You Can’t Ask Too Many Questions

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Recently I was helping my son manage the difficult and painful process of dealing with insurance companies following a minor car accident. After speaking to the insurance company, he explained to me what they had told him and where they were in the process. “Okay, ” I replied, “so what will happen next?” A blank expression greeted me. ” I don’t know. I didn’t ask.”

I imparted this piece of advice to him: You can never ask too many questions. In other words, if you don’t understand what someone is telling you, or they haven’t completely explained what is happening, why, and what is next, then you should keep asking questions until it is completely clear to you.

I remember exactly when this revelation hit home for me. I was a new manager in my other life as a banker, and my boss and mentor was joining me on a visit to a business customer. We both listened as our customer explained to us what was currently going on in his business and some challenges he was experiencing with his supplies. It definitely got a little complicated and I had trouble following his process and understanding certain industry lingo. After we’d left, my boss asked if I had understood what our customer was saying. “No,” I said with a laugh. He then advised that I should always ask questions whenever I didn’t understand. He explained that there was always a more down-to-earth way of explaining things, and most of the time people are happy to bring it down to your level. I think I had thought I would look dumb if I started asking questions, but when I thought about it, the opposite is true. Recognizing you don’t understand everything and having the courage to ask is a sign of confidence and intelligence. And the person you’re asking will appreciate that you are listening, and care enough about them to learn more.

I took his advice to heart and at future meetings started asking things like, “now what do you mean by that?” and “why is that important?” I discovered several benefits of this. Of course, I learned more about the business and how I might be able to help them. And I carried that knowledge with me to my next meeting, and all meetings after that. As my knowledge base grew, I developed confidence and was able to convey that to customers. I once had a customer tell me that he knew I was the best partner for him because I really seemed to understand his business. This, of course, was the result of years of asking questions. I also discovered that people really enjoy talking about themselves and their business, so they enjoy answering questions. This new strategy was definitely a winning one.

I think we’ve all been there. We get off the phone and think, “oh, I should have asked X.” Sometimes we’re just so happy to get to an actual person, that we let them off easy when answering one question. But often that’s not enough. Or, the answer to that first question might lead to several other questions. I’ve found that it helps to be prepared with a list, and also identify in your own head, exactly what you want to know. What is happening? What is next? How long should I expect it to take? Is there anything I can do to help or to speed things up? One of my favorite followup questions is, “When should I expect to hear from you?” There’s nothing worse than expecting a call the same day, and finding out, days later, that the expectation was more like a week. And don’t be afraid to pause once you get an answer–especially an unexpected one–to see if it generates more questions. Often, when we get the answer we wanted, we are quick to say thank you and move on, then later realize that we should have asked a followup question.

Although I thought I had learned my lesson those many years ago, I was again a victim of this myself recently. I just purchased a new home and had numerous projects to arrange. First up: a new septic system, which brought many questions. Most importantly, when could I expect the job to begin. When my contractor told me there were “a couple” of jobs ahead of me, I assumed he meant two. Let’s just say my assumptions were way off. I should have asked, “how many jobs is a couple? how long in weeks?” I spent a lot of time anxiously waiting by the phone and guessing as to arranging other things that were going on at that time that would be affected by this major project. Asking those questions up front would have made my early days in the new house less stressful.

I think the practice of asking as many questions as possible serves us well in all areas of life. With friends and family, at work, as a homeowner, with healthcare, and when considering important decisions in your life, like taking a new job, having children, or when to retire. There are some big decisions in life and some, once made, are irreversible, so you want to make sure you have all of the information needed to make the best decision possible for you.

Don’t worry about being a pain. Sometimes people assume we know certain pieces of information and so they don’t share it. In most cases, the person with the answers wants you to have the information necessary to make the best decision. And even if they don’t care about helping you, and get annoyed, too bad. You still need the answers. In cases like that, don’t be afraid to ask to speak with someone else. I recently had someone tell me that when she needed to call her IT department at work, she would recognize an unhelpful person on the other end and say, “sorry, wrong number!” Then hang up and try again later, with the hopes of getting a different person who would be more helpful.

So keep this strategy in mind. The next time you’re in a situation where you’re relying on someone else to relay information, don’t stop with just one question. Keep asking until you’re comfortable with all aspects of the process. And then you can relax for a few minutes. . . until another situation pops up and you can start all over again.