The urge to prove your worth to someone "above" you is the barrier. Picture them as an ordinary person and ask a human question.
The idea
We build people up in our heads until they stop being human. The investor becomes a gatekeeper, the CEO a mythical figure. Then we perform: get formal, drop credentials, rehearse impressive lines. That effort to prove we belong is the wall, and it blocks the very connection we came for. People do business with people they know, like and trust, and you can't build any of that from behind a wall. Marcus Aurelius pointed out that Alexander the Great was buried in the same earth as his slaves. Or, as the toddler book puts it, everybody poops.
How to do it
Notice the impulse to prove yourself: the credential, the big client name, the switch into formal mode. That's the wall going up.
Spend 30 seconds humanizing them. Picture them grocery shopping, burning toast, scrolling on the couch.
Drop one level of formality.
Ask one question that has nothing to do with business.
Share something real about yourself, even if it isn't impressive.
Example
I still remember the sweat. First-time founder, about to meet one of the best-known VCs on Sand Hill Road, pacing like I was about to meet the king. My mentor stopped me: "You know what that person is probably thinking about right now? What they're having for lunch." Years later I had coffee with a Fortune 500 CEO. We spent way too long trading travel destinations and commiserating about hauling our daughters to dance practice. That led to more conversations. Real ones.
Connect With the Whole Human: Treat prospects, colleagues and friends the same way, with genuine interest in the person behind the title and the professional facade.
The No-Ego Dinner: Keep the guest list secret and hold off on professional introductions until the next morning, so people meet the person instead of the title.
The 15% Rule: Share about 15% more than feels comfortable to crack the professional facade. People are waiting for someone else to go deeper first.
Show You Like Them: Lead with liking ("you matter") over utility ("you're useful to me"); use their name, ask about what they care about, and listen.