What 15,000 Microsoft people taught me about storytelling

Here are seven essential truths about business storytelling that I’ve learned in helping more than 15,000 Microsoft employees become better storytellers. The last one is the key to them all.

For the better part of three years, I’ve been obsessed with helping business people become better storytellers. It began as a passion project in 2015 while I was an employee at Microsoft, and it grew into such a monster that I struck out on my own this past January. (You can read about that here).

Now that I’m a consultant, I get to focus full-time on the pure art and science of the challenge – digging deep into research and working creatively with high-performance clients who demand hard results. It is rewarding work, as people consistently report improvements in both their business results and job satisfaction. Plus, I’ve been witness to some of the most jaw-dropping stories I’ve ever heard.

I sometimes spend days or weeks working with a team. I also do a fair bit of keynoting, which is a fun challenge. The topic is so substantial, encompassing so many aspects of a person’s working life, that it’s never easy to cram the right things into a one-hour block. Yet, those bite-sized presentations are worth it. Distillation is the heart of good communication, after all.

So, in that spirit, I’d like to share seven essential storytelling truths that I have learned in my work with professionals at Microsoft, and beyond.

Your thing is not a story

The first storytelling mistake that many people make is to assume that the thing that’s central to their job – the thing they’re getting paid to build or sell or deliver or fix – is a story. “We’ve gotta tell the story about the new Widgetator!” Wrong!

Products aren’t stories. Neither are cool features, services, analytics reports, messaging frameworks, or value propositions. These are all, of course, more than a little bit important. But they are all lifeless, inanimate things, no matter how many stock-photo faces of attractive people we slap onto them.

A story is more than a mere description. A story concerns itself with human experience. It lies at the intersection of that thing you care about and a human life that it impacts. Your job is to understand that intersection. Where and how do people engage with your product? What happens if they don’t? Critically, how do people transform – for better or for worse – by virtue of the fact that your thing is either added to their lives or does not yet exist to help them?

These questions take you directly to the landscape of meaning in people’s lives. This is not the place of metrics and measures. It’s the inner world of dreams and dreads, of hopes and fears. It is what people live for. It’s what their loved ones say about them after they die.

A simple question to ask, which will put you into the right frame of mind in the face of any vexing storytelling challenge, is this: “What is the human factor?” Think about this until you start to see faces and places, and go from there.  

Nobody actually cares about you

Another common mistake is to believe that people want to hear about you. They don’t, at least not at first. What they want to hear about is them – or, more specifically, about something that matters in a meaningful way to their personal wants and needs.

This is not to say that you shouldn’t talk about your experiences. You should. The trick is to find the ones that best resonate with the people across the table from you, ideally in a way that naturally leads to where you want to take them.

If, for example, you’re talking to an executive who is obsessed with cost-cutting, that story of how you learned the hard way about the value of a dollar might just do the trick. More than making you relatable, it makes you credible, as you dive into a discussion about finances or some other related topic.

The key here is that you must think about the audience first. What do they need? What got them out of bed this morning? What do they love, hate, dream of or worry about in the dark of the night? Start here; your own personal fabulousness can wait.

Stories connect people

Storytelling, above all, grabs the attention of another human being. It’s hard to imagine a a better bit of magic.

Stand before a typical room full of busy professionals, and you’ll find yourself competing with screens. You’ll see as many lids of open laptops as you will human faces focused on you. Gone are days when propriety demanded that people look like they’re paying attention to the speaker.

However, when you tell a story in a compelling way, people put down their screens. And they’ll do more than listen. They’ll look at your face. Their senses will be stirred. They’ll feel the emotion underlying your words. They’ll care about you, and what happens to you.

When the human mind gauges that a story is afoot, it holds distraction at bay to take in the pleasure or the trouble of a human experience being shared. Brains and bodies change, and time and space morph in ways that leave people wanting more. This opens the opportunity for engagement and influence.

Stories happen, with or without you

Many of my clients are leaders struggling with constituencies who remain annoyingly wedded to beliefs or assumptions that don’t exactly map to the three pillars of the team mission statement. They wonder why splashy events, colorful posters, and brute-force repetition fail to carry the day. Their problem is often not the story they’re telling, but rather the lack of any story at all.

PR professionals and savvy politicians know that “there’s no such thing as no comment” in response to scandal or disaster. Saying nothing invites people to assume the worst – and, too often, they will. A parallel hazard exists for anyone who leads a team, represents an organization, or deals with customers or stakeholders.

If you have responsibility for a situation involving disruption or transformation, and you don’t tell a story up front – rich with human motives and action – people will make up their own. And it won’t be good for you.

The human mind is wired for story in a profoundly improbable way. Character-driven narratives help us process the lessons and learnings of life. It’s an evolutionary benefit. But it’s a flaw as well. Because when we’re faced with chaos or problems for which we lack complete explanations, we invent narratives to make sense of things – and, likely as not, these narratives are completely wrong.

If you show a video of geometric shapes moving randomly around a screen (as researchers Fritz Heider and Marianne Simmel famously did a few decades back), most people will tell you they see a story of romance, bullying, betrayal, or escape. This is both fun and frightening. For anyone looking to lead other people in a time of change, the message is clear: It’s not optional to offer a narrative about what’s going on. The people you care about most are already doing it on their own – unless and until you give them something more compelling.

Telling a story means creating an experience

Think of any good story you’ve heard – a can’t-miss joke, a favorite movie, the book your parents used to read to you at night. They all share one amazing thing; they transport you to a different time and place. You can often visualize it vividly months or even years after the fact. Your job as a storyteller – even if only for a moment and even in the driest of circumstances – is to do the same for your audience.

Storytelling is the original virtual reality technology. Tell a story well, and you stick all sorts of information, both important and trivial, into the minds of your listeners. This is because our brains are optimized to imagine and recreate experiences of other people so that, functionally, we share their challenges and benefit from their lessons. We learn from another person’s trail or triumph without having to incur the actual costs.

To make your story an experience: 1) you need people – at least one character (who might just be you) to whom the audience can relate, 2) you need a place – a specific, physical location, at a specific point in time, and 3) you need a problem – some nettlesome challenge that’s disrupting somebody’s life, which gets resolved one way or another.

Leave out just one of these three factors, and you don’t have a story. Bring them together, and you can transport people out of their plastic chairs and boring conference rooms and into scenarios they’ll take pleasure in remembering.  

What’s obvious to you is not obvious to me

As a storyteller, you are in the experience-generation business. As such, you need to be explicit in naming and labeling every critical detail. A dash of physicality is essential. People love distinctive names and labels. They’re hungry for words that paint pictures, that convey action, and that bring the blemishes and beauty of an interesting character to life. It’s one thing to say, “The room smelled really, bad - just terrible!” It’s quite another to say, “The room smelled like stale beer and body odor.” Same number of syllables. Totally different impact.

Odds are, you’re really bad at this.

Not because you don’t care, but because these kinds of details are so patently obvious to you, so clearly visible in your mind’s eye, that you assume that everyone else sees them too. And so you don’t mention them. This cognitive bias, dubbed the “Curse of Knowledge” by Stanford professor Elizabeth Newton, creates a massive blind spot in our storytelling. We can’t imagine that the other person does not know what we know or see what we see. The ironic result is that they often never will, and stories are robbed of their power.

This is easily the number one issue I address in coaching. And it’s so easy to fix. Just remember to include simple descriptions, labels, names, and distinguishing features. In my workshops, I force people to write down all these salient details, and hold the list before them as they deliver their stories. Typically, I have to ask for such critical details as, “What was her name?,” “What year was it?,” or “Where did this happen?” People are often surprised to realize that they hadn’t actually voiced these essential details, which sit literally right under their noses.

It’s rare that anyone doesn’t fail to include at least one or two such juicy details. But this blind spot fades with awareness. And soon, even the driest of narratives pulses to life, with sometimes just the smallest bits of distinctive color and unique personality carefully mixed in.

There’s one secret at the heart of it all

The point of storytelling in business is to win people over. You want to guide someone – a stranger, a skeptic, a partner in love or war – to a new way of thinking, behaving, or seeing things. This bit of magic can only happen by first inhabiting other people’s worlds.

Until you find a way to make your interests relevant to someone who knows or thinks little about you, then the story you tell risks becoming an extended exercise in vanity. Sadly, the world is overflowing with these. The key to avoiding this and unlocking the powerful dynamics of story is to master empathy.

Empathy is the constant thread, woven intrinsically across each of the insights I’ve shared in this article. Empathy is the ability to step out of your own skin and imagine, in a deep and non-judgmental way, what it feels like and means to live a life that’s quite different from your own.

To build empathy, I walk my clients through a detailed process of identifying the demographics and psychographics of a target audience. I ask them to define a specific person – either an actual person that they well know or a prototype, an amalgam they create – and I tell them to give that person a name, an identity, and a history. Then I ask them to create a long list of salient details, everything from the person’s age and salary to his or her innermost dreams and worries.

Interestingly, people are frequently distressed by how little they actually know about the lives, values, and sentiments of the people in their audiences, some of whom they see or deal with on a constant basis. The good news is that the folks in your audience are usually willing, typically excited, to tell you all about the things that matter to them. You need only ask, and make time to listen. Odds are, they’ll be delighted to share it all. And, inevitably, it will come in the form of terrific stories.

Empathy, practiced well and often, opens new worlds of understanding and possibility. Empathy is at the hopeful heart of much of the economic transformation sweeping the globe. The lack of empathy is at the dark heart of too many social and political ills.

My deep belief, proven through hundreds of consults and workshops, is that storytelling is a function of empathy – and much, much more.