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Recently I watched a TED Talk with Simon Sinek about how great leaders think. There he presents a framework or a way of thinking that these leaders have. He coined that framework the ‘Golden Circle’ and argues that all great leaders communicate opposite to the way most of us communicate. Where most people go from talking about ‘what’ they do, through to (sometimes) elaborating about ‘how’ they do it to finally (almost never) about ‘why’ the do what they do, inspiring leaders start with the ‘why’ (Simon is doing a better job at explaining this). And that is ultimately what makes them the leaders they are.

I generally find a lot of sense and truths in what Simon is talking about, but there is another application to that golden circle that I think deserves some attention. That is the art of asking questions. There are 2 basic ways in which we learn: 1. by interaction and experience, and 2. by seeking knowledge from others. The former is a kind of reactive learning where we don’t have a choice about it and learn lessons from life (often painful lessons), where the latter is more proactive acquisition of knowledge, which is normally triggered by curiosity (or desire). But having curiosity is not enough to gain access to good information especially because today there are countless of questionable sources that supply bad information to the curious mind. However, knowing how to ask the right question will put the questioner at a certain advantage against these ‘junk sources’. 

Everything anyone will ever need to know is in one of these three questions: What, How and Why (WHW framework). And, as Simon points out, each question goes dipper than the former. So ‘What?’ is a question that scratches the surface (what do you do?) and helps you get to the next layer by raising those kinds of questions – the ‘How?’ questions (How do you do it?). Finally, after we understand what something is and how it operates (or came to be) we ask ‘Why?’ (why do you do it / why is it important / what is the purpose of it?). ‘Why?’ is the deepest question of all and it goes to the core of the subject matter – its purpose. In interpersonal interactions, getting to the ‘Why?’ may be a very personal and intimate experience so you should proceed with care and dig in carefully with ‘What?’ and ‘How?’ before getting to the why. But for yourself, it is important to ask ‘Why?’ often.

So, much of our learning is done by asking the right questions (and I will go farther by saying that inspiration stems from these questions) and because I believe that it is a crucial skill for entrepreneurs I will post different questions that I have struggled with in the past in the ‘Question bites’ page. Feel free to comment and add interesting questions of your own. Hope it helps.


I am helping an early stage internet startup to get first round financing to grow the business and hopefully explode in the world wide web. The first thing I did was to get the founder Ruthy, a smart business women with a contagious personality, to pitch in front of an angel investors forum. I got her a spot in a very short notice and helped her build a good 90 seconds pitch. Then I also coached her on the delivery. Needless to say she worked very hard all weekend long to be ready for Tuesday morning – and she was.

When we got in early in the morning the first thing I did was to look at the list of presenters. That day must have been the longest list I have ever seen in that forum, but her name was nowhere to be found. I realized that something was wrong. After confirming with the organizer that she was not going to present that morning, I was struggling with how to break the news to her and why was she not registered. It turned out that while she registered for the website, she didn’t complete her registration to present in that event. This was a bad situation.

I decided to just tell her the situation as it is and try to make the best of it. She was obviously disappointed especially after all the work she had done in building and rehearsing her pitch. But I reaffirmed her that she will get value from this experience.

Because she was not presenting, she was allowed to seat in on the other presentations, which turned out to be invaluable for two reasons: 1. after seeing “her competition” for the angels’ money, she became a lot more confident in her company (this is not to say that other companies were no good, many of them were really good, but so was her company). 2. she learned what it takes to have a good presentation.

By the end of a morning full of presentations, Ruthy had gained a lot of confidence and wisdom. After the presentations were over I introduced her to a few angels. Talking with the various angels, she essentially used the pitch that we had developed for her and she received positive, even enthusiastic response from them.

This was just the first step in a longer process to get capital from investors, but as they say “a journey of a thousand miles begins but with a single step”, we probably made (more like) 100 steps. The purpose was to prospect for an angel sponsor and we got some pretty good prospects. Success!

The lesson here was pretty clear to me: When things go wrong, it’s possible to make them better than initially anticipated – find the way.

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