!1) They must sound natural. Everyone can hear it when you’re reading from a list or a script. It just sounds awful. This makes me feel like I’m on the world’s worst sales call, which is damn close to the world’s worst fate. You make things sound natural through repetition. Practice your questions all the time. Practice them in your head, practice while you’re driving. Think about a call from yesterday and ask where you missed good questions. Play it over in your head, and then revise those sections mentally until they are perfect. !2) No salesy questions. I’ve banned any question that sound like canned “salesy” questions. If any slip through on our team I strangle them, drown them, and bury them in the desert. And then I turn my attention to the question. I never want to lose sight of the fact that this is a conversation about how to solve a problem, and I want my questions to further that conversation, not make my prospect roll his eyes. An example of a salesy question is what the sales books call a “tie down” question. It goes like this: “Having a secure house is important, isn’t it?” Barf. Everyone sees right through this manipulative question. !3) Actually ask the questions. You would be stunned at how often question asking is neglected, or how little time is spent on it. Paul Kenny, sales consultant and owner of Ocean Learning, says that the average time that elapses between the end of the initial chit chat and the launch of the pitch is about forty-nine seconds. Forty-nine! You couldn’t get much more than my name in forty-nine seconds. It’s the biggest missed opportunity in sales. !4) Ask open questions. There are three types of questions: * A selection question: “Do you want the red pill or the blue pill?” * A closed question: “Oh my god. Was that the dog?” * An open question: “How did you end up down there?” Open questions are the ones you want to favor. These expand the conversation and receive fuller answers. Closed questions are necessary, but when relied upon too much they invite short, clipped answers. “Do you want pizza?” invites one kind of answer, and “What are you in the mood to eat?” invites a completely different kind. Open questions that get a sales call going could be, “What prompted you to look at FogBugz?” or “Since you’re using Bugzilla but looking at FogBugz, can you tell me a bit about what’s not working for you now?” Sometimes you’ll get a short answer to an open question, but that’s fine; just ask another open question. !5) Ask questions until you understand everything you need to. I’ve seen reticence on the part of some sales people around asking repeated questions. They feel like the questions are intrusive and bothersome, and anyway, they’re straining like greyhounds waiting to start their product demo. This is a mistake. If your prospect describes an internal process you don’t understand, uses an acronym or jargon that’s foreign to you, or simply says something in an unclear way, keep asking questions until you understand properly. !6) Take notes. You think you are going to remember that conversation you had, but you’re wrong. Write your notes as soon as you get off the phone. Just make it part of your habit.