How to connect deeply with anyone – the 3 simple steps
It’s one thing to start a conversation (these are the techniques I use), but it’s a totally different skill to continue a conversation and form a connection with someone.
And that’s exactly the challenge one of my clients was facing this week. He said “I can start conversations just fine, but things just...fall flat after that. I’m interested in connecting with people but I just don’t know what to say.”
And I used to have the SAME problem, so my dating coach recommended I read How to Win Friends and Influence People. And I was skeptical, because I used to believe that my wheelchair and my disability prevented me from connecting with people, and there was no way to change that. But here was this book, that said I could connect with anyone, if I just got them to do the majority of the talking, about something they care about.
I just had to figure out how to make that happen. The book has some good guidelines, but not much more. So I had to do a lot of experimenting. A lot of trial and error. Some things worked really well (see below) and some things didn’t (don't jump straight into “so what are you most passionate about?”).
Fortunately, you don’t have to go through all the awkwardness and missteps to figure it out, because I’ve gotten it down to a science. If I want to connect with someone, I know I can make it happen.
So how do I do it? It’s not magic – it’s a simple 3 step process. Are you ready for it? Let’s go.
Step #1: ask a conversation-opening question
Step #2: ask probing questions to discover what they care about
Step #3: ask for a story about the topic they care about
There you go! The secret formula! Go on now…
Oh, you want to see some examples of how this might work? Well, I thought you’d never ask…
Example #1: start with “have you always done that?” [focus on the past]
It’s common to discover what someone does for work within the first minute of meeting them. “So what do you do?” is embedded in our culture. I hate it (here are better things to ask) but if someone asks you, it’s natural to ask the same (lame) question back. But then what? What if you are in two totally different fields? Do you just look at each other blankly?
That’s what I used to do, and then I discovered that asking “have you always done that?” was like a secret cheat code to getting people to open up. Because NO MATTER what they say, you can always ask some simple probing questions and understand what this person cares about.
Have you always done that job?
No, I used to do [other job].
Oh, why did you decide to make that change?
Well, I really wanted to move to Seattle.
Oh, why did you want to move to Seattle?
I just love the outdoors, and there’s nowhere where I can experience it year-round like I can here.
I hadn't thought of that. So which of your latest outdoor adventures made you think "I made the right choice in moving here?"
Last winter I went to…
And now you have learned about something this person cares about. You have discovered what is important to them (the outdoors, in this case) and if you keep talking about that, you will connect deeply. And once you know what someone loves to talk about, you can continue using it. I like to remember what that “thing” is for people that I meet, and whenever I see them again, I always ask about it. That’s why people love me, nbd.
Example #2: start with “do you always want to do that?” [focus on the future]
Whenever I get the sense that someone is not completely satisfied with a part of their life, this is my go-to question to open a conversation. Because I know they are asking themselves the same question, and hoping SOMEONE will finally ask them about it, so they can unload.
Do you always want to work in tech?
It’s good for now, but I have this crazy idea of becoming a chef.
A chef! How did that idea pop into your head?
Well, I really enjoy cooking for my friends.
Clearly, we need to be friends. But seriously, how does it feel when you create a meal that people enjoy?
It’s incredible! I feel like a mad scientist that has come up with the perfect concoction.
Which of your latest experiments are you most proud of?
Last weekend I made…
Talking about hopes and dreams for the future is another avenue for discovering what someone cares about, and again, the that’s the golden ticket to connecting deeply.
Success And Challenges
So how do you know when you’re connected to someone? The mark I go for is when they are willing to share a story with me, like in the examples above. The more personal the story, the deeper the connection. You can keep repeating steps #1-#3 to get at more personal stories.
Fair warning though, you may not always get there as quickly as the examples above, and that’s okay. Sometimes it takes a little bit more probing, because people are not used to getting so much genuine, focused attention from another human being. They may think you are just being nice, and not be willing to open up so quickly. But keep at it, and use open-ended questions [how…/why…/what was it like when…/how did you feel…/etc.]. If you give it a few tries and it’s still not going anywhere, you may have skipped a step in the beginning, or the person is just not in the mood to connect.
I love using this strategy to start flirting with a girl and find out if she is single. Allow me to demonstrate...
Have you always lived here?
I just moved back here from California about 6 months ago.
Ooh, was it because of a boy? (in a teenager-sharing-gossip voice)
This usually makes her laugh, and her answer lets me know if she is single. If she is single, I will ask her out (here’s the proper way to do that). If she isn’t single, it opens the door to talk about dating, and I can ask her how she met her boyfriend (here’s why you should always ask that).
So how did a 23-year-old, shy guy in a wheelchair go from zero success with women to dating 40+ women, getting his first kiss, losing his virginity, having 5 girlfriends, and being the life of the party wherever he goes? The strategies I still use, to this day, are spelled out in The 3 Step Guide to More Friends and More Dates – click the button below to download it (for free!) now.