Stop wasting money and make stakeholders happy with everyday storytelling

Ryan Bigge
12 min readOct 11, 2022

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A small investment in narrative can pay huge dividends

(Andy Healey co-authored this post, based on our 2022 Confab talk.)

Last summer, Andy Healey and I (Ryan Bigge) came across a Medium article that spoke to our (collective) souls: Slack is no place to write the Great American Novel. As author Kieran Snyder notes, “One of the most fundamental mistakes people make when sharing written information is choosing the wrong medium to share it.” In other words, your co-workers might appreciate a long email about a project update, but their eyes will glaze over at the same amount of content in Slack.

If you’re content designers like us, advice about where and how to communicate might seem obvious. But for many other UX people, the opposite is true. Pouring a novel’s worth of words into Slack is a prime example of how poor storytelling erodes the impact of your UX team. Another, harder to ignore example is a typical design review:

A line graph marked start / end on the x axis and good / bad on the y axis. The line’s progression indicates that the design review starts out fine, but quickly descends into bad due to missing context and feedback on the wrong things. The graph concludes with “no one leaves happy.”
A line graph showing a design review starting out well, then turning bad due to missing context which leads to feedback on the wrong things.

Forget about a smooth narrative arc. Too many design reviews are a drunken scribble of missing context, weird tangents, and byzantine plot points. Which means your team gets unhelpful feedback on the wrong things.

Sheer walls of text on Slack. Demolition derby design reviews. Taking inspiration from Lisa Maria Marquis, we call these everyday storytelling opportunities — moments where spending a small amount of time on narrative structure can pay huge dividends. And if your UX org isn’t great at everyday storytelling, it’s costing your company thousands of dollars every month.

That’s right: thousands.

Want to stop wasting money and make stakeholders happy? Keep reading.

We tell ourselves stories in order to get promoted

In October of 2019, Ryan was asked to oversee a new project at Shopify. The new thing was an extension of Shopify Capital, a service that lent money to merchants based on an algorithm. The idea went like this: what if Shopify lent brand new merchants $200 even if there wasn’t enough data to give them a traditional Shopify Capital loan? Turns out this wasn’t a terrible idea:

Screen grab of a Forbes article titled “Shopify wants to launch millions of small businesses and thinks $200 loans is the way.”
Screen grab of Forbes article about starter loans.

The final product used words, glorious words, to drive the user experience. But, as important, if not more important, everyday storytelling skills shaped those words into a successful project and launch. Skills such as:

  • Giving the product a non-stupid name
  • Leading content-first design reviews
  • Tailoring project updates to suit the target audience

Naming

Instead of putting a bunch of people in a room and letting them shout about their favourite name, Ryan tried a different approach. He sent out a survey to help the team to align on what they wanted the product name to accomplish, along with voting on descriptive and evocative names. As it turned out, no one could agree on a cool, evocative name. This probably happens more often than people realize, but usually there isn’t a pie chart to prove it:

Pie chart showing the results of a survey to determine the name for starter loans. Possible names included booster loan, seed loan, spark loan, and first-time loan.
Pie chart showing the voting breakdown for possible names.

Luckily, the team was able to align on a descriptive name — “starter loans.” (This was especially good news, since Shopify’s naming guidelines also recommend descriptive over evocative). Why put all this effort into naming a product, especially since it was an experiment? Well, because if you’re not careful, it’s really easy to pick a bad name. Satellite mode in Google Maps was almost called Bird Mode.

Two screen grabs that show Google’s uneven track record with naming products. The first is a tweet explaining how Satellite was almost called “Bird Mode” in Google Maps. The second is an information card from Google sheets introducing a feature called “people chips.”
Google has an uneven track record with naming products, as “bird mode” and “people chips” demonstrates.

As for people chips, well that’s a real actual thing.

Of course, not every product or feature needs a name. But when it does, it’s important to do it well. As you’ll see in a few paragraphs (aka foreshadowing) there were other, unanticipated benefits of good naming.

Content-first design reviews

Since starter loans was very content-driven, it made a lot of sense for the person driving the project to present updates during weekly design reviews. Ryan wasn’t perfect at this right away, probably because content designers are rarely asked to present project work. But after one or two meandering updates, he figured how to control, or at least steer, the narrative. This meant design reviews focused equally on visual and content fidelity. In this way, the refinement of content moved in lockstep with visual design. That meant content challenges weren’t left to the end, which improved the quality of content early and often

Bespoke project updates

Ryan was also able to tailor project updates based on channel, audience, and frequency. Weekly design reviews required less context as the project went on, while team-wide weekly updates via Slack were short bursts focused on how design milestones linked to product and engineering efforts. Once a month, the general manager was given a high-level update. Finally, after starter loans launched, Ryan gave a detailed recap to the entire Shopify Capital team at a live-streamed event. Each of these updates varied in length, context, and central focus, but they all leveraged everyday storytelling techniques to ensure the intended audience got what they needed.

Title slide for starter loans recap talk given by Ryan. The talk is titled “Start me up: why we created $200 loans.” In the bottom left corner of the slide is a Windows 95 start icon.
Title slide for starter loans recap talk given by Ryan.

As it turned out, everyday storytelling wasn’t just great for internal communications. When you have a clear, descriptive name for a product that has a clear and compelling story, you can compress that story down into five emojis.

Screen grab of a tweet from Shopify about starter loans, summarizing starter loans in five emojis: seed, water, sprout, seedling, and tree. “At the start of every business is a big idea that needs a little love to pick itself up and keep on growing and growing.”
Tweet showing a five emoji summary of starter loans.

The naming work Ryan did made it easier for the social media team to tell the starter loan story on a very different platform. And all that storytelling paid off — literally — with his first year end bonus. While that shouldn’t be the only success metric, storytelling for the win! As essayist Joan Didion famously wrote, “We tell ourselves stories in order to live.”

Well, we also tell ourselves stories in order to get promoted.

What’s the story, morning glory?

After Andy went from content designer to UX lead at Shopify, he gained a new perspective on the power of narrative. Last year, two designers that reported to him were getting ready to present at Fresheyes, a low-key weekly meeting for peer feedback. To protect their identities, let’s call them Designer1 and DesignerB. The day before Fresheyes, Andy asked them both if they wanted any support. DesignerB said yes, so Andy worked through a story template with them.

The result? Designer1 went first, showed some work in Figma, got asked lots of clarifying questions, and received some actionable and non-actionable feedback. Standard stuff. Then it was DesignerB’s turn. They started by telling everyone what they were going to share:

  • I’ll begin by giving you some context on what we’ll be looking at today
  • Then I’ll tell you the kind of feedback I need from you
  • The problem we’re solving
  • What the current experience is, and why we’re changing it
  • Then I’ll walk you through what we’ve been working on
  • I’ll explain how we’ll measure if it’s successful or not
  • And finally I’ll talk a bit about the next steps

Clear, concise, and engaging. The story they told answered 50% of the questions they would have been asked. This meant more time to gather impactful feedback. That session had a profound impact on the team and set a storytelling bar that inspired other designers to try and match. Afterwards, Designer1 told Andy that they’d felt like a novice designer presenting their work. Although Designer1 had done just fine, DesignerB demonstrated how a little bit of everyday storytelling goes a long way.

Screen grab of tweet from Ha Phan praising the value of storytelling in UX. “The thing that’s missed when people talk about storytelling is that good storytellers can break down complex problems in ways that make people care and understand. Good storytellers can bridge the mental model of systems and value. They know how to utilize markers in the story.”
Tweet from Hà Phan praising the value of storytelling in UX.

Good storytellers can break down complex problems in ways that make people care and understand. A clear story makes it easy for stakeholders to give useful feedback. Which in turn will help your team build a better product and to get it to market more quickly. Good storytellers also anticipate the questions their audience might ask:

  • Why are you showing me this?
  • What do you need from me?
  • How will we know if it works?

And they tweak their presentation based on audience: other designers versus stakeholders versus leadership — like Ryan did with starter loans. Which means fewer meetings and better results.

Storytelling maths

Now, as Ryan once said: “It’s hard to measure the value of good storytelling, but it’s very easy to show the cost of bad storytelling.” So let’s measure the easiest to evaluate factor, cost to time, by roughly calculating the cost of a design review. To keep it simple we’ll assume your designer has a salary of $100,000 per year, which is about $50 per hour. Add in a product manager, along with two stakeholders who earn a bit more (but are definitely worth it, wink-wink) and you’re at $300 for the review.

Slide showing the maths for four design review s. Cost the meeting is $300 and cost of implementing feedback is $400. Across four design reviews that adds up to $2,800.
Maths for four design reviews — $2,800.

After the meeting, your designer needs a full day to implement feedback. That’s another 8 hours, another $400. And since most projects require at least 4 design reviews to get sign off, you’re looking at a total cost of $2,800. Now, this is simplified example — many design reviews will have a content designer present, maybe a UX researcher or an engineer. And it assumes your company has a predictable and reliable digital delivery process that everyone has aligned on.

But when process goes awry, the potential for wasted money is shocking:

  • additional 6 week sprint needed to get approval ($)
  • team of engineers blocked for a week and unable to progress ($$)
  • designer getting difficult feedback and deciding to leave the company ($$$)
  • a new feature is too slow to market and customers move to a competitor ($$$$)

These kind of things can make or break an organization. But it doesn’t have to be this way. Let’s go back to the original example of 4 design reviews with a total cost of $2,800 — but at a company that has invested in everyday storytelling.

In this review, the designer uses Andy’s template and the people in the room provide focussed and actionable feedback. It still takes a day to implement that feedback, but everyone is aligned on what the next steps are. The team makes great progress. Instead of 4 reviews, they might only need 2.

Why? Well, the key problems are addressed directly rather than getting lost in the backwards and forwards of stakeholder hell. There’s no need to go back to the drawing board after several reviews as happens to some teams, because communication, and so the project moves forward faster. The cost just dropped 50% to $1,400. Cha-ching!

Plus you’ve established trust and credibility, so future reviews will go easier. Multiply those savings across the entire UX org, and you’ll quickly see that storytelling is a worthwhile investment.

How to Nurture Everyday Storytelling

By now you must be unbelievably excited about everyday storytelling. Hooray! Here are four things you can do to promote the habit at your company:

  • normalize it
  • practice it
  • scale it
  • enjoy it

Normalize it

When the Shopify UX blog went quiet in early 2018, Ryan decided to normalize storytelling by organizing a Hack Days writing marathon. He created some resources and offered typewriter support to anyone who wanted it. And in only two days, participants wrote 21 blog posts! Some were first drafts, but many were final, and all of them ended up getting published eventually. What better way to cultivate storytelling than by encouraging people to tell stories that matter to them?

Of course, your company might not offer Hack Days — so writing a blog post could be one of your annual craft goals instead. Heck, maybe your company doesn’t have a blog. In which case, you can fake it with an email newsletter sent to co-workers. Or just create a Google doc and share it. Or publish your NDA-approved thoughts publicly on Medium, like this.

Practice it

Shopify’s content design team had a variety of opportunities to practice everyday storytelling, from safe to intimating. Content critiques. Bi-weekly content design meetups. Company-wide Town Halls. Internal and external conferences. And any one of those venues might eventually inspire a blog post, like Gillian Massel’s article about content hierarchy.

There are also less obvious opportunities. Writing or editing a project brief. App release notes. Really, whenever you create or share information with someone, you can practice everyday storytelling.

Scale it

As your UX team grows, scaling storytelling becomes important. In 2018, Andy gave such fantastic talk about assumptions at Shopify’s UX Summit that people started asking him for storytelling advice. He put on multiple workshops in multiple cities — how to practise storytelling, the shape of good stories, how to keep calm in high stakes situations. He got great feedback, but the workshops weren’t sustainable, so he turned it into a series of short videos. That scaled.

Videos worked for Andy, but you could also use a slide deck, a google doc, or another method of your choosing. The key is to give everyone access to your everyday storytelling learnings, in a self-serve, easy to digest way.

Enjoy it

These and other resources were very helpful, but counterintuitively, by the spring of 2019, they were starting to backfire a bit. A sizeable number of content designers were becoming intimidated by the quality of presentations at our annual Content Design Summit and even at bi-weekly content meetups. This was not the intent of improving everyday storytelling skills. So Ryan and Andy decided to do something not at all intimidating and give the team a chance to practice ruining a presentation. Introducing: Worst. Presentation. Ever. A workshop where our content team could practise wrecking Keynote so they wouldn’t screw up when it really mattered.

A slide from the worst presentation ever workshop. It shows a variety of low resolution GeoCities era gifs.
worst. slide. ever.

We divided our group into teams, assigned a topic, and watched our content experts outdo themselves as they created intentionally awful talks. Every group was interrupted by laughter as they shared their worst efforts. And the exercise helped reinforce a 2022 study from the Institute of Fun that showed learning new things is 67% easier when it isn’t painful or boring.

While those horrible masterworks are trapped in a dusty corner of the cloud, the collective list of things to avoid survived:

  • too many words on a slide
  • tangents
  • speaking too quickly
  • poor contrast on slides
  • being patronizing
  • not prepared
  • poor timing (talk is too long)
  • title doesn’t match content of talk
  • being too insider-y
  • reading instead of presenting

If an hour-long workshop isn’t feasible, try starting a Slack thread of presentation pet peeves and create a worst ever Pecha Kucha. Remember: there are dozens of ways to wreck a presentation. The trick is finding the best way to capture and share them.

Storytelling across the org

Being at a fast-moving tech company can be disorientating and exhausting, but the flip side is an openness to initiative and new ideas. In case you couldn’t tell already, there isn’t a guidebook for everyday storytelling — we made it up as we went along. In fact, the official books on building strong teams through design operations are light on storytelling.

Screen grab of index from the book Org Design for Design Orgs showing that storytelling only has two entries.
Proof that storytelling advice is often missing in UX operations.

In an otherwise good book, the message is: storytelling is important, go figure it out for yourself. Which is a shame, because we see a lot of value in narrative — especially when you’re able to support the creation of overlapping and interconnected stories:

Diagram showing how stories can interconnect in a content design team.

This diagram of storytelling from above and below describes content design at Shopify, but there’s no reason it can’t be applied to your UX org as a whole. There are individual stories, project stories, stories about what it’s like to be a content designer, stories about the content team as a whole. Internal stories, external stories. Stories about how content design fits within UX. Stories within stories within stories. And the wonderful thing? These stories often reinforce each another.

Do everyday storytelling right, and your UX org will resemble an intricate masterpiece, like Inception. Do it wrong, and your UX org will turn into a confusing fiasco, like Tenet.

Storytelling played a huge role in the success of Shopify’s content design team. What about your UX team? Leave a comment or start a Twitter conversation with Andy or Ryan to learn how we can help your team get better at everyday storytelling.

Promotional tile for Ryan and Andy’s talk at Confab conference 2022 titled “Boost the value of your content team through storytelling.”
Ryan and Andy at Confab 2022!

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