Dumb Questions Smart Leaders Ask

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Guest Post by Phil Van Hooser

Back in 2005, I read an article in FORTUNE (June 25, 2005) by Geoffrey Colvin. It was entitled, “The Wisdom of Dumb Questions.” The title caught my attention. In the article, Mr. Colvin surmised that “dumb questions lead to smart decisions…” and that a dumb question can “…cut to the heart of the matter, posing a blunt challenge to someone or something–an authority, a policy, the established order. It can make people uncomfortable.”

That made sense to me and I started thinking: What dumb questions should I be asking that might lead me to smarter leadership decisions? I thought you might be interested in some of the “dumb” questions I now suggest proactive leaders consider asking with great regularity.

Dumb Questions Leaders Ask

Dumb Question #1: How am I doing?

This question was made popular by former Mayor Ed Koch. During his term of service to the City of New York, Koch was renowned for stopping average New Yorkers on the street and asking them this, his favorite dumb question. Why would he do such a thing? I think he realized how easy it is for leaders to become isolated, even insulated from the very people they are entrusted to lead. If he didn’t ask the regular “Joes” and “Janes,” his only other alternative would be to trust the opinions of his advisors–most of whom were even farther removed from the man and woman on the street than he.

Dumb Question #2: What have we screwed up lately?

All of us enjoy having rose petals strewn before us. In other words, we like to hear people bragging and commenting on all the great things we have done and are doing. But what do those kinds of accolades really teach us? Not much, I’m afraid. Praise is great for ego boosting, but rather worthless when it comes to building a foundation for continual improvement. Mistakes, errors, miscalculations, screw ups–those are the things that can really teach us something. Admit it; haven’t you learned more from your mistakes over the years than you have from your successes? Well then, why not spend some focused time seeking out areas where we seem to be chronically screwing up, in order to shine a bright light on those areas as we begin to repair them.

Dumb Question #3: What should we be doing better?

Maybe you really are doing a great job and people are honestly struggling to find concrete answers to your Dumb Question #2. Congratulations! You must be doing something right as a leader. Keep it up. But never forget that some wise person once said that “good is the enemy of great.” And it is. There’s always room for improvement and improvement should be our never-ending quest–to be great at what we do and how we lead. Therefore go out and ask your constituencies — the employees, customers, colleagues, partners that make up your professional existence — what they would like to see done at a better, higher, more sophisticated level. Their answers may prove to shake the comfort zones you have allowed to form around you. But their answers may also serve as the catalysts and motivation to jumpstart heightened levels of performance.

Dumb Question #4: What would you like for me to do about that?

This may be the dumbest question of all and yet the smartest one you can ask. Everyone has opinion. And even the lowliest of employee is known to openly and freely share opinions with fellow workers, family members, neighbors, even innocent bystanders waiting patiently in the grocery store checkout line–everyone, that is, but  you, their leader. Possibly the smartest thing a leader can do is to actively seek out the personal, specific opinions of others. Don’t be afraid to ask them Dumb Question #4, then shut up and listen. It’s nothing short of amazing what they might tell you–in startling detail. The chances are stacked in your favor that you will learn something from the conversation. And don’t worry; I know you’re thinking–what about the worst case scenario? What if they share suggestions that are unrealistic, unworkable and impossible? What then? My advice is to tell them so. In an honest, open manner, tell them what won’t work AND why. Most of the people we work with are reasonable people. If it truly is unworkable, based on your complete explanation, they will understand. And for those who just refuse to understand, at least they can never say you didn’t make the effort to explain things to them.

Here’s How It’s Done

Now that we’ve covered four dumb questions any leader can ask, maybe I should tell you how it’s done best.

  1. Don’t label your question as a dumb one before you ask it. The fact that you have the courage to ask the obvious questions may actually make you look brilliant in the eyes of others. It worked for Socrates: after all “What is virtue?”
  2. Don’t apologize for asking the question. Don’t dilly-dally. Don’t tip-toe around the question until it has lost its power, its uumph. Just step up and ask it. And ask it with sincerity and an open mind.
  3. Don’t worry about what the answer to the question might be. You can’t predict nor control the future–the answer will be what it is. You can begin to deal with it once it has shown itself.
  4. Don’t be intimidated if people don’t immediately offer a response to your question. Be patient. Let them process the question appropriately. After all, this may be the very first time their leader ever asked a dumb question–on purpose, at least.

PhillipVanHooserPhil Van Hooser is the Founder and Concept Director at Leaders Ought To Know.  He works with organizations that want to build leadership bench strength, performance and productivity. Phil’s clients run the gamut from Alliance Coal and Blue Bell Creameries to REEBOK, Wells Fargo and Westar Energy.  Phil’s latest leadership book, Leaders Ought To Know: 11 Ground Rules for Common Sense Leadership, is a must-read handbook for leaders feeling the pressure to perform. Phil is a past president of the National Speakers Association and a member of the Speaker Hall of Fame. He was recently named a “Top 5 Leadership Speaker” by Speakers Platform.  You can connect with Phillip @ phil@leadersoughttoknow.com