What should I even say!?
I’m just a nobody.
There I was… talking with an entrepreneur who had seemingly achieved everything possible.
Despite my fears, we ended up having a fun conversation.
How did I do it?
Years of experience talking with people more successful than me 🙂
Throughout my career, I’ve worked with some of the most accomplished entrepreneurs, including the first marketing director at Paypal. I’ve also built relationships with many other smart, driven people.
In this article, I will share how you can talk with people who are more successful than you — all without having to fake anything.
Accept that you will feel inferior
Talking with someone more successful can trigger feelings of inferiority. That’s completely normal! Our society has conditioned us to idolize and worship successful people, after all.
Rather than judging yourself for what you feel, try doing this instead:
- Tell yourself that “It’s OK that I’m feeling this way”
- Ask yourself this question: “How can I connect with him/her despite my difficult feelings?”
And if you worry about their judgment, acknowledge the thought and emotion for a moment. Then bring the attention back to the conversation.
Accepting how you feel — and aligning with your values despite the emotion — is key to having a healthier relationship with your feelings. Forget about the whole “fake it till you make it”!
(This approach is based on Acceptance and Commitment Therapy, which I’m a strong advocate for)
Value your own intelligence and wisdom
No matter how unsuccessful you feel, your ideas and insights are valuable.
If you told me this years ago, I’d have laughed in disbelief.
But here’s what I realized after years of talking with people more successful than me…
I always have something unique to offer them. Whether it’s a new idea, a little-known insight, or a relevant experience.
You don’t have to believe what I say — just consider the possibility that the more successful person will be interested in what you have to say.
Even if it’s a 1% possibility, how would you communicate differently?
This is how you start becoming more socially confident, no matter who you talk to.
See them as human beings
When we see successful people only for their accomplishments — vs. for their full humanity — we end up having superficial conversations.
Why? To cope with our inferiority, we often pretend that we are just as successful and we hide our vulnerabilities.
What we forget is this:
Even the most successful people have their own problems to deal with. They also have insecurities as we all do.
To get them to open up, consider the following:
- Share a recent challenge that you’re going through
- Ask them about their challenges
- Seek out their advice (more on this later)
A long-time collaborator of mine, Michael Simmons, shared about the power of vulnerability in an HBR article:
“The mistaken assumption is that if people find out who we really are underneath, they’d remove themselves from our lives. The reality is that if we share the ups and downs of our human experience in the right way in the right context, we build deeper connections. In doing so, we can break down the roles we play (e.g., client/customer, boss/employee, fundraiser/philanthropist) and connect with each other as humans.”
Treat the conversation as a learning session
When was the last time you talked with someone more successful and learned something valuable?
Seeing the conversation as a valuable learning opportunity helps you go from feeling intimidated to feeling curious. Here are various lists of questions to spark deeper conversations with them:
- 77 career conversation starters for employees, bosses, networking professionals
- 47 dreams conversation starters for adults and kids
- 54 goals conversation starters to spark deep conversations
And here are a few of my favorite questions to get their best insights:
- “What career/life advice would you give to your younger self?”
- “If you were in my shoes, how would you solve [a specific challenge/problem]?”
- “If you were to start all over again in your career/business, what’s the #1 thing you would focus on?”
Asking for advice benefits you in multiple ways. As Harvard Business School researchers explained:
“We actually view people who seek our advice as much more competent than people who forego the opportunity to seek advice… [And because] you’re making yourself vulnerable and letting people see that you don’t know everything, you can be trusted more.”
Useful phrases to keep the conversation going
These phrases are especially helpful when you get nervous, since they are simple and will work for any conversation you have.
25 useful phrases to keep a conversation going (and avoid awkward silence)