by Mark HuYoung
When you’ve spent a few decades wrangling deals, sitting in board meetings, and delivering leaders for the C-suite, one thing becomes clear: while business continually evolves, the truest currency remains human connection. Modern AI bots can schedule meetings, predictive algorithms can help recommend optimal lunch spots, and machine learning tools can automate reminders of every birthday from here to eternity. But nothing replaces the handshake, quirky banter, and genuine trust that get careers built and deals done.
Just last month, my team was closing a CEO search for a defense contractor. The finalist had all the right credentials on paper, stellar references, and even impressed our AI screening tools. But during our final conversation, when he casually mentioned how he’d personally called every employee on his team during his company’s last layoff, not to deliver bad news, but to check on their families, that’s when we knew we had our leader. No algorithm captures that level of emotional intelligence.
Still Wondering if Relationships Matter?
I get it. In today’s hyper-connected world, you might secretly wonder whether actual relationships are passing into obsolescence, buried under digital interfaces and clever chatbots. Don’t fire your emotional intelligence just yet. Technology makes it easier to keep score, but not to build trust. Every executive has a CRM, but only a few really know how to create those magic moments of being seen, heard, and understood, not just entered in a database.
Whether you’re a private equity dealmaker, an executive searching for your next adventure, or just that person navigating Zoom with coffee and optimism, let’s admit it: only real people build real trust. Only real people can laugh at dad jokes on screen or at least groan politely.
Many years ago I gave a particularly challenging board presentation to a skeptical private equity investor. My PowerPoint was flawless, the market benchmarks, past performance, and differentiators were pristine, but the room felt like a morgue. Then their managing partner’s phone buzzed with a photo from his daughter’s first day of college. I mentioned my own daughter was starting her sophomore year, struggling with getting reacclimated to the pace of school after a summer devoted to working at a kid’s camp. Suddenly, we weren’t acquaintances across a boardroom table. We were two parents sharing the anxiety of watching our kids spread their wings. The deal closed two weeks later, but the relationship started in that brief, unguarded moment.
The Science: Bonding Isn’t Just Nostalgia
Let’s toss out the idea that trust is corporate fluff, left behind with those cold sandwiches at teambuilding retreats. Science says our brains are hardwired for connection. Oxytocin, the “warm-and-fuzzy” hormone, floods when we truly engage with eye contact, empathy, a sly joke, or even a vulnerable story about locking keys in the car on a family vacation and having to call for help. Research backs it up: teams with real trust report higher creativity, lower stress, and a welcome break from Monday morning dread. Both neuroscience and psychology warn that loneliness is a business risk no tech upgrade can cure.
COVID, Remote Work, and Pajama Productivity
Remember COVID? Suddenly, the office was your kitchen, and snack breaks featured your pet or family members focused on crossword puzzles instead of passing by suspicious stale pastries in the breakroom. Sure, we proved productivity could survive in pajamas, but something was missing. Remote work came with spikes in anxiety, Zoom fatigue, and a longing for actual hallway conversations. Harvard found more than half of us felt anxious or isolated during the remote era, and 60% said work relationships suffered. Turns out, even introverts miss those rote “how was your weekend?” chats… and yes, even the mysterious breakroom pastries.
I’ll never forget our first virtual happy hour in June 2020. Nothing elaborate, just a simple “let’s catch up over drinks” Zoom call. But the magic happened when someone’s kid wandered into frame wearing a superhero cape, and suddenly half the team was sharing stories about their kids’ quarantine creativity. We stayed online far longer than planned, not because we had anything urgent to discuss, but because we remembered we were people first, colleagues second.
Technology: The Best Wingman, Not the Soulmate
Let’s be honest: I love technology. AI can recommend a hundred movies that fit my preferences before I’ve even had time to fire up Netflix. While I like my smart fridge, we’d have a slightly closer relationship if it could remind me where I left my coffee cup. But bots don’t notice when a colleague’s laugh is just a little off at dinner, or when a loved one’s “I’m okay” actually means “I need a hug.” Emotional micro-moments. Those are irreplaceable.
In a search for a CFO at a fast-growing tech company backed by investors, our platform flagged a candidate whose bona fides looked perfect for the client: Ivy League MBA, Big Four experience, all the right keywords. But during the final deep-dive interview, my colleague noticed something an algorithm wouldn’t capture: every time she talked about her team’s successes, her whole demeanor changed. She sat straighter, her voice got animated, and she used “we” instead of “I.” That’s when we knew she wasn’t just technically qualified; she was a leader who genuinely cared about developing others. She got the job, and fourteen months later, her team’s retention rate is 15% higher than industry average.
Tech is a tool meant to help us show up, not replace authenticity. Harvard researchers say meaningful relationships can be built virtually with genuine curiosity, vulnerability, and a dash of honesty. I’ve forged partnerships via LinkedIn comments and Zoom catchups that started as digital and ended as real-world camaraderie.
Practical Ways to Build and Keep Real Relationships
Here’s the cheat sheet, sharpened by board experience and blessed by research:
- Practice Active Listening: Put down the phone and actually hear people. Even a quick “Did that new plant survive?” in a virtual meeting makes connection memorable. I once closed a major client relationship because I remembered their daughter was applying to veterinary school and followed up six months later to ask how she was doing. That kind of attention to personal details builds loyalty you can’t buy.
- Be Relentlessly Reliable: If I promise a Tuesday call, it’s happening, even from an airport, volleyball game, or a birthday party with a bouncy house in the background. I once dialed into a critical board call from the sideline of my son’s rugby tournament, muted except when I needed to weigh in on a vote. My fellow board members joked about hearing the referee’s whistle and a lot of screaming in the background for years after, but they also remember that I showed up when it mattered.
- Get Curious, Ask Great Questions: Go beyond superficial weather talk. Ask about someone’s career path or the plot twist in their favorite book. During a particularly tense contract negotiation, I noticed the client had a first-edition Hemingway on his shelf. We spent ten minutes discussing “The Sun Also Rises,” which broke the ice and led to a more collaborative tone for the rest of the meeting.
- Share Appropriate Vulnerabilities: Be honest about project disasters and lessons learned. Authenticity (and a little humor) goes much farther than perfection. I once started a client presentation by confessing I’d accidentally sent the wrong version of our proposal the night before, the one with my personal notes still visible, including “this sounds like corporate BS” in the margins. Instead of being mortified, the client laughed and said they appreciated the honesty. We’ve been working together for close to a decade now.
- Regularly Reach Out: A “just checking in” text or unscheduled call often sparks better ideas and relationships than formal meetings. I keep a monthly reminder to text five people in my network with no agenda just a quick “saw this article and thought of you” or “hope the new role is treating you well.” Last year, one of those random check-ins led to a major search engagement when the recipient mentioned they sat on the board of a company that was looking for a new CEO.
- Give Real, Specific Recognition: “Nice job” is okay. “I noticed how you handled that crisis with calm humor. It helped us regain alignment with the client and kept everyone on track.” is unforgettable. After watching a junior associate deftly handle a difficult client call many years ago, I didn’t just say “well done.” I wrote her a note detailing exactly what she did right and copied her direct boss. Two promotions later, she still brings it up with other colleagues and mentees when projects get tough.
- Set Clear Expectations: Clarity is your armor. Who’s bringing snacks? Who owns the deliverable? I learned this the hard way during a multi-practice engagement where nobody clarified who was handling due diligence coordination. Three weeks of confused emails and duplicated work later, we instituted a simple rule: every meeting ends with a clear summary of who’s doing what by when.
- Tune Into Emotions: If someone seems “off,” don’t ignore or avoid it. Proactive empathy prevents a month’s worth of misunderstandings. I once noticed a usually chatty fellow board member being unusually quiet during a quarterly meeting. A quick inquiry during our break revealed he was dealing with a family health crisis. I asked our board chair to reschedule his committee presentation, and he never forgot that small act of consideration.
- Find Shared Interests: Whether it’s a mutual love of historical fiction, bad ’80s music, or premium wine, mutual ground breaks the ice and seals the deal. I discovered a potential client was a fellow bourbon enthusiast when I noticed a bottle of Pappy Van Winkle 20 in his office background during a Zoom call. We ended up scheduling our next meeting at a whiskey bar, closed a deal over neat pours of Weller 12 (close enough), and now exchange recommendations for rare bottle finds.
- Create Community (Physical or Virtual): Organize online “coffee breaks” or in-person meetups (happy hour, dinner, etc.). Teams that laugh together stay, and thrive, together. Our firm hosts weekly lunches where teams from every office gather physically and virtually to connect and catch up on what’s happening both at work and at home. What started as a way to stay connected became our best source of innovative ideas and cross-team collaboration.
- Lead by Example, Consistency Rules: The quickest route to trust? Show up, admit mistakes, stick to your word. Plus, self-deprecating jokes always play well in Slack. A close friend recently shared how he accidentally sent a voice clip to his entire senior team with a message meant for his executive assistant, who was worried about whether he’d make his flight on time. Well, it was more like a two-minute rant about being stuck in airport security behind a group of people who apparently packed their entire kitchen pantry in carry-on suitcases. Instead of pretending it didn’t happen, he leaned into it and provided some great comic relief. Now “airport security energy” has become shorthand for patience in frustrating situations for his team, and people feel more comfortable being human at work.
Advice for Remote and Hybrid Teams
The watercooler may be virtual, but the connection is real if you:
- Share your working hours and preferred ways to connect, so folks know when and how to reach you.
- Use video for real conversations. Yes, the camera adds a few pounds but multiplies empathy.
- Set up virtual hallways or chat threads for non-business banter. One of our clients created a #random-musings Teams channel that’s become their digital coffee shop. People share everything from last minute weekend adventures to their dog’s latest antics.
- Schedule regular 1 on 1’s, not just when problems crop up. In the early days of growing NorthWind, I would block 30 minutes monthly with every single team member just to chat: no agenda, no performance reviews, just connection. As we scaled, those conversations prevented more problems than any formal process or review ever could.
Why All This Still Matters
Businesses that invest in real connection outperform, period. Employees stick longer, clients refer more work, candidate ghosting fades. The “magic moments” that fuel resilience aren’t stored in your inbox. They’re found in candid chats, shared experience, and mutual laughter.
During the 2008 financial crisis, I watched businesses with strong relationship cultures weather the storm while others with purely transactional approaches crumbled. The companies that survived were the ones where people genuinely cared about each other, not just the bottom line. When layoffs came, teams rallied around each other. When clients tightened budgets, they stuck with partners they trusted. When candidates had multiple offers, they chose the company where they felt valued as humans, not just resources.
As AI handles the routine, trust and empathy remain power skills. Whether guiding a company, launching an investment fund, or dealing with the rigamarole of business travel, people go the extra mile for those they trust and the ones brave enough to share a joke or bring the snacks.
The Final Word
Embrace bots and ride the current AI wave, but don’t outsource your soul. Double down on laughter, empathy, and intentional relationship building. Your fortune, and your organization’s future, depend on being someone worth knowing online, offline, and in the moments that resist automation. If in doubt, bring the snacks. Maybe a bottle of the good stuff, too.
So, go forth, make a connection, and remember, algorithms might predict customer behavior and automation might streamline workflows, but nobody ever closed a million-dollar deal with a chatbot. Real, trustworthy relationships? They get you through everything.