Pushing back by teaming up

Has someone ever come to you with a design idea that you have concerns about? What do you do?

Early in my career, I'd just speak up and say so. Sometimes, that works. The problem is that when I showed concern again and again, I quickly became everyone’s least favorite person to bring design ideas to.

It's unfair to get frustrated when someone brings you an idea, but it's also irresponsible to just jump in and do what you're asked without exploring the problem. Pushing back is one of the most important things someone can do. It's a sign of a healthy team. So how can you make it feel better?

What if, instead of pushing back on the person, the whole team pushes back on the idea?

One of the things I learned from working with Scott Kubie was how to make worksheets that help my teams have important conversations. He does this all the time, and what's helpful about it is that instead of an individual asking questions and raising concerns, an external artifact is taking that on that burden. This makes pushing back a team activity, and keeps negative feelings to a minimum.

Here's a worksheet I made to evaluate new design ideas:

I work with the team to make this part of how we work, so that examining our ideas becomes a regular occurrence. That way, asking questions is normal and expected, not a discouragement.

I put things in the worksheet that I know will make the conversation more constructive and give me the answers I'm looking for. For example, I made a big area for user needs, because if we don't know what they are, I want that to be obvious. I do all this to instill these values in the larger team. Eventually, they become part of how we work.

What's important about this idea:

  • Asking the questions as a team. Get things out of the realm of two people disagreeing with each other.

  • Capturing the conversation somewhere. Most of my teams are remote so I share my screen and fill this out while we talk. We need to see what we’re agreeing to.

  • Adapting it to your situation. The questions my team asks may not the ones your team needs to ask. Make this activity your own.

  • Acting on what you learn. If you see that you don't know much about user needs, plan some research to learn about them.

What's NOT important about this idea:

  • Calling it a worksheet. Reframing the conversation is what's most valuable, doesn't matter what you call it.

  • Making it a PDF. The form doesn't matter. These questions could be part of your acceptance criteria or a step you take during backlog refinement.

You can download this worksheet yourself, or make a copy on Figma that you can adapt for your team.

You should invite everyone to your design critique

I recently attended a workshop on design leadership by Mia Blume where she described the difference between feedback and critique. She defines feedback as a quick, one-way reaction often grounded in opinion. Critique, she says, is critical dialogue grounded in objectives that helps us understand design decisions.

Unsurprisingly, most designers I've met want as little feedback as possible. It makes sense. The one-way nature of feedback doesn't give designers the time or space to provide context or articulate their decisions.

Meanwhile, people who don't have "Designer" in their job title are forced to make changes to design through feedback. Design isn't their craft, but they're heavily invested in the outcome. In fact, their jobs may depend on it.

When I plan a critique, I include Business Analysts, Product Owners, Subject Matter Experts, and Engineers along with Designers. I coach them on how to talk about design and give them guidelines to follow. Everyone learns from each other. Designers gain a better understanding of the business constraints. Engineers share technical ideas and limitations. All of this makes the critique more effective.

Here's what's on my screen during a remote design critique. I send links to the design in advance so that people can ask questions and start dialog even when there isn't a gap in the conversation.

These are the guidelines I give critique participants, building on what I learned from Mia Blume (take a workshop from her if you can!):

  • Let everyone participate. Every perspective on this call is important.

  • Ask questions if you’re unsure why something is the way it is.

  • Speak from objectives. Avoid phrases like “I don’t like that”.

  • Dig into the details. This is the time to talk through the nuances of word choice, button labels, error handling and more.

The whole team is responsible for what we create. By including them in the process, everyone has the opportunity to shape the design and the product is stronger as a result.

Practical content strategy: making the journey

This piece was originally published on the GatherContent blog.

I love the strategy part of content strategy. High-level planning makes projects more purposeful. It helps us figure out what we should be doing and informs how we do it. But a plan has to be carried out to be worth anything, otherwise it's just a collection of ideas.

A couple of years ago, my brother and a few of his friends took a bicycle trip across the United States. It's a journey of 3800 miles, so a lot of planning went into it. He researched the right equipment, planned a route, and talked with people who had done it before.

However, until he actually got on his bike and started his journey west from the East Coast, his planning meant very little. Once he and his friends dipped their front tires in the Pacific Ocean after weeks of riding, their plan was completely validated.

Content strategy is like that. You never want the contribution you make to your company or client to be limited to a stack of deliverables. It feels good to make a plan at the beginning of a project, but no matter how beautiful, detailed, or thought-out your deliverables are, if they don't shape the website, app, or product you're building, they're worth very little. That's why content strategy has to be practical.

Here’s a framework for practical content strategy. It starts with clarity, and as the project moves forward, communication, collaboration, and creation help you maintain that clarity.


Maybe your strategy doesn't take hold because the people you’re working with aren't on board. When this happens, it can often be because it's still your strategy. If you want the strategy to work, your co-workers or clients need to feel like they own it. It needs to be their strategy.

Clarity helps everyone see the strategy in the same light. Show people how the strategy benefits them. Demonstrate their role in carrying out the plan. People won't truly support something until they understand it, so make things as clear as possible.

Your clients/co-workers/employers/stakeholders/team need to feel like they're shaping the strategy, even if you're doing most of the work. Involve them, build consensus, then make sure that consensus is clear.


Communicating the strategy requires just as much thought and intention as the strategy itself. Remember, it's not about what works for you, it's about what works for your audience. Maybe you love having your strategy in a nicely formatted text document, but if you're communicating with a busy executive, chances are that document will get ignored at best and misinterpreted at worst.

Watch what works, and adapt the way you communicate the strategy. If the people you're working with respond well to snappy slideshows, put one together. If they enjoy a visual diagram or a business model canvas, make one.

I often use mindmaps to capture information during meetings and document their relationships.

Communication goes both ways, so be sure listening is part of your process. Listening to your stakeholders won't just help them trust you, it will strengthen your strategy. Their questions and concerns will help you clearly see the problems your strategy is meant to solve.


Even in-house content strategists suffer from seeing themselves as the experts who are there to do great work, then present that work to the stakeholders. For agency strategists, that kind of behavior is often built into the workflow.

However, this comes with a big risk. What if you spend hours creating models and templates, then the people you're presenting to don't like them? It's frustrating, it feels like a big setback, and you'll end up incorporating their feedback anyway. Why not flip the process around?

Invite your stakeholders to help you with strategy-defining documents and deliverables before that final presentation. When you need their approval down the road, they'll feel like they're approving their own work because they helped you create it.

Worksheets like this one help your stakeholders get involved while strengthening your strategic perspective.


When your strategy leads to real things that people can read, interact with, and buy, the best way to make sure everyone is following the plan is to help create those things.

I'm not saying you have to write every article or edit every page, but humans have trouble following even the clearest plans. When you help create the things you planned for, you're perfectly positioned to make sure everyone is sticking to the strategy.

If your strategy includes a style guide or a content pattern library, time spent on creation is an invaluable way to strengthen that documentation. Your hands-on work will reveal holes and edge cases you wouldn't have found otherwise.

Whether you call yourself a strategist or not, strategy is a necessity. But creating a strategy isn't enough. Putting it into practice has to be a big part of your skill set.

The projects we work on can be big, frustrating, and messy. But when your strategy helps people in real, practical ways, it's all worth it.

So don't just plan your content journey. Finish strong.

Find your people

Here I am, yet again, asking my co-workers a question that could come off as confrontational. I do this constantly during meetings, usually without realizing it. 

"Doesn't that feel misleading?" I ask the group, with some conviction. We were discussing interface copy for a new piece of software.

They take a moment to consider my perspective, and that moment feels pretty lonely. Speaking up at times like this isn't easy, but it's important.

What did I feel was misleading? The words. I care about words quite a bit. Thankfully, throughout my career so far, team members usually come to appreciate this sensitivity. We build better stuff as a result.

Apps, websites, and other digital products, mainly communicate using words. Words have the power to encourage, hurt, educate, sell, persuade, insult, inform, and more. Every team designing and building digital experiences should care about the words. Hopefully, they hire someone to care about the words professionally. For most of my career, that someone has been me.

No matter the job title, I feel like I’m always doing the same thing: I help people figure out what they want to say, then find a way to say it. Sure, sometimes I say it with images, video, or audio, but most of the time I use words.

The content conversation

The people who dedicate their careers to caring about the words are my people. When I first started doing this work, most of these people were calling themselves content strategists. I began to follow them on Twitter, read their books, share their articles, and learn from them as much as I could. Without the work of people like Kristina Halvorson, Nicole Fenton, Erin Kissane, and Tiffani Jones-Brown, I wouldn't have been able to get into this field at all.

In Spring of 2014, I attended Confab, the content strategy conference. Before the conference, they put out a call for speakers to give 5-minute lightning talks, and I wrote up a proposal. To my surprise, they invited me to give one. Afterward, so many kind people talked to me about my ideas and encouraged me to keep sharing them.

Here I am at Confab, talking about how to comfort stakeholders during a project.

Here I am at Confab, talking about how to comfort stakeholders during a project.

That's when I became aware of just how wonderful it can be to have a two-way conversation with someone who gets your work. Someone who's been where you've been. Someone who cares about the words just as much as you do.

Since that first Confab I've spoken at more conferences and I've met a lot more people, but I keep coming back to the content conversation and those who take part in it. I've found my people, and I want to keep learning from them.

As a white male from the Midwest, the content conversation has helped me learn from the perspectives of those who don't share that background. I'm so grateful for the people who've helped me see the challenges they face. Challenges that, before talking with them, I wasn't even aware of or sensitive to.

I've also found so much value in connecting with people who have different opinions about content work. Whether we're talking about word choice or methodology, it's invaluable to hear from someone who doesn't see it my way. It's not always fun or enjoyable to have these conversations, but my work has gotten better as a result.

The diversity of our field is a strength, not a weakness. However, the latest job titles and buzzwords in our industry push us toward a false feeling of separation.

While we may use different titles to describe our work, titles say very little about what we're interested in or passionate about. A content strategist might really need to have the word "content" in her title because she needs people to know she doesn't just care about words, but images and video as well. I need "user experience" in my current title because I need to be involved in projects early as a member of the design team.

Better content experiences

Since our work is so varied and unique for each person, what's our identity?

Regardless of the titles, the thing that pulls us all together is a belief that communication should be human, that language should build trust, and that we can use words to build better experiences and ultimately a better world.

While these ideals resonate with me, there's friction when I talk with someone who doesn't quite see it this way. They may be interested in harnessing the power of language, but their terms betray their motives. They plot "campaigns" and they've identified certain "targets" they'd like to "blast." If you find yourself captured by this type of content on the web, you're not imprisoned, but you'll have a hard time finding your way out.

However, the people who create misleading and unfriendly content aren't monsters. They need our help. We need to go beyond pointing out how awful it is. We can show how putting more effort into the content of that newsletter and making it worth the reader's time will actually result in a more loyal, engaged audience. Doing this is hard, but it's also worthwhile.

Jonathon Colman gave a great keynote at Confab Central this year. He talked about the wicked problems our world faces, and how it's hard for humans to deal with them. These problems are so wicked they seem impossible to solve.

He also left us with inspiration: We can use our skills and abilities to solve real problems. We can improve life for the people around us. We can make an impact on our world. I'm thankful for Jonathon and other members of this community who've helped me see that.

Community and encouragement

Content work is often thankless. It can be frustrating. It can feel like no one around you shares your ideals or thinks they're worth working toward. But that's what makes community so important.

So far, I've been shying away from calling the work we do "content strategy," because I think and hope this conversation is bigger than a single term or job title. The content conversation is about how people experience content, whether it's an error message in an app or a series of articles on an enterprise website. We need to realize that when we use words to build better experiences, we're all working toward the same thing.

At Confab Central this year, I met a lot of people who were doing content work with software just like me. I started a group on Slack so we could keep learning from each other. It's a small group so far, but it's been a great way to keep the conversation going. Here are few of the things we've discussed recently:

  • How to test content for usability

  • Writing humane Privacy Policies and Terms of Use

  • Portfolios for content professionals

We'd love to see it grow beyond the software focus it has right now, to include anyone who's interested in the user experience of content.

So how about it? Want to join the conversation?

Whether you join the Slack group or not, I encourage you to find your people and connect with a community. The work we do gets so much better when we help each other.

Thanks to Megan Whalin for her help editing this article.

A written record

One of the key components of every project I’ve worked on is consensus.

I’m not talking about consensus of opinion, although that’s great if you can get it. What I’m talking about is consensus of action: What’s the problem we’re trying to solve? What did we decide to do? Why are we doing it that way?

These conversations can be tough, but they’re important. They move the project forward. They’re a big part of the design process.

As tough as the conversations can be, having them over and over again is even tougher. Sure, it’s great to refine ideas, but at a certain point, your team has to embrace the solution you’ve chosen and get to work.

Meeting notes and project managements tools help keep a record of the conversation, but often, they aren’t an effective way to quickly understand design decisions. Style guides and documentation do a better job summarizing that information, but they usually appear too late in the project to help you build whatever you’re building.

What I’ve been trying recently is something in the middle. A living, changing, useful, consensus. It will look different for each project because the consensus depends on your goals and constraints.

Here are a few examples:

  • After analyzing user research with a co-worker, I transferred the contents of the whiteboard we used to a Trello board. Since the team is largely remote, the Trello board became the place where we kept refining and adding to our analysis. When we showed our research to other members of the team, the board became a valuable reference point.

  • While designing a website for a small non-profit, I sketched out the ideas that came up during a lunch meeting. My notes included a low fidelity wireframe, a rough voice and tone guide, message hierarchy, and a preliminary information architecture. After the meeting, I snapped a photo of the pages and emailed them to the group so they could use them during the next design iteration.

  • For a project that involved lots of interface writing and group meetings for approval, I created a content wiki for the project. We use it to reference decisions we’ve made as a group along with some reuseable boilerplate content. Since this project involved modifying a lot of existing copy, I also used the wiki to keep a running record of every content change we’ve made.

There are a lot of different ways to keep a written record, but a record isn’t the least bit valuable if nobody sees it. That’s why it’s up to you to keep referencing it. Keep pulling it out. Keep sending the link. Keep sharing your screen and walking people through it.

What I’ve found is that over time, the team will start to internalize the design decisions. If you’ve ever felt like the only person who understands what the group should be doing, that says more about you than it does about the people you’re working with. Give them a written record, point them toward it constantly, and soon they’ll be defending design decisions right along with you.

Work that touches

I can’t physically touch my work.

Well I could touch it, but it wouldn’t mean anything.

I could find the location of the server I’m working on, drive to the building, pull out one of the hard drives, remove the disk, and run my finger along it. The thing is, that wouldn’t tell me anything meaningful.

Those of us who build websites, software, and other digital products have to experience our work digitally through the devices we use.

So many people who work with technology have hobbies that are tactile. A previous co-worker started a miniature farm; he and his wife have a garden, raise chickens, built fencing for a pasture, and bought a cow. A developer I know learns everything he can about cooking. Another co-worker roasts his own coffee. Working in the digital space causes us to crave work we can actually touch.

Maybe we’re also craving work that touches us. Our work can’t touch us physically, but it can touch us emotionally. This is why I’m a fan of people like Aaron Walter and Nicole Jones. They recognize the power of creating something that isn’t just useful, it’s personal.

Our users have come to expect this, and the products that make it a habit are rewarded with something money can’t buy: memorability.

Whether it’s the transparent Letterpress release notes, Grubhub’s loyalty game that gives out free treats, or SplatF’s playful pagination, designers are constantly finding new ways to touch people.

We may not be able to touch our work, but that doesn’t mean it can’t touch us.

On reading well

For a lot of us, reading takes up a huge part of the day. I’m on a remote team, so when someone at work wants to tell me something, I usually read it. Reading is constant. It’s how words on the screen get inside my head. It’s easy. Second-nature.

Here’s the problem: I don’t think I do it well enough.

Reading is a whole lot like listening.

We can’t make great stuff if we don’t listen. We have to listen to our users, our coworkers, our clients, and our leaders. Listening well creates an exceptional experience. Listening poorly can make people despise, or, even worse, ignore you.

If listening and reading are so similar, why do we approach them so differently?

When we read, we’re typically in a hurry. We skim through emails and scroll through conversations looking for what’s important. How would you feel if someone you were talking to acted completely uninterested until they felt like you were saying something interesting? Because we have the advantage of not being seen by the author when we’re reading something, our behavior is different.

What if you were fully invested in everything you read? What if you maintained eye contact with your email?

While it may sound time-consuming, I’m willing to bet it would save you time every day. If you committed to reading with focus, you’d click fewer links on Twitter, your email replies would be more helpful and you’d have more accurate information. You’d also be less likely to overload yourself with distractions.

It’s always more effective to do something purposefully. Even something as common as reading.