By John O'Connor

In a lot of situations, I feel strongly that asking great questions can start a positive burn, a fire in another person to respond to you. Questions asked with great thought and context matter. If you ask me a question that you really want me to answer, I can tell if you find it compelling and challenging, that you authentically want to listen so that you are closer to an answer.

Most of the time, I can tell when someone asks or writes a question with the desire of knowing the answer. So many questions that people ask in marketing themselves or even marketing products seem rhetorical. Look at Linked In and all the questions that get posed on that channel. Many of them are rather self-serving; the writer does not care to know the answer. Others can be excellently posed, sincere and authentic. Underlying many questions that people ask is this – “Let me pose a question that elicits the response I want from you” or “Please notice that I am asking this question.”

It's harder to ask tough questions and enter into a dialogue. It's harder to engage in tough conversations without having made up your mind completely. It's more difficult to not get pat answers and have to look deeper into assumptions you have made about an issue. But what positive things can happen if you do it the "hard" way? What happens if in conversations or in blogs or in daily life you try to rise and ask the more difficult questions? Here are some positive, possible outcomes:

1. You will create a more authentic brand. 

2. You will interact with people from a point of integrity. 

3. You will seek and find better answers. 

4. You will learn more and become better at what you do.

5. You will develop a stronger reputation among people that matter. 

As an executive career coach and professional, I am sure I ask a lot of basic questions and common questions initially. But clients want me and need me to dig much deeper as I grow my relationship with them. Our best clients want collaboration, interaction, tough questions and, ultimately, strong, workable and credible advice. That's not easy to get to.

Ultimately, I don't want to ask just the easy questions, and I certainly don't want to come up with pre-conceived solutions that just benefit me. When I focus on me, I become short-sighted. I think we all do. I hope and believe my clients want authentic interaction, tough questions and for me to have their best interests in mind.

How can asking tough questions in your field and work life benefit you? Who in your life has asked you the toughest questions? Who in your life has asked tough questions, really listened and used the information to help you? The people that do can help guide you and help you secure your future.