“What do you want us to build?”

“I want two hundred million dollars. Can you build that?”

No one has ever died, to my knowledge, from asking a business executive a question. Sure, you may not have received the response you expected. Sure, you may have lost credibility or come across as ill-prepared (never stupid), but no one personally died from asking a question.

So why are technicians so afraid to ask business executives questions? In most cases, it is the fear of not getting the answer that one expected or wanted to hear. Get a sarcastic response like the two questions at the beginning of this article. You later discovered that the information was incorrect, invalid or incomplete and you are so far down the road that making the adjustment is costly in both time and money.

Do you want better answers? Well, why not ask better questions? To say that the business community never knows what it wants is an excuse. YOU have a responsibility to ask thought-provoking questions that help the business person think and provide thoughtful answers.

It doesn’t matter what role you’re playing. Everyone in information technology needs to learn how to ask good questions. Yes, that includes:

• call centers
• help desk
• Business, Data and Quality Analysts
• Project and Program Managers
• network engineers
• Technical, Solutions, Business and Enterprise Architects
• developers
• etc.

By the way, the business person will not remember the questions he asks, but he will remember that he asked good questions for decades. You build credibility by asking good questions. You build trust by asking good questions. You identify the level of risk (and risk tolerance levels) by asking good questions. You find the answers you need by asking good questions FOR DECADES!

So what are good thought-provoking questions?

The most common factor for good questions is requiring more than a four-word answer. The question requires more than a Yes/No/Maybe answer. The question requires more than a simple substantive answer (product, service or definition). Ask open questions.

The opposite is also a danger. If the question you ask is vague and open-ended, you won’t get the specific answers you need. Many executives are detailed thinkers. Asking broad concept questions will be very difficult for him or her to answer. The opposite is also true. If the executive is conceptual in nature, it is best to ask who you should talk to for a better understanding of the finite details.

Thought-provoking questions aren’t ones that could have been answered by a Google search the night before (if you did your homework). The question should illustrate that you did the basic research to learn about company policy, department strategy, and the personal goals of the person identified to answer the question. It is very easy to make clear that you understand this as long as you express it as “I understood that” Prayed “Am I interpreting this and how does it affect?”

Be careful, you don’t want to waste any executive’s time asking clarifying questions just to show off your knowledge. Ask questions that show curiosity to learn and understand rather than showing what you know. Rhetorical questions leave a bad taste in the mouth of every executive. Leave a feeling of being manipulated or insignificant because you are wasting your time. No business executive has time for you to brag about what you know. You are expected to know or do some homework to find the answer yourself.

Instead, business executives want questions that challenge their thought process. You want questions that make you think differently. Questions that help to think about a messy process or the consequences of a change of direction. He or she wants questions that can save money and time.

If you want to get the executive’s attention right away, start the conversation with a question. When you have a conversation that starts with a question, have a purpose. Know what answers you need (again, not the answers you want to hear).

Asking a question is important.

• An analogy is remembered long after the question is asked and answered. This means that more thought will be given to the question, the answer, and the questioner. Mentioning a correlation helps generate visual or audio reminders that help the responder quickly grasp your drift.
• A story describing a scenario is recalled. If you want the question and answer to stick… add emotional appeal to the description. If you’ve already done your homework on the person, you already know that certain stories can be offensive. (I was once asked a question where the questioner related the story of a lazy wife. Needless to say, the question and my opinion of the questioner were not well received. I remember him and the question in a negative way. more a decade later).

Opportunity often involves a great deal of work and a willingness to take a chance on something, the outcome of which may be uncertain. Learning how to prepare to ask thought-provoking questions is a skill that will give you better answers and prompts. Learning to prepare to ask thought-provoking questions will get you noticed by the right people.

Add clarity, purpose, and value to the executive with every question.