The Right Questions

In a recent workshop I led for high school students, I met a young woman who had just been awarded a prestigious scholarship. In recognition of this achievement, she had been invited to attend a luncheon at which she was to be seated next to Deborah Roberts of ABC’s 20/20. Naturally, she was excited by this prospect. I asked her what she planned to ask Ms. Roberts to maximize the opportunity. The question caught her off guard. After a moment of pause, she said, “I don’t know. What do you think I should ask her?”

In order get the right answers, you must ask the right questions. Many times we are quick to ask questions just for the sake of conversation. These questions normally result in a nice exchange, but they rarely leave the asker any wiser or the answerer any more invested.

Instead of asking surface-level questions, seek to find answers that will help you get where you want to be. I typically offer three guidelines when it comes to crafting the “right questions.”

1. Ask questions that will help inform your decisions. I knew that a school selection was on the horizon for my young friend, so I suggested her first question be, “I am getting ready to decide what college I am going to attend. Why did you select the school that you did, and how has that decision affected your career path?” Not only will this question show your genuine respect for the person it is directed to, but its answer provides insight that could guide you in your own decision making.
2. Ask questions that will open doors to wisdom. We have the amazing chance to learn from the experiences and the mistakes of pioneers who have gone before us. The second question I offered was, “Is there anything you would have done differently in your career? If so, how would those decisions have changed where you are now or how you got here?” Questions like this typically lead into a narrative, hosting innumerable points of wisdom. Equally important, shared stories help build memorable connections between people.
3. Ask questions that will provide networking opportunities. Lastly, I recommended that this young woman request permission to contact Ms. Roberts periodically for advice and counsel, asking something like this: “I know that there will be decision points along my journey where your wisdom and counsel would be invaluable to me. Would you mind if I contacted you periodically for your perspective?” (What honorable person would say No to this request?) This simple question could open countless doors. However, this type of relationship requires complete authenticity and respect for boundaries. Appropriate periodic contact with someone of this stature is probably two to four times a year. It could include an update on decisions and life progressions, or it could include a question on which genuine feedback is being requested. The keys are to (a) keep the communications brief and (b) refrain from asking for favors; ask only for counsel. This approach can yield a valuable mentor relationship in which the mentor has a personal stake in the mentee’s success.

There is not a person alive from whom you cannot learn if you only listen. If you are given the chance to engage in a dialogue with an individual who has insight to offer, it is a gift. When you raise questions that are strategic and thought provoking, you will always benefit from the answers if you listen carefully. Joyce Brothers said: “Listening, not imitation, may be the sincerest form of flattery.” Seek individuals who are worthy of your listening ear – and ask away.

-Clifford A. Bailey speaker, mentor, CEO