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:
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