PhotoCredit: Ballet West by Luke Isley ( cballet.org )

PhotoCredit: Ballet West by Luke Isley (cballet.org)

We were always expected to know the answers to the questions in school: “What year did World War One end?”, “What started World War One?”, “What treaty was signed at the end of World War One?” Raise your hand if you know the answer.

Don’t worry - there is not going to be a test!

When I went to law school it was even worse. Never mind raising your hand because this is the Socratic Method: we will just pick people at random to answer questions. The intention behind the Socratic Method was to encourage intelligent debate. In my classes it became an intellectual showdown between a few students desperate to show themselves and their class how smart they were.


I couldn’t stand it. I am not an answerer. I am a questioner and an absorber. I like to think about a question. I like to hear what other people think and I like to take my time coming to a conclusion. I don’t especially like conclusions. What I liked the most about studying law is that everything can be debated. There are very few matters of black and white. Most things live in the in-between. For most things the right answer is a matter of the specific facts and the circumstances. For most things the right answer is “it depends”.

So I prefer questions. The smartest people I know are not the people who know all the answers. They are the people who know how to ask excellent questions. I think this is an under-appreciated skill. I want to learn to be better at asking questions because in the question lurks the information that clarifies the dependencies.

How do you ask better questions? The first trick can be called the Dr Seuss trick. It’s the What, Where, Why and How trick. It’s simple, effective, and under-used. Sometimes you can literally ask someone “how?” or the more polished version, “I am not sure how we are going to achieve that?”. You will be over-run with additional information on the topic. One of my favorites is “what?” and specifically “what is your biggest concern as we commit to this strategy?” Another favorite is “what is the thing that gets you jumping out of bed in the morning?” and the sister question to that, “what wakes you up in the middle of the night?”

The second trick is the New York Times trick. This is the “please dumb this down for me and explain it to me like I am an 11 year old” trick. The New York Times is famously written for reading at an age of 11. I like this trick when I literally don’t understand a strategy and also when I think the strategy is over-engineered and a little too clever. Simplifying it allows you to poke more holes in it. Simplification also forces the communicator to rest less on their prepared argument and highlights how well they really understand the foundations of the idea or the strategy.

The third trick is the old classic “she loves me, she loves me not” trick. This is where you ask for the 5 reasons the idea could fail and the 5 reasons it is likely to succeed. It’s a variant of the Pro/Con list and the idea is to pick a big enough number that it starts to get hard thinking of why it’s a good idea and why it’s a bad idea. It’s only once it gets hard that you start thinking of extreme and out of the box reasons. I think the extreme and out of the box are much more likely to happen than we think. The extreme and unlikely also get you thinking differently and so often are the source of really great ideas.


My husband Mark is an artist, a sculptor, and he once commented to me that he spends more time standing back and looking at what he is making than he spends actually working on the piece. I have always felt that was one of the more valuable business lessons I have ever learnt: I needed to spend more time standing back from my challenges than working furiously on them. More time ON the business than IN the business. In much the same way I think we all need to spend a lot more time thinking we don’t know the answer, and asking the questions, than pretending we have it all figured out. No matter the context, knowing what questions to ask is a much surer sign of intelligence than knowing all the answers.