Fostering Deep Connections with Jennifer Hill
16 Dec 2025 · 30 min
Jennifer Hill describes a "golden triangle" of connection between self, others, and purpose. She walks through tools like heart-focused breathing for self-regulation, matching people to roles based on their motivators, and how proactive confrontation builds trust instead of eroding it.
Questions this episode answers
To have connected 1 billion people deeply to themselves and others by the time she dies.
24% (described as an unprecedented 24% globally).
Project Aristotle (2012): studied 38,000 people in 182 teams and found psychological safety as the top factor.
OM App — omapp/survey (spoken as "OM app forward slash survey").
jennifercahill.com
Chapters
Foreign.
Hi, I'm Susan Drum, and welcome to the Enlightened Executive, where your personal evolution sparks your leadership evolution. Each episode we feature groundbreaking techniques and strategies to help you get the edge in personal and leadership effectiveness. This episode is brought to you by Meritage Leadership. At Meritage, we strengthen leaders and empower teams to achieve high performance. Go to meritageleadership.com to learn more. Are you curious about your development path to enlightened leadership? Take our free 5 minute quiz@susandrum.com to discover your superpower and the roadblocks that could get in the way of effective leadership. Today we're talking about cracking the code for connection, and my guest is entrepreneur keynote speaker and coach Jennifer Hill, who is arguably one of the most connected people I know. Jennifer successfully exited her first company focused on legal recruiting in 2018, and she was recently accepted as a member of Deepak Chopra's Evolutionary Leaders Circle, a group of thought leaders who come together to support a shift in consciousness. She's hosted over 20 TV episodes with Chopra and Don Hoffman called Conversations at the Intersection of Cutting Edge Science and Spirituality. Jennifer's current project is Optimatch, a SaaS company she founded, and it leverages her superpower, which we're going to get into in a moment. She also hosts a podcast called Regarding Consciousness and is speaking at Chopra's Sages and Sciences. All right, welcome, Jennifer. I'm so excited to have you on the podcast.
Thank you so much, Susan. And big shout out to our mutual friend Joss, who connected us a few years ago. From the first day you and I met, it was just kismet. I just love you as a human being.
Oh, thank you. Love you. Love Jocelyn Herman. She's amazing and so excited. She got us connected. And one of the things I'm really struck by is your mission in the world. Can you share what that is?
Yes. Our mission, our dream, is that by the time I die, we will have connected 1 billion people deeply to themselves and others. And that is my life's work. It's what I do every day, whether I'm podcasting, whether I'm appearing on somebody else's podcast, keynoting, or it's what we do every single day with our technology. Optimatch. What if we could all find psychologically safe relationships where we could feel heard, known and understood and be our authentic selves? And it really starts, Susan, with accepting ourselves. When we begin to accept ourselves, that allows for acceptance and deep, meaningful connection to others.
I love that and I'm so moved by that because I really believe the very same that it is always starts with your relationship with yourself. And if you want deep, meaningful connections with those outside, you've got to do the inner work to heal some of the parts that are at war within yourself. And the more you create peace internally, the more you'll create peace externally. So excited to have you on. Share with us what you mean when you say connection.
When I talk about connection, Susan, I like to think of it as the golden triangle of connection, as we just referenced deep connection to self, connection to others, and connection to purpose. And I've really found that connection to self is the cornerstone to all of that. And what I mean by the word connection is a sense of engagement. If we look at the world right now and the loneliness epidemic being at an unprecedented 24% globally, across the world, it's not just a US thing or a Europe thing or wherever. We're all impacted by this loneliness epidemic. And it really begins with us. Because although we have all these fabulous devices that allow us to listen to podcasts and be on zoom with one another, we've disconnected and disengaged with ourselves and with life and with one another. And so our dream, my vision, is to re engage people. Let's plug ourselves back into the circuitry that is the life vitality. That is connection.
Absolutely. And why do people struggle with connection? Like you said, we have all these devices. There's a way that can be connected to more people than ever before, and yet we have this loneliness epidemic. Why do people struggle with that?
I'm going to give you a really surprising answer, and it's going to be steeped in a little bit of science. So most of us are aware, Susan, of our amygdala. Right? Our amygdala is that fight or flight side of our brain. It's that lower part of our brain, that reptilian side. Well, what a lot of us don't think about is we have three parts to our brain. We have the amygdala, the lower part of the brain. Then we have the midbrain, which is the mammalian part of the brain. Am I safe? Are you like me? Can I trust you? And then we have the higher part of the brain, the executive functioning, the creativity, the capacity for love, kindness, compassion. And yet what most of us don't realize is that the higher brains can't function until the lower brain first feels safe. And I found that in a post Covid world, the reason that we're seeing these epidemics of loneliness perpetuating the world right now is because we don't feel safe or amygdalas are running the show. We're not having a relationship with my friend Susan or my husband or whomever it might be. I used to do a popular talk on this called how to deal with an office Jerk. And it was very funny. I remember I'd be doing these trainings at law firms and conferences and I'd say when you're dealing with somebody who's upset, you are not dealing with an upset 45 year old or 57 year old or an upset 25 year old. You're dealing with an upset 4 year old. And yet our upset 4 year old, our amygdala is fighting with their amygdala. And then we all disconnect and feel lonely and sad and fearful and so what if we could quiet that amygdala? What if we could spend time in self reflection to better understand how we're motivated, how those around us are motivated. Just the other day I had something where I noticed I got triggered, you know, such as life. I'm building a tech company. I love what we're doing. It's amazing. And as tech sometimes happens, something didn't work. So we had this big new engagement we were doing. We were super lit up. I was like jumping up and down for joy right before I like while I get on the call with our C suite team. And then as soon as we get on the call, something had went awry with it and I'm like, you know, and so in that moment, a lot of us as leaders, what I've noticed we do, Susan, if we don't have tools for self regulation to apply in that moment to probably amygdala, then our amygdala is going to run the rest of that board meeting. So then when we quiet it in that moment, I used one of my favorite techniques, which is heart mass, heart focused breathing. Nobody is wiser. I'm literally having the conversation with our executive team. And instead of verbally vomiting on the team, or as I affectionately call myself, when I was building my first company, I did not have any of these skills and I often refer to myself as, hi, I'm Jennifer Cahill. I'm a recovering jerk. Nice to meet you. Because I used to let that amygdala run the meeting where you can bring your awareness. You can pause in that moment before you send that angry email or say the thing that you're going to regret and just pause. Allow a few deep breaths in and out. I like heart focused breathing. There's wonderful Tools out there, box breathing, vagon breathing, anything to quiet that lower reptilian brain. And then we regain access to that higher consciousness. And, and I think a lot of us in business relationships and friendship and romantic, we're often coming from a reactive place rather than a proactive place. And the more that we can learn to be, use our consciousness to be proactive, use techniques and tools to be sure that we provide for our own needs, and we're not trying to take energy from the people we work with or the investors or whomever it is. Then from that place, place, we become the sexiest human on the planet. I tell people this all the time because you're no longer trying to take energy. You become the most investable person, you become the hottest person in dating, no matter what you look like physically. Because so often we're always trying to take energy from one another. So I think the secret, a long winded answer to your question of what is connection? The secret to connection is to provide for yourself first. Put your own oxygen mask on first, engage with yourself first, and then that will give you the tools that you need to make meaningful engagements with others.
Yes. And when you're triggered, that, that should be a signal to yourself. Whatever comes out of your mouth at this point is not going to be from the highest reasoning part of the brain. It's a reptile, so it should be. And what's interesting is I think when people get triggered, the first place they go is looking external. You triggered me. You did this to me. You know, life is happening to me. And instead, if we could start to train ourselves, oh, I'm triggered. I got to go within and take care of something internally because anything I do from here will not be at the highest level of consciousness and will not actually produce the results that we really want.
It's the antithesis of it. It's really. I used to teach this to job hunters when they would go into the interview. So so often I remember people, whether it was executives or general counselors or whomever it was, people would want to just sit and share their sob stories. Oh, this person happened. And then this company blew me off. I was on a call with somebody in the last week and I was really surprised that they shared a story with me about how somebody like lied on a contract or pulled the contract. But it was like a big crux of their story. And something I've learned is that if we make something significant, it becomes significant for those around us, those we lead, those we work with. But if we can make something Softer. We can soften our language, soften the experience of it, maybe light. Latcha, you know what? We had this little pitfall the other day, but we learned from it and it was a great learning opportunity. I think us as leaders, if we can constantly be reframing that even when our team says something, often as leaders, we're put in a position where our team might misspeak, speak, or they might get angry with one another and we put too much attention on that, then that can create greater frustration and turn, you know, make a mountain out of a molehill. Yet our perspective, which is something I like to talk about a lot, really directly correlates to how things show up for us in business.
And so tell me, what advice would you give to leaders who may be dealing with conflict on their team? I know more recently we did a survey in a company that I'm working with, and that was the number one concern of managers. How do I deal with conflict on my team as a leader? What would you say to that?
Great question. This is exactly what we focus on at Optinage and what I do with our own clients and so forth that we coach on. This is number one to help people realize that the others on the team, no one on the team, is misbehaving. That is step number one. I think it's so tempting as a leader to say, oh, well, this person said this, this person said that. So to be neutral and just come from a place of we're all motivated differently. That's what I've been studying for 20 years, is human behavior, first in recruiting and now with optimatch. And what we found is if my motivators and your motivators are adverse to each other, then that could cause what we call a potential accidental adversarial relationship. So to any of you out there who have conflicts in your team, number one is get curious. Number two is help to understand whether you're using our software or somebody else's software. Understand what motivates your team. There is a plethora of resources out there. Our studies and research have shown us that motivators tie in directly to how easily and psychologically safe people feel. I think it was Google who did a study on this called project Aristotle in 2012, where they studied 38,000 people in 182 teams. They found out unequivocally, the number one secret is psychological safety. So when you're about to go in and if you are about to be the one who is conflict managing a situation, I would say step one is to sit down with each party as individuals, or if it's multiple people, sit down one on one before you go into the conversation. Now I'm actually going to backtrack and I'm going to give a very high level because this is enlightened executives. I'm going to give you an even higher level tool that I only give to my favorite clients. I'm just teasing. I give to everybody. I love this. It's a tool that is a kabbalistic tool I learned years ago and I've since modified for my coaching clients called proactive confrontation. So half of the world's conflicts could be avoided if we just one waited for better timing. So according to the kabbalist, they say that when we're in conflict with somebody, step one is to ask which when we're about to have a conflict resolution conversation, ask internally. Ask your own inner knowing which intuition has been proven time and time again, Is this the right time for the conversation? Even if you don't consider yourself intuitive at all, we feel it, you know, that conversation, whether it's your spouse, your CEO, your employer, you feel it vividly and viscerally. Yet often we don't listen to it. So step one is to ask ourselves, is this the right time for the conversation? So step two, if it's not, pause and wait for a better timing. And step three, if it is the right timing, I always encourage our clients to pause and to imagine having the conversation with the person at the heart level first. Now you can have amazing results. I like to quote a friend of mine, Amy, on this. This is one of my favorite stories, and it's not business, but you'll appreciate it. She's also an executive coach, and we were traveling around last year together. And she tells me a story I'm sharing with her about proactive conference confrontation. She says, ah, Jen, we teach that to all of our executive clients too. Can I share a story? I said, please, Amy, go ahead. And she's like, we had this guy Tony, and Tony is like Italiano, and he's like angry and frustrated because his kid was being bullied at school. And she said, listen, Tony, can you just pause? Can you just imagine having a conversation with this kid who's bullying your kid? Just imagine at the heart level having this conversation with them and tell them all the things you wish that they were doing differently. So Tony, you know, acquiesces. He spends some quiet time and reflection. And Susan, no conversation took place in reality. But literally on Sunday, two days later, who shows up at his door, but the little kid who's bullying his kid who came to apologize. And I've seen this happen in business. I have to be careful for confidentiality of who I share about it as well. But when we take the time to proactively have the conversation, oftentimes it can make all the difference. And radical accountability is one of our biggest values at optimatch and what we do. So my. Even my own co founder that one day said to me something, he said, jen, you know, I have the experience that you're not treating me with the respect that you used to because you helped me sell the last company, and that you're treating me like an employee instead of a co founder. And I was like, wow, I'm so sorry. I did not realize that. So when we get confronted with things like that, it's important not to defend, to get curious and say, wow, okay, well, when did you first notice that? Okay, let me feel into that. And for me, I use muscle testing. And I checked myself, and sure as heck, he was right, Susan. Within moments, I didn't defend. I was like, you're right, Jules. That's not what I'm committed to. And I'll immediately work on this. And we were able to resolve it in 20 minutes instead of ending a partnership or having it go a different direction. And so I think radical accountability on the leadership side and on the team side, conflict management is taking that time to really just tap in and imagine having that conversation. And then when you do have the conversation, go through a process of clarification. It's a technique I learned years ago from a brilliant woman named Alison Armstrong. Changed how I run businesses. She said, great partners always use a process of clarification. And in order to say, oh, well, tell me more about that. So how did that occur for you? And half the time, you can resolve most conflicts by just getting down to whatever the breakdown is in communication.
Yeah, I think following up with, how did my behavior occur for you? Let me understand how you translated that. And I couldn't agree more. I just want to go back to something that you said, which is around really understanding what motivates your team. I mean, it's why I'm so deeply steeped in the enneagram, which is foundational around what is the core driver or motivator, not behavior. Because I think problems show up when we interpret people's behaviors through our own motivation, our own lens of what we're motivated by, and we can't understand it. Well, they may not be motivated by the same Thing, they're motivated by something else. And once you under start to understand that, you start to build the empathy. Oh, now I understand why they did what they did. If this is their motivation, and it's okay that they're motivated by something different. In fact, the best teams are, what I say, cognitively diverse teams. You're going to have some conflict. And that's where the best decisions come out of. Because if it was all up to you all the time, I guarantee you wouldn't have the best decisions all the time. Like, we need each other. It's fundamental. And the best teams leverage each other in this really powerful way. So, so many good things that you touched on there, particularly around thinking going into this, like, proactiveness around the conflict and visualizing what you want to occur as a way to pave the path to get there. Look, athletes visualize crossing the finish line. We spend a lot of time like, well, what if they say this and what if they say that? And it's almost like, don't go there. Go to the place of imagining the conflict being resolved and how did it get resolved? And play that out in your mind. That's one key piece. And the other key piece is that curiosity that you mentioned going in and saying that certainly, you know, if somebody's triggered by your behavior, well, that wasn't my intent. Like, I didn't want to trigger you, but let me understand what it was so I can either shift that behavior, clarify what the intent or motivation was, and maybe show up with a different behavior that will still accomplish the intent that I had. Right. And so this deep curiosity and learning, I think, is key to creating the type of connection we're talking about.
Yeah, 100%. I mean, that's what we do. It's funny, people always ask. We call our types in optimatch fruits, lychee, apple, mango, pear, or what we call lamp. When people always say, well, why do we call it fruits? And it goes back to that adage of what you just mentioned. It's literally sometimes like one person speaking apple and another speaker speaking orange. Even though we're both speaking English, we can't hear each other. And I had that happen with one of our vendors in the last several months. Nice guy, does a good job for what he does. I won't say what it is he does. And thank God at the beginning of this, I. At the beginning of that call, I've been working with him for about six months. And I said, oh, would you mind answering our matching question so anybody can answer it? If you want to see how your team's motivated, you can go to ohm app Forward slash survey and it gives you a free report or give your team member one at least. And I suggest that to him. On the beginning of the call, and we're talking about a few things, at the end of the call, something happened where I literally asked him a question and my co founder is on the call. He says no, and I'm like, okay, well, I really need your help with no. And I'm like, this is really no. And it's just like it was going to lead to hours of extra work. So I get off the call and I'm noticing I'm starting to get triggered myself. And I'm like, why is this happening? And then I remembered he answered our matching questions. And in our system, it's 0 to 40 points and 40 is the highest that you can get. It's. I think we've only ever seen a 39. I don't know if I've ever seen somebody be at 40. And one of the categories we measure is called Apple, which is are you motivated by facts and information? Well, this guy, it turned out, was a 37 Apple. Now, what we found in doing our research is that when you get into the higher apple numbers, a high apple is often a no first before they're yes. And it's not personal. And I kid you not, Susan, the moment I saw his results, I went from being angry and frustrated and like, ready to fight to being deeply compassionate and going, oh, shoot, he's just motivated differently. This is just a high apple who's a no first before he's a yes. It's not personal. And I think that's where the pain comes from, is that we take it personally. It goes back to the Four Agreements, one of my favorite books, books of all time. Oh, so good. What if none of it's personal? What if nothing is ever personal? Joss is so good at teaching that I love our friend. Joss teaches. It's like I was in a class with Joss a week or so ago, and somebody in the class said, oh, this person ghosted me. And Joss was so great in her coaching. She said, well, in reality, nobody ghosted you. So she's like, what happened was you texted somebody and they didn't text you back. And then it became a thing that you called ghosting, which often can disempower us. So I like to look at what are the perspectives that we see the world through. Actually, Julian, my now co founder, was the Business coach who helped me exit the first company, and he saved me. In one scenario, there was a person I was working with, Susan, and I was very frustrated. Have you ever had that where somebody screws up once, they screw up twice, and by the third or fourth time, you can't even hear them because you're just looking for the next disappointment to happen?
Yeah.
So I had already gone down that slippery slope with this one particular person who had been an early hire. And Jules comes in. He says, jen, what if the reason that she is a disappointment is because you are looking for her to be a disappointment? And I was a little bit indignant. How dare you. I have all these reasons why. Evidence. That was my exact word. Legal recruiting evidence. I was like, I have all of this evidence. He said, great. How's that working out for you? I was like, really crappy. And so he said, good, here's what I'm going to invite you to do. He said, for one week, you don't even have to tell her you're doing it. All you're going to do is write down one thing that she does well a day. That's all. You just have to look for and find one thing. Don't even have to tell her. It's just for your own indulgence. So it's hard when you're frustrated or angry or looking for the bad in people. It's hard to shift your perspective at first. So the first day was like spitting venom. Trying to figure out something that you appreciate became easier. Third, fourth, fifth day. But the seventh day, Susan, she was doing amazing. And I'm proud to say that that is a woman who took over the company after I sold it and is still there six years post acquisition. And that was all out of that experience. So something I like to suggest to the executives I work with is to imagine that our perspective is like a giant, enormous black warehouse that is pitch black and you cannot see a darn thing except for a tiny pin light that's like on a miner's helmet. So all you're going to see, if you look to the right, you'll see what's to the right. Left, you'll see what's the left. Up, down. You get it. And that ties into neuroscience, which tells us that every moment of every day, we're only perceiving a hundred bits of information out of 11 billion bits of information that hit us. Us. So what are we choosing to put our attention on? If we look for how our executive team, our board members, our. Our employees are misbehaving we can absolutely prove ourselves right. That's what we're designed to do as human beings.
Yes. And it's. It has to do with what we're motivated by, to look at. Right. At the. The analogy I use is like, as human beings, we think we're chameleons and can see it all 360 degrees, but we can't. We actually have a central vision and a peripheral vision. And really, it's really only the central vision that we see much or we think we see. And wherever we point our head, that's what we're motivated by. That's what we see. But there's so much behind our head we don't see. I don't know what's going on behind me. And yet we interact with the world as if we're seeing 360 degrees. And I think the awareness for a lot of leaders that the way you're perceiving the situation may not be how it actually is in reality like that. And so what it does is, again, open up that curiosity to say, what is the blind spot? What is the piece that I'm missing? And how can I go in asking more questions about this circumstance than not right.
And assuming the worst? Like, what have we all looked for the good in everything and everyone? And yes, you do do have to have hard conversations. I've had to fire more people than I can count in my life. And half the time, now that I've developed myself as a leader, I've actually had people thank me for firing them. Because if we do it in a way that is compassionate and clear. There was a method I learned from Allison years ago where she had talked about, you know, you ask somebody the first time to do something and you say, hey, I need your help. Susan, can you help? I need this project completed by Friday. What do you need from me? Very simple, right? Well, if the person doesn't do it, in Allison's method, she encourages people to increase their pressure. And by the end of it, most of us don't actually increase pressure. We just blow up and blow a fuse when somebody doesn't get us the report on the day they said. And then it's disempowering for both parties when somebody does wind up getting terminated, though. I remember one guy, I had to. Well, I was going to fire him, and he wound up quitting, like two weeks in. It was just a very bad mismatch hire. We all make mistakes, and it was hilarious because I remember the huge accounting firm that had acquired our company. He goes into HR's office and she's like, I'm sorry, blah, blah, blah. Is in my office. Did he get fired or did he just quit? I said, no, he just quit because I just went through this process with him. It saved us workers, comp and staff. But the guy just got clear it wasn't his right for him.
Yes, yes. What's one piece of advice or an action item that you would suggest leaders take tomorrow to build deeper connection with themselves or with others that they lead?
I would say one of my favorite techniques is inner child work. And I do it with every single CEO I work with. I got to teach it at a law firm conference earlier this year. It was such a joy to get to work with 200 people on this. It's very simple. It's not rocket science. You can look at a picture of yourself at a 4 year old, 5 year old, 7 year old. The age is not important. Important. Or you can envision yourself at whatever age, he, she, they, them, whatever it is you imagine yourself at that age or look at yourself at that age. And I like to put my right hand on my heart, my left hand on my abdomen. And it's the last thing I do every morning right after I meditate and I check with myself, Susan, and I'll say, how are you feeling today? And it's really interesting. On the one hand, I'm autistic, so I have a little bit less connection, connection to my feelings sometimes. So I'll put my right hand in my heart and say, how are we feeling today? And my inner child will say, we're sad. And I'm sitting there as 43 year old Jennifer going, we're sad. Shoot. What are we sad about? But I don't even know. But I've also talked to people who are neurotypical who have said they have the same experience because so many of us don't realize we get triggered by something. And then I love it was so cute. My mom just sent me an article about this the other day. She's like, honey, it was like some really prominent news article saying, did you know if you hug yourself for 20 seconds a day, it can create greater oxytocin and happiness. Happiness. And I was like, I do that every day, mom. So like the last thing I'll do is I'll just hold myself. And I ask myself every day, you know, what do you need? How are you feeling? You are loved and you're cherished, you're accepted. And when I do that, then I find that the five year old in me is not running my board meetings. Yeah, yeah, exactly. And to have compassion, the last little bonus add on here is the next help time that you see somebody and they're getting upset or maybe it's one of your team members. See them as their four year old self or five year old self and then that will help you to come from a more compassionate place in how you deal with it rather than saying, oh, why is this 54 year old person throwing a tantrum? They're not 54 in this moment. You're dealing with a 2 year old. And if you can fill with them and give them compassion, it all begins with self though. It goes back to the golden triangle of connection. Whatever we give to ourselves, we can provide to others and to the world.
Well, thank you so much for joining me on the show today, Jennifer. This was wonderful. Could you share how people can learn more about you and your work?
Yeah. Thank you so much, Susan. So if anybody wants to try our survey, it's complimentary online, OM app, forward slash survey and it's free to go ahead and take it there. And otherwise you can find me on LinkedIn. Our website is om app. Or if you'd like to find out about working with me as an executive coach, you can go to Jennifer Cahill.com.
Thank you so much. And if you like this episode, you're not going to want to miss my interview with Moshe Gerst, whose life mission is to assist in awakening the world to a higher consciousness. Let's all lead the way. Hope you enjoyed today's episode and I'd like to point you to the next important step. Hit the subscribe button to get notified when we release new content. I'll see you on the next episode of the Enlightened Executive.
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