Have better conversations about content design

Nick DiLallo
Nick DiLallo
April 9, 2024

The best way to move design projects forward? Talking.

Honest, meaningful conversations are more effective than endless async Figma comments or lengthy Slack back-and-forths. Conversations let the entire design team dig into details together and share different perspectives. They’re a forum for discussion and agreement.

But conversations can also be frustrating. Lots of opinions. Too many voices. Endless swirl. Without intentionality and care, conversations can spin out or become unproductive.

I’ve been lucky to help launch complicated, content-heavy products that have billions of users—the kind of products that require ongoing alignment between writers, designers, engineers, and product managers. One reason those projects were successful? The way we structured conversations during the design process to drive consensus and decision-making. These are the techniques that I’ve found most helpful.

Getting the right people together

Involve stakeholders from the beginning

This is the first step for any conversation. To keep projects moving forward, you’ll need to get the key people together. Conversations without decision-makers don’t lead anywhere. You’ll be left wondering what’s approved or what happens next. In my experience, having the same meeting multiple times isn’t the answer. It causes more frustration and swirl. If you need to reschedule, reschedule.

Be strategic about group size

Exploring something new and not ready for the whole team yet? Sometimes a small group is the right move. Maybe there’s another writer, product manager, or engineer you can connect with first. Other times, it’s better to gather with the bigger group. The whole team should be at the project kickoff, as well as at key milestones, like the readout from the first round of user research.

Invite specific people and ask for their thoughts

Many of the most brilliant and insightful people I know tend to keep quiet. But when they’re in the conversation and I ask for their feedback, they always say something helpful that unlocks the project. Give everyone a chance to weigh in. If there’s someone whose opinion you want, go ahead and ask directly. 

Of course, be respectful. Don’t make anyone uncomfortable. It can be hard to share an opinion—especially a dissenting or unpopular one—in a big meeting with senior leaders. Sometimes I’ll privately ask people afterward if they have anything they want to add that we didn’t have time for. And if they don’t, that’s completely okay.

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Deciding what to talk about

Get aligned on the big picture

Conversations about content design are often proxy conversations about strategy and business needs. The first few discussions for any project should be about challenges and opportunities:

  • What are we fixing? 
  • Where are users confused? 
  • What are the engineering constraints? 
  • Why are we even doing this thing in the first place?

Discuss ideas without looking at designs

It’s okay if conversations are just that—conversations. No decks, no interfaces, nobody sharing their screen and showing work. Just people talking and getting on the same page. It’s tempting to start designing solutions and creating content frameworks early on. Try holding off until you’ve talked everything through as a team. Once you’re all aligned, you can get to work.

Explain the business impact

Once you’re looking at designs, ladder content decisions to business goals, revenue, or strategy. Explain how you solve real user needs and keep your company operating more efficiently. It’s often as simple as adding another sentence or two to your explanation of any interface. Instead of simply saying, “This UI shows the seat number,” add the thinking behind it: “Research shows that users want to know the seat number. It’s also our most common customer support question.”

Give every conversation a purpose

You can’t talk about everything in every meeting. Choose a specific part of the content design to discuss. It can be something big, like a new content framework or an evolved brand voice. But it can also be something small, like a single button or the best way to format currency. The idea is to keep conversations focused on where you are in the project—and where you need to align. 

If you’re leading the conversation, set expectations

Let everyone know where you’re all headed. Add a few bullet points or give a quick summary at the start of the conversation. If there’s a key decision you need to align on, make that clear. I’ve also found it helpful to start by explaining what you won’t be covering. A clear setup keeps the conversation on track and lets people know what’s coming. Nobody needs a plot twist in a design review.

Ask for the feedback you want

Are you looking for reactions to specific words or larger themes? Is now the time to talk about all the edge cases, or are you getting aligned on the core user experience? Explain what will be most helpful to get things unblocked. 

Moving the design team forward

Show content design in the interface

It’s impossible to evaluate design in a spreadsheet. Even simple interfaces seem impenetrable when they’re put into rows and columns. For a better conversation, show the content design as it will appear in the app or website. Doing so will help everyone understand the bigger context and full user flow.

Looking at one file means conversations about content design can also include thoughts about the brand and product design. I’ve found that feedback about writing can sometimes be solved by changing the interface:

  • Does the headline feel too formal? It could be the traditional serif typeface. 
  • Does phrasing seem weird? Maybe it’s the odd button placement.
  • Is that text hard to read? The type size and line height might need adjusting.

Other deliverables and formats might come later as you get closer to engineering handoff or need to prepare for translation. Stick to a single, unified presentation file when you can.

Explain trade-offs

There’s never one single solution for an interface. For a more pointed conversation, it can be helpful to bring a few options. Explain what each of them does well and what each is missing.  It’s important to frame this as a conversation about pros and cons. For example:

  • Short sentences are easier to read. They also include less information. 
  • Funny writing can make an app feel fun. But humor is harder to translate. 
  • More info can create a personalized experience. Gathering it can feel invasive.

Great content design means deciding what to keep and why. Talking about trade-offs helps the team make more thoughtful content design decisions.

Have a point of view

Even better than having multiple options is having one you like the most. Trust your instincts and abilities. Write exactly what you’d want to see in the product. Show it to the team and explain what you like about it.

Favoring just one option can feel counterintuitive. For a long time, I thought being flexible and open-minded was the way to present work—share a few ideas and let the other people choose. But that approach makes conversations more ponderous, like picking a restaurant with a few friends who all like everything. Flexibility is good, but we’ll eat much faster if someone says they’re craving sushi.

Talk about something else

Many of the most helpful work conversations I’ve ever had haven’t been about work at all. They’ve been about family, what we’re reading, or what’s happening in our lives. Sure, we’ll meander back to design talk at some point, but only when it feels right.

A formal design review with senior leadership is not the place to get off-topic. But do what feels right in a more casual setting among trusted team members. Give a conversation space to wander and explore. Come back to talking about content design when it feels right. Sometimes, if you want to move forward, it helps to change the subject.

Putting it all together

The way we work is always changing. Today, distributed design teams collaborate across locations—and across time zones. There are more ways than ever to communicate. There are countless options for project management software. But there’s still no replacing a smart, thoughtful conversation.

So the next time you feel like you’re spinning out, try talking things through. Instead of avoiding tough conversations, have more of them. Get the right people together, talk about what’s important, listen to each other, and make decisions as a team. It’s the secret to great design.

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Nick DiLallo

Nick DiLallo is a writer based in Brooklyn. He specializes in helping companies integrate writing with design to launch great brands and digital products. His approach blends copywriting with UX writing, and he’s written extensively about the way good writing can help make the internet better for everyone. In his career, he’s worked at top digital agencies like Huge and Work & Co. And he’s worked with some of the world’s most admired companies, including Apple, Etsy, IKEA, the MTA, and Planned Parenthood.

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