The Power of the Obvious Question

When faced with an intractable or complex problem, it's easy for leaders to get bogged down in the minutiae when trying to come up with a solution. Another trap is to go binary - it's either this or it's that - too soon in the decision making process. Rather than opening up options and possibilities, we sometimes try to solve complex problems by settling for the least painful of the most obvious options.

It's at times like this, that's it's helpful to have someone in the room who can step back, get up on the balcony and ask some questions that seem obvious in retrospect but maybe weren't asked because everyone else was too close to the situation at hand.

There was a great example of this in a recent Newsweek article by Holly Bailey and Evan Thomas on Vice President Joe Biden. Here's an extended excerpt that paints the picture:

"Joe Biden had a question. During a long Sunday meeting with President Obama and top national-security advisers on Sept. 13, the VP interjected, 'Can I just clarify a factual point? How much will we spend this year on Afghanistan?' Someone provided the figure: $65 billion. 'And how much will we spend on Pakistan?' Another figure was supplied: $2.25 billion. 'Well, by my calculations that's a 30-to-1 ratio in favor of Afghanistan. So I have a question. Al Qaeda is almost all in Pakistan, and Pakistan has nuclear weapons. And yet for every dollar we're spending in Pakistan, we're spending $30 in Afghanistan. Does that make strategic sense?' The White House Situation Room fell silent. But the questions had their desired effect: those gathered began putting more thought into Pakistan as the key theater in the region."

What obvious questions do you need to ask to help your team challenge their assumptions? Are you even the best person to ask those questions or is that role better played by designating someone on your team to play the role of devil's advocate? What are the pros and cons of either approach?