Welcome to the first week of challenges. You begin this program by learning how to start a conversation with anyone you want.
Let me ask you a question:
Have you ever gone to a social gathering by yourself?
Maybe you’re on a business trip and end the day with a drink and some food at a bar, hoping to have some fun as well.
Maybe you just moved to a new city and attend a young professionals social mixer to mingle with new people and hopefully make some friends.
Or maybe you attend a marketing seminar to connect with like-minded people.
These are great opportunities to meet new people and have a great time.
You befriend the bartender and flirt with the cute girl next to you.
You meet other successful people at that mixer who are around your age and seem adventurous just like you.
Or you go to that seminar and meet someone who’s really into email marketing, become friends, and later become business partners.
But, as we all know, it doesn’t always work out like this.
We sit at the bar alone, staring out our beer, constantly sipping it because we don’t know what else to do.
We go to the seminar, watch the speakers, then walk around aimlessly looking for a way to get a conversation started, only to end up against the wall staring out our phone.
Or we go to the mixer, take one lap around and leave, because the thought of being alone with no one to talk to fills us with anxiety that’s so bad, we just can’t handle it.
I’ve been in all of these situations. And they can be extremely painful. But I also know that you can overcome them.
So this week’s goal is to get you talking to strangers. Because when you learn how to start conversations with anyone, your life can improve dramatically.
Instead of having anxiety when you go to a social event alone, you’ll be excited wondering what possibilities await you. And you never know who you’ll end up meeting – it may just be a new friend, client, business partner, mentor, boyfriend or girlfriend.
Before You Begin
Before you start this week’s challenge, read this article I wrote on how to start a conversation with a stranger. It’ll give you an excellent primer on the strategy for talking to strangers.
All four of this week’s challenges require you to talk to strangers, so you’ll need to go somewhere you can find plenty of people you don’t know. I recommend going to a mall or shopping center, or some other area where people amass.
The goal is to teach you to proactively start conversations with strangers. If you’re just standing there and someone asks you a question, that doesn’t count. You want to start conversations that wouldn’t exist otherwise.
Lastly, I talk about contextual statements and questions a lot, so you need to know what I mean.
Contextual questions and statements are relevant to the environment or situation.
It’s asking someone at a coffee shop if they know which drinks are good. Or telling someone you love the cold weather right now. Or asking someone if they know where the nearest restaurants are.
You’re not going to say that the pyramids in Egypt are spectacular when you have no reason to bring them up. The other person will look at you funny and wonder why you just told them that.
Basically, contextual statements and questions are not out of the blue. They make sense in the context of the situation.
Now, let’s get to your challenges for the week.
Week 1 Challenges
Challenge 1: Start 15 conversations with people who are paid to talk to you by asking some version of “how’s your day going?”
People who are paid to talk to you are people who are working (getting paid) and need to help customers (you). These are baristas at coffee shops, checkout clerks at various stores, servers, bartenders, the people who walk around the store to help you find things, etc.
You can do this while you’re going about your day, or you can go somewhere like a mall or shopping center and knock a bunch out quickly.
Here are some examples: when you’re getting your coffee, don’t just order, also ask how their day is going. Or go to the mall, walk into a store you like, find someone to help you out, and ask how their day is going.
This is pretty simple for most people, but it’s still a good practice. It’ll help you get in the habit of starting conversations with people that you normally interact with (ordering food, buying groceries, etc.), instead of just transacting.
What success looks like: To complete this challenge, you just need the people to respond to you. Even a one-word response like “good” or “okay” will do.
Bonus points: Ask a follow-up question to dig deeper. If they say they are doing well, you might ask, “What’s been the best part of your day so far?” or something else along those lines.
Challenge 2: Start 15 conversations with people who are paid to talk to you by asking a contextual question.
Similar to Challenge 1, you’re going to talk to people who are paid to talk to you. But this time, you’ll start the conversation by asking a contextual question.
Make sure you are prepared and come up with your question before you go into the store or walk up to the person.
The question can be personal: You can say to a barista, “I’m curious. Do you drink way more coffee because you work here?”
It can be about the store: “When do you guys usually have your biggest sale?”
It can be about the weather: “What do you think of this hot weather we’ve been getting?”
It can even be about you: “Can I get your opinion? I’m getting a haircut in a couple hours and am curious what you think. I’m cutting the sides short for sure, but should I keep the top pretty long like it is now, or should I take a good amount off?”
As long as your question is relevant to the situation you’re in, it should work.
When coming up with different options, ask yourself this: Will the stranger understand why you are asking them this question, or will they wonder why you are asking them?
If they are wondering why you are asking them, it’s either not a good question or you aren’t prefacing it with something like, “I’m curious…” or “Can I get your opinion…”
What success looks like: You just need them to answer your question.
Bonus points: Keep the conversation going! You already started it with something that interests you, so respond to their answer with your own thought, opinion, story, or question.
Challenge 3: Start 15 conversations with random strangers in public areas by asking a contextual question.
You are using the same type of conversation starter as you did in the last challenge, but now you are starting conversations with random strangers instead of people who are paid to talk to you.
These can be people in a coffee shop, walking through the mall, shopping for groceries, hanging out in a bar, or doing anything else in a public area. But they can’t be coworkers, classmates, group members, or have any affiliation with you at all.
If you don’t know them, they aren’t working to help customers and you have no affiliation with them, they are valid.
Again, you want to be prepared. If you’re shopping for shoes, you can ask the nearest person (who’s not an employee) for their opinion between two shoe options.
If you’re in line for coffee, ask the person behind or in front of you if they know which drinks are best.
If you’re walking around a mall, ask someone if they know where something is, like a good restaurant or coffee shop.
Just make sure it’s contextual and the other person isn’t wondering why you’re asking them.
What success looks like: Again, you just need them to answer your question.
Bonus points: Again, see if you can keep the conversation going!
Challenge 4: Start 15 conversations with any strangers by giving them a compliment.
You aren’t hitting on anyone and you aren’t trying to get them like you. You’re just offering a nice (and true) opinion that you think they’d appreciate hearing.
Since you can only compliment them on what you can see (you can’t tell them they have an awesome personality because you don’t know them yet), this will likely be something they are wearing or holding, like something they just bought.
Or it could be more general like their style. But you want to compliment things they can control. Not their looks, but their style. Not their eyes, but the way they do their makeup.
Or you may see them do something, like help someone who just fell, give money to a homeless person, or help an old lady across the street, and you can definitely give them a compliment for those actions.
Your goal is to go up to someone you’ve never met and give them a compliment. They can work at a store or be a stranger in a public area. It doesn’t matter as long as you don’t know them and you are the one starting the conversation.
Here are a few examples:
“Hey there, I really like those boots. I’ve never seen a pair quite like those.”
“I noticed you just ordered a Manhattan. It’s probably their most underrated drink here. You obviously have good taste.”
“Your 4 Sons shirt is awesome. Do you go to the brewery a lot?”
What success looks like: They just need to acknowledge your compliment (usually with a thanks).
Bonus points: Dig deeper. Ask them where they got whatever you complimented, or how they learned how to do it, or some question that shows you were sincere about your compliment and interested in discussing it further.
Wrap Up
The goal of these challenges is to get you more comfortable starting conversations with strangers. You want to be able to strike conversations wherever you go (if you want) because it livens up your life. You never know who you’re going to meet, what you’ll learn, or what kind of fun you’ll have with other people.
After completing these challenges it should be a little easier for you and you should realize that it’s not as hard as it seems in your head.
Once you complete them, congrats. You can now do something that many people fear.
And you’re also ready for Week 2. Click below to move onto the next challenges.