Gen Z is redefining online dating.

I was recently interviewing for a role at one of the big dating apps. Throughout the process, I was asked how I would write to resonate with Gen Z. I’d read up on the company and the industry and I knew it was a big concern. Gen Z is frustrated with dating apps and shifting their usage. As the biggest generation and one that includes ages 18 to 28, it’s a critical audience for dating apps. But there are big challenges to overcome.

First, there are the declining marriage and fertility rates worldwide. Then, there’s the political divide in the U.S. which has made it harder for men and women to connect. Gen Z is less worried than previous generations about being single and they’re pickier. They want to align with potential partners on a lot of issues before they even meet. They’re risk averse and have really high standards. Those who use dating apps feel that the quality interactions aren’t there, or that people aren’t as committed, so they get tired of looking and give up. At the same time, there’s a renewed interest in meeting people in person through hobbies and activities. (The one bright light of hope!)

So how can content design help? Given Gen Z’s complicated relationship with dating, maybe the offering also needs to change.

My approach has always been to ask how people are secretly hoping this experience will change their lives. I say “secretly” because these aren’t always things people are aware of or would admit to other people. We all go about our lives hoping certain things will happen but also worrying about other things happening. The gap between those things signifies where the transformation needs to happen.

Most transformations happen over time, moment by moment. If I’m going to help a dating app create some of those moments, I need to know what people want, show them it’s possible, and take steps to deliver it. I do that by first uncovering the universal truths that inform their expectations. Then I find out what they value and what they’re concerned about. Then align every experience with those values. For Gen Z especially, it also must be inclusive to everyone. The days of designing for an “average” user are over.

And in the dawn of an AI revolution, why not consider and explore something totally different? These same principles can be used to imagine fresh ways to meet their needs and exceed their expectations.

We’re all human beings.

My number one rule of content design is to respect the humanity of my audience. Gen Z, like every other generation, are human beings first. Life experiences — such as growing up, making a living, and falling in love — are universal. All generations have hopes, overcome challenges, raise children, and face death. Gen Z might have a unique view and experience of these events, and that’s the first place to start.

We crave experiences that are profoundly human, genuine, and trustworthy. We’re delighted when apps are smart or predictive and know what we want. We love when they integrate into our lives and feel like an extension of what we’re already thinking or doing. And when they manage to convey the warmth, humor, and realness of a good interaction, we become fans.

I like to think of every UX interaction like helping a good friend in a time of need. Listen when they need to be heard, ask questions when they need help figuring things out, smile and make them laugh when they need cheering up.

I focus on the Truth.

In my screenwriting program at UCLA, we were encouraged to write the Truth (with a big T). Let’s say you’re watching a TV show. Jim and Phil are leaving a Super Bowl party and Jim says his wife died in a car crash on Super Bowl Sunday. He says she was killed by a drunk driver who eventually went to prison. We got all the relevant info but it doesn’t convey how Jim feels.

Now what if Jim and Phil are leaving the same party and we see that Phil has had too much to drink. Phil tries to get behind the wheel of his car to drive home and Jim flies into a rage. They’re both shocked by his reaction when Jim breaks down and shares how guilty he feels that he wasn’t with her that day. It’s not about the details of what happened, it’s about the emotional truth behind it.

What are the universal truths of dating that transcend age, culture, or religion? Love, connection, safety, and belonging — these are things a dating app should strive to provide. But we also need to address their opposites — loneliness, loss, fear, and anxiety. It’s a delicate balance. Can I people find love and connection while dispelling their fears and anxiety?

I look at every experience through that lens to make sure the app is telling the truth. Is there an illusion of safety, or actual safety? Is there a promise of love, or real love? How can I create true connection and foster belonging? What features, interactions, and communications will support those goals? Which ones will detract from it? If I know the core needs of people using an app, I can prioritize those above smaller more granular ones.

Uploading photos, for example, is a critical step to using a dating app. But what concerns might people have? Could photos compromise their safety? Could they make them feel judged, instead of belonging? Could they diminish their chances of finding love? If so, I need to address those realities and think about other paths to success.

It’s crucial to understand the emotional needs and concerns of an audience and how they think. Then we can find the best ways to fulfill those needs.

Most apps are global.

If an app is available in 140 countries and 60 languages, it needs to be usable by people in a myriad of cultures. Generation is only one way to segment an audience, and it may not be as relevant in some places as privacy, safety, or religion.

What we say is infinitely more important than how, when it comes to global audiences. I ask myself what questions or concerns people might have. What do they need to know right now? What can I save for later? What shouldn’t I save because it would compromise trust, safety, or comprehension? What should I leave out because it raises more questions than it answers? I look for potential dangers or traps that people could fall into and avoid them. Then I ask customer experience to write or add to an article to help people if I fail.

Inclusivity means making sure everyone, regardless of abilities or situation, can access and use the app. Everyone should feel that the app is for them or can easily be tailored to their specific situation. Gen Z has a much bigger awareness of and appreciation for inclusive experiences than previous generations. Even if they don’t personally need or use a feature, they’ll applaud you for including others. For a consumer app, that could mean designing for a lower level of tech savviness or accessibility — especially in emerging markets. It might mean providing an offline version so people can keep using it on the subway. Or adding settings to increase font sizes, turn off sounds, or control who sees what.

It’s a big generation.

The dating life of an 18-year-old is quite different from a 28-year-old. One is beginning their life as an adult. They don’t know what they want yet and aren’t looking for a serious relationship. The other will have more experience and could be deciding whether to get married or have children. Or they might already have kids, be divorced, and are getting back out there. Are they men, women, straight, gay, bi, cis, trans? There’s a range of needs and emotions to design for.

What they likely have in common are their values. How they see the world and how that view differs from previous generations. From my own observations, Gen Z values transparency, inclusion, and social responsibility. They’re digital natives who’ve grown up on social media. What their peers think is important, and their peer group extends beyond friends to influencers on TikTok, YouTube, and Twitch. Their community is global. It includes content creators, influencers, and celebrities who speak out on the issues they’re concerned about — like climate change and mental health.

I can use Chat GPT to find out that Gen Z values authenticity, diversity, and creativity. And that they’re concerned about work-life balance and financial stability. They embrace technology but worry about screen fatigue and privacy. And they really want to make meaningful connections.

If the company making the dating app values those things too, we’re miles ahead. But it’s not enough to just say it, those values must be prioritized in the product. From my own experiences in tech companies, I know there’s often a constant tension between what the company wants and what customers want. When companies put making money above the needs of their customer, they eventually lose those customers. But if you actually change their lives for the better, they will happily pay.

“Be one with the force.”

Values aren’t constant. They’re variable and contextual, and not always predictable. To be confident that I can address any situation, I need to understand and feel what my audience is feeling. That means spending time in their mindset. I’ll read articles and books, spend time on apps they value, and stay up to date on the trends, conversations, and issues that matter. I’ll spend as much time with my audience in person as I can — whether in user testing, focus groups, or the wild. Most importantly, I’ll stay curious and open to new information.

When working for Dropbox, Facebook, and eBay, I met people all the time who wanted to talk about features I was working on. A few minutes after meeting them, they’d tell me everything about their experiences — good and bad. There’s nothing like hearing unsolicited feedback from real people! It’s timelier and more relevant than any research or journalism on the topic.

Solicited feedback works as well. When I wrote for college students at Chegg, I often conducted tone tests on sensitive topics and tried different approaches and language. I always learned new things about how they thought and felt by hearing their reactions to words I’d written.

Values drive interactions.

When connecting with Gen Z, it’s not about using their slang or referencing popular culture — though that can be fun in moderation. It’s about understanding their motivations and concerns, to design meaningful interactions. The words I choose are in service of that. They’re packed with as much authenticity, humanity, and value as I can provide.

Just as important as language is how the app behaves. The features we choose should be informed by our audience’s values and meet their expectations. Keep in mind that people live online and offline, and every interaction they have creates expectations.

From what I know so far, I’ll prioritize things like direct, real-time feedback, suggestions, and notifications. I’ll brainstorm interactive features that let them be creative and express themselves, while enriching their experience. I’ll find ways to personalize the experience, so they get exactly what they’re looking for. I’ll look for opportunities to instill a belonging and community. I’ll focus their time on quality over quantity. I’ll build in options to connect on the issues and voices that matter to them. Then I’ll add acknowledgment, assurances, and celebration in all the right places.

Ask the hard questions.

We know Gen Z is pickier, prone to “slow dating,” and more concerned with their well-being than being coupled up. But they still want meaningful connections. Are dating apps meeting their needs? If not, how should they evolve? Maybe we should think beyond photos as the primary means of attraction. Can we use AI to help mimic how people connect in real life? Is there a way to make it feel less transactional and more organic? Can it be more fun? Can we remove the anxiety? If success is measured by coupling, it’s statistically doomed to mostly fail. What if the primary outcome is self-discovery, learning who we are, and becoming a better, happier person?

Challenging basic assumptions and asking hard questions is the most important part of product design. We can’t be afraid to do it. It helps us focus on what matters. It prevents us from launching features that not only fail to connect but alienate our audience. It opens the door to new ideas and directions.

To sum it up, it’s about values.

Connecting with Gen Z means getting a deep understanding of their values, experiences, and expectations. It’s about more than following trends or using cultural references. It’s about addressing real needs in a way that aligns with what’s important to them.

I focus on universal human truths through their perspective and ask the hard question: Am I creating experiences that will change lives?

A content design approach for connecting with Gen Z was originally published in UX Collective on Medium, where people are continuing the conversation by highlighting and responding to this story.

A few years ago, I turned down a job at a place I loved to take on the challenge of being the first content designer (also known as content strategist or UX writer) at a growing company.

During the interview process, I focused on whether I could do the job and how much the people interviewing me seemed to value the role. There was so much I didn’t know to ask. I accomplished an astonishing amount in 2.5 years, but it was hard, frustrating, and a little lonely at times. It seemed like I learned everything the hard way.

When I went to Meetups and met people doing the same thing, our experiences were different but our learnings were eerily similar. I thought at the time that I would write a book about how to do it, when I was done, but “done” eluded me.

Creating space for a new function, building a team from scratch, and making it a valued part of a company is a journey that never really ends.

That said, you only have one opportunity to begin. This article is about how I would do it, if I were beginning it again.

👋 Figure out who your friends are

Who are your allies and sponsors, the people who believe what you do is important? You need people at the leadership level who believe that words matter and are worth paying for.

If there’s only one person at the company who believes in your role, it’s going to be rough going. If that person leaves the company shortly after you get there, who will champion you?

In the interview process, ask who supports the role and who’s going to help you ensure success. Whose idea was it and why? It’s important that you also make sure they understand what the role does and haven’t built their support on a false sense of what you bring.

Set up one-on-ones with your allies and sponsors. Ask why the role is important to them and collect stories of when words mattered in their lives. Ask them who the influencers are, the most important people for you to win over, and see if they’ll make an introduction.

Plan to:

• Meet with your sponsors on a regular basis, and ask for help
• Get ideas from your allies on where you should focus your work
• Bounce ideas off your friends so they can offer advice and support

🚌 Put together a roadshow

Make a presentation* that explains your role, why it’s important, and how you work. Present it to as many influencers as you can. I like to find out what experience people have with content design. It’s a great opener; you’ll find out immediately whether they’re already fans or are starting from scratch.

Include examples; it’s the best way to communicate what you do. Before and afters are really effective.

Show how writers impact information architecture, usability, and tone. Show specifically what content designers did and how their work made an impact.

It doesn’t actually have to be your work though it does help to establish your credibility, especially if you did the work at a reputable company. Otherwise, make sure you mention other companies you’ve worked for. Let people know that you’re experienced and worthy of trust.

Then ask what opportunities there might be on their team to improve their metrics with words.

Plan to:

• Explain in one sentence what you do and why it’s important
• Modify your presentation to answer any questions you get
• Add quick wins to your presentation as soon as you can

*Special thanks to Andy Welfle for helping me get a presentation started.

💸 Show the value of the role

In those early months, you can’t do everything and if you try, you’ll burn out. You’ll also set a precedent that you’re superhuman and it’s hard to pull back from that. During your roadshow, find an existing problem that’s been measured—something that can be improved with copy. It doesn’t need to be big, but it needs to be doable without too much design or engineering effort.

It could be rewriting a screen to increase conversion. Or adding a line of copy to decrease customer service calls. Or rewriting messaging to help people complete a task. Get the baseline performance, before your intervention, and then after. Make sure you’re testing a metric that’s important to the company. Ask a product manager or data scientist on that team if you aren’t sure.

Brand new products and features are fun to work on—and most definitely benefit from writing—but without measurable improvement, you’ll be hard pressed to prove your contribution.

You’ll win your peers over by being a collaborator but you’ll win the company over by getting results.Start small and take on bigger projects as you go. The key is to collect wins and case studies.

Plan to:

• Do some major convincing to get your updates tested
• Take screen captures of everything you work on before and after
• Find a key project, one where there is already company energy, excitement, and opportunity

🎤 Talk about your progress

As soon as possible, your roadshow needs to start incorporating your progress. Show people that you’re there to make an impact, and that you’re ready to scale and lead a team.

Early on, ask what the requirements are for growing the team. Find out what your success metrics are. Are they achievable? Are they reasonable? Who’s as invested in you are in your success?

When you have success metrics you can all agree on, clearly articulate what you should receive as you achieve them: Time to work on foundational projects, credit for the work you’re doing, and a bigger team. Or maybe you want access to a certain team or project. Ask to work on it, come up with ideas, and lead the discussion.

Look for opportunities to present your progress and wins at team meetings or all-hands. Help people see what’s possible with a team.

Plan to:

• Identify the places where content design can make an impact, and build on small wins
• Outline exactly what your new hires would work on and why it’s important
• Talk about big trends in the industry and how your team can help make the company more competitive

🌱 Grow the team

A company needs to start somewhere but one person does not make a team. Without help, you’ll soon be drowning in requests.

You want to make sure your company is thinking beyond the start. Is there a commitment? Is there momentum? When will they hire more writers, and how many? Will they report to you or will you all report to a design manager? One of you needs to be the head of that team or you’ll have no power.

Get it in your contract: 1–2 hires within 6–12 months. That gives you enough time to create guidelines, set expectations, and build a foundation. Hire contractors if you can get the budget. Establish as quickly as possible that this function requires a team. You can’t work in a vacuum for long — you’ll need other writers to bounce ideas off of, collaborate with, and prioritize with.

Plan to:

• Hire contractors on your own or coach the recruiters on what to look for
• Create process, documentation, and guidelines
• Write a mission statement to help people understand where content design can take the company

In the year and a half since this experience, I’ve been contacted a half a dozen times to start a team somewhere else, and I’ve been much more wary. It takes a lot of confidence, passion, and fortitude to start a team. Don’t assume that whoever is hiring you has a plan beyond that, or that they know what they’re asking for. This is a journey you’ll own, so make sure you do what you can to set yourself up for success.

This article is Part 3 of 3 on finding great UX Content Strategists for your team!

In my 3+ years managing UX Content Strategists, I’ve had the privilege of giving several people their first jobs as UX Content Strategists (also called UX Writers or Content Designers). I’ve successfully hired with internal recruiters, talent agencies, and sourcing candidates directly.

The qualities I look for include an interest in people and communication, experience as a writer, and an ability to work with designers and researchers to create impactful user experiences.

I start with resumes and have considered candidates with a variety of backgrounds including marketing, SEO, conversion optimization, community management, and customer service. See article 1 of 3 in this series.

The portfolio review and phone screen let me dig deeper into whether candidates have the right mindset and experience, which determine whether I’ll bring them in to meet the team. Read article 2 of 3 in this series.

Finally, I bring candidates in to meet with a multidisciplinary group of designers, researchers, product managers and/or product marketing managers. This article is about how those interviews are generally conducted and what I look for.

The “onsite” interview

The interview process usually lasts about a half day. The goal is to get input from teammates and partners on strengths and weaknesses they perceive in the candidate — to help determine whether they’ll succeed in the position.

The interview typically consists of:

• A presentation by the candidate
• One-on-one interviews
• An onsite exercise

All of these involve some prep work, both for the candidate and the interviewers. I’m a big believer in prepping candidates for what will happen onsite and making them comfortable, and prepping interviewers to see what the candidates have to offer.

I see no benefit in watching people fail because they were nervous, unprepared, or our expectations were not aligned. I much prefer giving people a chance to shine.

The candidate’s presentation

This is potentially the most difficult and nerve-wracking part of the interview for me. In the course of our work as writers, we’re often trying to build trust and win people over so the better we are at it, the better we are in our jobs.

It’s important that candidates present well and connect with people in the room through their work.

Unless instructed otherwise, presentations are expected to be a case study of 1-2 projects that show a range of skills with projects that are most relevant to the job, and within the last 3 years. I ask candidates to look for projects with parallels to the size of company/team, industry, user, or type of projects—to make it easy for the team to imagine them working there. I also like when candidates include a slide or two about themselves in the beginning to show what they, personally, bring to a role.

In the presentation, I’m looking for:

• An ability to present clearly, concisely, and convincingly. Presentation counts so spend time making it look good, practice, and get feedback.
• A demonstration of the problem to be solved, use of data, and rationale for the solution. It’s also nice to see results if you have them!
• Thorough content and copy considerations, explorations, and choices. Be prepared to talk about your process and who you worked with.

More established writing teams might rely entirely on other writers to assess candidates, but I’ve asked researchers, designers, and product managers to interview as well. It helps to have an understanding of these roles and what they’re looking for, so candidates can anticipate their questions.

One-on-one interviews

A few days before the interview, I send an email to my interviewers to prep them. They’re busy so I try to keep it brief. My email goes something like this:

Hi [name],

Thank you for agreeing to help me interview UX Content Strategy candidates! You’re interviewing [candidate name] on [day, date].

Because it’s a fairly new field, my candidates may have limited direct experience even though they are experienced writers. I’ve already assessed their writing and determined that they have the writing qualifications.

What I’m looking for from you is an assessment of their ability to:

- Ask questions to determine what’s best for the user

- Collaborate with designers

- Give and receive feedback

- Create copy tests and incorporate research findings in their work

- Articulate and advocate for their point of view

[Candidate’s name] has a background in [brief description of where they’re coming from and how I see it relating to what we’re looking for]. Their resume is attached for your review. Let me know if you have any questions!

Thank you,

Writing exercise

I like doing this as the last part of the interview process. After the presentation and the interviews, it should feel easy. I’ve already spoken to the candidate a few times and I intend for this exercise to be a casual conversation. But it is a risk because you’ve already spent people’s time interviewing.

Many companies send out a writing exercise in advance and ask candidates to complete it on their own, then have existing staff evaluate, sometimes blind. I myself have completed these exercises a half a dozen times and have “passed” and have “failed.” I’ve also graded them. Though we try to be scientific, different writers will evaluate the exercise differently.

If you have a lot of qualified candidates, it’s an effective hurdle. But for people new to the field, I prefer the onsite exercise for a few reasons:

• I get to see the way my candidate thinks. What kind of things might they come up with that I have not have thought of?
• I get to see how quickly they can assess a situation. Anyone, given several days or a week might be able to come up with good copy, but what can they do on the fly? What questions do they ask?
• I get to see how they solve problems and how collaborative they might be. What do they notice, what do they miss? How do they deal with a lack of information? What would they try?

If I see that writers have a sense of curiosity, know what questions to ask, and can come up with ideas, I’m confident they can learn the mechanics needed, on the job.

In my hiring, I’ve skewed towards candidates who can lead strategic content thinking from concept to execution as well as execute copy but it’s worth nothing that larger teams might have different needs. Some products require rigorous process, adherence to guidelines, and detailed copy systems. That type of writer may not do well in this on-the-fly exercise.

For the exercise itself, I usually show a live product that has not had a writer on it and ask how they would improve it. I’m looking for a rapid fire assessment. What do you see? What do you want to know? What stands out as a bad experience? What opportunities for a good experience have been missed? I’m not expecting candidates to write copy, I just want to know what they notice and what they don’t, what’s important to them.

This part of the process excites me the most. I’m always amazed at how similarly—in some ways—people drawn to this role think, and yet how creatively different we can be in how we approach things. This is where I start to see what kind of impact this person can make on my team.

The final decision

How the candidate expresses themselves in their presentation and in the exercise is critical, as is how easy they are to converse with. I’ve found this to be important with other interviewers as well.

These are some of the reasons I’ve had to pass on a candidate, despite their work experience:

• Inarticulate or too long winded
• Took too long in the setup, not enough time on their work
• Doesn’t listen or stop to ask for questions
• Didn’t answer direct questions
• Can’t describe their process
• Made assumptions about the job that may not be true
• Doesn’t have experience with other writers or designers

On the other hand, there are so many factors that go in to a hiring decision. A candidate can make a great impression and still not get the offer. All anyone can do is present ourselves, our experience, and our expectations in the best and most relevant way and hope that when it’s a match, everyone will know it. My goal is to create transparency so candidates and employers can do just that!

When Netflix launched their Black Lives Matter collection, my first reaction was “Oh, cool!” I had seen something similar on Amazon and was thrilled to see more new content. I spent 15–30 minutes reading the descriptions of every single show and movie and adding them to my list. Halfway through, though, I had my second reaction, which was: “Wait a minute, where did all this content come from? Has it always been on Netflix and I just haven’t seen it, or did Netflix go out and acquire it because there’s suddenly an interest?”

If the former, it made me wonder if the reason I hadn’t been exposed to it sooner was the sophisticated algorithms that are used to recommend content similar to what I’ve already watched. I remember the first time I realized just how polarized experiences could be. I was at a guy friend’s house to watch a movie and he pulled up his Netflix. There was the same interface I have, with rows and rows of recommendations, except I didn’t recognize a single movie or show! Much of it was still original Netflix content, very popular, recommended, etc., except that his feed was filled with action movies, male comedians, and gritty crime shows, none of which had made my feed.

This is how “echo chambers” are created, a term used to describe what happens on social media when people are shown increasingly similar content by increasingly similar people over time.

Our views narrow as our consumption narrows and we artificially experience the world in one particular way, rather than recognizing the multitude of experiences, perspectives and truths that coexist in our world.

To be fair to Netflix, of the 30 or so movies and shows in the Black Lives Matter collection, I had watched 4 and 2 were on my watchlist, so some had already trickled into my recommendations. But it took an enormous amount of pressure and attention to force businesses to surface this content to people who haven’t asked for it. How are we supposed to expand our horizons and be inclusive if our digital world is dominated by such algorithms?

After adding the shows to my list, I went back to my homepage. In just that half hour, my perspective had completely changed.

All of a sudden, my recommendations and list seemed obscenely white and embarrassing. I imagined what it must be like to live in a world that feels like it belongs to someone else.

I admit that in the past I have skipped over “black shows”, assuming that I wouldn’t be able to relate and intentionally choosing things more familiar, easier. Then, I read an article by a Black woman saying that she’s been forced her whole life to read and watch content that she couldn’t relate to. Whoa.

I started watching a show called Pose. It takes place in the late eighties and centers on gay and trans Latinx and Black youth living in New York, most of whom are runaways, disowned by their families. They form new families, take care of each other, and compete together in balls — where people dress to certain themes and walk and pose for an audience and judges. At first, it was so different from my usual fare that I wasn’t sure I could watch it, but I loved the music and the costumes, and I got hooked on the stories and their world became my world.

After a few episodes, I felt my perspective shift again while following a storyline of a beautiful trans woman who lives in fear of being “clocked” or found out. All she wants is to be a “real woman,” and to pursue her dreams or have a relationship like a real woman could. Her vulnerability in the face of prejudice and a world that can’t tolerate ambiguity, is heartbreaking.

It made feel thankful for the simple gifts of being born a woman, being happy to be a woman, and having a real woman’s body, even with its lack of perfection.

The show tackles an amazing array of universal human situations—making a living, pursuing dreams, being noticed, looking for love—as well as specific hardships facing this community. My best friend in high school was a gay man. We lost touch sometime during college and when I reconnected with him, he said he’d gone through the darkest days he could imagine, losing friend after friend to the AIDS epidemic. I remember feeling the weight of that statement and not knowing what to say. We never spoke again, the gap between us was just too large. Pose gave me the opportunity to relive that time and try to see it from my friend’s perspective.

As a girl, I remember being confused about drag queens—were they were men who wanted to be women or men who just wanted to dress as women? I frankly couldn’t understand why anyone would want to wear all that makeup and heels, but the first time I saw a female drag show, I was transfixed. I suddenly wondered what could be more powerful than a woman claiming to be a man, and getting all the respect and benefits that the identity warranted. In Season 2, one of the “butch” characters explains to another that it’s okay to be manly and embrace their feminine side.

In that moment, I understood the power of being able to claim all the sides of ourselves and, again, saw life through a different lens.

Though the show felt a bit corny at times, because the characters often say and admit things that people in real life don’t, I bawled at the end of every episode. Pose tackles huge themes like love and family, life and death, ambition and opportunity, fairness and kindness—as well as violence, hatred, injustice, and indifference. And though life is harder and grittier than the show, sometimes we need entertainment to show us what true courage, love, and change can look like.

There’s so much to love about this show, including the fact that it stars 5 transgender actors. Just give it a watch! Though Pride Month is over, I find it reassuring to realize the immense victories of the LGBTQ+ community over the course of the past fifty years.

My friend Elektra sums it up perfectly at the end of the second season:

“It takes guts to step out of your comfort zone and into the shoes of another. We should all do this more. If we did, we would make a better world.”

Everyone knows brands are important, though perhaps not everyone agrees on whether brands are created or built. Maybe it’s both. The reality is, all brands have to start somewhere but does a name, logo, and feeling really matter? For a startup, they can make all the difference in the world!

A good brand can help people understand what you’re offering, remember your new product, and envision your success as a company.

A couple of years ago, I started as a brand strategy advisor with Bipronum—a startup with a revolutionary way to organize people, achieve goals, and move business forward. I’d worked with them to solidify their positioning and messaging, but really wanted to tackle the name and develop a visual brand that was as exciting as the product. It was obvious to most people involved with us that the brand could do much more, but without an agency or a design team, I didn’t dare take on a rebrand myself.

Then, the stars aligned, and my preparation met opportunity, propelling a small but scrappy distributed team to create a name, logo, look and feel that would ignite our team around a fantastic new brand.

This is the story of how we did it.

A brand challenge

Our first name and logo were defined in the very early stages of the product, as they so often are for startups. But people couldn’t consistently pronounce it, it wasn’t very memorable, and it didn’t mean anything.

After creating an innovative and valuable product, the name was starting to work against us.

In the last two years, we’d learned a lot about what makes our product different from the plethora of collaboration tools out there and the value we offer. Now, we needed our brand to reflect this.

Our product resonates best with:

• Freelancers and independent consultants who drive business — not work — without a fixed team, inside and outside corporations, and across their networks
• People who want to design their own business interactions, and need to flexibly and continuously meet opportunities as they arise

While we always knew that a new brand would make a difference, we didn’t expect that our customers and partners would respond as quickly and enthusiastically as they have!

The beginning of a journey

We started this rebrand process a full year ago, when I completed our first brand messaging architecture which included a vision statement, a set of brand attributes, and key product features. Everyone agreed that we needed a new brand but without a designer on the team, we could only focus on a name.

Those explorations, around a few of the themes that regularly came up, yielded several names that we liked, but most only reflected one aspect of the product, not the whole experience. Additionally, it was hard to put the name to the test without an accompanying logo, look and feel.

Some of the names we considered:

In late October, Kristy Mapp joined the team. A visual designer with a diverse background as a photographer and interior designer, one of her first tasks was to rebuild our website. As she got to know the product and the brand, she began playing around with ideas for a new look.

One day, Tim Bussiek, the CEO, asked Kristy to create a key visual for a deck he was putting together for the editor of one of the biggest women’s magazine in America. He wanted to convey how the product could empower her mostly female team of creative professionals to drive their success inside and outside their organization. Kristy created this image to represent business people achieving business success together.

Having a designer who could visually brainstorm for us was proving to be incredibly valuable! But this infusion of female energy and ideas into a product that had thus far been concepted and engineered by men, was really the leap forward we needed. Tim and I were so inspired by the image that Kristy made, that the three of us began to dabble with name ideas that expressed the user as a superhero, masterminding their next big moves.

Some names we came up with:

• Max, Maxwell, Super Max
• Rocket, Jet Pack, Action Pack, Slipstream
• Phone Booth, Get Smart
• The Salon, Great Hall

Ensuring a focused approach

Before I knew it, we were diving into a real rebranding effort. And while I was thrilled that we were finally doing this, I also knew we needed to do it right.

We had two driving forces. 1) Finding the right name and brand and 2) Moving quickly.

We couldn’t afford to spend months and months on this, but we also couldn’t settle for something that didn’t meet our criteria.

Our new brand needed to:

• Be interesting, different, and memorable
• Reflect our brand attributes and the diversity of users
• Resonate with and excite our team, customers and partners

I started by putting a deck together about the product experience and brand attributes, around our company mission:

To empower people to create and repeat business success with others in a visual, achievement-driven environment

From big picture to big idea

Without a creative agency to work on this, Kristy and I presented the deck to the team and asked them to submit images that expressed the feelings of brand attributes for our mood board. Our images ranged from abstract and technical, to organic and personal. I even threw in pictures of friends and family in moments of triumph or celebration.

From there, Kristy created a few color palettes and we chose one that was most familiar and looked most like our exploration thus far.

During a brainstorm session, Kristy came up with the name “Pilot” and it immediately resonated. We loved the idea of men and women charting their course to reach a destination, and taking others along. We loved the aspirational aspect of it and the idea of soaring above everything. Kristy mocked up some logo ideas and I reviewed the name against our brand attributes. It worked!

Why Pilot works:

• Personal > Your ingenuity put into action
• Freeing > The sky is wide open, where do you want to go?
• Easy > Pick a destination and fly on autopilot!
• Efficient > You’re in control, no training required
• Rewarding > Flying is still a special experience

We added the color palette and logos to the deck then shared it with the team. They liked it too! But there was a concern that Pilot was too specific, had too many other possible meanings, and wasn’t unique enough.

Though we really liked Pilot, I started thinking about alternates:

• Skypilot, Aviator, Captain
• Flier, Aeronaut, Aerialist
• Eagle, Soaring

Ready for inspiration

Then one day, it came to me: Hi-flier. It was less specific than the other options but more aspiration. I just knew it was the right word for our empowered entrepreneurial professionals.

I looked up the definition of Hi-flier and almost fell off my chair. It was identical to how we had described our users. I made a few tiny tweaks to create our own unique definition.

Hi-flier: A person who puts their ingenuity into action to create business success

I shared it with Tim, and he immediately loved it for being even more about ambition and achievement. We floated it past Kristy and we all decided that we didn’t lose anything by giving up Pilot as all of the rationale worked for Hi-flier as well. But with Hi-flier, we gained the aspirational sense of soaring above it all. Next to it, Pilot felt clunky and grounded.

Getting feedback from friends

Kristy updated the preliminary logos and we were ready for feedback. I finished up the brand deck and we sent it to a group of our trusted friends and partners for their thoughts.

Half of the feedback was just positive — great direction, makes sense, love the work! The other half let us know that we weren’t quite there and needed to refine the concept further. I challenged us to address each of these:

• Mood board lacks cohesiveness. A few people wondered which brand attributes we thought each image represented and challenged us to cull them down to ones we really feel convey the brand. Could we choose just a handful of images that we agree convey the brand values?
• Colors don’t represent the brand values. A designer suggested that in looking at this for freedom, flexibility, and skies the limit, the dark blue, orange and gold didn’t seem to convey those qualities. Could we revisit the palette for lighter, brighter, colors?
• Name and visuals look retro. One person said it reminded them of the movie Catch Me If You Can. Another said Hi-flier reminded them of the 1950’s Radio Flyer wagon. The militaristic aspects didn’t resonate. Could we dial back the airline look and make it feel more modern?
• Balance between individuals and teams. Two people thought that Hi-flier put a lot of emphasis on the individual and didn’t indicate a partnering product. Could we convey the collaboration aspect with the messaging?
• Messaging sounds ambitious. There was another comment that Hi-flier might be ambitious and not in line with how people think about business. Her concern was that people want their work to be more relaxing. Could we create a sense of rising above it all that feels effortless?

Outside-in gave us the perspective we needed

In a one-hour sync session, Tim, Kristy, and I made some quick decisions based on the feedback to whittle down the images on the mood board, spend more time talking about why the images supported the brand attributes, and redo the colors.

We selected 10 images that represented the ambition, optimism, and ingenuity of our audience. From there, Kristy created a new color palette. We reviewed the colors and discussed the attributes of each until we had ones that best expressed the brand.

How the colors express the brand:

• CALI BLUE — The color of opportunity
• CHARCOAL — The color of confidence
• CADET & POWDER BLUE — The colors of freedom and self-expression
• CLOUD — The color of possibility
• GOLD — The color of success
• CORAL — The color of excitement

Now that we had forward motion, Kristy could finalize the logo using the new colors and a font that felt more in line with our concept. During this final round of design, we found ourselves learning even more about our product and our brand.

With Hi-flier, we went all in on the idea of achievement, the entrepreneurial spirit, and rising above it all. This is an app for people who are motivated to optimize their efforts and achieve more.

The logo has wings and leans forward to express the idea that people who use Hi-flier will fly, with a perpetual forward motion. The use of the dot in the center, instead of the dash, correlates to our shortened brand mark and represents a point on a journey. Our confidence color used in the name sets the tone for achievement while the gold in the dot and wings, represents the individual success of each user.

Though our focus is still on ‘everyday business success,’ the action is now ‘fly.’

Our new tagline is: Make your everyday business fly!

I added a few slides exploring terms we could use in the product to enhance the feeling of being a hi-flier:

Audience testing

Then, we updated the deck and ran it by current users for their reactions. Here are a few.

An independent consultant, formerly with McKinsey, who runs a business as an efficiency expert said:

I like the idea of seeing it from a higher level, I want to see over everything

I don’t care about all the details, I just want to know where things are

I’m okay with the idea of boasting, I want to be a Hi-flier!

A group of college students in Michigan, who are using Hi-flier to collaborate on projects, gave this feedback:

It’s good to sound ambitious

The brand and terminology bring the app to life, and lets me know what to expect

‘Mission Control’ instead of ‘Notifications’? Cool!

A product manager who develops online services such as eBay, said:

I like the aspirational feel of being able to achieve anything

Work should be easy, and this looks breezy and flexible

There’s something so cheerful about the “Hi” in a bubble, it’s optimistic

We were elated to hear confirmation of what we had set out to achieve!

The name and brand communicate our offering of an app that supports people’s ambition and organizational talent for business success.

As expected, the brand also gave us a unified direction for messaging using hi-flying as a simple and effective guiding idea.

Time to celebrate

We hit it! With a combination of preparedness, inspiration, and skill, we finalized the brand and showed it to the team. From there, we moved very quickly. I created a timeline for how to roll it out, Tim researched and secured a URL, and Kristy put together ideas for how it would look on our website, in email, and in the product.

Our new website is up, with our new look and feel, at www.hi-flier.com but ideas of what we can do with this brand just keep coming. Stay tuned to see where this small but scrappy distributed team will go using Hi-flier!

Hi-flier’s brand journey — from bland to evocative was originally published in Hi-flier on Medium, where people are continuing the conversation by highlighting and responding to this story.

This article is Part 2 of 3 on finding great UX Content Strategists for your team!

About 2 years ago, I was brought on to build a UX Content Strategy team at Chegg®. Building a team from scratch is no small feat. From integrating into the existing design process and creating guidelines for content strategy, to helping design a great user experience and writing clear, concise copy, the biggest challenge can be growing the team.

This is a fairly new field, so managers often find themselves sourcing talent from the same small pool of experienced candidates. We often need to expand our searches to people with related, but not direct, experience. Since starting my team at Chegg, I’ve hired several content strategists this way.

There are 3 steps to my process:

1. Pre-qualifying. I look for candidates with creative background and experience writing user-facing communication. I ask them to answer 3 questions in writing to determine their interest in user experience and ability to apply content to it. Read article 1 of 3 in this series for more!
2. Phone screen. The next step is to dig deeper into whether they have the right skills. I do that with a phone screen to talk about their experience, and follow up by asking for writing samples. This article is about what kind of questions I ask and what I look for in their portfolio.
3. Interviewing. At this point, I believe I’ve found candidates who can do the work. Now, it’s a matter of how they present themselves and whether I, and others on my team, believe they will succeed at Chegg. That’s what my next article is about.

PRE-QUALIFYING RESUMES

I’ve considered candidates with a variety of backgrounds including marketing, SEO, conversion optimization, community management, and customer service. Each of these positions contains a critical aspect of content strategy such as talking directly to users, listening to what they want, aligning with what they’re looking for, and solving their problems.

But a job title doesn’t guarantee demonstrated skills and the ability to use those skills as a UX Content Strategist.

It’s a very good sign if candidates have already thought about how to use their experiences in the new role. It shows me that they’re motivated, have done their homework, and will likely be good at the job.

It’s quite common to see a wide range of strengths among content strategists based on their experience and interests, but there are a few demonstrated skills that I feel are critical to success.

The demonstrated skills I’m looking for are:

• Advocating for the user
• Making a business case for content strategy
• Collaborating with designers
• Designing or utilizing content tests

DIGGING DEEPER IN THE PHONE SCREEN

After reviewing resumes, I set up a 45-minute phone screen with candidates to get to know them and dig into their experience.

The first question I ask is “Why do you want to be a UX Content Strategist?” The answer to this question alone can often give me enough context to know whether they can apply their experience to content strategy.

I’ve found that best candidates have had a experience doing what’s best for the user and realized that it’s something they have a passion for. Then, I walk through their resume with them to try to assess the demonstrated skills.

Advocating for the user

There’s nothing more important to UX Content Strategy than being able to advocate for our users. I’m looking for fierce advocates and defenders of positive human experiences.

Working on the art team at a big publishing company, one of my hires had noticed that art content (which is usually in a horizontal, rather than vertical format) didn’t display well in their eReader. Without a user experience team, she and a few co-workers built a prototype of how the eReader could be modified for art books and got approval from the business leads to test it with students at a local university.

By identifying ways to improve an experience and taking the initiative to get validation from real users, she demonstrated that she would do what’s best for the people who use our products.

Making a business case for content strategy

My second hire came from an online education company as a community manager, where she heard from users about the problems they were having with the product. She rewrote instructional copy to improve usability, and in cases where users were happy, she made recommendations on how to use that momentum to deepen engagement.

When she noticed a lot of questions about how it worked, she proposed a redesign of the homepage to feature the overview video, that had previously been a few pages in. To get the change made, she had to build a business case and demonstrate how she would measure success.

Being able to articulate the impact communication changes can make, and convince product leaders in the language of business, is critical to being able to advocate for users.

Collaborating with designers

Because content strategists work closely with designers, one of my requirements is experience giving design feedback, taking feedback on their writing and ideas, and being able to collaborate with designers asynchronously and in real time.

One candidate I interviewed had worked extensively in journalism. She described her process of ideating with designers, writing copy and making suggestions for imagery, and then reviewing the final product together for any additional updates. It was clear that she understood the importance of getting alignment, being accountable to a team member, and working together to find the best solution.

A candidate who hasn’t had experience iterating with designers is one I probably would not consider because that relationship is too important.

Designing or utilizing content tests

While it’s certainly not a deal breaker, I prefer candidates who have had some experience testing copy, or getting feedback from users on their copy, in terms of performance and comprehension. I want to know that they can use data to improve their writing.

With a background in marketing, my first hire had a lot of experience working with conversion funnels and had regularly written and A/B tested copy variations. Tweaking copy based on the results and applying those learnings to future copy was a regular part of her work. Her ability to plan, execute, and track copy tests and leveraging results over time showed me that she could systematically find the right wording for an audience.

She later used that skill on the job when she pored through student’s tweets about Chegg and mirrored their language in a rating modal. She tested four versions on a scale from neutral to 100% student to find which they would respond to, and the result was a 2-fold increase in our app store rating.

THE ROOKIE PORTFOLIO

Next, I’ll ask for their portfolio. But what kind of samples should writers provide if they haven’t done UX content strategy?

Primarily, I’m looking for short form content to make sure they can write clearly and concisely, bonus if it’s in a digital medium. It could be website copy, emails, social posts, banner ads, articles, or even a personal blog. Sometimes they’ve even “dabbled” in UX writing with an error message, banner, tooltip, or form. All of that is good to include.

I may ask for specific pieces that they mentioned on our phone call — such as a spreadsheet where they documented subject lines to test and the outcomes of those tests, or a piece of instructional copy that they wrote for an internal team.

Though the samples can vary, candidates should be able to talk about how their work has helped people understand, use, and enjoy a product or experience.

If candidates don’t have any of these samples, it will be hard for me to consider them so it makes a difference whether they’ve made an effort to advance their understanding of UX content strategy by joining Meetups, online groups, or taking classes.

One person I screened was doing a daily UX challenge and had included that work in her portfolio. The sample work demonstrated her thought process, ability to do UX writing, and interest in learning and improving.

These are the qualities I’m looking for in writing samples:

• Concise and clear writing
• Good grammar and consistent usage of punctuation, capitalization, and terms
• Straightforward, conversational language
• A personality or brand voice

I often ask for a quick follow-up call to discuss their samples. In that call, I’ll want to know more about how the problem they were solving, how they approached it, and their explorations. I may ask about any guidelines they followed, what kinds of testing they may have done, and the copy decisions they made.

Finally, I’m ready to bring candidates in to meet the team in person for a portfolio presentation and 1:1 interviews!

Check out Part 3 of 3 on finding great UX Content Strategists for your team!

Screening candidates who are new to UX Content Strategy was originally published in Chegg®UX on Medium, where people are continuing the conversation by highlighting and responding to this story.

How to find great UX Content Strategy candidates

This article is Part 1 of 3 on finding great UX Content Strategists for your team!

A little over a year ago, I was brought on to build a UX Content Strategy team at Chegg®. Charting this course has required doing lots of project work, creating guidelines and process, and demonstrating the value of the role, but there is also the job of actually building a team.

Anyone hiring product-focused content strategists knows that strong candidates can be difficult to find.

In the last few weeks, I’ve seen job notices posted in a Content Strategists’ group on Facebook, for roles with Dropbox, Indeed, Tableau, Mailchimp, Facebook, LinkedIn, and Shopify in locations all over the country. And these are just the big companies, companies you think wouldn’t need to advertise.

That’s how hot this field is right now. While many of these companies are hiring their first content strategist, Facebook hired their first 9 years ago and has doubled the size of the team every year. That’s how new this field still is.

Companies are selecting candidates from journalism, PR and creative writing to fill job openings. And though more and more people with writing backgrounds are taking steps to position themselves for roles in UX Content Strategy, they don’t necessarily have the experience.

That means screening candidates with relatable skills and experience in order to determine whether they can do the job.

But what is the job of UX Content Strategy?

Content strategy for digital products uses three disciplines: User experience + content design + microcopy writing.

User experience is the foundation. This is essentially empathy, translated into actual experiences with a product. Does your candidate effortlessly think and feel from the users’ perspective? Can they articulate what makes a good user experience?

Content design is the most critical aspect. When done well, this is unseen but it’s the conversational structure of the user experience. Content strategists helps determine what the content is, in what order it appears, and where it’s placed in the design. Good content design can make or break user comprehension, conversion, and satisfaction.

Microcopy writing is the bread and butter. More editing than writing, we often need to convey information, feeling, and direction in just a few choice words. Determining the right words, making sure they’re consistent with the rest of the user experience, and being able to test and validate choices requires someone dedicated to the discipline.

In an ideal world, your word wizard would be an ace at all three, but it may not be possible. So it’s important to know your needs.

If your priority is innovation, look for a UX Content Strategist who’s quick with interesting ideas and has an instinct for what makes a great user experience. You want a writer who uses content to push design further.

But if you have a product with a ton of functionality and use cases, you might want to focus on someone with a strong showing in content design. “What happens every step of the way and do users have the information they need?” Your content strategist will also need to organize the copy for all the different states, including errors and confirmations. You want a person who lives their life by lists.

It’s important to know which skills you need most.

Here at Chegg, we serve students — mostly college students — and while they love cool and funny content, they are also stressed and need our help. It’s a privilege and a responsibility to make sure they have a great user experience.

Understanding what makes a great user experience and the role of content and copy is essential for success at Chegg. I also look for curiosity and a willingness to try new things, with the hope that my hire will help the team think out of the box and take risks with copy.

I’m looking for people who understand the role of content in a good user experience and who can communicate clearly and concisely.

To find out, I ask for responses to 3 questions in a written format.

Here are the questions:

1. What are 1–3 apps — phone or desktop — that you think have a good user experience and why?

It’s important that candidates use digital products daily and have plenty of experience booking and purchasing online, interacting on social media, and consuming digital content. We want people who think about user experience and can articulate what makes a good or bad user experience.

I look for references to specific functionality, copy, or design that delighted them, and maybe even ideas on how to improve. They don’t have to understand everything about how user experiences come together, but they need to understand what it looks like when it’s working.

2. What do you see as the purposes of content within the user experience of an app?

What I’m looking for here is twofold: 1) An acknowledgement that content isn’t just copy, and can be data, images, links, buttons, or navigation; 2) An understanding of the different functions of content which, on the most basic level, are to entice, inform, instruct, and inspire.

Sometimes, I’ll get a response that describes content as only words and as more of a narrative — like in brand or marketing copy. I won’t completely rule that candidate out if they show promise in other areas, but it is a bit of a red flag. If we just fill in words or think of content as a one-way narrative, we haven’t done our job.

3. What experience do you have writing microcopy? What experience do you have testing content in user research? What experience do you have defining or working with terms?

Writing microcopy is an art. As the famous quote goes, originated by philosopher Blaise Pasqual, “I would have written a shorter letter, but I didn’t have time.”

Choosing the right few words—simple enough to be understood by everyone, clear enough to prompt the right action, and phrased to elicit the appropriate feeling—is work and requires knowing when to write more, less, or use no copy at all. If candidates have written email, Facebook posts, or banner ads, they’ve probably worked with these concepts.

Relatable skills can also include getting direct feedback from users on copy and modifying it, or doing A/B testing on copy variations. Adhering to brand standards, getting legal approval, or using specific terms for SEO also demonstrates experience in choosing just the right words. The context might be different, but the skills are the same.

When I get thoughtful responses to these questions, I get really excited about what adding this person to my team could mean for Chegg. Now it’s my job to get them excited.

Check out Part 2 of 3 on finding great UX Content Strategists for your team!

What to look for in UX Content Strategists was originally published in Chegg®UX on Medium, where people are continuing the conversation by highlighting and responding to this story.