The One Career Move That Can Get You Into the C-Suite
Life + Money

The One Career Move That Can Get You Into the C-Suite


In today’s hyper-competitive workplace and still-recovering economy, few workers are comfortable letting their colleagues or customers know they’re not experts at everything they do.

​Yet admitting you don’t know it all – and more importantly, asking questions to learn more – is not only the best way to learn, but the only way. With growth and development come greater and more valuable contributions to your organization – and new potential for success.


“None of us can afford to be complacent in a world filled with smart customers, great competitors, powerful purposes, and a host of new and creative business models and offerings,” says Washington-based business advisor Alan Gregerman in his new book, The Necessity of Strangers: The Intriguing Truth About Insight, Innovation, and Success.  

That’s why asking questions – just as “a relatively clever and somewhat renowned guy named Socrates” once did, reminds Gregerman – is the key. 

“He had a great gift for asking very important questions that sparked equally important conversations,” says Gregerman. “Those conversations, rather than quick answers, sparked a sense of collaboration in exploring ideas and possibilities.”

Gregerman cites the example of L-3 Communications, a leading defense contractor. It saw the opportunity to grow its business in unmanned aerial vehicles – as long as it asked questions of its numerous business units. Senior leadership raised two vital questions: Did they want to play a role in “building a brand new UAV from the ground up,” and what abilities would they draw on to make it happen? From there, new business opportunities emerged as ideas, people and technologies were brought together for a common purpose.  

Today’s leaders must set the example, say the experts. Doing so allows individuals at all levels (as well as the teams they work on) to speak up.

“Every really great leader is a great teacher, and the best teachers bring out the best in their students by asking questions,” says career counselor Michele Woodward. “If a leader doesn’t know the answer or wants to foster innovative brainstorming, all he has to do is start asking probing, thoughtful questions.”


This builds trust within the team – and a feeling that the team is “doing something meaningful.”

In his book, Gregerman emphasizes that it’s “leaders who build cultures of conversation, engagement and possibilities.”

He suggests a team’s key questions be made public within the organization to emphasize the importance of collaboration. That way, “coworkers [can] connect and share their best thinking… They might have a very different view based on the work they do or some other aspect of their lives they’re particularly passionate and knowledgeable about.”

And they might just “stretch our thinking” and allow for new answers, fresh ideas and further success – “if we’re open to it.”