I've interviewed many of tech's biggest names (Gates, Schwartz, Chambers, Ballmer, etc) for my video show, ScobleShow.com.
Some things I've learned: 1) Don't go for "gotcha" questions. These people all are very astute at answering questions (at Microsoft they prepare execs for the press by doing "rude Q&A" sessions). They'll turn your rudest question into something they want to ask. That strategy never works and usually ensures you won't be invited back. 2) Instead, ask at least one question they've never been asked before. With Gates I knew he'd been asked any question I could come up with so I turned it around: asked him what he'd ask the world's richest guy if he were in my position. 3) Do your homework. Know what your interviewee will probably say BEFORE he/she says it. 4) Listen. My best questions came AFTER they said something and I asked for more in depth. Best followup? "Why do you say that?" 5) If you hear jargon ask them to clarify. Often times this brings up some interesting stuff. For instance, if I were interviewing Marc Zuckerberg, founder of Facebook, and he talked about "the social graph" I'd ask "some of my listeners don't know what you mean by 'social graph', can you give us a short definition and explain what you mean by that?" 6) Have a thesis for the interview. If you interview someone interesting there are 100 ways you could take the interview. I'd focus it on one theme and try to get them to tell a story with your questions. Lead them down a path. If you're asking Gates about how he took over the operating system business, for instance, I'd ask him a question about his high school/college experience, then early days at Microsoft, then ask about the DOS purchase, etc etc. 7) Have an outline of questions to ask, particularly if you'll be nervous. With Gates I started out very nervous, but then I calmed down and my brain started working again. That's when you can start having a conversation and not just going off of your prepared questions. 8) Listen, listen, listen. I always look my interviewer in the eyes and try to give them 110% of my attention. That leads to a better interview. When I'm distracted or not totally focused for some reason I find interviews don't get as interesting. 9) Start out with stupider questions just to get you both going. That's why I ask EVERY INTERVIEW "who are you?" and "what do you do?" Those two questions aren't really all that important, but they both get us going and also give your heart a chance to calm down (if you're interviewing someone famous) and also get you into the listening mode. Often times people will say something interesting in response to the "what do you do?" question. John Chambers, CEO at Cisco, for instance, talked about his being a father. That opened up a part of his life that makes for great conversations. 10) Listen, listen, listen. It's amazing when I listen to podcasts and I can tell the interviewer isn't really listening and isn't asking for clarification of jargon, or more depth on something really interesting that was put on the table. "Can you explain more about what you mean by that?" I really hate it when an interviewer is clearly NOT having a conversation and, rather, only has 10 questions that were prepared and is rushing to get through those. Use your prepared questions as a guideline, or a way to start a conversation but DO NOT be a slave to them. That's the quickest way to a boring interview that sounds stiff and stupid. (out of 600 interviews I've done I've only gone into two with prepared questions for just that reason). PR people, by the way, will ask for your questions in advance. I always answer that I don't prepare questions in advance, but will give them some examples of things I'd like to talk about. Again, talk about themes, not specifics. "I'd like to talk with Steve Jobs about the development of the iPhone and the design process that led to that." Hope these help you with your questions. Robert [Non-text portions of this message have been removed]
