The five greatest questions to ask a person.

As a talker, and the son of a talker, over my lifetime I have been in a lot of conversation, but also have seen a lot of conversations and I have concluded that there are better questions than others. There are also certain questions that cut through a five-minute conversation and honour a person much greater with fewer words. So, lets explore some of those in a blog entitled.


1. What do you like doing?

– Usually when you first meet people you ask the traditional:

Whats your name? Where are you from? How old are you? (and in some cultures) Are you married?

and then it gets to the first red flag “What do you do?”

Which in most people’s heads translates to, ‘how can I label you the best/ what do you spend most of your time doing/ what part of this cog that we call existence do you fit as?’ Most of the time we think its normal, and quite legitimate to minimise our first few questions to these. Because if we know what a person does, we know what kind of person they are right?


Ten years ago I started working as a petrol station attendant. A very flexible and perfect job for what I was actually trying to do with my life which was play as much music as I could, and hang out with young people as a positive influence. But if you asked what I ‘did’ your picture of me would be quite skewed. I have another friend who is very good with computers, freakishly good in fact, but his passionate loves are not in computers. Like a carpenter who makes shelves because he knows how to and can sell them, my friend fixes computers.

Asking what you ‘like’ doing, may in fact end up with them telling you their job. But only if they enjoy doing it. Most of the time you will get strange looks from people who aren’t used to being asked what they like doing, and then they will get comfortable and tell you A LOT about what they enjoy doing, because they enjoy doing it. Years ago this would take me ten minutes to get to because I would always subtly try to find their loves and then ask questions about it. But now, I just ask what their loves are and then give them space to talk forever about them.

remember: in a conversational competition, the person who speaks the least…. wins.

2. Who are you? – is next.

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