Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change

CHAPTER 3

THE GENERAL’S CHARGE

Strategic Questions

BILL AND MELINDA GATES didn’t just wake up one morning and decide, over a bowl of organic oatmeal, to throw themselves and their money at the fight against malaria. They knew the terrible toll of the disease—symptoms that usually appear within two weeks of the mosquito bite: fever, chills, headache, and vomiting. They knew that, if not treated within twenty-four hours, the illness can become acute and kill. They’d seen the data: The disease was afflicting up to 300 million people a year. Most were pregnant women and children. Most were in Africa.

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With their vast wealth and giant foundation, they were looking for philanthropic investments that could make the biggest difference for the most people. At a forum of more than 300 health and political leaders in 2007, Melinda Gates called for an all-out assault: “Advances in science and medicine, promising research, and the rising concern of people around the world represent a historic opportunity not just to treat malaria or to control it, but to chart a long-term course to eradicate it.”

The call to eradicate malaria led to one of the most ambitious mobilizations of research and medicine in the world. Researchers and doctors made tremendous progress—in just a few years deaths came down 50 percent—but if the campaign actually eradicated the disease, it would save millions more lives and untold suffering. It would unlock immense potential in places where the disease is a debilitating curse on families, communities, and entire countries. Defeating malaria would be an epic human achievement. Like other ambitious undertakings, it requires huge investment, commitment, strategic alliances, massive time allotments, and boundless energy. But how did the Bill and Melinda Gates Foundation and others determine that an ambitious campaign against Malaria was feasible and could succeed? What did they ask about objectives, resources, hurdles and challenges that made them come down on the side of an all-out assault? They posed big, strategic questions.

What is the extent of the problem?

What will it take to succeed?

Are we up to the challenge?

In Chapter 2, I showed you how diagnostic questions help identify a particular problem that’s defined by a unique set of symptoms or circumstances. Strategic questions ask about the bigger challenge and the long-term goal—about stakes, opportunities, costs, consequences, and alternatives—as you focus on the big picture. They help you set your sights, clarify objectives, and consider obstacles as you think about future benefits and consequences.

Set Your Sights

Perhaps you’ve been invited to join a startup venture. You like the people. They have a couple of years of funding. The business plan is exciting. There could be a big payoff. But the idea is untested and the competition is moving fast. You’ll have to leave your corporate job, and there’s no job security in the startup world.

Maybe your partner is lobbying for a move across the country to get out of the rat race and reboot your lives. The idea has appeal. But you’re not sure what you will do out there, or how much of a real difference the move will make. Truth is, you’re not loving life right now either, but this would be a quantum leap into the unknown. Will the change be worth the effort? And what about that paycheck you now get reliably every two weeks?

Your company is considering a major investment in a product that it believes will increase market share. You have to weigh in. Something is needed because the competition is eating your lunch and just launched a brilliant ad campaign that brought it a ton of buzz. Maybe the new product will make a difference, but it will require a huge investment, a lot of your time, and a big marketing push. It seems pretty cool, but there’s no guarantee it will be the blockbuster you need.

These are all-in moves that come with a daunting list of pros and cons and plenty of unknowns. They call for fundamental changes and new ways of thinking. They require questions that look over the horizon.

“Strategy, by definition, is about making complex decisions under uncertainty, with substantive, long-term consequences,” Freek Vermeulen, associate professor of strategy and entrepreneurship at the London Business School, wrote in the Harvard Business Review in September 2015. Vermeulen crafted an elegantly simple description of a word that almost everyone overuses and poorly understands. But by asking strategic questions, you can define and articulate your long-term goals. As you challenge your assumptions, you weigh the investment and risks involved. These are tough questions, built on a few overarching principles. Like an imaging satellite miles above the earth, strategic questions start wide and zoom in to see the landscape in detail.

Get the big picture. Define the challenge or opportunity. Ask why it matters. Articulate the goal. Does it reflect your values? Who else cares? What are others prepared to do? What does it look like from 60,000 feet?

Know what you’re up against. Recognize that you have a worthy opponent, whether it’s a person, place, or, in the Gates’s case, a disease. Give it credit. It’s the biggest obstacle that stands in your way. Ask what your opponent can dish out and what you’re willing to take.

Define your plan. Determine the tactics that will help you achieve your strategic goal. What are the next steps and the steps down the road? Who does what? And how will you measure success along the way? Know that tactics may change even as your strategic interests remain constant.

Challenge yourself. Hold your plan or proposal up to the light and look for holes. Play out different scenarios. What haven’t you thought of? What can go wrong? Can you explain and defend the strategy with facts, or is emotion driving you? Force yourself to stop and ask about options and alternatives.

Define success. Can you explain what success looks like? How will you know it when you achieve it? What will it take and at what cost?

A Strategic Approach

Before the Bill and Melinda Gates Foundation committed time and resources to the global fight against malaria, it posed a set of demanding questions to assess the dimension of the challenge. The foundation had published the “Strategy Lifecycle” as a sort of handbook of strategic questioning. The guide could serve as a template for just about any big decision, or campaign.

The Strategy Lifecycle posed a series of questions organized in three phases: Lookback and Scoping, Strategy Choice, and Execution Plan. “Look Back” and “Scoping” questions sought to learn from previous experiences and to define the history and dimensions of the issue.

What are the lessons from prior strategies and implications for our future work?

What is the nature of the problem?

What are the most promising ways to address the problem?

Strategy Choice questions got specific, tied directly to the challenge and what was needed to accomplish the mission.

How do we think change will happen?

What will we do and not do? Why? What are the trade-offs?

What is the role of our partners?

What are the financial requirements?

How will we measure our results?

What are the risks?

The answers to these questions helped set the parameters of the undertaking, and they exposed the risks. The team then asked how and what it would take to achieve the defined goals.

What is the timing and sequencing of initiatives?

What resources are needed?

The foundation’s strategic questions helped clarify decision-making and provide coherence to a campaign that pitted ambitious ideas against a formidable foe. The Gates Foundation launched its campaign and became a transformational leader in the fight against malaria. It spent billions of dollars to create new partnerships, launch massive public health campaigns, distribute insecticide-treated bed nets, and fund indoor spraying, more rapid diagnostic tests, more accessible treatments therapies, and a lot of research into improved medication. It helped turn the corner on malaria, especially in sub-Saharan Africa. The World Health Organization’s World Malaria Report 2014 estimated that malaria mortality rates had decreased by 47 percent globally and 54 percent in Africa since 2000. Researchers reported progress on a number of other fronts, including single-dose treatments and, possibly, a vaccine that would prevent the disease altogether. Optimists believe the disease can be eradicated by 2030.

A General’s Command

Strategic questions deepen understanding and clarify objectives. By asking more, you set benchmarks and assess risk. You examine opportunities and expose vulnerabilities. You become a better thinker and a smarter leader. You avoid the constraints of near-term distractions and stay focused on the essential, long-term goals. To dig into strategic questioning with someone who has done it for a living, I crossed the river to Virginia to pay a visit to General Colin Powell.

Headquartered in a nondescript office building just off the George Washington Parkway, the general still had the bearing of a military man. Taut and trim, he looked much younger than his seventy-odd years. He greeted me warmly with a big smile and an outstretched hand. I wanted to learn about his version of the strategy lifecycle—how he had brought military discipline together with intellectual curiosity to clarify the mission and set strategy at a time of war when the stakes couldn’t be higher. I wanted to know how this retired four-star general had used questions to define and execute a mission. I wanted him to explain success. And failure.

I had first met Colin Powell when we were both much younger. He was a rising star and had just been named President Ronald Reagan’s national security adviser. He took the job in the wake of the Iran-Contra scandal, an unmitigated disaster that threatened the Reagan presidency. Lieutenant Colonel Oliver North and others had hatched a secret scheme, run out of the White House, to sell arms to Iran in exchange for American hostages and funnel the profits to anticommunist guerrillas in Nicaragua. The convoluted mission violated U.S. laws as well as the president’s solemn pledge never to negotiate with terrorists. It was a mess.

I was a young White House correspondent with an untested news organization called CNN. I became consumed by the story and the deepening scandal—following every move of the independent counsel, months of congressional hearings, and leaks from sources trying to influence public opinion and the investigation itself. The scandal ruined careers and tarnished the Reagan presidency. Several senior officials resigned or were thrown overboard.

Reluctantly, President Reagan finally acknowledged, “Mistakes were made.”

Powell was a calming influence. He was brought in to help repair the severely damaged ship of state. He stayed above the chaos and proved adept at managing it. I remember his first White House briefings. His unflappable demeanor and disarming ability to pivot from tough guy to humorous answer man established him as a confident and credible power player. His direct, sometimes playful relationship with the media made him a go-to person for a comment or quote.

Everybody, it seemed, respected Colin Powell. He would serve three other presidents—George H. W. Bush, Bill Clinton, and George W. Bush, breaking barriers as the first African American in some of the most influential roles in the U.S. government.

When I visited his office all these years later, Powell’s roles in government service long finished, I was struck by its modesty. The picture windows looked out on the GW Parkway, not on the grand avenues or monuments of Washington that so many crave in order to assert their place in history. Inside, there was no wall of fame heavy with pictures of Powell in uniform or alongside world leaders, no reminders of famous battles or personal glory that are so common in the offices of “formers” across this power town. The most prominent object was parked next to Powell’s desk: a bright red Radio Flyer wagon, the symbol of America’s Promise, the youth organization Powell founded nearly twenty years before.

Colin Powell was a key player in America’s two wars against Iraq. In the first, he was chairman of the Joint Chiefs of Staff, the principal military adviser to President George H. W. Bush. In the second, he was secretary of state, the top diplomat in the cabinet serving President George W. Bush. Powell was not the principal architect or the leading voice in either war—there were many other forces and personalities at work in both—but he played significant roles. The questions he asked—and did not ask—stand as examples of how strategic questioning can shape decision-making at a time of crisis.

Powell explained that his approach to strategic questioning was honed through his military training. During his student days in the Reserve Officers’ Training Corps (ROTC) he learned to start with a rapid and accurate “estimate of the situation,” so he would know what he was up against. Suppose there’s a hill to be taken, Powell said, the first thing the young infantry officer or the old corps commander needs to do is ask:

What’s up there?

How many enemy?

What’s the weather going to be like?

How much time do I have?

How much equipment?

How much food?

What’s my ammunition supply rate?

What’s the enemy doing?

How dug in is he?

What’s his ability to reinforce?

Once you assess your opponent’s ability, Powell explained, you devise a plan that includes tactics and timelines. Your success in taking that hill will depend on having asked the right questions so you have the most accurate “estimate of the situation” possible.

As Powell rose in the ranks, his world expanded well beyond the hill to be taken. Increasingly, he had to think about winning the war, not just the battle. He developed strategic questions designed to look at the big picture, articulate goals, and challenge his thinking and that of his commanders. Powell’s strategic questions asked decision-makers to peel back groupthink and conventional wisdom, recognizing Vermeulen’s definition of strategy and the stakes of “complex decisions under uncertainty, with substantive, long-term consequences.”

Eight Yeses

Powell’s big test as a military leader came after Iraq invaded Kuwait in August 1990. Saddam Hussein’s invasion was a sledge-hammered move in a fragile region, a dictator’s crass grab for power and territory. By occupying Kuwait, he also posed a threat to Saudi Arabia, America’s oil-rich ally. President George H. W. Bush declared that the aggression “will not stand.” The president wanted a recommendation. The first questions, Powell explained to me, sought to define the mission.

“The early argument was what do you want to do? Do you just want to protect Saudi Arabia so that the Iraqis can’t move south? Or do you want to kick the Iraqis out of Kuwait? And is there anything else you want to do? You want to go to Baghdad? And we needed to get those questions answered … before we made a plan,” he said.

There was no appetite to go to Baghdad, least of all from Powell. He told the president that if the United States pursued Saddam and marched into Baghdad, “You are going to be the proud owner of 25 million people. You will own all their hopes, aspirations, and problems. You’ll own it all.”

So the Pentagon went to work, putting together a military campaign, Operation Desert Storm, to liberate Kuwait. Planners considered Iraq’s military capacity, topography, roads, ports, waterways, weather, and the location of civilian populations. They looked at American capabilities and the contributions allied forces could make. Before proposing to the president the deployment of half a million American troops to push Saddam Hussein back across the desert, however, Powell asked his strategic questions to see what they would reveal through the long lens of diplomacy, politics, and war. He wanted to know about goals, resources, consequences, rationale, and risk. Having experienced Vietnam, he asked whether the American public would stand by a war in Iraq if it got costly and difficult.

Powell posed eight strategic questions looking at the big picture, challenging assumptions, and defining success. Only if the answers to all were positive, he believed, could the president confidently launch a full-scale invasion to liberate Kuwait.

Is a vital national security interest threatened?

Is the action supported by the American people?

Do we have genuine, broad international support?

Have the risks and costs been fully and frankly analyzed?

Have all other nonviolent policy means been fully exhausted?

Have the consequences of our action been fully considered?

Do we have a clear, attainable objective?

Is there a plausible exit strategy to avoid endless entanglement?

The answers were all compelling and affirmative. The big-picture questions made clear the threats to national and global security. Iraq had broken international law and was sowing instability in a region that provided much of the world’s oil and access to some of its most important shipping lanes. Public support appeared solid, with the U.S. Congress voting for military force and three in four of Americans supporting it, according to a Gallup survey at the time. The international community was on board, too. UN Resolution 678 authorized all necessary means to push Iraq out of Kuwait. Several countries in the region, even some that were normally hostile to Washington, signed on as active coalition partners.

Powell’s challenge questions drew definitive responses as well. Intelligence from U.S. sources, as well as from Iraq’s neighbors and America’s closest allies, painted a consistent picture of Saddam’s intentions and capabilities. The option of diplomacy had been tried through intermediaries, the United Nations, and direct talks with the Iraqi foreign minister. America had consulted every country in the region, along with more than two dozen coalition partners. Military and political leaders had considered every contingency they could think of, down to the frightening scenario that Iraq might sabotage its oil fields, which ultimately, it did.

Finally, Powell’s questions intended to define success produced clear answers and finite, achievable goals with a realistic exit strategy. The result was a mission—Operation Desert Storm—designed to push Saddam out of Kuwait and force him to comply with international law and UN resolutions. This would not be an open-ended occupation or an exercise in nation building.

The war began with a punishing barrage from the air. American and coalition bombing pounded Iraq’s air defenses, military installations, and government headquarters, which were quickly destroyed. By the time U.S. and coalition forces rolled into Kuwait on the ground, Iraqi forces were on the run. Though Saddam hung on to power, the mission had been a success.

The ground war lasted just 100 hours. Colin Powell’s star was never higher.

Failure Is an Option

When a leader fails to know where he is going, refuses to listen to what he doesn’t want to hear, or relies on faulty information, bad things happen. If nobody asks or answers challenging questions, flawed thinking may go unnoticed or unaddressed. Colin Powell experienced the dark side of decision-making when he and others didn’t ask enough tough questions leading up to the second Iraq war.

In the aftermath of the terror attacks of September 11, 2001, Powell, then Secretary of State, was surrounded by hard-liners, led by Vice President Dick Cheney, Defense Secretary Donald Rumsfeld, and several influential senior policy makers. Cheney and the others argued for a muscular American military response. After Afghanistan, home to Al Qaeda, they viewed Iraq as a logical target. They accused Iraq of harboring weapons of mass destruction, in direct violation of commitments to destroy them made after the first Gulf War.

Still reeling from the 9/11 attacks on New York’s World Trade Towers and the Pentagon in Washington, D.C., the public strongly supported this administration’s plans for military action against Iraq. The administration assured the world that the intelligence was credible and the Iraqi threat with respect to weapons of mass destruction was real. But behind the scenes, the really tough strategic questions that should have been asked were unwelcome.

Have the risks and costs been fully and frankly analyzed?

Have the consequences of our action been fully considered?

Do we have a clear and attainable objective?

The questions Powell posed before the first Iraq war, more relevant than ever, were glossed over or not pursued. Powell himself contributed to the drumbeat to war in a dramatic 2003 appearance before the United Nations.

“Leaving Saddam Hussein in possession of weapons of mass destruction for a few more months or years is not an option,” Powell declared. “Not in a post–September 11 world.”

As experience would later show, however, Saddam didn’t have weapons of mass destruction. The intelligence was wrong. The administration hadn’t asked the right questions of the right people. I asked Powell about the price he and America paid for that failure. For the first time in our otherwise friendly conversation, he bristled. The information he got was bad, he said. It had gone to Congress four months before he went to the UN. Congress had seen the formal National Intelligence Estimate, the comprehensive report prepared by the CIA, and reached the same conclusions. Influential senators on both sides of the aisle including John Kerry, Hillary Clinton, John McCain, and Jay Rockefeller, the chairman of the Senate Intelligence Committee, all lined up behind the report. The president cited it in his State of the Union speech. Vice President Dick Cheney went on national television with it. Condoleezza Rice, the national security adviser, referred to it when she told CNN that Saddam was closer to a nuclear device than anybody thought. “We know that he has the infrastructure, nuclear scientists to make a nuclear weapon,” Rice had said, adding ominously, “but we don’t want the smoking gun to be a mushroom cloud.”

“They all said this is solid stuff and believed it,” Powell told me.

They were all wrong.

Particularly egregious was the assertion that the Iraqis had biological weapons laboratories that they could move around and hide from weapons inspectors and spy satellites. It was Exhibit A for the CIA. But it was based on a single source, an Iraqi defector code-named Curveball. He’d told his story to German intelligence. American agents never interrogated him. Only after the invasion did we learn that Curveball had lied.

Why didn’t anyone realize Curveball’s story was full of holes? What questions should have been asked, and by whom? Why didn’t alarm bells ring when officials realized Curveball had not been interrogated by American agents? More than ten years after the fact, Powell was still steaming mad.

“The friggin’ director of the CIA should have asked! He should have asked his people, ‘What do we really know about this? … Where did this come from? Is it multiple-sourced?’”

As secretary of state, Powell didn’t push back hard enough. The power players—the vice president, the secretary of defense, and others—drove the decisions. They didn’t ask the right questions either. The U.S. mission in Iraq turned into a costly open-ended commitment riddled with unintended consequences and terrible casualties, resulting in an ugly and inconclusive outcome.

“Yes, a blot, a failure will always be attached to me and my UN presentation,” Powell wrote in his book, It Worked for Me. “I am mad mostly at myself for not having smelled the problem. My instincts failed me.”

In his office, far from the cameras and the lights, the retired general and former secretary of state seemed subdued and regretful that his long and distinguished life of service to the United States, his record of breaking barriers and standing for integrity and honor, had been sullied by a mission that he and others did not submit to the kind of scrutiny and strategic questioning it deserved. His UN appearance and his insistence that Saddam Hussein represented a clear and present danger still pained him.

“I’m the one left holding the bag with respect to all this crap and it’s in my obituary,” he said to me. “And so be it.”

Washington is a town of towering purpose but also towering egos. It is a place where people assess you by your connections and your access to power, where you are only as useful as your last job title and the network you bring with you. Taking responsibility for failure and screw-ups is not a common trait. It’s too easy to accuse someone else, duck the tough questions, or change the subject. Powell didn’t do that. He acknowledged when an operation had gone wrong and he took responsibility where it mattered. He should have been a louder voice and insisted that difficult but strategic questions got asked along the way. Whether anyone would have listened to him is another matter. But he knows he should have tried. That’s a lesson from him and for the rest of us.

Getting Personal

In the mid-1990’s, when his star dominated the political horizon, Powell considered a run for the White House. The pressure from supporters was intense. The calling seemed clear. Powell’s first book, My American Journey, was a bestseller. America’s victory against Saddam Hussein in the first Gulf War, and the four stars on Powell’s shoulders, made him a hero. His story was inspiring and he enjoyed unparalleled stature and authority. He looked like a modern-day Eisenhower, a leader who could bring precision and discipline to Washington, along with star quality and diversity to the Republican Party. The very hint of a Powell presidential bid drove cable news shows and op-ed columns into a frenzy. I was the anchor of a daily show on CNN at the time, and we could barely keep the pundits and politicians away from the microphone. Everybody wanted to weigh in. It was TV heaven, but the spectacle was short-lived.

Powell asked his strategic questions, this time on a much more personal level.

One, do I have an obligation?

Two, do I really want to do it?

Three, do I have the passion to do it?

Four, do I have the organizational ability to do it?

Five, am I going to enjoy campaigning or will I be good at it?

Six, what is my family’s view of this?

Could he answer each question in the affirmative? No, he didn’t have the passion. And no, his family was not on board—especially his wife, Alma, who had suffered bouts of depression over the years. To submit her to the unending ordeal of a campaign and the intense and public pressures of the White House should he win were beyond what he could reasonably ask. The world would never see a Powell candidacy.

Instead, Powell would serve as secretary of state in one of the most wrenching periods in American history. There would be speeches and books and boards. And when it was all over, he would have his regrets but he’d still have his integrity, service to country, and his general’s bearing. And he would proudly display that little red wagon in his office, dedicated to America’s Promise.

Challenge Yourself

Strategic questions are vital company at any major crossroads, professional or personal. They are deceptively simple questions that illuminate complex decisions characterized by great risk or uncertainty. They are healthy questions that call for answers about purpose and the big picture.

You may decide, like Colin Powell, that the answers need to be unanimous and affirmative. Or you may be comfortable with a more ambiguous response. After all, some of the best ideas and strategies have been built on hunches or whims. But strategic questions prompt you to examine the terrain broadly, to estimate the situation from which you can proceed with a better sense of capability and destination. Whether you are considering a major business move or a big investment of your own time and resources, thinking about the long-term consequences and goals—asking why, where, and how—will help you to better clarify the stakes and the prospects. At a major crossroad, pose a variation of these questions to yourself or the group:

Does this course of action advance my interests?

Is there a calling, a bigger purpose?

Does it feel right—is it important, consistent with my values?

Do I have the passion to do this and stick with it?

Can I define “success”?

Do I have the tools to achieve it?

Have I calculated costs and benefits, risks, rewards, and alternatives?

What are the consequences for my emotional, intellectual, and spiritual well-being?

Would the people closest to me think this is a good idea?

If this ended up in my biography (or obituary), would I be proud to see it there?

As the Bill and Melinda Gates Foundation considered its campaign against malaria, the answers to their strategic questions pointed to a need, a capability, and a plan that justified a massive global campaign. They have since worked with doctors and scientists, governments and nongovernmental organizations (NGOs), community organizers and ordinary citizens to make significant progress against a deadly disease. Big and bold and ambitious, their all-in strategy produced results that justified the cost and the risk. Their strategy, well considered and executed, attacked the right problem and was built on the right questions.