The #1 Reason Authentic Business Storytelling Is So Difficult

“So, let’s go around the room—everybody say something about yourself so we can get to know each other.” This request is common at work and elsewhere, but it’s totally ineffective. That’s because when we are with strangers or acquaintances, it’s tough to talk about ourselves in genuine and relatable ways. Authentic business storytelling is incredibly difficult.

And the higher the stakes, the harder it is.

For instance, in job interviews, you can almost guarantee the interviewer will ask you, “so… tell me about yourself.” A job offer depends on how well you can connect with the hiring manager.

Sharing who you are makes you naturally relatable. It makes people trust you. And the better people know you, the easier it is for them to digest your message.

But even knowing the benefits, it’s still ridiculously hard.

Why Is Authentic Business Storytelling So Difficult?

It’s easy to warm up to someone who is clearly sharing from their heart. It’s even easier to sniff out the faintest whiff of inauthenticity. But when it’s your turn, it’s hard to convey your true self.

Hands down, the hardest barrier to overcome is that, quite frankly, it takes guts to talk about ourselves in ways most people will find compelling.

The story a client recently shared brought an epiphany:

When I was in first grade, I cried every day. My parents didn’t know that initially, but my teacher tried everything in the book and it didn’t work. Nothing worked. Eventually the teacher had to have a conversation with my parents. 

My dad was a very no-nonsense kind of parent. He said, “Look, you’ve just got to stop. You’ve just got to stop crying. And you have to ask yourself, ‘what is the problem and how do you solve it?’”

Eventually the crying faded away, but that became my mantra in life. Whether I’m working with my teams, working with clients, and even as this pandemic and lockdown make me feel like crying every single day, multiple times a day, this mantra has carried me through. I have asked myself, “what is the problem and how can I solve it?”

Sharing a story like this takes courage. It’s far more personal than reciting your resume— but you wouldn’t have problems telling this story to a good friend, right?

And why not? Because with your good friend, you trust this person, you have a shared history and you have expectations that give you some assurance that they’re not going to ridicule you. They’re not going to make fun of you. If anything, they’ll be empathetic. They’ll ask you questions and reciprocate. You rest on this trust, this shared history, and this expectation as you open your mouth to tell a story.

The relationship you have with the audience makes some things easier to share than others. But what if you don’t have any relationship with the audience yet?

Storytelling = Forward Thinking

Here’s what separates leaders from everyone else. All relationships have a starting point. They start because someone decided to do something, maybe subconsciously, but often consciously.

And if you start with the mindset, “Listen, I barely know you. We don’t have a shared history. We don’t have expectations. We definitely don’t know if we can trust each other, but I’m just going to talk to you and approach our communication as if we already have trust. As if we already have some shared history.”

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That’s what separates leaders from everyone else. They take the lead at the start of relationships. They lead with thinking through, “what kind of relationship do I wish to see?”

The magical thing is that humans like to reciprocate, so by taking the lead, you do often start to build this kind of trust.

Now, the downside is, not everyone reciprocates. Sometimes you might even get ridiculed. But if you consider yourself a leader, you cannot expect to be rewarded without taking some risks.

This still gives you the option of deciding whether or not this is an audience that is worth the risk. Maybe you meet someone at a cocktail hour or at some conference, and you have to decide. You can’t be exerting yourself all the time, but if you’re interviewing for your dream job, or talking with someone you wish to establish a partnership with, then by all means think about what kind of relationship you wish to lay the groundwork for.

It turns out, sharing an authentic story isn’t about emotional vulnerability at all. It’s about being forward-thinking. As a leader, you are constantly thinking ahead. Sharing your true self is part of that.

What else makes it difficult? Here are four more obstacles to authentic business storytelling and how to overcome them.

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