Making Authentic Connections

Hardly a day passes when I don’t talk with someone trying to solve a gnarly issue. I listen, gently probe and try to understand what they think are the issues. As I get to the source of the problem — usually, the issue underneath the issue, the root cause — I wonder how I might help.

I never tell them what to do; no one likes that. I usually relate a story of someone “just like them” and what they discovered and did. Or I connect them to someone they would benefit from knowing and who might advance the cause better than me.

Some recent conversations come to mind:

  • A C-suite leader at a major firm shared her challenges. It became evident that she needed to meet the CEO of a top digital agency I know. I connected them. Both said it was a great fit. They are now working on pricing.
  • A tech/ops CEO texted me with a question, and I connected him to the editor of an industry publication. Each had what the other needed.
  • Recently, I coached an executive on the rise on how to be effective within a new organization by thoughtfully influencing bosses, reports, colleagues, and competitors within and dealing with the inherent political BS.

My definition of authentic connection

Some describe what I do as networking, but it’s way beyond that. In my observation, most people who “network” (air quotes) show their hand. They’re evident in their self-interest and quick to ask for a lead, referral or sale. Please don’t do that.

Connecting authentically means understanding where someone is stuck, learning what matters to them, and creating a richer connection and deeper relationship. As a result, you develop something of real value — a relationship built on mutual commitment and trust — one conversation at a time.

I recently recorded a podcast with a colleague. Beforehand, he admitted he wasn’t comfortable “doing these” and said, “I’m only on this podcast because I trust you.”

Connecting with others is an exercise in earning trust. I never abuse that trust. The connections I create often have little immediate benefit to me, financial or otherwise. I revel in conversations and getting to know people; I discover something new every day.

How’d I get here?

I am an inveterate connector. It’s in my bones. I inherited this from my mother — my father described her as “vivacious.” She would walk into a room and become someone’s, or everyone’s, new best friend. She asked questions, listened closely and was genuinely interested:

  • Where are you from? Oh, do you know so-and-so?
  • Tell me about your family. How are the kids? What are they doing?

These weren’t idle questions. She was always trying to find common ground. Quick to smile and laugh, she was delighted by other people’s stories. What some would call “small talk” flowered into people telling her their life stories.

Beginner tips on listening (or the practice of listening)

I’m describing a practice, an ability that can be learned and honed over time.


  • Give your full attention to what people are saying.
  • Refrain from distracting yourself by formulating your next brilliant thought. Shut up. Listen.
  • No one-upmanship. Do not compete as to who has the best story.
  • Ask questions that reveal the layers of others’ fears, joys, concerns, history, prejudices and priorities.
  • Take your time. You don’t need to know everything all at once.

As I wrote in another “Reflection,” it’s about being “more interested than interesting.” It takes practice; it’s never one-and-done. It also takes being willing to be vulnerable. I find this comes more naturally to women than to men. Don’t be afraid: tell someone about yourself. Share. Be authentic. It’s the cornerstone of trust.

Building trust in remote work

Some say the shift to virtual meetings limits our ability to create authentic connections. It may, particularly for people without many former coworkers and colleagues to lean on. However, I can get to know someone as well on video chats as I did making the rounds of offices and conferences.

Hosting my podcast, WealthTech on Deck, has helped. It’s given me more opportunity than ever to learn what makes people tick. The time before and after the microphone goes live is invaluable — two people preparing to reveal themselves. As the red light goes on, my questions are designed to help listeners – and me – to really get to know the guest:

  • What’s your role? What are you excited about now?
  • How’d you get started? Tell me about your career journey.
  • What do you do outside of work that you are passionate about that people might find interesting or surprising?

I will often prompt them with nothing more than, “Really, that’s interesting.” And I mean it. Then, they reveal more and more. A C-suite friend once said, “I can’t believe they tell you all that stuff.”

A compass to becoming a ‘connector’

I learned great lessons from a friend who went to a dude ranch for a family vacation. When he praised the owners on what “great conversationalists” their children were, they said, “We don’t teach them to talk. We teach them to listen.”

Their lesson? Use these four points for launching a conversation:

  • Location — Where are you from? Is that where you’re from originally? How did you end up here?
  • Vocation — What do you do? How did you get into that? What do you enjoy about your work?
  • Relation — Tell me about your family. How’d you meet your spouse? How old are your kids/grandkids? What are they up to?
  • Recreation — What do you do for fun? Hobbies? Vacation plans? Where was your last trip?

When you genuinely listen, you remember what others say. Bringing up something they said in a future conversation confirms that you heard them. What they said mattered. By listening, you bring them alive, earn their trust and make a difference for them and you.

Related: Overcoming Challenges in Organic Growth within Wealth Management – Insights from Steve Gresham