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Five Great Questions

Updated: Mar 30, 2023

One of the key character qualities I look for in others is the ability to ask questions. Some people prefer to talk and rarely ask any questions at all (see Killing the Me-Monster blog post). Their focus is squarely on themselves or their knowledge on a subject and can be due to insecurity, pride or just a general lack of self-awareness. Additionally, some are content to remain silent and let others carry the conversation. This can also be due to insecurity, lack of self-awareness or just plain laziness. Either way without adjustments, over-takers tend to be avoided and the silent types ignored.

What can really set someone apart is not only their willingness to ask questions but making the effort to ask really great questions. Even if this is not a natural tendency it can be developed with some awareness during conversations as well as intentional effort ahead of time. In order to be interesting to others be interested in others.

Here are five questions I have found to be very effective in stimulating rich conversation and communicating sincere interest in others:

1) What was your high and low for the past _______ (week, month, year)?

2) What are you really excited about right now?

3) What does success and failure look like in your job?

4) Have you ever thought if you were not in your current career what you would do?

5) What do you hope will be different in a year? What can you do to make that happen?

Each of these questions helps to get past surface information and discover what people see as really important. Be prepared with answers if they turn around and ask the same questions right back. As a result, conversations should be more interesting and the asker will be, too.

See Power Question Collection blog post for more questions.

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