Tag Archives: advice on tough questions

How to Ask a Tough Question

The question I asked Hillary Clinton at the Yearly Kos Convention has generated lots of attention.  I was moved by the number of people who approached me and said, “great question!” and now it’s starting to change the narrative of Hillary’s campaign in the mainstream media – as evidenced by this AP article.

But I’m not asking people to thank me. I just did what anyone else is capable of doing – holding politicians accountable by asking a very pointed question that drives the message home. My question was no accident. It was well-prepared, and I put a lot of thought into it. You can too if you take the following advice:

Before I begin, I want to emphasize that this is not about “catching” Hillary in more embarrassing situations. All politicians should be held accountable by asking tough questions, and Hillary supporters are free to follow my advice when you ask Barack Obama or John Edwards. If they can’t heat from us, they don’t deserve to be nominated. This advice is appropriate for all politicians if you ever get the chance to ask them a question.

(1) Do your homework: This may sound obvious, but having a well-prepared question written in advance allows you to think it through and be confident when you ask it. The opportunity to ask Hillary Clinton — or George Bush or Bill Clinton or Al Gore — doesn’t happen every day and you should never walk into the room without having memorized the question you are planning to ask. I had worked on my question for 2 days. Do your research. Think it through. Plan it carefully.

(2) Never ask an open-ended question: Politicians are trained to “stay on message.” That means they answer the question they want to give. It is infuriating to hear politicians get asked a question and then proceed on a long-winded stump speech with their standard sound-bites, but that’s because they have a particular message they want to get out. Questions that force them to answer “yes-or-no” require them to take a particular stand and make the news, when they would rather the news be a regurgitation of their three-point message.

(3) Avoid follow-up questions: Usually you need to ask follow-up questions to really get the politician on record – but chances are you will not have that opportunity. I certainly didn’t when I asked Hillary Clinton, but I was told that John Edwards allowed follow-up questions during his break-out session. If you can get away with it, do it – but always plan your question around the assumption that you won’t. Some Hillary supporters are mad at me that I asked a four-part question (which was “rude”), to which I say – grow up. If I could have broken up the question into four follow-ups, I would have.

(4) Ask an original question they don’t expect: Politicians and their consultants spend hours obsessing over the perfect sound-bite to answer tough questions they expect to receive. I could have asked Hillary about Iraq – and someone else should – but unless my question had been brilliant, she probably would have had a pre-arranged sound bite. Think through about an issue that has not been a part of the campaign, but don’t make it so esoteric that the media (or the audience) won’t understand what you’re talking about.

(5) Avoid sounding mean and shrill: Coming off as angry or hostile to the candidate is self-defeating. You will only please people who already don’t like the candidate, and it will alienate the others. Be polite and respectful. I started my question by thanking Hillary Clinton for her willingness to repeal “Don’t Ask, Don’t Tell” because I believe that we should give credit where credit is due (incidentally, it’s also why I clapped when Hillary said good things.) It also makes your question more effective because you don’t sound like a jerk.

(6) Find a good strategic place to sit: The most brilliant, well-thought out question in the world will be useless if you never get called on. When I walked into the Hillary session and saw the number of people, I doubted I would get the opportunity. Arrive early so you can get a good seat. If you can’t be in the first three rows directly in front of the podium, get a seat next to the aisle – which is what I did.

(7) Wear a bright shirt: While I certainly didn’t plan this part, I was wearing a bright red shirt when I went to her break-out session. Peter Daou (her Internet Director) called on me as “the man in the red shirt” when he had called on all the other questioners by their first name. I honestly believe that it’s the reason I was called on. I know it sounds ridiculous, but I’m serious. It works.

I’m not giving this advice because I seriously doubt the Clinton campaign will ever give me the chance to ask another question. I just believe that as bloggers, we have a right to have our voices heard and our questions answered. We may have some “access,” but we certainly don’t have the millions of dollars to go to an elite fundraiser where you can probe a candidate with follow-up questions. Even at most fundraisers, you don’t even get those chances. We’re also not media celebrities who can get an hour-long interview with the candidate.

Finally, if you get the chance to go to an event where the candidate will be taking questions, send me an e-mail at [email protected]. While I would much rather have John Edwards or Barack Obama win the nomination than Hillary Clinton, I have not chosen a candidate – although I’m leaning towards Edwards. I believe all candidates should earn our support.