A Checklist For Sparking Deeper Connections

Life feels better when we live it with people we love. 

This is because it’s in our togetherness that we create the memories that last. 

The moments spent laughing so hard that your belly aches! The beautiful tears that roll as you support each other through the pain. The intimate conversations that keep you up all night long. 

These are the moments that we remember. Moments that touch us so profoundly they often change us.

No wonder connection is one of the most beautiful energies we can cultivate in our lives. 

Brene Brown defines connection as “the energy that is created between people when they feel seen, heard, and valued.”

How do we create this energy in practice? This checklist is here to help.

1. Lead with vulnerability. 

At an intuitive level, we want to fit in and belong. This ancient coding stretches back to the days when our ancestors needed to be inside the tribe to survive. If you became an outcast, your survival was at risk. 

The challenge is our ancient brain still holds this fear. It’s why we can wear a social mask or hide the parts of ourselves that feel ‘too much’. But when we’re always holding something back, it’s harder for people to know us. 

Vulnerability is a willingness to be more exposed with your truth. It’s a desire to show who you really are. Vulnerability can be a superpower, because when you lead by example, you permit others to take more visibility risks themselves. 

In turn, our connections can deepen because instead of connecting on superficial grounds, we get to connect through our hearts. 

2. Break the ice. 

Meeting someone for the first time can feel awkward - especially if conversations aren’t a key strength! The trick is to find common ground. People like people who are like themselves! As soon as you find something that resonates, the conversation [and therefore connection] builds momentum. 

It helps to have some icebreaker questions in your back pocket. 

“What do you do?” is a little too cliched! Also, because people often equate ‘doing’ to their work, it can spark an uncomfortable conversation if this isn’t a topic someone wants to explore. 

Asking about someone’s passions or hobbies can be a better way to kick-start a conversation. And if you want an entire deck of icebreakers, you’ll love this tool! 

3. Then ask deeper questions.

Most conversations are surface level. We dance within our comfort zones and what doesn’t scratch the edges too much. 

Deep-dive conversations can be uncomfortable. It requires vulnerability. It demands that you explore topics, memories, thoughts, and ideas that you may not have fully processed yourself or ignite a fear of judgement if you were to share them with others. 

However, on the other side lies the possibility of a deeper connection. 

When you share the depths of who you are, you give yourself a chance to be fully seen, heard, and valued. When someone knows what’s under the surface, you instinctively cultivate a deeper sense of understanding, compassion, respect - and even love. 

For sure, you want to feel safe in a deeper conversation, and it’s crucial you cultivate a level of trust with someone before you go there. But when you find the people to whom you’re willing to bear your all, the connection that follows is exquisite. 

For deeper dive conversations, we love the Deeper Talk Deck.

4. Hold space

Your head can only hold so much insight at one time. That’s why space holding is a little piece of magic. When you create and hold space, you create a receptive void, and that void is ripe to be filled with thoughts and feelings. 

Sharing who we are is a beautiful thing. 

And the ability to hold space takes the resulting connection to new depths. 

We’ve all had experiences of talking with someone who’s only listening so they can figure out what they’re going to say next. 

It’s why we know the difference when someone is genuinely interested in what we have to say. 

Knowing someone is interested permits you to share even more. As a result, the thoughts in your mind unravel as you speak them out. It’s how conversations can create clarity, new ideas, and closure - as well as deeper connections. 

5. Practice the three levels of listening. 

Level 1 is internal listening. This is when you interpret what you hear in relation to what the words mean for you. 

Level 2 is listening to understand. At this level, we’re less distracted by our own stuff and more interested in what the other person is communicating. 

Level 3 is global listening. This type of listening takes level 2 to new depths by weaving in intuition. If you’ve ever had a hunch that someone is leaving something unsaid and you raise that, you’ve been listening at level 3. 

When we cultivate the skill to dance between the three types of listening, we get to hear the people we love at a deeper level. In turn, your connections strengthen. 

6. Be authentic. 

Every human has instinct and intuition.

It means we can often feel when something is off. 

Authenticity helps build trust in your relationships. It allows someone to trust you, instead of doubting you. 

Real talk - where you strip away the fakery and say it as it is can be such a relief! In our social age, we’re bombarded with other people's social highlights, and it can be hard to know what’s real and what’s shared to create a particular impression. 

Authenticity helps us sink into what’s real. 

And that deepens our connections exponentially. 

Brene Brown also said that “connection is why we’re here; it is what gives purpose and meaning to our lives.” 

We can often shy away from connection because it means we have to reveal who we really are. 

But without it, we feel a sense of loneliness, isolation, and separation. 

The ability to spark connections with others is a skill we can master. I hope the suggestions in this checklist empower you to feel closer to the people you meet in your life.

Conversation Decks For 
Sparking Deeper Connections