For You to Understand Their Issues: “Come prepared. Find out as much as you can about my issues before you even walk in my door. However, don't pretend like you know exactly what my issues are. How can you? You don't even know me. If you ask some intelligent questions and add value, I'll open up, and we'll have a meaningful conversation -- and I won't see you as a waste of my time.”
Do your research and arrive at the prospect's office knowing the broad outlines of their strategy, the major initiatives they have going on, and the key trends and challenges they are facing in their industry. Then, use that information to ask intelligent questions that slowly draw the other person out. Ask questions that reveal what they are most concerned about— what their agenda of three to five critical priorities, goals, or needs is. It's often better to ask indirect questions that get the client talking about their issues than blunt, generic ones like “What are your priorities?” In a meeting with a prospective client, you are trying to build trust and identify an important issue you can help them address. The challenge is to get them to open up about their true priorities and frustrations. You do this by adding value in the conversation and through thoughtful, informed questioning.
Questions to Help You Understand a Client's Issues (the more tailored these are to your specific client and their industry or job function, the more effective)
1. What are your most significant opportunities for growth over the next several years?
2. I'm familiar with the broad outlines of your strategy… my question is, how are some of these initiatives, like becoming more market-focused and reducing your cost infrastructure, affecting your own particular area?
3. How will you and your area be evaluated at the end of the year? What are the major goals you're being asked to accomplish by your leadership?
4. What exactly do you mean when you say…(“ risk-averse,” "problematic," “dysfunctional,” “challenging,” etc.)?
5. What would your best customers say are the main reasons they do business with you?
6. Why do your customers leave?
7. How have your customers' expectations changed over the last five years?
8. What's the driving force behind this particular initiative (e.g., what is behind the drive to reduce costs, design a new organization, etc.? or, Why did you decide to do that?)?
9. What would “better” (risk management, cost controls, organizational effectiveness, etc.) look like?