A Surefire Path to Success? Ask Smart Questions


One of the perks of my job is that I am fortunate to sit in meetings with the leadership of the organization – President/CEO, COO, CFO, VP’s, directors, whomever.

I sit at the table and am part of teams that make decisions that affect the organization and its thousands of employees, both immediately and for years to come.

This isn’t a humblebrag, because I’m often the lowest-ranked and least experienced person in the room and, as such, usually don’t say a word. Yet, being in that position allows me to take everything in. I’ve worked for global multinationals and not-for-profits. I’ve been in organizations that make a lot of money and I’ve had my salary frozen for a few years. I’ve seen it from all angles. And while I’ve learned a great deal in my fifteen year career, I’ve noticed that every successful person and strong leader – regardless of their age, race, gender, education, or background – has had one thing in common: they ask smart questions.

They look, listen, and observe. They read the room, the tenor of the meeting, and can foresee where it’s headed. Based on that, they’ll make a seemingly basic inquiry that will lead the discussion in the direction they want it to go. If it’s already headed where they want it to go, the question will further propel the group in that direction; if it is not, then the question will subtly shift the discussion back to where they want it to be. A question can be a thread to pull on and the best ones get everyone in the room thinking and, like a brainstorming session, often open the door to more – and better – ideas or solutions.

Questions are important, and not only because they help you expand your knowledge and education. If you’re in the early stages of your career, a good question not only shows that you’re an active listener and engaged in the discussion, but also illustrates what you can bring to the group and the organization without being so gauche as to say it directly. Say little, so that when you do speak, it carries more weight. If you think of it in Godfather terms, you want to be viewed as Michael Corleone, not Sonny or, heaven forbid, Fredo.

Occasionally, the questions to which I’m referring are specific and detailed, but more often than not, they take on a general tone. The best are framed not as accusatory or even explanatory, but rather as educational. Those in leadership will begin with a qualifier such as, “I’m no expert in this field,” or “Forgive my ignorance,” and then will pose a query that proves just how much they truly understand.

A declarative statement pushes people away, but an interrogative one pulls them in. Put another way, “a question,” as Ryan Holiday said at the end of his appearance on Brian Koppelman’s podcast last year (1:00:10 mark), “is disarming.”

So the next time you find yourself hoping to make a good impression or are eager to contribute something, ask a question that clearly was posed with some thought.

You will never be disappointed in the reaction.

Christopher Pierznik is the author of nine books, all of which are available in paperback and Kindle. In addition to his own site, his work has appeared on XXL, Cuepoint, Business Insider, The Cauldron, and many more. Follow him on Facebook or Twitter.


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