What Iran's Mistake Teaches Us About Navigating Uncertainty
There are many lessons to be drawn by thinking leaders from the current conflict between Israel and Iran, but one of the most important things it exposes is the risk of committing to one possible future when it is impossible to know what the future actually holds.
Iran's leadership became convinced that Israel's obvious preparations for war were a bluff intended to force it into a negotiated settlement to dismantle its nuclear program during its upcoming talks with the United States, which had been scheduled to begin this weekend in Oman. As a result, it failed to take the steps necessary to prepare its defenses (such as they were) and – more importantly – move senior military leaders and scientists to secure facilities.
This made them easy targets for Israel, thanks to its robust intelligence network.
What Iran failed to do was plan for both possibilities – that Israel was bluffing and that it was not. Taking what steps it could to secure high-value targets while also preparing for the upcoming negotiations with the U.S. would have cost it little and almost certainly reduced its losses from Israel's initial attacks.
That is why I emphasize the need for leaders to adopt plans with optionality.
A man walks past a billboard displaying images of top Iranian commanders and scientists killed in ... More Israeli strikes early Friday, in Tehran, Iran, Friday, June 13, 2025. (AP Photo/Vahid Salemi)
It is worth noting that there was nothing inherently irrational in the conclusion the Iranians drew. Indeed, Israel came to a similar one when it saw Egypt and Syria mobilizing for war back in 1973. Like the Iranians, Israel concluded this was just political saber-rattling, designed to force them into concessions at the negotiating table. Israel mistakenly believed that their backers in Moscow would prevent them from launching a full-scale attack, just as Iran mistakenly believed Washington would restrain Israel.
What was irrational in both cases was failing to allow for the opposite to be true.
That is why it is essential for leaders – in government, in the military, and in business – to develop plans and strategies that allow for uncertainty and ambiguity. Decision-support methodologies such as red teaming help leaders do just that.
In my work with clients, I always advocate for the simultaneous pursuit of diverse options. Committing to only one course of action is a recipe for disaster in today's volatile and uncertain world.
Of course, pursuing multiple strategic options simultaneously requires careful management to avoid confusion, resource dispersion, or indecision. Leaders must rigorously prioritize and communicate clearly, ensuring optionality does not devolve into paralysis or inefficiency. But when done correctly, maintaining strategic flexibility remains undeniably advantageous.
Again, this is as true in business as it is in the military.
The ability to successfully navigate complexity and ambiguity is the most essential skill for leaders to cultivate. So, make that a top priority for your own personal development so that you can be the leader your organization needs today.
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CNN
26 minutes ago
- CNN
Analysis: Trump's strike on Iran marks a momentous moment — and gamble — for the world
Donald Trump has thrust Iran, the Middle East, the United States and his own presidency across a fateful threshold by attacking Tehran's nuclear program. A midsummer night in June 2025 could come to be remembered as the moment the Middle East changed forever; when the fear of nuclear annihilation was lifted from Israel; when Iran's power was neutered and America's soared. But if Trump's gamble fails to destroy Iran's nuclear program — despite his claim to have 'obliterated' it with US air strikes — an often-lawless president could have set the United States and the world on a disastrous course. The risk now is that the Iranian regime responds by attacking US forces, targets or civilians in the region and the conflict escalates into a full-scale war. The president has therefore made a huge wager on global security and his own legacy. He has no way of knowing how the consequences will play out after lining up the US squarely behind Israel's attack on Iran. The president who came power vowing to end wars looks as though he may have started another one. Trump on Saturday night warned Iran's leaders that if they didn't absorb the American assault by B-2 bombers on three key nuclear sites — and do nothing — far worse is to come. 'Iran, the bully of the Mideast, must now make peace. If they do not, future attacks will be far greater,' Trump said in a Saturday evening address from the White House, flanked by Vice President JD Vance, Secretary of State Marco Rubio and Defense Secretary Pete Hegseth. The US airstrikes represent a ruthless and unilateral display of US military might and presidential power and a stunning culmination of 45 years of poisoned US relations with Iran since the Islamic Revolution in 1979. But it's easy to start new wars; it's much harder to end them. In the Middle East, especially, the tactical assumptions of US presidents that they can contain the fallout of 'shock and awe' military action often get exposed as tragically naive. Trump — who has constantly pushed against constraints on presidential power at home — sent US forces to war without acquiring the consent of Congress or properly preparing the American people, and after declining to enlist allies. On Thursday, he said he'd make a decision on what to do about Iran within two weeks — but in the end, he didn't wait that long to strike. The president also did not present evidence of his claims that Iran was weeks away from acquiring a nuclear weapon to the public or to the rest of the world. And he repeatedly dismissed assessments from his own intelligence community that Iran was still years away from a weapon. And he has no way of knowing for sure what comes next. 'If anyone tells you that they know where this is going, the good optimistic (possibilities) or the most pessimistic … they have no idea what they are talking about,' Brett McGurk, a senior US official who worked for Republican and Democratic administrations on the Middle East, told CNN's Anderson Cooper. 'Nobody knows,' said McGurk, who is now a CNN global affairs analyst. The short-term questions now concern the capacity and willingness of Iran to hit back against US targets in the Middle East and elsewhere. And despite Trump's declaration of total success for the mission, it is unclear whether the US strikes will have eradicated all of Iran's stocks of enriched uranium, which it might have hidden, and which it might still be able to use to make a rudimentary nuclear device in the future. No senior US leader wanted Iran to get a nuclear weapon. But such unknowns were some of the reasons why Trump's recent predecessors chose not to take the massive risk of striking Irandespite years of proxy warfare between the two powers, including Tehran's support for militias that were responsible for the deaths of hundreds of US troops in Iraq. Administration officials say that Trump does not view airstrikes against Iran as tantamount to the US assaults on Iraq and Afghanistan that led the United States into wars from which it took 20 years to extricate. Still, Iran now gets the chance to decide how to respond and whether it embroils the US in a new war. The immediate danger is that, even in its weakened state after days of Israeli air strikes, Iran could attack US bases, personnel, and even civilians in the Middle East and elsewhere — and drag American into a bloody conflagration. Iran's leader, Ayatollah Ali Khamenei, has now been comprehensively humiliated on an issue — Iran's self-declared right to enrich uranium — that is regarded as central to his regime and his nation's prestige. It's therefore hard to imagine that a spiritual leader who is the guardian of the revolution will do nothing to respond. But Trump is warning Iran will hit back at its peril. 'There will be either peace, or there will be tragedy for Iran, far greater than we have witnessed over the last eight days. Remember, there are many targets left,' Trump said in his address. Despite the serious degradation of its missile arsenal by Israeli strikes — and of its proxies Hezbollah in Lebanon and Hamas in Gaza, which would once have rained missiles on Israel in response to strikes on Iran — Tehran does have options. It could seek to provoke a global energy crisis by closing down the Strait of Hormuz, a vital transit choke point for oil exports. It could target US allies in the Gulf. It may seek to weaponize proxies in Iraq and Syria to attack US troops and bases in the region. Any of these options would inevitably drag the United States into reprisals that would risk setting off a full-scale US-Iran war. The political impact of Trump's strikes inside Iran is also unclear. Some experts wonder if it could set off political eruptions that threaten the survival of Iran's revolutionary regime. Israel has made little secret of the fact that that it hopes its onslaught will cause the downfall of a government that has threatened to wipe the Jewish state off the map. But such a collapse of the government could lead to an even more hostile and dangerous regime, perhaps led by elements of the Islamic Revolutionary Guard Corps. If the Iranian state were to dissolve, civil war could break out and disastrous instability could spread far beyond Iran's borders. The fear for many Iranians will be that a humiliated regime will respond by doubling down on repression against its own people. The desperate legacy of the Iraq and Afghan wars — which opened with spectacular US military successes but then went on for years, killing and maiming thousands of Americans — hung over the prospect of US military action. It took the best part of two decades for the US to find a way out of those conflicts. Successive presidents have wanted to divert resources away from the Middle East to Asia and the challenge posed by China, a rising superpower. The Iran conflict doesn't have to turn into a repeat of those wars. The Middle East has changed in recent months at lightning pace. Iran's regional power has been seriously eroded by Israel military action following the Hamas attacks on Israeli civilians on October 7, 2023. And predictions that Trump's killing of Iranian defense chief Qasem Soleimani in his first term would ignite a regional inferno did not come true. But Trump has set the United States on a new road with an uncertain end. He ultimately decided that the risk posed to Israel, the United States and the world from a potential Iranian nuclear bomb was more disastrous than the cascade of consequences that could be unleashed by an attempt to stop it. Trump's action will only deepen concerns of critics who believe Trump is grasping for unconstitutional, unchecked power that is antithetical to US democracy. After all, the president has initiated a new conflict at a time when Iran did not pose a direct threat to the United States. Trump's record of serial lying and eroding of the mechanisms of US democracy will also make it far harder to convince the public that he did the right thing. Trump has now also set a precedent for unilateral American action that potentially infringes on international law and the principles of the US-led international system. It is likely to be used by strongmen and tyrants everywhere to justify unilateral military action against smaller nations. Trump is also testing his standing with his ultra-loyal political support. He has now repudiated one of his few previously rigid political principles — that the era of US presidents launching new wars in the Middle East on the basis of questionable intelligence is over. The potential of a US strike on Iran had already split the MAGA movement. That said, Trump has also long been consistent that he'd not allow Iran to get a nuclear bomb. The American assault on Iran's nuclear plants, however, represents a massive triumph for Israeli Prime Minister Benjamin Netanyahu, who has been pushing for the military eradication of the sites for decades. Netanyahu effectively started a war against Iran just over a week ago that he knew that Israel could not finish, since it lacks the bunker-busting bombs the US used on Saturday night. He bet, correctly, that after Israel disabled Iran's air defenses, Trump would take the chance to try to wipe out Iran's nuclear program once and for all. Trump's decision to strike Iran set off an immediate political storm in the US. Senior Republicans on Capitol Hill immediately offered their backing. House Speaker Mike Johnson and House Majority Whip Tom Emmer praised Trump in statements. 'The military operations in Iran should serve as a clear reminder to our adversaries and allies that President Trump means what he says,' Johnson said. But top Democrats accused him of breaking the law, infringing the Constitution and plunging the US into a new Middle East conflict. Virginia Sen. Mark Warner, the top Democrat on the Senate Select Committee on Intelligence — who, like other Democratic leaders, was not informed before the strike — slammed Trump's decision to strike Iran, 'without consulting Congress, without a clear strategy, without regard to the consistent conclusions of the intelligence community, and without explaining to the American people what's at stake.'
CNN
26 minutes ago
- CNN
Analysis: Trump's strike on Iran marks a momentous moment — and gamble — for the world
Donald Trump has thrust Iran, the Middle East, the United States and his own presidency across a fateful threshold by attacking Tehran's nuclear program. A midsummer night in June 2025 could come to be remembered as the moment the Middle East changed forever; when the fear of nuclear annihilation was lifted from Israel; when Iran's power was neutered and America's soared. But if Trump's gamble fails to destroy Iran's nuclear program — despite his claim to have 'obliterated' it with US air strikes — an often-lawless president could have set the United States and the world on a disastrous course. The risk now is that the Iranian regime responds by attacking US forces, targets or civilians in the region and the conflict escalates into a full-scale war. The president has therefore made a huge wager on global security and his own legacy. He has no way of knowing how the consequences will play out after lining up the US squarely behind Israel's attack on Iran. The president who came power vowing to end wars looks as though he may have started another one. Trump on Saturday night warned Iran's leaders that if they didn't absorb the American assault by B-2 bombers on three key nuclear sites — and do nothing — far worse is to come. 'Iran, the bully of the Mideast, must now make peace. If they do not, future attacks will be far greater,' Trump said in a Saturday evening address from the White House, flanked by Vice President JD Vance, Secretary of State Marco Rubio and Defense Secretary Pete Hegseth. The US airstrikes represent a ruthless and unilateral display of US military might and presidential power and a stunning culmination of 45 years of poisoned US relations with Iran since the Islamic Revolution in 1979. But it's easy to start new wars; it's much harder to end them. In the Middle East, especially, the tactical assumptions of US presidents that they can contain the fallout of 'shock and awe' military action often get exposed as tragically naive. Trump — who has constantly pushed against constraints on presidential power at home — sent US forces to war without acquiring the consent of Congress or properly preparing the American people, and after declining to enlist allies. On Thursday, he said he'd make a decision on what to do about Iran within two weeks — but in the end, he didn't wait that long to strike. The president also did not present evidence of his claims that Iran was weeks away from acquiring a nuclear weapon to the public or to the rest of the world. And he repeatedly dismissed assessments from his own intelligence community that Iran was still years away from a weapon. And he has no way of knowing for sure what comes next. 'If anyone tells you that they know where this is going, the good optimistic (possibilities) or the most pessimistic … they have no idea what they are talking about,' Brett McGurk, a senior US official who worked for Republican and Democratic administrations on the Middle East, told CNN's Anderson Cooper. 'Nobody knows,' said McGurk, who is now a CNN global affairs analyst. The short-term questions now concern the capacity and willingness of Iran to hit back against US targets in the Middle East and elsewhere. And despite Trump's declaration of total success for the mission, it is unclear whether the US strikes will have eradicated all of Iran's stocks of enriched uranium, which it might have hidden, and which it might still be able to use to make a rudimentary nuclear device in the future. No senior US leader wanted Iran to get a nuclear weapon. But such unknowns were some of the reasons why Trump's recent predecessors chose not to take the massive risk of striking Irandespite years of proxy warfare between the two powers, including Tehran's support for militias that were responsible for the deaths of hundreds of US troops in Iraq. Administration officials say that Trump does not view airstrikes against Iran as tantamount to the US assaults on Iraq and Afghanistan that led the United States into wars from which it took 20 years to extricate. Still, Iran now gets the chance to decide how to respond and whether it embroils the US in a new war. The immediate danger is that, even in its weakened state after days of Israeli air strikes, Iran could attack US bases, personnel, and even civilians in the Middle East and elsewhere — and drag American into a bloody conflagration. Iran's leader, Ayatollah Ali Khamenei, has now been comprehensively humiliated on an issue — Iran's self-declared right to enrich uranium — that is regarded as central to his regime and his nation's prestige. It's therefore hard to imagine that a spiritual leader who is the guardian of the revolution will do nothing to respond. But Trump is warning Iran will hit back at its peril. 'There will be either peace, or there will be tragedy for Iran, far greater than we have witnessed over the last eight days. Remember, there are many targets left,' Trump said in his address. Despite the serious degradation of its missile arsenal by Israeli strikes — and of its proxies Hezbollah in Lebanon and Hamas in Gaza, which would once have rained missiles on Israel in response to strikes on Iran — Tehran does have options. It could seek to provoke a global energy crisis by closing down the Strait of Hormuz, a vital transit choke point for oil exports. It could target US allies in the Gulf. It may seek to weaponize proxies in Iraq and Syria to attack US troops and bases in the region. Any of these options would inevitably drag the United States into reprisals that would risk setting off a full-scale US-Iran war. The political impact of Trump's strikes inside Iran is also unclear. Some experts wonder if it could set off political eruptions that threaten the survival of Iran's revolutionary regime. Israel has made little secret of the fact that that it hopes its onslaught will cause the downfall of a government that has threatened to wipe the Jewish state off the map. But such a collapse of the government could lead to an even more hostile and dangerous regime, perhaps led by elements of the Islamic Revolutionary Guard Corps. If the Iranian state were to dissolve, civil war could break out and disastrous instability could spread far beyond Iran's borders. The fear for many Iranians will be that a humiliated regime will respond by doubling down on repression against its own people. The desperate legacy of the Iraq and Afghan wars — which opened with spectacular US military successes but then went on for years, killing and maiming thousands of Americans — hung over the prospect of US military action. It took the best part of two decades for the US to find a way out of those conflicts. Successive presidents have wanted to divert resources away from the Middle East to Asia and the challenge posed by China, a rising superpower. The Iran conflict doesn't have to turn into a repeat of those wars. The Middle East has changed in recent months at lightning pace. Iran's regional power has been seriously eroded by Israel military action following the Hamas attacks on Israeli civilians on October 7, 2023. And predictions that Trump's killing of Iranian defense chief Qasem Soleimani in his first term would ignite a regional inferno did not come true. But Trump has set the United States on a new road with an uncertain end. He ultimately decided that the risk posed to Israel, the United States and the world from a potential Iranian nuclear bomb was more disastrous than the cascade of consequences that could be unleashed by an attempt to stop it. Trump's action will only deepen concerns of critics who believe Trump is grasping for unconstitutional, unchecked power that is antithetical to US democracy. After all, the president has initiated a new conflict at a time when Iran did not pose a direct threat to the United States. Trump's record of serial lying and eroding of the mechanisms of US democracy will also make it far harder to convince the public that he did the right thing. Trump has now also set a precedent for unilateral American action that potentially infringes on international law and the principles of the US-led international system. It is likely to be used by strongmen and tyrants everywhere to justify unilateral military action against smaller nations. Trump is also testing his standing with his ultra-loyal political support. He has now repudiated one of his few previously rigid political principles — that the era of US presidents launching new wars in the Middle East on the basis of questionable intelligence is over. The potential of a US strike on Iran had already split the MAGA movement. That said, Trump has also long been consistent that he'd not allow Iran to get a nuclear bomb. The American assault on Iran's nuclear plants, however, represents a massive triumph for Israeli Prime Minister Benjamin Netanyahu, who has been pushing for the military eradication of the sites for decades. Netanyahu effectively started a war against Iran just over a week ago that he knew that Israel could not finish, since it lacks the bunker-busting bombs the US used on Saturday night. He bet, correctly, that after Israel disabled Iran's air defenses, Trump would take the chance to try to wipe out Iran's nuclear program once and for all. Trump's decision to strike Iran set off an immediate political storm in the US. Senior Republicans on Capitol Hill immediately offered their backing. House Speaker Mike Johnson and House Majority Whip Tom Emmer praised Trump in statements. 'The military operations in Iran should serve as a clear reminder to our adversaries and allies that President Trump means what he says,' Johnson said. But top Democrats accused him of breaking the law, infringing the Constitution and plunging the US into a new Middle East conflict. Virginia Sen. Mark Warner, the top Democrat on the Senate Select Committee on Intelligence — who, like other Democratic leaders, was not informed before the strike — slammed Trump's decision to strike Iran, 'without consulting Congress, without a clear strategy, without regard to the consistent conclusions of the intelligence community, and without explaining to the American people what's at stake.'
Yahoo
27 minutes ago
- Yahoo
Pres. Trump speaks after U.S. strikes three Iran nuclear sites
President Trump addressed the nation Saturday night, hours after he posted on Truth Social the United States completed attacks on three Iranian nuclear and military his address, President Trump said "Our objective was the destruction of Iran's nuclear enrichment capacity," and went on to say the strikes "totally obliterated" Iran's nuclear attack marks the United States' entry into the conflict between Israel and Trump described the strikes as a "spectacular military success" and said in his social media post that all of the planes involved were safely on their way post was written by Rachel Sherman. Sign in to access your portfolio
