Category: Designing

Tool builders

August 15th, 2026
July 14, 2024 @ 2:29pm – San Francisco, CA

A computer is… the most remarkable tool that we’ve ever come up with. – Steve Jobs

Beware brand-new time-sucking beta-rollout crap. – Bruce Sterling

Right now everyone I know at my job at a software company is building things, including tools. A few years ago, a designer might have found some spare time to code up a plugin that helped to speed up a manual workflow. Now they are pushing code to production and creating bespoke apps. All you need are some agents and some agency.

One type of tool I’ve noticed a lot of people using and creating are “skills”. Skills don’t really take any technical skill to make. But they are useful. They “teach Claude how to complete specific tasks in a repeatable way, whether that’s creating documents with your company’s brand guidelines, analyzing data using your organization’s specific workflows, or automating personal tasks.”

Some skills are developed and used privately. For example, another designer told me about a skill they made to turn any text into something that sounds like something they would say. Other skills are shared out publicly, so that lots of people can use them, like a whole marketing team or the entire company.

Skills that are designed for many face the same usability issues that any type of software has. The developer simply can’t know everything about the “user”, or how they will end up using their program.

In most cases this mismatch or misunderstanding of mental models results in sub-par user experiences, wasted time and general confusion. Users might send emails, stop using it, or worst, suffer in silence. But by talking to users, testing, making smart assumptions and iterating, many of these issues can be resolved and avoided. It’s not easy, but it’s not rocket science either.

With the skills and other new tools we make, we must do the same. Even if there’s only one user. It’s the users who are the ones who are needed to actually use, test, stress and push the builders to make improvements that meet their needs.

Are you building something? Consider:
- The whole world might not need access to your tool straight away. Roll it out slowly, or test with small, private groups of people.
- Make it as easy as possible to get feedback. Better yet, sit down with someone who’s actually using your tool and listen and watch how they use it.
- Allow healthy competition. Great software wouldn’t exist if we stopped after building one messaging app, to-do list or browser.
- Sometimes it’s better to buy. Even a company like Google, filled with some of the best internal tools (and tool builders) still relies on software built by other professionals.
- The whole world might not need access to your tool straight away. Roll it out slowly, or test with small, private groups of people.
- Make it as easy as possible to get feedback. Better yet, sit down with someone who’s actually using your tool and listen and watch how they use it.
- Allow healthy competition. Great software wouldn’t exist if we stopped after building one messaging app, to-do list or browser.
- Sometimes it’s better to buy. Even a company like Google, filled with some of the best internal tools (and tool builders) still relies on software built by other professionals.
We shouldn’t put up with broken, inferior tools. Let’s make sure we’re not building more tools for other people to put up with too.
Designing like a spreadsheet

November 14th, 2025
November 1, 2025 @ 5:56pm – Porepunkah, Australia

Nudge. Change position. Change label. Undo. Redo. You hit a wall. You think about deleting everything and starting from scratch.

Then, an idea hits!

You race after it, leaving a stream of frames and layers behind you. Looking over your canvas filled with colourful shapes, you feel like you’ve really diverged in a creative way.

But have you actually made progress? What decisions did you make exactly? And are you any closer to a solution? Often, it’s not clear. And sometimes there’s a sinking feeling that you’ve actually gone backwards.

This random, slightly automatic way of designing can make it difficult to feel confident about what you’ve made, and can be painful for your collaborators. Engineers can’t find the ‘latest’ design and design crits and reviews can suffer from murky rationale. Not great.

A method to the madness

Inspired by another designer, who was much more methodical and measured than me, I started to experiment with a different way of working.

It looked something like this:

Each new approach is labelled (eg. “Full width panel). Variations or iterations related to it are also labelled and grouped together.
Then, when you’re ready, you create another direction and branch into related solutions from there.

Why this worked for me

At the time, I had started to work on product experiments, usually described as “growth design”. This meant I was thinking about smaller changes to workflows that could be built and tested rapidly.

Every solution also required a strong prediction or bet about how it would move a metric, expressed as something like “If we do X, then Y will happen, because X”.

Using this structure, I could organise my design file like a spreadsheet, with each hypothesis followed by a series of ideas. Once I felt I had exhausted that line of thinking, I moved onto a different hypothesis and another “row” of executions.

I remember reading about how designers at Spotify worked in a similar way. They called it “thoughtful execution”. Spotify designer Annina Koskinen explains why it’s important to explore multiple hypotheses (rows) and multiple executions (cells).

“Any problem or opportunity can be addressed in multiple different ways with varying results. That’s why it’s important to create multiple hypotheses per opportunity to see which one leads to the most desirable results. Each of the hypotheses can have several solution executions, so you can’t prove or disprove a hypothesis by just trying out one design solution.”

Aside from being a helpful way to organise and keep track of experiment solutions, I noticed a few other benefits:

1. More creativity

We have funny rules in our heads about what counts as creativity. For me, I thought I had to be kind of messy and impulsive to find these lightbulb moments. I don’t think that’s true. Sometimes a little more constraint can force us to think out of the box (like the repetition of crazy 8’s).

2. More buy-in

Working from goal to hypothesis to solution gave me a chain of reasoning that helped a lot when I was presenting work to stakeholders. It’s easier to gain consensus progressively, at each of these stages (a bit like going from lo-fi to hi-fi). It can be much harder to find agreement when we present a piece of work that has a lot of different ideas and assumptions baked into it.

3. More intentionality

By labelling screens with a “why” (hypothesis) or a “how” (execution), I’m forcing myself to ask:
- What’s actually different here?
- What problem am I trying to solve that the last one didn’t?
- What am I actually exploring here? What do I want to see?
That little pause and questioning can help prevent you from doing and re-doing the same thing over and over.

With a bit of structure in place, it makes it easier to work effectively with tools like Gemini. Gemini can help suggest new solutions for existing hypotheses or generate altogether new hypotheses you may not have thought of.

Putting it to work

In general, I’ve enjoyed less chaos in my Figma files while keeping (I think) my creativity intact. So if you’ve ever felt yourself spinning wheels, re-doing stuff, losing track of decisions, try out this method.

Most of us where I work at Xero are designing complex tools and workflows with lots of moving parts, and we don’t have the need to test different dimensions in this way. But if you’re designing more specific changes or in a high-traffic space like a check-out flow, designing a bit more like spreadsheet might work for you.
Is this co-design?

October 24th, 2025
December 29, 2023 @ 7:01pm – Jiaoxi, Taiwan

When we set out to co-design, we’re usually intending to get clear on a strategy or approach, find alignment across different groups and discover some new ideas together. If we’re putting together a formal workshop, we might plan, re-plan, create activities and facilitate the best we can.

And often these types of things work well. But the expectations don’t always match reality. Ideas can get a bit lost in translation. Some participants invariably feel left out, or misunderstood. And worse, the designer might end up creating something altogether different. It’s like the workshop never happened.

For some of those reasons, it’s natural for a designer to want to work in smaller groups, or by themselves, avoiding this way of working entirely. There’s less overhead and you can move faster if it’s just you and some focus time right? But less collaboration doesn’t work great either. Whenever I’m designing alone for too long or with limited input from other collaborators, I hit a dead end pretty quickly.

No one should design like this, even if it feels easier or more comfortable in the short term. I often think of this quote (now five years old) from Bob Baxley, reflecting on Apple’s review-heavy design culture: “If you ever found yourself sitting at your desk by yourself with your headphones on, stressing ’cause you felt like you had to figure it out on your own, something was really broken.”

Meet me halfway?

To make co-design more palatable, effective and integrated into our ways of working, we need something to fill that middle ground, somewhere between intensive multi-day workshops and flying solo.

Recently, I found myself in a cross-functional group that had formed to help with product growth. We wanted to test out a lot of little experiments and see if any helped customers to get onboarded and set-up faster. This shared goal had given us valuable alignment to begin with, but we still needed to decide what experiments to run and how they should work. We had limited time and a big backlog of experiments to flesh out. How were we going to work together?

Once or twice a week, we’d come together to ‘frame’ or ‘shape’ an experiment. We’d discuss the problem it would solve, risks and a few possible approaches. It was never longer than an hour, and it was purposefully unstructured. There might be some ideation or diagraming or maybe we’d spend most the session on the right problem to solve.

Initially, I found this working session really frustrating. I’d think, shouldn’t the designer be doing this? How can we start to design without exactly understanding the problem? There wasn’t any time to optimise or improve the activities. I had the typical fear (of designers) that we were rushing into solutions, and we were! But we also needed to agree (or disagree) and commit, so we could move onto the next experiment and keep moving.

But slowly, I started to see some benefits. When it came time for me to actually design something, I was no longer starting with a blank slate. Many of the edge cases that would have me spinning wheels had already been resolved. And design reviews were more effective, since everyone had shared context and had already contributed significantly to the concept. I didn’t feel like I was shouting down a one-way telephone line.

Why did it work?

I think this sort of framing activity worked well for us because:
- Everyone involved was responsible for driving the same goal
- We’d already prioritized the rough idea, so we could focus purely on the how rather than the why
- Each experiment was scoped to no more than two weeks to build, so there was a natural expectation for designing to be similarly fast
But most importantly, it succeeded because we allowed it to, without forcing it. If this was ‘co-design’, we never labelled it such. We need to allow co-designing to express in ways that are appropriate to your particular team or project. If you’re designing a new product from scratch, co-design will likely look very different. And that’s ok! It’s easy to get attached to how you think alignment and agreement should look. But if we’re too rigid in how we expect collaboration to happen, it probably won’t.
Working well with others

September 14th, 2025
September 4, 2025 @ 11:47am – Melbourne, Australia

“A huge percentage of the stuff that I tend to be automatically certain of is, it turns out, totally wrong and deluded.”
— David Foster Wallace

Whether you are making shoes, advertisements about shoes or shoe-making software, it’s likely the work is getting done in a group or a team.

Since 2020, this way of working has become especially important. Engineers and designers can no longer reliably chat at a desk or gather around a whiteboard. Those conversations have migrated online to collaborative software, like Miro and Figma.

If you’re used to working alone, it can be overwhelming to see all this work in progress. Miro boards filled with sticky notes, spaghetti diagrams, screenshots and other design detritus. What used to be private thinking is now facilitated in real-time workshops, with dozens of stakeholders calling in, watching, listening and co-designing together.

I resisted this type of collaboration for a long time.

I was critical of workshops and dismissed them as “UX theatre”. I thought they were inefficient and believed there was better ways to use my time. I didn’t think stakeholder management was my job. I was wary of politics, group think and other barriers to creativity. And when I had no other choice, I turned my criticism inward, lamenting my own facilitation skills or introversion. I thought, maybe I’d like collaboration if I was actually good at it.

There might have been some truth to these concerns. But what if it was less about collaboration being a mess, and more about my own need to be perfect?

Anti-teamwork

A perfectionist is usually defined as someone who has set high standards for themselves or others. At their core, they need to look good and be right. And at first glance, a perfectionist in the team will look like and sound like a normal person. They’ll bring their skills, help out and try to work together. But because of this strong, often unconscious need, they tend to prevent, rather than encourage healthy collaboration.

Firstly, a perfectionist cares more about how they look, rather than the shared goal of the team. They’ll often lose sight of the overall goal, and instead tend to focus on little things that don’t really make much difference.

The perfectionist is usually driven by a harsh ‘inner critic’ that nags and nitpicks them hundreds of times before they critique or blame another person. But when they do, harsh criticism will make their team feel judged, shamed and less likely to share ideas. Hypocritically, a perfectionist can’t bear to be criticized.

A perfectionist thinks they are right. This rigid conviction comes at the cost of creativity, listening and general respect for others. If you believe you are right about something, why listen to someone else? Conviction taken to extremes is behind every totalitarian regime and fundamentalist religion. Due to their predictable righteousness, a perfectionist will struggle to sit with uncertainty, ambiguity without an “irritable reaching for facts and reason.”¹

A perfectionist can’t handle being ordinary. They think in black and white terms; their output is trash that needs to be exceptional. They live in a fantasy world and need to return to reality, where the rest of their team is waiting. Marie-Louise Von Franz connects this attitude with a “sudden-fall” dream, which she says “generally coincide with outer, deep disappointment when one is suddenly faced with naked reality as it is.”²

Lastly, a perfectionist doesn’t know how to fail. If something doesn’t turn out how they planned, they blame or find ways to avoid responsibility. Without owning (and learning) from these mistakes, they have failed to fail, or what I’m coining inauthentic failing. They’d be better off to “get back up… to celebrate behaving like a human—however imperfectly—and fully embrace the pursuit that you’ve embarked on.”³

It’s easy to wave off perfectionist tendencies if you’ve got them. I’d filed most of mine under positive sounding interview answers like attention to detail, working too hard or caring a bit too much.

Collaboration can be chaotic. For a perfectionist, this collaborative world can feel like hell and they naturally want to defend against it viciously. That’s where all the ranting, blaming and burning the midnight oil comes from.

But rather than blame brainstorming or lame ice-breakers, I would have been better off noticing my own perfectionism – and how it makes collaboration nearly impossible.

To truly collaborate, and to actually get things done, one must accept the messy Miro board, the antithesis of perfection, the ordinary, imperfect nature of life itself.
1. https://en.wikipedia.org/wiki/Negative_capability ↩︎
2. Marie-Louise von Franz, The Way of the Dream: Conversations on Jungian Dream Interpretation ↩︎
3. Marcus Aurelius, Meditations ↩︎
Light pollution

July 19th, 2025
July 18, 2025 @ 12:54pm – Melbourne, Australia

“The cave you fear to enter holds the treasure you seek.” – Joseph Campbell

“We have to acknowledge that we hate those things and only those things in the world that we first hate in ourselves.” – Ken Wilber

If you look up at the night sky in a city, you’ll see a couple of stars. There’s the constellations you’re familiar with, and a few others here and there. You may have seen the sky full of stars, but that’s probably not the sky that you experience most of the time. It’s limited, but it’s your sky. In a similar way, we are habitually identified with a certain type of consciousness, our ego. This is the attitude, thoughts, beliefs, that we have grown up with and grown used to.

It’s been developed for good reasons, because an ego helps us to relate with others and get things done in society. But because of how the ego is developed, unconsciously, and in response to stuff that happens in childhood, it is naturally going to be a little bit narrow. As we’ve grown up, we’ve made all these little choices about what is good, what is bad, and so on. It’s been in our interest to try our best, but we’re always operating off limited information. So our personalities end up a bit limited too.

The ego is missing some stuff. It’s probably over-indexed on certain things, under-cooked in other areas. It’s a house designed with very little oversight. Some of us spent most of the time designing a sleek infinity swimming pool. Others spent a lot of time getting the kitchen right, but forgot to plumb the bathroom. Some rooms are lit up with seductive mood lighting, others have no electricity.

In this imperfect process, as we double down on the things we believe to be important, we’re also doing a lot of shoving away of the things that are deemed dangerous or difficult, or that don’t particularly help us to navigate the world.

This stuff becomes what Jung called the Shadow, the “dumping ground for all those characteristics of our personality that we disown”¹. Deborah Stewart, of This Jungian Life podcast, describes it as “the underbelly of the ego…that’s hard to look at… hard to feel really connected to…loaded with feelings of disgust, profound discomfort, and a feeling of wanting to push it away.”²

Although the ego and the shadow have such differing relationships with the conscious mind, they both constrain us. We are constrained by identification with some things and rejection of other things.

The Constraint of the Ego

I was collaging with some friends. I hadn’t made a collage in a long time. I thought it would be easy, but I found it very difficult to create a composition that I liked. I was selecting and cutting out images from magazines. I thought I was being clever. I thought I had a good eye and aesthetic. I’m a designer. I should be good at this.

But I was stuck. I was jiggling around pieces like a jigsaw puzzle. Nothing was fitting together. My friend D saw this and asked what I was doing. I said “I’m trying to move it around so it looks right.” She replied, “What’s right? It’s a collage.” She had a point. What did right mean? And why was that important? Why not just have fun? Why not make something silly, or shocking, or bright turquoise? No, for me, I need to get it right.

A few pieces of ripped paper shone a bright light on what’s habitual for me, what I identify with. The need to be careful, considerate, aesthetic, minimal. I pick pleasing things. I take care and attention and time. That’s my ego.

There’s no right way to do a collage, of course. That’s like saying there’s a right way to make a song. And I got more interesting results when I used colors that I don’t normally use, or if I used my left hand, or closed my eyes, or if I ripped things really quickly, or if I ripped instead of using scissors.

The Constraint of the Shadow

When I buy something at the supermarket, I don’t make small talk. I place my things down on the counter, my phone bristling ready to pay. I move on as quickly as I can. I want to be efficient. I don’t want unnecessary attention on me. I don’t want to slow down people behind me.

Now, sometimes, when I need coins for the laundry in my apartment building, I need to ask for change. It’s not possible to move by quietly like usual. I have to stop and say “Hey…” I have to ask someone to do something for me. In a way, I have to admit that I need help, or that I don’t have my life completely organized and together. Those are things that I would rather not look at directly. Things that my habitual side really can’t stand and pretends don’t exist. That’s my shadow.

And there’s a lot of defense mechanisms when I’m pushed into those shadow areas, even with something simple like asking for change. For some people it’s “hatred, disgust, avoidance, criticism, accusations, attacking.”³ In this case, I’ll get irritated. I’ll try and avoid it. I’ll roll my eyes. I’ll think about finding a machine to do this so I don’t have to think about it again. I’ll feel bad about holding up the line and apologize a lot.

Just like the ego constrained my collaging attempts, my shadow also prevents me from spontaneously asking for things.

There’s no need to blow up the ego, or to live out your shadow all at once. That would be reckless and dangerous. These functions have been carefully created for practical reasons. But we need to watch them closely. Watch how they shape our behaviour and most importantly how they constrain us into tight spaces.

We can try to stop squeezing ourselves between our (self-created) likes and dislikes. It’s not comfortable there and never will be. We need room to move. Like Viktor Frankl famously said, “between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.”

We can look up at the sky and we can say “hey, I kind of know this isn’t the full sky, right? I kind of know that light pollution is blocking some stuff. I know there might be more out there.”
1. Robert A. Johnson, Owning Your Own Shadow: Understanding the Dark Side of the Psyche ↩︎
2. Episode 55 – Identifying & Integrating the Personal Shadow,” This Jungian Life ↩︎
3. Episode 55 – Identifying & Integrating the Personal Shadow,” This Jungian Life ↩︎