There's no one right category for any given question. The final category is really irrelevant. What's important is creating the widest possible range of open-ended, thought-provoking questions that might help to surface relevant issues. Of course, you have no way of knowing which questions will yield useful information and which won't. One of my clients described a time when a project-focused question from her list prompted her customer to reveal a key language translation issue in a global project. Therefore, the best course is to emulate Sam the cop-guide, prod, and probe to gather as many facts as possible.
But as you do so, let your inner psychologist pay attention to how customers respond to each question. Do they frown? Wince? Smile? Shudder? Laugh heartily? Laugh nervously? Do they start speaking faster or slower, or in a louder or softer voice? Do their eyes widen? Do they bolt from the room?
These reactions may have nothing to do with the project, so don't jump to conclusions. But if you notice a reaction that seems curious, or is a striking change from previous behavior, you might do as Alan the psychologist does. Ask, "What concerns you about that question? Does that question trigger something for you?" Then ask the person to explain. Or as Alan suggests, simply ask, "What is that about?"
Balance project-focused questions with questions regarding customers' perceptions, expectations, hopes, fears, and so on. Consider these questions:
- What is the most troubling aspect of this problem for you?
- What is unusual (or unique or striking) for you about this project?
- What is the most important aspect of this problem (or the ultimate solution) for you?
- What is your biggest fear (worry, hope, aspiration) about this project?
- What is important to you in how we work with you on this project?
- What have you experienced in past projects that you'd like to see (or avoid) in this project?
- What will you be looking for when the system has been implemented that will enable you to feel it's successful?
- What will your management look for?
These questions focus on what's important to the customers, matters that, if not detected early in the effort, can lead to dissatisfaction with the outcome even if all the facts of the case are addressed. Some of these questions will feed the cop's need to know the facts; others will generate reactions for the psychologist to inquire about. Both can strengthen your understanding of the undertaking.
As you conduct your information-gathering sessions, ask questions from both the cop and the psychologist perspective. You might be surprised with the wealth of relevant information that surfaces.