Why it works series - An analysis of Whimsical’s user experience
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Why it works series – Whimsical’s User Experience

Woah! Experience Director, Greg, here and this is my first post in our fledgling Why it Works mini series. For my article, I thought I’d go uber-meta and take a look at the user experience of one of our favourite user experience tools, Whimsical.

Flight of whimsy

I have a leaning towards learning through play and creativity. I’ve grown up with technology and love so much about ways to be productive and efficient. But one particular area I’ve struggled with over the years is that mid-point between professional documentation and visual creativity. Humans are visual learners, a lot of what we learn as kids is from watching other people and seeing the world in action. Our memories are often visual and the more senses we use to experience a situation, the better we will remember it.

I suffer badly from Imposter Syndrome so I have often leant on more traditional academia as my ‘True North’, to the detriment of my more creative pursuits. A few years back, I decided to foster a working life that not only made space for creativity but actively encouraged and could demonstrate the benefits of it: drawing, visual expression, music, rhetoric, poetry – these aren’t just nice flourishes in our existence, they are the very essence of how we learn and evolve.

But what the heck is user experience and why should I care?

User Experience is a term that gets bandied about a lot these days, especially in tech circles. A former colleague of mine simply calls it ‘design’, and he’s right. Good design should be about beautifully crafting a solution to someone’s problems, making their life easier, better somehow. The challenge is that, all too often, ‘design’ is seen simply as making something look pretty or colourful – something purely superficial. For me, ‘user experience’ is simply about shifting the focus back on the person, the human at the centre of why we’re doing any of this. I’d rather solve someone’s problems than simply sell them a product. This also builds trust and loyalty – products come and go, relationships last longer.

Mkay, so what is Whimsical?

Whimsical calls itself ‘The Visual Workspace’, and I’m inclined to agree. They currently offer four core tools: flowcharts, wireframes, sticky notes and mind maps. Now, depending on your life choices, those might not sound particularly exciting but in my world those tools bridge the gap beautifully between extensive, abstract documentation; hard-core coding; and design tools like Photoshop or Illustrator. Each of which have a place, sure, but for too long there was something missing in my working life: a lightweight tool to help me communicate some complex ideas in an effective way. 

You may have heard the term show don’t tell – I could explain what your website will look like, comprehensively document what features it will have, how the pages will connect together, blah blah blah; but nothing quite hits the mark like a clear visual that neatly demonstrates all of these points, especially if I haven’t had to spend three weeks perfectly crafting something in Photoshop or coding a beta website only to find out it’s not quite what you were thinking. 

I had a professor once who liked to tell his students that there were only 10 different plots in all of fiction. Well, I’m here to tell you he was wrong. There is only one: “Who am I?”

– Miss Ritter, The Amazing Spider-Man

Who am I?

Whimsical cuts through the BS. It’s visual but not too fancy, it’s neat and digital but not too rigid. I am Goldilocks and this porridge is just right.

Image credit – Monika Grabkowska on Unsplash

The past few years have seen unprecedented growth in web apps – when was the last time you opened up the desktop version of Word? Hell, nah! Everyone uses Google Docs and the world is better for it. Why? Well, web apps are easy to distribute, generally collaborative, accessible and platform-agnostic. But abundance isn’t the same as quality and I’ve tried way too many of these new tools – most of them are trying too hard, a lot of them aren’t trying hard enough. I’m Goldilocks, remember? 

One of the things I appreciate about Whimsical is that they live their brand values. At Matchstick Creative we believe in the power of identity. It’s why we feel so strongly about tone of voice and why your brand isn’t simply your logo. Steve Schoeffel, co-founder of Whimsical, wrote a piece for one of my other brand crushes, Inside Design by InVision, about how important it was for them to define their identity, their core traits and values, before they did anything else. They aren’t trying to compete with the big guns: Adobe, Microsoft, Google or even Sketch. Their idea was ‘to make visual collaboration awesome.’ Their core tenets were speed, simplicity and beauty as they felt that those values were missing from the other tools on the market. They were right. Those values are exactly why I continue to choose Whimsical over other tools I’ve tried. They are why our Content Director and Founder, Ruth, loves any chance she gets to use Whimsical. *SPOILER ALERT* Ruth is not a UX Designer. 

Image credit – Kate Murray, Handled with Care Design

In our workshops, we often hear people say ‘I can’t draw!’, it’s usually accompanied by a sense of shame or that drawing is childish – grown-ups use words. Drawing is something we do as kids but are generally steered away from as we get older and ‘more professional’. Fuck that. Yes, drawing can make you feel vulnerable but it’s also something unique and personal – which is almost priceless IMHO. Whimsical helps people who don’t consider themselves designers to create professional visuals and sate those creative desires we all have but rarely feel empowered to pursue. Yes, I am the Experience Director but Ruth created the wireframes for our new website and they were absolutely perfect. I repeat once again, Ruth is not a UX Designer. How powerful is that?


Whimsical knows the value of user experience – their tools help other people create great user experiences. It’s what they do. Before founding Whimsical, Steve Schoeffel was a product designer and Kaspars Dancis was an application engineer. They understood the problems they were trying to solve because they had lived them, it’s who they were. 

An old friend

A good friend helps to steer you in the right direction if you’re feeling lost or anxious. Whimsical does this by making shortcuts obvious and visible. They often use the same shortcuts used by most of the common design tools. When I open up Whimsical, I just get started and crack on. I don’t need to learn how this software works, it’s second nature. 

Users don’t care about design for its own sake; they just want to get things done and get out. Normal people don’t love sitting at their computers.

–  Jakob Nielsen, Nielsen Norman Group

I want to add a new element, I hit ‘E’, I want to add text, I hit ‘T’. I hit ‘B’ for a button – you get the picture. Anything more complicated and there’s a handy search function. They know you can’t have a shortcut for everything so they focus on the most common elements and actions that people need in a particular context. The ancient Greeks had two words for time: chronos, the sequential passing of time; and kairos, the opportune time for action. Whimsical has put the effort into understanding what will be most useful in a particular time and place. This is hard to do and hard to do well. Whimsical makes things seamless and intuitive. Something you might not realise is that they optimise left-handed shortcuts, this blog post explains why, but you can probably see for yourself from this image.

Perfection is achieved, not when there is nothing more to add, but when there is nothing left to take away.

–  Antoine de Saint-Exupéry, French writer and aviator

Whimsical doesn’t have every font and colour combination under the sun, it doesn’t have every potential page element, shape, browser window, device frame – it has enough for you to make a point, to demonstrate a concept. It knows why it exists and it stays true to that.

Aside from the user interface, Whimsical shows their investment in user experience in other ways. Before Christmas, I received a refreshing email. Whimsical were choosing to put privacy first and were no longer going to use tools like Google Analytics to track every minute interaction by their users. In the tech world this is a big deal. It’s often said that Data is King but maybe Respect is Queen and as we step into an era where people are more discerning in their choices about which brands and services they support we might find that the king is dead. Vive la reine! (Long live the queen!)

What can you learn from Whimsical?

  • Know who you are – it’s easy to try and be everything to everyone and it might seem admirable but invariably without a sense of identity you end up being nothing to nobody. A bit of self-confidence goes a long way – you’re beautiful and unique, own it!
  • Be clear on your ‘why’ – Whimsical felt something was missing in the visual communication landscape, they had insight and direct experience of this so they had the authority to work on a solution. Where do you think you can make the biggest impact and why do you think that? A workshop might help…
  • Stay true to your values – this doesn’t mean be a stubborn mule but be authentic. Understand what motivates you and your team. Find out where your shared values are. Teams work best when they’re focused on a common goal.
  • Don’t be afraid to make the bold play – you might surprise yourself and everyone else. This isn’t about being reckless. A lot of people are afraid to use their voice, to share their opinions, their experience because it might be different to someone else who has the authority, the position of power. The people in charge aren’t always right. Adobe XD probably wouldn’t exist if it weren’t for young upstarts like Whimsical, Sketch and Marvel. You might not always be right but dust yourself off and try again. We have a mantra of Improvement, not perfection – Whimsical make little tweaks all the time.

Need a hand figuring all this shit out?

Speak to Greg or Ruth about one of our workshops and we can help steer you in the right direction. No pressure, no stress.