesign leadership development programs to include explicit training in recognizing and navigating dilemmas, rather than focusing solely on problem-solving techniques.
- Create organizational mechanisms; red teams, dissent channels, structured uncertainty reviews that surface conflicting signals before they become crises.
- Reward managers who raise well-framed dilemmas as much as those who deliver clean solutions, building on the idea that destigmatising failure is a prerequisite for organisational learning.
Our Final Word: Hold the Courage to Remain Uncertain
The mother in our opening story never resolved her dilemma. She carried the tension of it through nearly 100 countries, across decades, through hostile waters, desert, civil wars, uninhabited islands, and a fourteen-year-old alone in Paris. She would not have described herself as a leader. But the posture she maintained, honest about risk, deliberate in her trade-offs, unwilling to pretend the tension was smaller than it was, and courageous enough to act anyway, is precisely what the best organisational and governmental leaders demonstrate in times of genuine peril.
The pressures on leaders in times of great change are immense, and most of them push in the same direction: toward premature certainty. Boards want clarity. Media demand positions. Competitors exploit any signal of hesitation. And within every leader is a deeply human desire to reduce the weight of tension.
The Hormuz crisis and the AI people dilemma are, on the surface, very different challenges. One involves the physical security of global energy infrastructure. The other involves the ethical obligations of corporate institutions toward the people they employ. But both share a common deep structure: they are dilemmas, not problems. They cannot be solved. They can only be navigated, with honesty about the trade-offs involved, with sustained attention to the values in tension, and with the organizational capacity to hold that tension productively rather than collapsing it into a false resolution.
The leaders who endure, who build organizations and institutions that outlast crises, are precisely those who have resisted the pressure toward premature certainty. They have built cultures, grounded in psychological safety and adaptive capacity, that can tolerate and support productive tension without collapsing into false clarity or paralytic ambiguity. The dilemmas before us today are not going to yield to decisive action alone. They require something rarer and more difficult: the sustained, disciplined exercise of judgment in the face of genuine uncertainty. That is the leadership imperative of our time.
Oh, and thanks, Mum.
References
[1] Heifetz, R. A. (1994). Leadership Without Easy Answers. Harvard University Press.
[2] Heifetz, R. A., Linsky, M., & Grashow, A. (2009). The Practice of Adaptive Leadership: Tools and Tactics for Changing Your Organization and the World. Harvard Business Press.
[3] Martin, R. L. (2007). The Opposable Mind: How Successful Leaders Win Through Integrative Thinking. Harvard Business Press.
[4] Edmondson, A. C. (2018). The Fearless Organization: Creating Psychological Safety in the Workplace for Learning, Innovation, and Growth. John Wiley & Sons.
[5] Shanahan, Roger (16 March 2026). A Middle East security analyst, Al-Jazeera https://www.aljazeera.com/economy/2026/3/16/strait-of-hormuz-which-countriess-ships-has-iran-allowed-safe-passage-to