I’m Not a Real Conversation, but I Play One on the Internet

Writing in a conversational way

This blog post is part of the Trailhead content creator series. Follow The Trailblazer publication to read the entire series.

I’ve been helping my team teach a class for Salesforce employees who write for Trailhead. First-time Trailhead writers are enthusiastic but sometimes a little anxious, so we try to make the class fun. We tell stories and crack jokes, and we talk about how to use storytelling and humor to engage Trailblazers and help them relate to what they’re learning.

At some point during the class, someone raises a hand. “What if I’m not funny?” Others nod and look worried. “It’s hard to think up jokes.”

“Yeah,” someone else says. “And what if I don’t have any good story ideas?”

That’s OK, we tell them. Jokes aren’t required. You don’t have to be funny. And you don’t have to tell stories, either. Just write in a conversational way.

We give some concrete pointers: Talk directly to Trailblazers, we say. Connect by saying you and we. Be informal and brief. Use contractions. Pick everyday words (shows, for example) instead of jargon (provides visibility into) or big dictionary terms (illuminates).

Just be conversational, we say. You’ll be fine.

Many writers in the class seem relieved. But a few look like we’ve reassured them that their kitten isn’t going to grow up to be a strange and terrifying liger after all. It’s just going to be a regular — but no less terrifying — lion.

In other words, they still have concerns. Because maybe writing in a conversational way isn’t always so easy.

Think about it. Real-life, face-to-face conversations can be hard. If they were effortless, we wouldn’t need etiquette books. You’d never find yourself with a group of strangers answering get-to-know-you questions like “What’s your superpower?”

And Trailhead isn’t face-to-face. It’s online. When you write, you can’t see readers’ reactions. You can’t hear them chuckle or gasp. You don’t know if they’re late for the bus or if they’re holding a sleeping baby on their lap.

When you want to strike a conversational tone and you’re writing instead of actually conversing, you’re at a disadvantage.

Still, there are things good conversationalists do that you as a writer can do, too. When you do those things, you’re writing in a conversational way.

Let’s review them.

Good conversationalists take stock of the situation.

When you meet a good conversationalist at the dentist, and he’s cleaning your teeth, he doesn’t ask you open-ended questions about your hobbies or your siblings. He asks you if you’re comfortable or if you’d like to rinse, and he leaves it at that.

When you bump into him later at a dinner party, that’s when he asks you for all the details about your new electric guitar and your sister’s private detective agency.

You go to the dentist’s office and the dinner party for different reasons. A good conversationalist knows this and adjusts the conversation accordingly.

Writers also take stock of the situation, but instead of meeting readers in different physical places, they connect through different types of content.

For example, at Salesforce we’ve learned that people who want to accomplish a task will search for a help topic or consult an implementation guide. They want to do the job and get back to work. There’s no time for stories or jokes. They’re not in the mood for conversation.

When they want to learn something new or practice a skill, they come to Trailhead. They have more time available — usually 20 minutes or more. So we tailor the writing to make the time enjoyable and encouraging.

We might tell stories or make a few jokes. Sometimes it’s nothing fancier than using a friendly tone.

Good conversationalists pay attention to who they’re talking to.

When a good conversationalist meets the new family next door, she might mention where the nearest parks are and what day of the week the trash is collected.

She doesn’t volunteer this information to just anyone. Longtime residents already know, and people passing through the neighborhood on their way to work don’t care.

Writers do something similar. They write with their audience in mind.

Trailhead has content for different audiences: admins, developers, and business users. Each audience comes to Trailhead to learn different things.

Admins want to know how to set up and maintain their org and help their users be productive. Developers want to understand the platform and tools they can use to create great apps. Business users want to work smart with technology, customers, and colleagues.

In each of these groups, some people are just starting out, while others have advanced skills.

In face-to-face conversations, we sometimes misjudge how much the people we’re talking to know. Either we say too much (maybe that family moved from down the street, so they already have the park and trash situations under control) or not enough (it’s a family from outer space, and they have no idea what “parks” and “trash” are).

It’s even easier for writers to get it wrong. How can you figure out what your readers know when they’re not standing right in front of you?

In class we recommend that writers do two things: meet and talk to people in their target audience, and practice thinking with a beginner’s mind. Experts can forget what it’s like to be a beginner. Clearing your mind — working to unknow all the things you know, just for a little while — can help writers see their topic with fresh eyes.

The situation and audience change, but good conversationalists stay themselves.

Good conversationalists vary what they say and how they say it, depending on the situation and the audience. They themselves don’t vary. What kind of person they are, what they value — these are constants.

In writing, we say that what changes is the tone. What doesn’t change is the voice.

Even though Trailhead isn’t a person, it does have a voice. Whether a module is for admins or devs, advanced learners or beginners, Trailhead’s voice is casual, positive, and inclusive. It’s respectful. Sometimes it’s playful or a little silly.

As a Trailhead editor and teacher, I’m really proud of what our writers accomplish. They make Trailhead sound like a person, someone you’d want to have a conversation with. That’s their superpower.

Maybe it’s your superpower too.

Interested in learning more? Come to our session at Dreamforce and learn how to write the Trailhead way.

How to Write the Trailhead Way

• Tuesday, October 4; 2:30–2:50pm PT
• Moscone West, Admin Meadow Theater

Can’t make it in-person? The session won’t be streamed, but we’ll be posting the materials afterward on the Success Community in the Trailhead group.