Ask This Question To Connect With Your Hair Stylist

Are you sick of asking your stylist dead-end questions?  So was I.

I had a very lively haircut yesterday.  If you had seen how it started, you’d never believe how it ended – it started out in complete silence.  I was silent because I did not want to ask my stylist the same dull questions that I usually asked.  They rarely amounted to anything worthwhile.

Getting a haircut is great practice if you are shy when meeting new people.  You’re stuck in a chair for a solid 10-15 minutes (or maybe more if you’re female).  I realize that many smart people have a “go-to” stylist that they know and know won’t destroy their hairstyle, but I’m not that smart yet.  Every haircut is a gamble.  😀

I’m not shy when meeting new people, but I find the typical procedure rather formulaic and boring. Wouldn’t it be nice to just skip to the chase and really get to know someone?  How can we do that?

Yesterday, I found out how.

*Snip snip*  So….

Woman's Haircut

"You wanted the Vin Diesel, right?"

Sitting in the chair – losing hair on purpose for once – there was no conversation to be found.  As I said before, I did not want to break the silence just to ask the same lame inquiries that I usually go for.  The lame inquiries I speak of:

“How long have you been cutting hair?”  2 years.

“Do you like cutting hair?”   Sure.

THREE words total can answer both of those questions in full.  This time, I wanted to go deeper and learn more about the person behind the clippers.  So I tried a new one and it worked out very well!

“When did you decide to cut hair?”

To give you an idea of where that took things, she stopped cutting my hair several times just to talk and make eye contact – we were really connecting.  At different points we were both talking about our deepest passions in life.  This happened almost immediately after asking that question.

She talked about her passion first – mentioning she lived in Florida and had a home design business. Now in North Carolina, she didn’t have any clients and so she cut hair.

She said that she was scared and hesitant to start her business.  I should have suggested that she read about failure and living with the vigor of a shipwrecked sailor.  Seriously, I wish I would have. It may have helped her.

After talking a bit about her story, she took an interest in my story and I ended up telling her about how I graduated college last year, moved away, and eventually moved back in with my parents.  I explained that I was going to help people with computers to make money while I work on my blog (passions!).

Me: “Have you considered having an online presence for your business?”

Stylist: “I have no idea about any of that.”

I gave her some basic first steps to setting up a website so that she could do more research for herself.  I thought of offering my computer services to her, but my experience outside of WordPress blogs is minimal and that reminds me I need to make some business cards (any recommendations?). The next time I go in there, I might see if she’d be interested in my computer skills.

Why This Question Provokes Deeper Conversation

On the surface, this question seems somewhat plain, but it actually conveys great interest and encourages your conversation partner to open up.

Whenever we make a decision, whether it is to work at a factory, start a blog, or move to Texas, there is an underlying motive.  The question being discussed targets that motive. The question again (in case you forgot) is…

“When did you decide to cut hair?”

It takes her back to the point in time that she decided to pursue what she is currently doing. Whatever the answer is, it will be meaningful to her and an integral part of her story.  Possible answers?

1. A couple years back, she had the credentials and needed the money – though it wasn’t really what she wanted to do long term.  This was the case for her, and it naturally brought her to talk about what she truly desired to do for a living.

2. A couple years back, she realized she loved cutting hair and was passionate about it.  It was her chosen field.  If this was the case for her, she would have enjoyed talking about what first ignited her passion for it.  People love to talk about their passions if someone is willing to listen.

When I think of when I decided to blog, I don’t think of a date – I immediately think of the reason for that decision at that time.  “I want to be judged on my own ability for once, I love to write, and I want to help people think actively.”  My decision was made after having been rejected by hundreds of companies for months without reasonable cause and without being given a chance – another major part of my story.  That struggle gave me the desire to make something myself. This question is the gateway to our stories.

What if I just asked her why she styled hair?

It sorta kinda gets to the same idea, but the focus is not on her passion.  “Why do you style hair” only shows interest in the hair-styling aspect of her life and doesn’t encourage her to open up about her real passion if hair-styling isn’t it.  Her full response might be: “To make money while I try to figure out my design business.”  She only mentions the design business on the side because she thinks I only wanted to know why she styles hair.

On the other hand, the question I did ask probed to see if hair-styling is her passion or not. If it is not, then she knows that I’m interested in what she really wants to do.  This was clearly evident from her response!  It was a great experience to see a mundane haircut turn into a lively conversation about passions.

How To Do This When You Meet Someone

I already knew her profession, but when you meet Jim for the first time, you would need to first ask, “What do you do?”  Once he responds, “I’m a farmer,” then you can ask him the follow up question, “when did you decide to be a farmer?”

1. Farming runs in his family, so he decided to continue the tradition.

2. He enjoys the lifestyle, working outside, and being close to nature.

3. He believes it is important to directly provide food for his family (subsistence farming) and does not want to be dependent on others for food.

All of those possible answers are interesting and have to do with the Jim’s story and passions! When you inquire about someone’s decision to do something, you’re inquiring about their worldview and motive.  When it involves something as important as their career, you are bound to discover what they are truly passionate about.

Now I ask you the question – “When did you decide to _____?”   You may fill in the blank and answer in the comments if you so please.  🙂

About the Author

I'm lazy, but you can call me Stephen. When you're as lazy as I am, you need superior strategies to live well. My strategies are so effective that I'm productive every single day. As the world tries to figure out how to always stay motivated, I create strategies that don't require it.

Hugo Martins

“When did you decide to play guitar?”

When I was about 13 years old. I had a friend about 3-4 years older than me and he played guitar. I loved the way he was connected with the instrument and music itself so I decided to experiment and I got hooked. I play guitar ever since.


Hey Hugo,

I’m jealous of that (yes, I play guitar hero). Music is such a wonderful thing! Sometime I’d like to get into piano. Anyways, that’s a great story. It’s really interesting that seeing another musician connect with his guitar made you curious enough to try it out for yourself.

Grammar (per your request): “I have played guitar ever since.”

Hugo Martins

I suck at guitar hero, I am forced to believe that it is a problem within the game because I am really good at playing real guitars 😛



My friend who is a great guitar player says the same thing! I play guitar hero on expert :-P… I’d have to work at real guitars for a while to get good at them.

Hugo Martins

The thing is: when you are playing guitar you feel the music, the rhythm, the emotion so you may from times to times change the beat, rhythm,etc.

When playing guitar hero the notes are not always according to the song beat and us, guitarists, fail at them because we play them with the song.

I hope you understood.


Hey man,

Another great post! The truth is, people love to talk about themselves! But as you said, particularly when it come to talking about their passions. It’s amazing how a slight change of words in a question can completely alter its meaning and it’s expected response. “When did you decide to…?” is a great question and it brings people back to the mental and emotional state that they were in when they decided to do it. This usually makes them feel quite passionate about what they do, either because they love it with a passion or hate it with a passion when you ask them the question several months or years down the line.

I’m sure it gave the hairdresser a more interesting day because I can imagine that many of them have the same bull small-talk conversations day-in day-out. Good business mindset, perfect way to start working towards the “Know, Like and Trust” and build a relationship.

A tip on business cards, spend a little extra for the thicker slightly bigger ones. 🙂


Yes, that makes perfect sense!


Hi Robert,

I was pretty surprised at the dramatic difference. Then I started analyzing why and wrote this post. You nailed it when you said it “brings them back”…that’s what gets people so excited when you ask them.

I could perceive that she (as well as I) really enjoyed the conversation. Haha, I thought of business too because she could have become a client of mine very easily if I decided to offer my computer services. There was definitely already some trust there in a short amount of time.

I will keep your tip on business cards in mind. Thanks very much Robert!

Brandon Yanofsky

I started creating companies and businesses when I saw what a challenge it is. And if there is ever anything I come across that can’t be easily done, I have to figure out how to do it.

So that’s when I started my first company and began playing the strategic game of creating a business.

A few businesses later, it’s what I still do.


That’s great Brandon. I respect a man that seeks out challenges instead of backing away from them! I love the strategy involved in blogging/business.

I’m writing that guest post for you right now.

Armand Polanski

@Robert I have to agree with you, people do love to talk about themselves.

One way to sell a person almost anything effectively is making them talk excessively and as the listener, our job is to keep on asking questions. Question that can’t be answer by a yes or no but if we do, add the famous “Why?”.


I think their are no difference when you use “Why?”,”When” or any other way of asking a question.

Context is important because the questions you ask will reflect your intentions to the person being.

Thank you for another great post!

Great Post! I like how well you told the story.


its so funny, you can say a few words in just about any language and most can pick out a few, but say search engine optimization and people look at you like you are crazy!!!!!!


Hahaha, you’re right. SEO is completely foreign to those not involved with websites!

Archan Mehta


Thank You. This is a great article. I agree with your ideas.

However, I just think you are using conversation as a way to meet chicks, get a date.

Please stop using these cheesy pick-up lines, dude, chicks are paranoid these days and may decide to go to the police and get a restraining order against you.

You should seriously consider re-christening your blog as Don Juan blog or blog Casanova.

Just kidding, of course, as usual. Then again, what else is new? Cheers.


Haha, she was at least 10 years older than me, so you’re waaaay off. 😛

But maybe this is a good pick up line. Hmm…

Angus Finlayson

Great post Stephen!

That’s the difference between using closed and open questions when conversing… questions which can be answered with a one word answer are a definite no-no if you want any meaningful dialogue.

Open questions deliberately seek out longer, and therefore more meaningful answers. People are also far more likely to talk about their feelings and opinions and less likely to think about answering with set specific details.

I love the way you see and interact with the world Stephen… keep up the great work.


P.S. Have you looked at the free business cards from VistaPrint? They have a .com for the USA. They’re great cards, you can use your design and they’re good quality and you pay for delivery only. They make their money by trying to upsell at each stage of the process, so as long as you keep in mind that you only want the free cards it won’t cost very much at all. 🙂


Hi Angus! It’s nice to see you here. 🙂

Ah, you nailed it. Open-ended questions are definitely the way to go. I’m surprised I didn’t think of the term when writing the post, but I’m glad you did!

Wow, I really appreciate that statement. That’s very encouraging for me.

I did look at Vistaprint (first). I designed a free card and then saw that the shipping cost was artificially inflated (still cheap) and the delivery time was one month from order! From what I’ve seen, I could get a similar deal at a Brick and Mortar store and have the cards the same day. I’ll definitely keep them in mind though – as I liked the customization options for design. Thanks for your help.

I appreciate your comment, Angus.

Matt R

Hey Stephen,
It reminds me being a university student.
“Hey what classes do you take, what’s your major, what do you want to do with that major?”

“Hey what do you do, what made you become ____?”

It’s like the version of the same question that works for the general public (especially after you graduate from college for example.)

Great post!

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