AI Playbook Undeniable Speaking Trainings About Blog Subscribe Work With Me
← High Performance Center
Being · Routines and Relationships

How to Build Relationships

You build relationships by going first, giving with zero expectation of receiving, and staying connected in ways most people skip. I call it being a Master Relationship Builder. It comes down to five philosophies, a few conversation openers, and simple daily habits like taking a picture together and sending a video message.

TL;DR
  • A Master Relationship Builder leads the relationship and gives first.
  • Ask yourself what you are willing to do that others are not.
  • Open with "Tell me something awesome that happened in the last week."
  • Send one voice or video message a day so people can feel you.

What is a Master Relationship Builder?

A Master Relationship Builder is someone who leads the relationship, gives without any expectation of receiving, and does what others are not willing to do to stay connected.

A friend once sent me a voice message asking what helps me stay connected with people so seamlessly. My answer started with one line: I love collecting awesome people.

Some people stand out the moment you meet them, and most of the time that moment is where it ends. It takes two to tango, so I choose to lead. I am the person who says, "I noticed that you're awesome, and I would love to continue this relationship."

I love collecting awesome people because you never know where it might lead.

Rob Cressy

What mindset builds strong relationships?

Five philosophies run through my mind every day. I blend the second and third, because together they are one brand building principle.

  • What am I willing to do that others are not? This is a standard. Most people will skip this level of effort, so simply doing it makes you stand out.
  • Everything you do reflects your brand Everything you do is also an opportunity to create a positive brand interaction. The key word is opportunity. Staying in touch lives on my get to do list.
  • How am I going to stand out? Everybody sends a text or an email. Audio and video messages let people see you, hear you and feel you.
  • How can I be a go-giver? Ask "how can I help you?" and give without any expectation of receiving.

What am I willing to do that others are not?

That first question is about your standard of excellence. You are accountable for the relationships you create in your life.

What is the Ultimate Conversation Starter?

The Ultimate Conversation Starter is one question I ask almost every person I meet: "Tell me something awesome that happened in the last week." It works because there are a million ways to answer it.

It started after a night out with my friends. My wife asked what was going on with Jeff, and all I had was, "Oh, he's good, not much new." That cycle kept repeating, and I realized most of my conversations held very little of substance. So I started asking this question.

Many people struggle to answer at first, so lower the bar with examples like amazing sushi, a Cubs game, or a promotion at work. You can also widen it to the last month. Be ready to share your own answer, because people naturally ask it back.

What do you say at an event or conference?

Set your intentions ahead of time. I once went into a three day business event with three phrases as my blueprint for every conversation. I had just completed 75 Hard, so vision was top of mind for me.

IntentionWhat to ask
Your vision"Talk to me about your vision. What does your three year vision look like?" This is the thing that lights people up.
Fresh eyes"Is there anything you would love some fresh eyes on?"
Rapid expansion and success"What does that mean for you? What are you working on?"

Like attracts like, so people bounce each question back to you.

How do you build relationships step by step?

  1. Write "who" in your planner. I write those three letters every day, an idea from the book Who Not How by Benjamin Hardy and Dan Sullivan. Who do you want to connect with, and who can you help?
  2. Go first. When someone stands out, tell them.
  3. Take a picture together. Text it to them on the spot with your number. It takes about five seconds, and your face takes them right back to that moment.
  4. Send a voice or video message. A good vibes message takes me 10 seconds: "Just want to send some good vibes your way."
  5. Make your compliments about them. Open with "you" and say what you notice. I once told a barista, "You have great color coordination today."
  6. Track your conversations. Conversations are one of my top metrics of success.

How do you stay in touch without feeling overwhelmed?

I skip the CRM for my personal relationships and stay on one frequency every day: who could I shoot a message to? A simple version I learned in Jesse Itzler's community is the three minute rule. Once a day, message three people, one minute each.

You rarely know what somebody has going on in their life. People have written back to tell me a message arrived on a challenging day and helped them a ton.

How do you build relationships in the AI era?

Staying connected is becoming a superpower. Most people will outsource more to AI and have less human connection. I am team AI, and I am human first and heart first. Let AI draft, and keep the judgment and the heart human. I share more in how to use AI for relationship building.

Do this today

  • Send one video message. Pick one person, record a good vibes message, and repeat it once a day for the next seven days.
  • Ask the question. Start your next conversation with "Tell me something awesome that happened in the last week."

Listen to the episode

The Undeniable Leader · February 24, 2025

Mastering The Art of Connection: Building Relationships In A Digital World

Follow the show: Apple Podcasts · Spotify · All apps

Read the full transcript

In today's digital age, maintaining meaningful relationships can feel hard and overwhelming because there's so much going on in our lives and being thrown at us on a daily basis. So what in the world is the secret to staying in touch and connected with people and how can it be both seamless and easy? And what I want to do is share some tips about mastering, sharing the art of connection and building relationships in a digital world.

And the inspiration behind this is I received a message from my friend Francis who sent me a voice message that said, Rob, you come across as someone who is really good at staying in touch with people and staying connected. And that's something that's important but also very hard to do getting back to all the messages and all of the things. And I would love to have it. And I would love to have it become more seamless and easier and make it about the connection. What helps you stay connected so seamlessly? And what I wanted to do was share an in-depth response to Francis and I figured I'd share it with you so that it can help.

And I'm going to frame this a few different ways. And let's start with the foundational framing. Number one, I've got a background in sales of over the last 20 years. So staying connected, following up, standing out and being somebody who is likable and having multiple touch points for interaction. That is something that makes you a world-class salesperson on top of being top of mind for whether someone's going to purchase something or give you a referral.

Number two, I've got a background in improv, which is something that I learned and I believe in yes and. So I build on top of ideas. I'm there to support and build others up. And I also like to have fun and create and collaborate with other people.

And then number three is I'm an entrepreneur with super big dreams. And I'm always working on increasing that know, like and trust factor. And it's oh so important. So I'm somebody who wants to be memorable, stand out and do so in a way that leads with my heart so that you can feel me.

And then the last part about this is I love collecting awesome people. And one of my goals this year is to create more beautiful relationships. And this has been something that's been a part of my DNA for more than the last decade. And I love collecting awesome people because you never know where it might lead. And there are certain people that you're going to meet in your life that are going to stand out.

And this is something that is oftentimes a vibe, an energy, a level of conversation, a connection you have, or a shared experience. And so often you might meet somebody at an event or at a game or just passing through in life. And that can just be the end of it where it's like, wow, if we had an alternate universe where we lived in the same place, we would have been best friends.

Well, guess what? Why let that just end right there? Because it does take two people to tango. And it just so happens I am going to lead and be that person who says, hey, I noticed that you're awesome. And I would love to continue this relationship. And this does not mean that this has to be heavy. It doesn't have to be all of the time. It just means in the back of my mind, I'm going to sit there and say, you know what? I remember specific things about this person.

So for example, Francis, when I met Francis, she is full of good vibes. She has an aloha spirit living in Hawaii. And immediately I gravitated towards her warmth and the way that she made me feel. So I naturally said, wow, there's something special about Francis. I want to stay connected with her. And then I followed her on social media. And after that, I was like, wow, she is just as amazing as I thought when I experienced her on, I believe we first connected in Jesse Itzler's community with Build Your Life Resume.

So with this, I'm going to do my part in this dancing. At the same time, it does take two to tango. And not everybody is going to be in your life forever. People are oftentimes in your life for seasons. And part of this will be their ability or willingness to stay connected with you.

And this is something that's probably one of the harder things for someone like me who really does care about people. One of my declarations I speak is, I am that I care the most. And boom, my heart comes out of my chest right here because I truly do care about people. I truly want the best for them. I do want to connect. This comes from a place of love and positive energy. But at the same time, if someone is not going to do their end in that, that's the hardest part. But guess what? I give without any expectation of receiving.

So what I'm going to do to sort of break this down is share five philosophies or prompts that create my mindset around the art of connection and being a world-class relationship builder. And then I'm going to peel the layers on each of these to really make this very practical and simple for you so that you can implement this in your life.

So number one, what am I willing to do that others are not? Number two, everything you do is a reflection of your brand. Because number three, everything you do is an opportunity to create a positive brand interaction. Number four, in a digital world with so many distractions and so much going on, how am I going to stand out? And then number five, how can I be a go-giver? So that's what's going through my mind on an everyday basis around connection and relationship building.

So let's peel the onion on each of these things here. Number one, what am I willing to do that others are not? And I know by design, most people are not going to do everything that I'm sharing right here. So immediately, just the energy, just the intention in the way that I show up, most people are not going to put this level of effort to it. So just simply doing this is going to have me stand out.

But more importantly, I'm not most people and neither are you. And to me, this is a standard that if I have big dreams and goals and I want more amazing, beautiful people in my life and I want more connections, then I'm going to go above and beyond to make sure that I create that in my life. Because I am accountable and so are you for what you create in your life.

So for me, this is an ownership side of things. And of course, with this ownership side, you know the majority of the world will not be doing it. So it's really important that number one, this is a standard. You want this. So if you notice yourself not staying connected, well, is this something that you actually want? For me, the answer is yes. And then with number two and three, I'm going to blend them together because this is a brand building principle for me that I teach and I coach all the time.

So part of that in the brand building from your heart philosophy is everything you do is a reflection of your brand. And everything you do is an opportunity to create a positive brand interaction. And the key word here is opportunity. Because Francis said, Rob, I want this to be easy and seamless. And I hear the word flow almost like a ribbon in this because how I think about this. So this is an opportunity, not an obligation. This is not on my have to do list. This is on my get to do list because I love interacting and creating with amazing people.

So if you can look at this as an opportunity, then your lens becomes, huh? What are all of the opportunities I see of the people that I can create with and connect with? Many of them that you meet, but some of them that you haven't even met yet, which is why some of these mindsets and processes are so important and foundational.

And one of the things that is so simple that you can immediately do that is a hallmark of almost anybody who ever met me in person anywhere is taking a picture with them. So for example, a few weeks ago, I was at the Ultimate Experience in Arizona. And there are two of my friends that I met for the first time in person after three and a half years, Fiona Ross and Dominic London. And of course, I was like, we have to take a picture of this memory.

Why? Number one, I just want that for the rest of my life. But number two, I am now the ability to share that on all of my socials and on all my platforms. And I can tag each of them. And I have the ability to say a nice compliment about how much each of them means to me because both Dominic and Fiona are such kind-hearted and wonderful people. And I want more of the world to know how kind-hearted and wonderful they are. And the simple thing is, boom, you sit there, take a picture, and this becomes part of your process for when you meet new people.

And here's the next level of this. And this is the mastery level. We already said very few people are going to do this, but very few people are about to do what I tell you that I do here. So when you meet somebody new at a conference or in everyday life, and you exchange phone numbers or your social handles, and especially if you're at a conference where you're going to be meeting a high volume of people, and not everybody's going to remember every person and every connection. Therefore, I want to take a picture of that person and lock it in. And that way, when I send them a text message with my number, boom, I also include a picture with ourselves.

So for example, let's take this picture with Fiona and Dominic. Let's say I just met them for the very first time. What I would do is I would go on Facebook, and I would create a group message chat between the three of us and say, I loved creating with you guys. You're the best. Let's make sure to keep this conversation going after the fact. Boom. Send that picture right there. Immediately, they can go on for the rest of the three days of that event and do their thing.

And when they come back to a text message or a DM from me, they're going to see, oh, there's Rob. I remember them because I know what I was wearing. I remember that connection and the energy of how he made me feel. So boom. Nice and simple with that. And I estimate that over the Ultimate Experience event, I took 50 photos of people, each one locking it in, sending them that DM. Boom. Now I'm memorable. And I can remember that moment as well.

Next thing. In a digital world with so many distractions and so much going on, how in the world do you stand out? Well, to me, this is a very simple thing. And it comes from one of my foundations of being a prolific and master creator is I'm going to send audio and video messages. Because guess what? The easy thing to do is that everybody does. Just send a text message or just write an email, AKA hiding behind your keyboard. It's not a bad thing, but guess what? It is what everybody else does. And I don't want to be like everybody else.

So I knew this just from sales as well as just building my own business. And I want to create more beautiful relationships with more amazing people doing amazing things. So how in the world are you going to stand out? Anybody can receive a text message. Can't really feel a ton. Yeah, I can use some words to make you get an idea of me. But you sitting here watching this or listening to this right now, you can feel me. You can hear me. You can take that energy and be like, wow, I have an idea of what it might be like to have a conversation with Rob right now. That's what I want to transfer.

And especially if you've cultivated this personality for yourself and it doesn't have to be mine, but I'll even use Francis. Francis has such a warm and gentle and kind spirit. And she uses words like aloha and sending love your way. And man, you can feel the way that Francis talks to you. And it's one of the amazing things about her is that warmth. Man, that's why I want to keep staying connected to Francis is because I just want that little dose of Francis. And then, wow, thank you so very much for that warmth. And even if she's just sharing a story on Instagram, boom, I get a little piece of her in my day every single day.

And this is something that so few people are going to do. And I encourage you to ask yourself this question. How many people in your DMs and your text message right now are sending you an audio or a video message consistently? Hey, maybe you're someone where this happens all the time. Great. But I'm guessing for the overwhelming majority of people, very few people are receiving this.

And I know this from my own perspective, that there is a handful of people, let's call it five or less, that we're consistently trading audio messages together. But the majority of the people, I never receive anything whatsoever. Then we're going to flip this. How many people listening or watching right now are actively sending these to people consistently across the board? Once again, my guess is very few. Ding, ding, ding, ding, ding.

... holding you and everybody else back. Once you get past that and you lead with your heart and you just be you, man, Mr. Sunshine going to sunshine. And you just shine that light on everybody that you meet. And once again, the way that you become world-class is by asking yourself, what am I going to do that is both different and world-class?

But then here comes the next thing that a lot of people say is, but Rob, how in the world do you remember all of this? If you're doing this all the time for a decade at a time, isn't it hard? Isn't it overwhelming? What in the world do you do? You could use a CRM like many sales professionals do. That's great on the business side. And I have that, but no, I do not use a CRM for my relationship building and staying connected with everybody.

And for me, I like to think of this as sort of like an omnipresent thing where every single day I have the intentions of, I want to connect with more people who want to be exceptional and have good vibes and positive energy. And I know the more I give out, the more I'm going to receive right there. So with this, I'm always on this frequency of like, Hey, who could I shoot a message to?

And this is going to lead to the last part here before we get to the action item is how can I be a go-giver? Foundationally for me and how I create, how I show up every single day and the way that I interact with every single person in my life, whether you're a friend, a client, or someone that we're just friends with and connected with on social is how can I help you? And back to the movie, Jerry Maguire, help me help you Rod. So for me, I come from the mindset of being a go-giver. I'm going to give without any expectation of receiving whatsoever.

But I know this to be true. One of my superpowers is energy, my ability to create it in myself, as well as transfer it to others. And the best way that I can transfer this to somebody else is by using video and using voice because now you can see me, you can hear me and you can feel me.

And with this, and this is so important, you never know what somebody has going on in their life. Social media may make us think that everybody's lives are puppy dogs and rainbows, but I can tell you from experience, including present day, the last week is that that is not the case. That there is always something going on in everybody's life, whether you realize it or not.

And you never know the positive impact that you're going to create in somebody's day just by sending them a good vibes message and be like, Hey Francis, just want to send some good vibes your way. Want to let you know that I'm thinking about you. I love the consistent, positive energy that you're always putting out. Hope you have a great day today. Boom. Takes me 10 seconds. Francis has of course received messages like that from me and I have no expectation other than just shining my light on that person.

But guess what I've learned after doing that for decades is that I will receive messages out of nowhere or relatively because I sent the message that says, Rob, thank you so very much for this. You do not realize how much this means to me. I was having a challenging day. A family member got sick or somebody passed away or I lost a client or I've just been having a tough 24 hours or a tough week. And this really helped me a ton.

You hear that message one time and you're going to be like, I'm doing this forever because this is no longer about us. It's about other people. What we can do to be a positive force for good in the world. Because could you imagine if this is the frequency that the whole world operated on? And yes, the whole world might not operate on this, but guess what we have the opportunity to do? We ourselves can be that one of one who believes in being that positive force for good in the world.

One of the things that I've spoken into existence and I've stepped into as an identity is I am a leader of a global movement and my word is heart, our ability to create from the heart. And imagine if the way that you thought about mastering the art of connection in relationship building was you led with your heart. You wanted to help fill up somebody else's heart. And with this, this is why I love voice and video so much.

And the last part on this here is all around connection points. You want to be somebody who is a person of value. Once again, this goes back to the collecting awesome people side of things. Awesome people aren't sitting there living boring lives doing nothing. No, they're out there living full lives, taking risks, being bold, happy, energetic, connecting with other people.

So with this in mind, it's like, well, how in the world do I create all these connection points to allow more amazing, beautiful people to come into my life? Well, for me, this is simple. This is by design. Why in the world do you think I'm creating this video and podcast right now and live streaming this? Because I know that we can take our voice and our message and we can just amplify it in the world. It's no harder for me to click live stream and this go on Facebook, LinkedIn, and YouTube all at the same time right now. And then I can go chop, chop, chop, and turn this into a podcast.

And guess what else? One of the things I love about being a relationship builder, as well as somebody who hosts a podcast is I always have something of value to give to somebody. When I meet somebody new or awesome, and I know I've done a podcast with Francis and I'm going to have Dominic London and Fiona Ross on my podcast. Immediately I can say, Hey, let's deepen our connection. Let's book a 30 minute conversation and let's go deeper. Maybe we'll go live together. Maybe it's just a podcast, but now I've got something of value that I can give to them because everybody loves to talk about themselves.

But more importantly, I love, and so do the people that I get down with. We love getting together and talking and creating. And it just so happens we can do so over a shared space in the form of a podcast. So it's such a simple, immediate opportunity to be a go-giver, a relationship builder, and a connector. Snap of your fingers.

So wrapping a bow on this right now, how in the world do we make mastering the art of connection and building strong relationships in a digital world light, easy, effortless, and consistent? So nice and simple here. Number one, write this down in your planner every single day. What I write down in mine is three letters. W-H-O, the word who. And this comes from the book Who Not How by Benjamin Hardy and Dan Sullivan.

We don't have to figure out how in the world we're going to make our dreams and goals and visions happen. Instead, who can I connect with? Who are those people out there in the world that can help me accelerate my dreams, my visions, my goals, introduce me to new people, become clients of mine, become referrals? Who can I help out there? So every single day, I just write down the word who, and I put a little arrow up because I say look up and love up. So that's my intention every single day of, hey, who do I want to connect with? Who do I want to shine my light on?

Because number two for me in what I do in my business as the leader of a global movement, as a creator, as a coach, and as an entrepreneur. Conversations are one of the top metrics of success for me because I know the more conversations that I'm a part of, the more great things that can happen from them. So I want to spend more time in conversations. So that would be the next thing for you is if you want to be better at this, then start tracking how much are you spending time in conversations.

And then here's an action item for you, and this is such a simple one. What I would love for you to do is once a day for the next seven days, send one video message to a person, anybody that you want, and then watch what happens. I promise you with 100% certainty, you are going to learn something great when you do this. Maybe you got to get past your comfort zone of not sending video messages because you're not used to it. But more importantly, I want you to feel the love that is going to come back to you.

And one of the things that I learned being a part of Jesse Itzler's communities that was so simple, he calls this a three-minute rule where once a day, you just message three people, one minute each takes you three minutes. That's the other way that you can do this. Nice and simple.

So staying connected in this digital world is going to become a superpower because most people are just going to outsource things to AI, and they're going to have less human connection. And despite the fact that I am team AI, I am human first. I am heart first. So when you are one of those people, we are looking for opportunities to build deeper connections with other people. All it takes is the right framing, the right mindset, creating a standard for yourself, and then shining that light and heart on the rest of the world.

Transcript cleaned up for reading.

Keep going

Work with Rob

Create your next level with AI on your side

Coaching, keynotes and workshops for high performers and leaders who want AI working for them, the human-first way.

Coaching · Speaking · Workshops