It starts back in 2015 — well, technically before then, but Skyscanner onwards was where my career really started to get interesting. I had just given up my role as a Senior UX Designer at Skyscanner to come work at a Barcelona startup of 12 people to lead design.

Fast forward to today and that startup I joined which had less than one year of runway is now worth $2.7B. I'd like to claim four-years-worth of hard work contributing towards that achievement.

From 12 to 750, now what?

With TravelPerk outgrowing its position as a startup, I began working with another Barcelona-based company looking to revolutionize the hospitality management sector — Amenitiz.

Working with three co-founders, I designed the first version of the product, supported with branding and marketing and worked with the team through their critical go-to-market stage.

Staying on for a couple of years as a product and design advisor gave me a great opportunity to see things evolve while continuing to play a part in supporting the companies growth. Amenitiz has since secured it's series A round and now employs more than 300 people globally.

Alongside advising Amenitiz, I took on the challenge of becoming an Executive, joining Boatim as their Chief Product Officer. Despite the fancy title, I was very much in the weeds each day working closely with our team of around 15. Along with our CMO, I helped set a vision, deliver our go-to-market strategy and did it all whilst still pushing pixels and managing our small product and engineering team. Talk about context switching — this was next-level, even for me.

Climbing the ladder

After a number of years building products from scratch I pursued an opportunity to work at a larger organization. With the tech org alone being almost 300 people, I joined the team to become highly focused on craft as a Lead Designer. I wanted to move away from management and see what life was like outside of the chaos of startups and the time-suck of people management.

My IC stint was short-loved and after only a few months I was promoted to Head of Design and later to Director of Product Design where I had the pleasure of leading an amazing team.

However, moving further and further away from the craft and focusing more on team culture, organizational structure and — let's be honest — managing all the politics that come with working in larger orgs, there was a large void forming in my professional life which I desperately wanted to fill. I learned a lot there as a manager and a leader but it's not what I set out to achieve working there.

That Goldilocks moment

After almost 3 years working as a Lead, Head of Design, and finally Director, I slid down a few rungs of the ladder to go work at Sona as a Senior Designer in a 50-person startup where I could focus on craft again.

It was a great experience working with a new tech stack in a new industry, however, that team quickly doubled within the year and after only 2 years the product was already pretty well established — to the point that the need to support legacy parts of the codebase were a real drain on product acceleration and innovation.

I had found myself in a startup, working day-in, day-out designing, speaking with customers and doing what I thought I wanted, but just like Goldilocks' porridge it just didn't feel right. On paper, I had found what I was looking for but there were some aspects that I was still seeking — but what were they?

Be clear with yourself

After countless conversations with my partner and some personal reflection, it was clear that what I was seeking was something even earlier stage. When I looked back at TravelPerk, Amenitiz, and Boatim I was working with teams who were under or had just broken double-figure head count.

In those experiences, I was thinking about sales, marketing, customer support, engineering, product, and of course design. As a designer, your job is to solve problems and create value for people both externally — your customers — but also internally. Design can play a pivotal role in supporting and growing out other functions and I felt that was a big piece that I was missing at Sona.

For example, when TravelPerk was launching new products for customers or looking for ways to optimize the customer support experience for our customers and our agents, I was able to play a very active role in leading and supporting those initiatives.

Perhaps those conversations with my partner and some self-reflection sent out a little something into the universe as it wasn't long until I received a message that would set the stage for my next career move.

Here we go again

So, here we are today, three months into my new role as founding designer at Pensero. How did I get here? Luck and good timing you could say.

Not actively looking for a role, I was approached by a former colleague, grabbed a coffee and had a few calls with his co-founder. Within a week or two, the very thing that I was looking for had just appeared right in front of me.

I arrived as the 7th person on the team, and of course, the only designer. I’m deeply involved in the product, committing to the codebase weekly, joining sales calls, supporting marketing efforts, and exploring our product-market fit. I have arrived.

After some time away from writing, I would really like to use this new chapter to catalogue my journey as a founding designer, now against a very different, AI-filled backdrop that has disrupted many industries and roles in the past year or so.

If you are reading this and would like to learn more about working in startups or would like me to focus future articles on specific topics, feel free to reach out and connect on LinkedIn.

Until then, have a great week!

Moving from an apartment to live in a van and downsizing my wardrobe was so refreshing. Similarly, downsizing my digital tools has simplified my life significantly.

Operating system

Starting off strong with a product which weaves itself into almost every aspect of my day — I have continued to find even more use cases for Raycast than before. Raycast has been a game-changer in simplifying my workflow. I'm using it daily to:

• Search for and capture design tickets (via Linear) without losing context or focus

• Find files and screenshots on the fly saving lots of time

• Grab various snippets from my clipboard history

• Translate on the fly

• Jump into meetings at lightning speed

• Stay focused on the task at hand

• Jump into daily notes with a key press

• Chatting with various AI agents

• Plus so much more...

Another core part of my daily operating system is of course a solid browser, and after being an early adopter, I am still a huge fan of the Arc browser. Reluctantly making the switch from Android to iPhone, I now appreciate a far more seamless handoff between devices. If you still haven't heard of Arc, it's definitely worth checking out.

Design tools

Still holding strong this year is Figma + FigJam. I am interested to see what the team at Penpot deliver over the coming months and years but with so many useful features, I am really enjoying being back in the weeds with this powerful piece of software.

Sure, it has some funky quirks and suboptimal workflows but the pros far outweigh the cons for me. For example, leaning into the evovling Dev Tools has changed how I document and handover design files to my Engineering team.

FigJam is useful to keep everything together under one roof but I did enjoy using Whimsical for white-boarding last year for some time.

Note taking (+ personal todos)

After a number of years tweaking and customizing Obsidian, I had a brief stint with Bear notes (now that I was fully on the Apple ecosystem) but I found it to be a little too lightweight coming from Obsidian.

I have finally landed on Craft in 2025 as my go-to note-taking app. It's lacking in a lot of ways when it comes to shortcuts and organization but one thing that has been a real game changer with their v3 is the way that they have handled daily notes and tasks in the product.

Previously I would use a todo app, and a writing app which would often overlap but in messy ways. Now, Craft has really helped to streamline those two needs into one app.

Calendar

Notion Calendar (formerly Cron) has been a powerful addition to my working day. The keyboard shortcuts, speed and design make this a pleasure to use each day.

Email

After many years and some trials and tribulations with other email platforms, I always find myself coming back to Spark. It's a powerful combination of great design, great shortcuts that helps me to keep on top of my inbox.

Coding

Call it a sunk-cost fallacy, but I have spent a bunch of time finding the best workflows and setups when I need to do some coding and VSCode is still coming out on top this year. With integrated terminals, git and an ability to heavily customize it to suit your needs, I have yet to find something better.

Honorable mentions

These apps may not be front-and-center of my day-to-day work but they certainly help to keep things swimming along when needed

• EagleApp continues to be a great for capturing and organizing visual goodies from the internet

• Grammarly continues to keep my spelling in check

• LastPass because my memory sucks (though I am keeping an eye on Apple's new standalone password app)

• CleanMyMac continues to keep my machines running smoothly

• Loom continues to be a solid companion to my remote workflow

Wrapping up

As I embrace a simpler digital life, these tools have become essential in streamlining my workflow and enhancing my productivity. I’m excited to see how these tools evolve and how they will continue to shape my creative process in the year ahead.

What tools are you using to simplify your digital life? Feel free to reach out and share!

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Whilst designing the MVP for each feature or user flow has its merits it can also box us into a close-minded view of what our product could be. Sure, we do not have time to build all the parts, but having an idea of what those parts could be can help frame our thinking in new ways and get the team bought into a longer-term strategy of how we get there.

Working backwards from this exploratory venture, we can cherry-pick the parts that make sense to build right now. The benefit here is that we now have a broader view of how future parts may connect with this smaller part that we are focused on.

So, what is wrong with MVPs?

The typical approach to product design can often get us stuck in the "MVP loop." We focus so much on getting the minimal viable product out the door that we forget to think about what comes next. What is the bigger picture if this release is successful?

Too many products are made up of many scrappy MVPs, and it shows. Things can feel disconnected and inconsistent. Because there is no broader vision and a lack of thought being given to how the parts connect the product can often evolve spawning scrappy MVPs on top of scrappy MVPs. What you end up with is a product that is devoid of any sort of vision or craft.

That’s not to say that products cannot succeed by following an MVP-led approach, but at some point it has to be a conscious decision that the team makes as it could well lead the company down the path of being a feature-full but scrappy product.

Having recently migrated from Obsidian to Bear for my note-taking and writing, you can quickly get the sense that one product, while feature rich, can be a little overwhelming and complicated to use whereas the latter “just works”.

Bear has truly taken steps to ensure that every piece of the product works seamlessly with the other parts towards a cohesive vision — it is evident across platforms too. Obsidian on the other hand is very very powerful, with lots of things that kind-of work across platforms — it feels like you are using a product with a lot of MVPs.

Where would you like to go?

Imagine stepping into a taxi and answering that question above with:

“Just round the corner is fine, and then we’ll see where to go next.”

Your driver would likely kick you out pretty soon after, and you would have a very inefficient ride to a destination that you have yet to decide upon. Seems ridiculous right, but we do this a lot when building products.

So, next time you are working on a new feature or workflow — try to carve out some time to really stretch your mind farther into the future and see if you can craft a future state that can help provide direction to your team and yourself as you take those turns to get there.

Just like in the taxi analogy, you may find that some roads are blocked or that the traffic is too bad — justifying a change in direction. These are the MVP decisions, the small steps that you take along the way but at least you have some semblance of where you are heading towards.

Of course, there is a caveat

This is not some foolproof, magic bullet that will work for everything, all of the time. Reflecting on the axiom that you may have to solve the wrong problem first before you find the right one, there is a high chance that your extended vision of the product is not what is actually needed, at least not in its entirety. This is OK.

Considering the OODA loop where we can Observe, Orient, Decide, and Act we can continue to review and adjust against the vision that we had just as we would keep an eye on those turns and the traffic that lay ahead.

If, half way through your taxi ride, you realise that where you are heading to has permanently closed down, you will likely change your plans. Same is true when building product. At the first opportunity you recognise a need to adjust — adjust.

Wrapping up

While there is no perfect way to develop products, I find that rewiring my thinking to work backwards from an ideal future state has been extremely powerful in providing direction for today’s decisions. It helps team members connect the dots and see the bigger picture.

Being able to pull on this idea, has also helped to align the team and allows them to consciously and subconsciously move towards that direction, allowing their individual contributions to contribute to that future vision.

This can be far more powerful than having folks pull in different directions along the way, shipping solutions that are based on short-term thinking.

Try it out and let me know how you get on.

Powering this week's thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this week’s:

The personal wall

I was chatting with a colleague recently during our mid-year reviews and they mentioned this idea of "the wall". In this context, it was a reference to a fabricated idea that we sometimes impose on certain situations.

As professionals, it's normal that we will, at some point in our careers, suffer from some level of imposter syndrome. This topic has been well-discussed across many forums so I won’t digress on that.

The idea of “the wall” takes a similar angle but I found that after my colleague shared this analogy it resonated much more as a concept. It feels clearer in identifying what the problem is — maybe it's because I'm a visual thinker. For me, visualising imposter syndrome is much more challenging and abstract.

In that discussion with the colleague, we spoke about how people create a sense of stagnation, that they cannot be involved in certain projects, or feel that they shouldn't. In those circumstances, we need to take a step back and ask ourselves "Why?".

Through a simple pause and a quick reflection, we may come to understand that the only thing that is holding us back from progressing or getting involved in something is in fact ourselves. We have built a wall around us.

Unless many people have repeatedly told you not to get involved or contribute to something, then perhaps that wall is nothing more than a mirage that you can simply walk through.

Where's my sledgehammer?

Next time you find yourself facing a wall, doubting your ability to take on a new challenge or to get involved in something, ask yourself: “Who built that wall?”. If the answer is you, reach for your metaphorical sledgehammer and do yourself a favour.

Take one big swing and smash a hole through those misinformed beliefs that you “can't” or '“shouldn't” do something. Save your energy, and punch a hole just big enough for you to walk through, no more. Don’t overthink it or worry about cleaning up that mess of bricks on the floor — save your energy for any future walls that you may find along the way.

It's your growth

I know some statements have been made flippantly — like it's just that easy — but sometimes it is. When it's not easy, at least pausing to identify the source of friction or perceived blocker is a great first step in moving through the problem and coming out the other side stronger.

Maybe that first hit of the wall doesn’t punch a hole through it, but simply acknowledging there is a wall and taking a strike will begin to weaken it, and that too is a good step towards removing the wall.

As a junior designer in my career, I felt that it was my manager’s role to make me grow. In hindsight, this was a very flawed stance to take. Of course, my manager was there to support my growth, but it's not in their control what I do, or do not do, with each passing day. Sure, they can ask questions, and coach you along the way but it is ultimately you that takes the steps.

So, next time you approach a wall, take a pause and reflect on where that wall came from and see what's in your power to get around it.

Powering this week's thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this week’s:

In attending a recent presentation from Heather Hepburn on Accessibility at Skyscanner, she shared some final thoughts on how to drive accessibility standards across an organisation. As it turns out, the approach to tackling driving accessibility forward in an organisation and rolling out a design system has a lot of overlaps.

Top tips for successful adoption

1. Raise awareness

2. Get leadership buy-in

3. Make someone responsible

4. Build a Champions network

5. Educate everybody

6. Audit your products

7. Test with disabled people (or design system users)

8. Track metrics

9. Build into your process

10. Embed into your culture

Design systems enable accessibility

Not only is it great that the approach for rolling out accessibility is the same approach that can be followed for building your design system, but we should also understand that design systems inherently enable accessibility.

A product, or website, is made up of various styles and components laid out in a specific way. If that product or website uses a design system, a large part of the decision-making has been handed over to the system.

If the design system itself has not considered accessibility, anything that relies on it is in a less-than-optimal place. Or, put another way: shit flows downstream.

To prevent your poor users, standing at the mouth of the river, from a "shit experience" consider how you can push decisions and adoption right up to where key decisions are made. In doing so, you are not only building better products, but you are also building a more inclusive culture. That's a win for everybody.

Thoughts?

How are you tackling accessibility at your company? Is it something that you struggle with or is it baked in? Please share any thoughts or comments on the topic below and let me know if you’d like to dive deeper into the topic of systems and accessibility.

Powering this week's thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this week’s:

Related Config 2023 picks

A new phase for Design

Having worked on both sides of the developer and designer side of the fence, I always enjoyed dancing between the left and right sides of the brain. I loved that when the creative block hit or when I was being too subjectively critical of my designs I could move over to the developer side and switch on a much more logical way of thinking and working.

Since building my first design system, I have always aspired to keep the two worlds of design and code as closely coupled as possible. Whilst some tools are doing this in different ways (I'm looking at you Webflow, Framer, and UXPin) Figma has just dropped one of the most significant updates in a while — variables.

What is a variable?

Whilst a lot of designers working on systems may be more familiar with the term "token", Figma interestingly went with "variable" for this new feature. In both cases, a variable is a named container that holds a value.

In Typescript, a variable represents a specific location in memory where data can be stored and retrieved. Variables are used to store and manipulate values of different types, such as numbers, strings, booleans, objects, or functions. In Figma, we are limited to storing RGBA colors, numbers, strings, and booleans.

Column layout example

In Figma, responsive design has always relied on plugins and a system of hacks to recreate certain responsive behaviours. This is not great, as you need to ensure folks have the right plugins installed and can remember all of those hacks in the moments that they need them. It doesn't scale well.

I'd like to share an example of how you can use variables to improve your workflow and align your designs more closely with code.

1. Set up your fixed-size variables

First up, define the unit size that you work with. Most folks, including myself, follow an 8pt scale. Setting these fixed values will help to ensure consistency in your design as it will prevent folks from relying on guessing the scale that you are using.

Note the keyword here "fixed". These are immutable values that should never change. In Javascript, it would be the same as using const instead of let.

In Figma, you'll want to click on the “Local variables” button and add a new collection called “Fixed Units”. This is where we will add all of the units of measurement that will remain static, but which we can reference later.

I've used a scale of 0, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 32, 45, 64, 96, 128, 160, 180 which gives decent flexibility at the lower end and covers all the common larger sizes that you will likely work with. Of course, this list can be adapted over time.

2. Set up your responsive breakpoints

With our fixed values created, we can now assign some of these variables to our responsive sizes. We will want to create a new collection called “Responsive Units” to create a separation between these two concepts. By using this new collection, we will also be able to use "modes" to help us decide how our various units should scale across different breakpoints.

Inside this collection, let's start by defining some common layout units. These are:

• containerWidth

• containerPadding

• columnSpacing

It's common to use camelCase in TypeScript so I will stick to that for even more alignment between designers and developers.

Next up, we will want to set some viewport widths and heights. This way we can have a standard set of heights and widths to use in our design. Figma offers a tonne of frame sizes out of the box but there is no way to limit or recommend which ones to use across the team. This should help with that.

3. Create your column layouts

With some of the basics in place, we can now set up our columns using Figma's native column and grid feature. Here we are going to set a standard 12-column layout and use 16 (which is the same as our fixed unit of 2) for the columnPadding.

For the containerSpacing , we will start off with a default of 8 (or a fixed unit of 1) which will be used on mobile. With our 12 columns now set up, we know what our containerWidth will be and we can add that value in there.

4. Create your column sizes

Now for the tedious part — with your columns visible and set up with the correct padding and spacing, measure out the width that each column will be and create a variable for all of the column widths from 1 through 12.

Within your Responsive Units collection, you can organise your variables into groups. This can be done using the / notation as you are typing the name, or by selecting multiple variables and using the right-click context menu to group several items.

The three groups we have created are called Column, Container, and Viewport respectively.

5. Add your responsive breakpoints

Here comes the magic. With all of our responsive variables set in the default mode, we can go ahead and rename that first mode column to sm. We can then create 3 more for md, lg, and xl. These will loosely represent mobile, tablet, small laptop, and larger desktop displays.

Choosing a set of values that works for your context and your customers you can build out each column until it looks something like this:

6. Set up some test frames, and watch the magic

Lastly, to ensure that everything works as planned, you can create some example frames which each have a different mode set. You can do this by setting a mode via the contextual menu on the layers section on the right panel.

To make life easier, I created a small guide that also displays each of the variables as dynamic text and also color codes the various responsive sizes. This way, you can quickly view and test your layout across different device sizes.

The last step will be to publish this for your team to allow them to follow a more consistent way of sizing and laying out their UI.

That's a (flex) wrap 🤦

I could go into a lot more detail on many more exciting ways to use this and likely will in the future. Until then, I hope this has offered a bit of an insight into how variables can be used as a core part of your design workflow, which will also help your engineering friends.

Any comments or feedback, please feel free to leave them below.

Powering this week's thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this week’s:

The act of setting a goal will not get us there alone. It takes effort. We need to build habits and discipline that will help us to stay focused on reaching where we want to go. This got me thinking about a visual analogy that I could use and share with others when it comes to setting and pursuing goals.

Let’s imagine that you have reached a milestone in your life or a point where you need a new and interesting challenge. You are on the edge of a (not too high) cliff by the edge of some clear blue, comfortably warm water.

1. Look to the horizon

Pause for a moment. Where are you right now? Where do you want to be? The simple act of thinking about those two questions will help you to focus your sights on a horizon — on a goal. Like the horizon, which appears around 3 miles away, don’t set your goals too far. In doing so, you could increase the number of variables that you will face along the way. Focus instead on attainable and visible horizons.

2. Dive into the water

Now that you have seen where you want to go, you can take that first big leap in the right direction. At first, as you enter the water, it can be confusing and discomforting. There’s a change in temperature, splashing sounds, and the impact of hitting the water. This is that uncomfortable start that we sometimes experience when we set new goals. There are unknowns and details that need to be figured out. After all, it’s there is an ocean between us and where we want to be. Anything could happen.

3. Start swimming

After your momentary disorientating submersion you have returned to the surface of the water, found your feet and have begun kicking. You start to pick up a good pace, moving forward and gaining momentum. You regulate your breathing, find a good rhythm and settle into the swim. It feels good.

4. Lift your head

You’re moving forward, that’s good — but are you moving in the right direction? With your head down and only focused on moving forwards it’s easy to lose track of the big picture — of the horizon. There are also winds and currents and other factors that can steer you off course over time. Lifting your head from the water, taking a pause from the kicks and the strokes allows you to check in. Is the horizon still where you think it is? Are you reaching closer? Do you need to course-correct at all?

5. Swim again…

Armed with the confidence that you are on the right track and taking stock of your energy you can continue swimming towards your goal which is getting closer and closer. You will want to repeat the cycle of swimming and pausing to lift your head. Create habits to repeat the act of lifting your head to ensure that you are on track and that you are spending your time and energy wisely.

Closing thoughts

Why not keep this analogy in your head next time you are thinking about goal-setting or goal-tracking? Ask yourself when was the last time that you paused to take stock and check on the horizon.

It’s all too easy to just keep our heads down and swim aimlessly. It feels good to move and to move forward. But, you can be moving forward and be off-course — moving further and further from where you ultimately want to be. Find a rhythm that works for you to pause and lift your head.

Now, where did I put those swimming goggles?

Powering this week’s thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this week’s:

We can all recall that moment when our basic freedoms were removed and we were forced to stay home. In Barcelona we experienced one of the strictest lockdowns. As someone who does not fair well with “sitting on their arse” it was a largely uncomfortable period for yours truly.

That being said, being constrained in a moment by external factors, unable to distract yourself with the usual day’s activities does had it’s upsides. It forced us all to pause and allowed us to reflect — on a lot of things. Take the “Great Resignation” as an example of what a pause to our usual routines can cause.

When we pause, it gives us time with ourselves and helps us to formulate our thoughts and process our emotions without reacting in subconscious ways.

Pauses help us to be more deliberate.

Last week I took a pause from writing. It wasn’t planned, but it was needed. When I am having conversations with folks, I am trying to pause more to ensure that I am actively listening instead of filling air time. When experiencing emotions, I pause to take a breath.

Each pause is an opportunity to look within, to reflect. It allows you to be more thoughtful in your next steps.

Here are some pauses that you can try out:

Micro-pauses

• Take a breath before responding

• When feeling emotional, take a deep breath

• Before doing something, ask why this matters to you

Meso-pauses

• Walking your dog

• Taking a proper lunch break

• Journaling your thoughts using pen and paper

Macro-pauses

• Going on vacation (summer is just around the corner)

• Taking a sabbatical from work

• Dedicating significant time to your hobbies and interests

When was the last time you took a pause?

Powering this weeks thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this weeks:

Analogue tools

I’d say that my first signature relationship with a sketchbook was when working at Skyscanner. Back then, it was a 200-person flight search comparison site. Shortly after joining, I was tasked with leading the design for our upcoming hotel’s product — in steps the sketchbook.

It would not be uncommon to see me wandering around with a dog-eared sketchbook hanging out of my jean pocket. With a trusty fine-liner pen, I could quickly sketch out an idea and begin to visualise it in the moment. No booting up laptops or looking for chargers — just pure and simple pen and paper.

These rough sketches and accompanying notes would serve as discussion starters for product managers and engineers to test for feasibility, invite early feedback and iterate on concepts. It was by far the fastest way to get an idea out of my head.

Pros

• Cheap and easy — simply pull it out of your pocket and away you go…

• The tactile sense and connection with a rough texture like paper help to reinforce the fact that this is a rough idea

• The battery will never run out on your sketchbook — though your pen might run out of ink

Cons

• Easier to lose — because it’s cheap, you may not treat it less carefully

• When you need to repeat elements and patterns, it can be laborious

• Harder to share with colleagues who are not co-located

Digital tools

Working on the design of iPad apps I bought my first iPad mini back in 2013. Back then it wasn’t much of a design tool, but I did buy a third-party chunky rubber-tipped pencil that got me wondering about trading in my sketchbooks.

Fast forward a few years, and I am now on a 12.9” iPad with the latest version of the Apple Pencil which does invite a far superior sketching experience. Having tested a bunch of apps, I landed somewhere between Concepts, Sketches, and Paper.

They all had their pros and cons but the one I found most interesting for full-blown exploratory work was Concepts. It was just much more powerful as a drawing tool and offered an infinite canvas, which is not something offered by Paper or Sketches.

Setting up the tooling, you could easily recreate that “sketchy” aesthetic but now in digital form. Working in TravelPerk I began to lean more heavily on the iPad as a way of being able to more easily send digital versions off to colleagues or attach them to Jira tickets.

Pros

• All sketches can easily be collated in one place

• Easy access to a range of drawing tools and colours without carrying around a backpack of pens and markers

• Easy to reuse and rearrange elements with little effort

Cons

• Reliance on products and services that have proprietary formats

• The danger of getting too polished and taking more time than needed

• The distraction that comes from using any sort of digital device (even with “do not disturb” turned on)

Purpose-built sketching tools

Kicking off a component exploration recently, I had my iPad to hand and wanted to take a look at what was out there. I had previously explored an app called Mockup and decided to give it another try.

What’s nice about this app is that it brings the best of sketching on the iPad with the welcome constraints and “roughness” of sketching on paper. You are offered a limited, but powerful toolset. It feels like the Goldilocks “just right” balance.

One significant boost to the creative process is that it’s easy to create new phone, desktop, or even watch frames so that you can get to sketching the contents and not the surrounding chrome. I know, it doesn’t take long to draw a rectangle representative of a screen, but that’s not what you should be focused on. This tool helps you get to the content part faster.

In addition, you can easily save and reuse pieces of UI or icons for later reuse. I’ll continue to explore this in more depth and report back. Watch this space!

Pros

• Purpose-built and encourages focusing on wireframing at speed

• Just enough tools to entice you over to the digital realm without being too distracting from the task at hand

• An expansive set of UI elements and icons allows you to focus on the parts in-between

Cons

• Still falls prey to the distractions of working on a digital device

• There are some quality-of-life improvements that feel missing (like dragging to change the order of screens)

The wrap-up

In short, it’s great to see the evolution of sketching tools and the different ways in which we can capture and express ideas. With the rise of AI-generated drawing tools, it will be interesting to see how this next phase of ideation will play out.

That being said, despite all of these shiny new tools at our disposal I find there is always an attraction to that tactile feel of a sketchbook. There is a romantic element to the old sketchbooks that gather dust and lose colour. Their roughed-up edges hint at the type of life they have lived. This is something yet to be created in the digital world.

Powering this week's thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week.

I know I have shared Fred Again previously, but I was fortunate enough to be given a ticket to Primavera Sound in Barcelona by my beautiful partner and was a first-hand witness to this epic scene (below). As the first beat drops on of the best songs, there’s a power surge, but the crowd keeps the vibe going. Epic!

Being an Oculus Quest 2 user, I have experienced and used a similar type of device — but Apple’s take seems to be (virtual) worlds apart. Here are my top three takeaways from the event.

Connecting to the real-world

One of the first details that I noticed, which I love, is how they have tried to incorporate the real world into the experience. Rather than completely disappear into a virtual world you can still experience real life while using the device.

Remember those floating torsos during the Quest demo? With Apple’s Vision Pro, it seems that you have the option to scan your face and use that recording as a photo-realistic 3D model of your face which can move realistically in a spatial environment, like a FaceTime call.

In addition to you appearing (almost) real to others when you put your headset on, it appears that your immediate surroundings are also at hand. When you put the headset on, it appears that you are placed in the room in which you are sitting. The UI and various floating screens and widgets appear within that space, customisable to suit your needs. This way you can enjoy the benefits of a spatial UI experience without the nauseating disorientation of being transported into a space-ship or some other 3D-rendered scene.

If you do opt for a more immersive experience though by placing yourself into a completely virtual reality, when someone approaches you, the headset will detect this and begin to fade them into view. This connection to the real world in a seemingly seamless way seems to address some of the biggest challenges of prior VR headsets. No more bruised shins from walking into the coffee table!

What’s more, the person on the other side of the device will also be able to see from looking at the device what level of immersion you are in through the ability to see your eyes or not. These visual cues that lean on real-world patterns, like eye contact, help to make this all feel a little less alien.

Using your body as navigation

The next thing that caught my attention was the input method used for navigation: it seems that you navigate simply by looking. It's no longer point-and-click; it's now look-and-tap. With your eyes fixed on a piece of UI, which will react to your gaze, you simply tap your thumb and forefinger together and an outward-facing camera will capture your intent to "click" on that UI element.

Having fumbled around to grasp the Quest controllers, this simple extension of body-as-an-input takes an interesting approach to solving the challenge of interacting with a virtual world using physical inputs which are hard to see.

In addition to look-and-tap, there is of course voice input. Being a Scotsman though, I struggle to get excited about voice input given that more than a decade after being first introduced to it, most devices fail miserably to actually understand what I am saying. I’ll be curious to see what the alternative option for voice input will be.

Deep immersion

Lastly, I’d like to touch on how they have tackled the sense of immersion. As mentioned earlier, when you pop the headset on, you can still be in your current physical space. With a quick spin of a small watch-like crown, you can choose the level of immersion you’d like. I found this an interesting and light-touch way to move between real and virtual worlds without needing to remove the headset.

In addition, they also introduced a collaboration with Disney and some truly immersive experiences. It looked like the pause screen on Amazon Prime but on steroids. Instead of just showing who is on the screen you are spoiled by complementary visualisations and rich, interactive information.

The most striking example of this was the basketball action replay where the court seemed to appear out of thin air onto the coffee table in front of you. The level of detail and seamless transition from watching the game to watching an action replay was truly impressive. I’m sceptical about how much of that experience will make it into the final product when it launches, but that would be a real game-changer.

Dear Santa...

Despite all of the hype, we still have some time to wait before we will see these in real life. Apple announced that sales will start in the US in early 2024 with other countries following later in the year. So no surprises this year from Santa! That being said, even when they do land they come with quite a hefty price tag of $3,499 — ten times as much as the Oculus Quest 2!

Powering this week's thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this week’s:

On TickTick, my default way of working was to drag my tasks for the day — ordered by priority — onto the calendar and place them in the gaps between meetings.

It worked but it wasn’t perfect, so I went searching for some alternatives.

In steps Sunsama

As a designer, I appreciate that the tool feels well-designed and simple. It feels light to navigate and the interactions are snappy. The attention to detail is amplified by the heavy, and well-considered, use of shortcuts across the app. Within minutes, you can be set up with your connected calendar and be ready to plan out your days and weeks.

Meetings = To-dos = Chunks of time

First off, let’s acknowledge that meetings and to-dos are essentially chunks of time spent focusing on something, I have always tried to find the best way of reflecting that reality in the tools that I use but it has never felt fluid — until now. In my previous post, I shared why most to-do apps fail. Spoiler: it’s because they don’t recognise this fact in a streamlined way.

Sunsama, by contrast, has baked this thinking into their DNA. In fact, after you sign up you will be fed a series of emails from the team that elaborate on their principles and how to think about and plan your days. These folks get me — they really, really get me!

Visualise your time with colour coding

For those who want to easily see things at a glance, colour-coding your tags and calendars will immediately help you to get a sense of your day. I use colours to differentiate life, work and this writing project. Within each of those I also have some further colour breakdown to help easily visualise where my time is going.

What’s especially nice is that the colour coding is subtly reflected through the tag list, the time marker on the list item and also the calendar itself. This subtle, but powerful continuity allows you to quickly scan and see where your time is going and if you are perhaps context-switching too much.

Re-wiring the process

We all have our own flavours of planning and organisation. I thought mine was pretty good and well structured, though there were days I would slip and simply jump into “doing” mode. The reality for me though is that there are long-term strategic topics to plan, team goals to be supported, individual work to be done on specific projects and, of course, a sprinkling of admin and meetings for good measure.

Start with the end in mind

When kicking off the week, Monday for me, Sunsama prompts you to set weekly objectives. I’ve been aiming for no more than three to help stay focused. Just this simple prompt to think beyond individual tasks has been a huge help. It forces me to think about where I want to be on Friday afternoon.

This prompt also plugs in nicely with the Most Important Things (MITs) ritual that was introduced to the team a few weeks back which has helped to reinforce this habit. Put simply, you set some high-level objectives for the week which your tasks can then be linked up to. This way, you will be able to see if you are actually focusing on the big picture vs doing busy work.

Make time for planning

Now that we are clear on our goals for the week, we can now go a level deeper and look at each of the days and the work that we will do. The Kanban view of the days and tasks helps you to easily move things to later in the week (there are also shortcuts for that).

The attention to detail in the overlap between tasks and time is evident throughout the app. It’s super easy to set expected timings against certain tasks. For example, sending an update to the team should take no more than 10 mins, but working on a strategy doc could easily eat up hours of work. Having this “honest conversation” with yourself quickly grounds you in the actual amount of time you need. When you see this all laid out in front of you, saying no becomes much easier.

When planning, you can see below that you are immediately dropped into a view that compares your task list with your calendar. You can also choose to pull certain meetings into your tasks list — ‘cause let’s face it they are all “chunks of time”.

Be realistic

Now that we have added some tasks and dropped our meetings onto the list we can see that the meetings alone will take up 2h 40m of my day. Now it’s time to timebox the tasks to check if we are being too ambitious.

Taking the example below you can see that when I start to estimate the effort for each task, the time counter updates. As another nice design detail, it starts off grey if things are reasonable (less than 6 hours). When you’re in the 6 – 8 hour range, it will turn yellow and once you are past that 8-hour mark, it becomes amber.

This small, but significant, visual cue acts as a reality check on your plans. When this happens, you are one shortcut away from sending some of those tasks to the next day.

In addition to surfacing the true time needed in order to complete your planned tasks, Sunsama makes it easy to schedule that work directly on your calendar. Simply pressing X while hovering over a task will find the next available slot and block out that time for you. It will even split the work, so if you have a mid-morning meeting that cuts through the amount of time you need, Sunsama will add a chunk of time before the meeting and the remaining chunk after.

If you try and over-subscribe, it will kindly suggest that you are perhaps being too ambitious and should maybe defer some work — another nod to their attention to detail when it comes to realistic planning.

Reflect often

I’ve found that the more you intentionally reflect, the faster you can accelerate learning and wean off of any bad habits or distractions. Once you complete your plan for the day, Sunsama offers to add a “Daily Shutdown” at the end of your day. This is a moment for you to reflect on your plan vs the reality.

Did you overachieve or underachieve?

Is there something completed today that you would like to share more broadly?

Having this handy ritual to end the day helps to keep us intentional in our day-to-day. Then, when the end of the week rolls around, we can easily look back and see the breakdown of where our time went.

Was your week spent on the right things?

Did you focus on the objectives?

Having this quantitative analysis helps to remove those perceived biases that may lead you to think you spent a disproportionate amount of time on one area vs another. It also acts as a great primer for going into the following week.

Remove the noise

One of the biggest challenges I had in TickTick was that work that was not tackled as planned would keep stacking up in an evergrowing list to the side. This created a sense of anxiety and brought focus to what was not done vs what had been achieved. In Sunsama, if you have a task that rolls over for 5 days or more, it’s simply moved into an archive folder.

This way you don’t lose track of those tasks but if they were being constantly deferred perhaps they were less important than the other tasks you decided to work on anyway. The concepts of setting a daily time budget, shifting tasks to the next day and filtering out untouched work really sets the tone and a new way of thinking when it comes to managing your workload — and it’s a refreshing one.

Stay focused

So, you have planned your objectives for the week and your plan for the day. You have removed all of the noise and are ready to get to work. A final feature, and an integral part of succeeding each day, is to stick to your focus, and this is something that Sunsama does very well.

When you are diving in, tapping the T key will take you into “Today” mode where you will only see today’s tasks and today’s calendar. All are neatly laid out as planned. From here, you can simply head on over to the top of your task list and hit the spacebar to enter into focus mode. This also adds a floating bar above all windows that shows a clock of how much time you are spending vs your estimated time.

But wait, there’s more

In reality, our work is spread across many places. Historically this would mean that I would have to manage my own task list and, in addition, review and manage work in other tools like Jira.

With Sunsama, I am now able to get a unified view across these different tools, including email. This way, I can bring all of my work into one place and objectively plan the best way to tackle it vs blindly ignoring all other streams of work.

The wrap-up

I have spent a lot of time over the years trying to hone my organisational skills and I aspire to be lazy in the sense that I am able to do more work with less. This is why I seek out tools like this, to help streamline my workload and help me to be more efficient and effective in the way that I work. To summarise the key benefits that I’ve found by using Sunsama I’d call out:

• The constant reminders and prompts to create realistic plans

• The honest reflection of workload reflected across your tasks and calendar

• The importance of running regular reflections and creating a continuous learning loop with yourself

• Lastly, creating a sense of clear focus and being vigilant with how you are actually spending your time

In addition, I like to celebrate good products which have clearly put a lot of thought into it. From the way the shortcuts have been set out — using Q, W, E, R, and T as the main shortcuts for each task was not coincidental.

On top of that, the contextual support and advice along the way and the well-timed email digests show that the team have thought long and hard about what good, focused productivity looks like.

Just to be clear, I am not affiliated in any way with Sunsama — I just think it’s a well-executed product that I wanted to do a write-up on. I hope you found it useful!

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Powering this week's thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this week’s:

Planning is more than prioritising

Many tools allow us to prioritise our work and categorise it in different ways, which certainly helps to give some clarity about what we should be picking up next. In my experience though, what would often happen was that each list would grow independently and the high-priority work would simmer at the top of each list.

If I was lucky, I would skim the tops of the list and get through the high-priority work but this inevitably meant that anything less than urgent would simply get nudged further and further down the list and enter the "long overdue" pile. Something else was missing in my workflow.

When planning your work, you should also be looking to understand what *type* of work it is. High-priority work could simply be time-sensitive. But it could also be highly strategic. Seeing tasks through this additional filter will help you to better organise and arrange how you will tackle your list.

Time is everything

Without time, we cannot get through our todos — fact. To acknowledge this, I recommend plotting your tasks on your calendar as a way of helping to frame the task in the context of your available time. Taking this approach in the past few years has been a real game-changer in how I view and manage my tasks and overall workload.

You have 24 hours in a day and before each day starts, you already have a number of deductions on that time. Sleep, your daily commute, family commitments, meetings, etc. These all take up a portion of your day. What's left is the available time where you can plot your tasks. Oh, and you'll of course get surprise distractions too!

Most apps fail to make this task-to-time. connection and simply treat time as a due date which can often be ambitious and unrealistic. Instead, see tasks as blocks of work that need to slot into the gaps in your life. Will one block of time suffice? Will you need multiple? Have you factored in the cost of context-switching? Pausing and reflecting on these points should help you to plan your days ahead.

More to come...

I have recently been experimenting with a tool which frames my work to be done in a different, much more intentional light. I’ll cover this in more detail in next week’s post, so make sure you subscribe to avoid missing out!

Until then, if you have found any methods that help you tame your todos, please drop a comment or reach out to chat 💬

Powering this week's thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this week’s:

Most Important Things

After rolling out the One Big Thing ritual to the team, it wasn’t too long until that one big thing became more than…one. Was the system broken? Is it impossible to focus on just one thing? Short answer — no.

Having to decide between a few things and label one as the thing that matters for that week can pose a challenge. How was this resolved? The team would simply add the two or three things that they were working on which were big and important for that week. Does that mean that they are not focused? No. It simply reflected the reality of their weeks.

This gave me pause to consider if we were framing and discussing the week in the right way. I’d come across the concept of Most Important Things (MITs) in the past and considered rebranding our ritual to something more fitting. This week we kicked things off, and the early signs are good.

I’m not so sure about this

In addition to rebranding this Monday ritual, I’ve also explored adding some additional context to each “thing”. The first piece of metadata that has been added is a confidence indicator. What do I mean by that? Like most things in life, we can be sure of some things — like death and taxes — but we can’t be so sure about everything. This is perfectly OK.

What’s not OK is to misalign your expectations or those of others, when it comes to your confidence. If you strut into the week certain that you will smash all of your goals, that’s great. If you gently tip-toe into the week, unsure of what will unfold — that’s something worth talking about.

So, in addition to sharing what our MITs are for the week, we each share a confidence score alongside each. 1 being the lowest, 3 being the highest. I borrowed the thinking from the hill chart idea that I came across via the guys over at Basecamp.

Put simply, at position (1) you are staring up a hill, with no idea of what the journey to the top will look like, let alone what’s on the other side. When you reach position (2) you have gathered enough context and information such that you can confidently see the path ahead and can plan accordingly. Position (3) is the sweet spot. It’s that downhill acceleration to the finish line.

Not everything can be 3’s and that’s OK. So, if something is a (1) or a (2) you can signal to your peers that you have some doubts and that surprises may appear. It’s a micro-communication about how you are feeling about a particular goal.

On being explicit

Building on the metadata and additional context, we’re also trying to be much more explicit. Not, Snoop Dogg style. More for clarification. It’s simple…if you need help with something — say it. If you are blocked by something — say it. By just offering up that reminder, it helps the team to ask for help or to escalate something in good time reducing any last-minute surprises.

By having this ritual on Monday morning, we have plenty of time to rectify any challenges before the end of the week.

Why, why, why

Lastly, and probably most importantly, we now focus on the “why” of each MIT. For something to be the Most Important Thing for that week, it must have a good reason, right? I’ve never worked somewhere where I have had nothing to do, luckily. Staying busy is not the problem. Focusing on the right things is.

Going through the exercise of sharing why something matters is cathartic in the sense that you can hold up a mirror to any subconscious feelings of importance and look objectively at it to see how much it really matters.

Break it down

Adopting this new way of stating our focus gives each week a sense of purpose and divides what could be a 3-month project into smaller bite-size chunks. It trains our minds and our habits to seek out the work that matters, that has a good “why”. It makes it OK to put other things aside.

Leading by example, here were my 3 MITs for this week:

Be accountable

One of my colleagues, who is not a morning person by admission, told me once about how she would get up at 6 a.m. to go to the gym with a friend. Would she still go if it were not for her friend? No (she confirmed). So, how is this possible? She has an accountability partner. This is why we will do better when we form part of a class or when we know someone is expecting us to turn up. We don’t want to disappoint. Stating our MITs for the week creates this sense of accountability and allows others to ask about those things.

Given that I normally have my 1:1s with my team at the end of the week, I can take that opportunity to run a mini-retro and see how they got on compared to their plans. Doing this cyclical work of setting weekly objectives and checking in at the end of the week has been working wonders for me to stay focused and prioritize meaningful work.

As a manager, this also presents a great opportunity to learn and optimise each week versus waiting until mid-year or end-of-year review cycles when a lot of the detail often gets forgotten about.

Why not try this with your team and share some feedback

Powering this week’s thoughts…

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this week’s:

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Top 5 time-savers

Window resize

Let’s start with the most relevant one. As soon as I start my day, and the computer, I have all my usual apps open to help me get through the day. Depending on the task at hand, I may need to see some things side-by-side, and for that, I turn to the “Window Management” app.

By typing, I can easily split, resize and configure all my windows in a couple of keystrokes. To make life even easier, I have some shortcuts to get me there even faster. Here’s my setup:

With a window in focus, I can quickly whip one over to the left two-thirds and have another to the right as the last third. This is great when I am on a call in the browser and I want to follow along on Figma. Here’s how that looks in action:

Join a meeting in less than 1s

Working remotely has definitely made it easier to quickly jump into that next meeting. No more running up and down stairs, waiting for elevators or frantically knocking on doors to evacuate the squatters from your booked room. However, you still need to jump to your calendar tab — or open it — and then move the mouse to the event, click, open, join the meeting and wait for it to load.

With Raycast, I simply hit my ⌘ + Space shortcut to bring up Raycast and hit Enter and voila — I’m in the meeting.

Pro tip: Since Arc has launched its new Air Traffic Control feature, I can now define where to route all my Google Meet “traffic”. For me, this lands in a Space I have named Rituals, which is where I have all my weekly meeting agendas ready and waiting for me.

Copy and paste

Simple, but powerful. After checking, I copied 50 things to my clipboard yesterday — and that was a quiet day. Traditionally after you copy something it gets stored on your clipboard. But sometimes you want to retrieve not the last link, word, or hex code, but the second-last, or even that one from earlier in the day.

With Raycast it’s a breeze. I’ve set up a ⌃ + ⌥ + ⌘ + C shortcut that drops me right into my Clipboard History. From there, I can simply navigate through everything I have copied in chronological order, or I can search through everything I have copied. This works for both text and images and saves me a tonne of time each day!

Word definitions and synonyms

Sometimes I find myself writing and using a word that feels right but I’m not sure if it’s the right use given the context. In those moments I simply copy the word, hit ⌘ + Space and paste. By default, it will offer up the Define Word app. Hit Enter and I can now browse through the results and check the various definitions to see if it makes sense.

Pro tip: Because I have Spanish set up, you will also notice that I get examples in Spanish for each word that I look up.

Calculator

Last but not least, when doing some brain gymnastics to figure out how much something costs, or working out measurements for day-to-day things, you can do simple (or complex) equations straight from Raycast. As an added benefit, hitting enter closes the window and copies the result and it is now saved to that Clipboard History I mentioned above — nice!

But, that’s not the only thing you can calculate. You can also calculate things like “Days until…” which can be useful when counting down to a big day.

Another example would be figuring out the general distance between points. For example, did you know that the distance from new york to London is 12,932? Well, now you do.

Powering this week's thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this weeks:

Do as I say, not as I do

This was a phrase my dad would often remark when I called him out on something growing up. It used to frustrate me trying to understand these double standards that he held himself to. It seems that this flaw can also be observed in the world of research.

I was chatting with a research colleague, reminiscing on past research efforts, what we learned and the impact that it had on the respective projects. It was inevitable that at some point we would touch on a shared experience that’s all too commonly observed when doing research. Hearing someone say one thing and watching as they do something completely different.

He shared a particular example of how people generally share concerns about privacy and see this as important. But when undertaking some research the reality is that they give less shits than was first understood. This observation saved the company a tonne of time and money by not investing in something that in reality, was not needed.

I could also speak of countless times when people have described, in detail, how they would approach a task only to go about it in a completely different way.

People often share feedback or remarks based on what they think we want to hear as a safeguard against offending someone or entering into some sort of confrontation. This is less than ideal when you are trying to understand your users and customers.

Here comes the curve

What’s a good argument without an exponential curve of some sort? I appreciate there are many flavours in which to view this, but I wanted to find a simple narrative, so here goes:

In some companies or teams research can often be seen as an overhead, a slow-down, or a “nice to have”. The reality is that research, done well, can save costs, prevent risks, and identify new business opportunities. It’s a — relatively small — investment that almost always guarantees returns.

Let’s take a look at each stage above in brief:

1. You run a research study that sets out to test some early assumptions. You test competitor products, shadow people, or run generative interviews. You prove the assumption wrong, gain an understanding of the real need and use that to drive the next stages of the project.

2. The team works on a prototype to respond to the problem. They work quickly and iteratively and test their ideas as they go — tweaking the details and ironing out some gotchas that were missed before.

3. Now things get serious and a larger team gets involved. They build the product following production-quality standards, rigorously testing and then launching the feature to thousands of customers.

4. Customer support articles are updated, sales teams alter their pitches, and the marketing team spends tens of thousands on advertising and publicity.

5. Customers adopt the feature, love it, stick around for the long term and share your awesome product with friends and family.

A real need was validated, tested, and launched to bring value to the customer and revenue to the company — win, win.

The alternative

You skip the first parts. Build a feature based on loose, untested assumptions, get the whole team involved, add a lot of code and processes and then — BANG! People don’t use your feature. Even worse, it frustrates them. It highlights that you don’t understand them and their needs, and they leave. Not only is this a bad situation to be in, you have also created a bunch of technical and process debt that will one day need to be unpicked — at an additional cost of course.

A quick look at the rollout of the Twitter check marks reveals how not to do things.

Simply being a degree or two off at the start can have a significant impact at the end of a project. Invest in research and pay attention to what people actually do, observe what they need, and give them what they want — not what they say they want.

This weeks playlist

So, on Sunday I dusted off my “aggressive” inline skates and set off down to the beach to stretch my legs and get the blood pumping. As a teen, I was big into the skate scene and would watch all the videos religiously. Aside from the tricks, the soundtracks were often epic.

I was elated to find this little gem of a playlist before setting off. Enjoy!

After working with tech for more than 2 decades, I've learned that you can apply the same principles when facing off against digital bullies. You can use their distracting blows to your advantage.

Trigger future conversations

I’m sure it’s familiar to you also…you have a chat with someone, discuss some follow-up steps or ideas and then fail to ever do so. It’s normal. We can often be overwhelmed juggling many things that it’s easy to forget. Sure, I could create a task and follow up on that, but I often find myself looking at those tasks while scratching my head. What did I mean by that? The context is lost.

Rather than capturing a task and following up on it later in the day, week or — dare I say — month, why not just start the conversation today?

Here are a couple of use cases where I have used Slack’s scheduled message feature to make this tool work for me and not against me.

Out-of-office 1:1s

Just because I may be heading out for a long weekend doesn’t mean that I give less f*cks about my team. Whilst I might be sipping on a chilled glass of something on a Friday afternoon, they may still be slogging away, wrapping up their work week.

As part of my ritual before signing off for a holiday where I know I will miss a bunch of 1:1s with my team, I line up some check-ins that are sent out during the time we would normally meet.

I must say, I was pretty thrilled to see this brought a moment of joy to them that day. What’s more, I was able to come back the following week with some context that would have otherwise been lost.

You see our brains are terrible at recalling emotions and memories as more time passes. So, had I come back and asked “How was last week?” it would likely get a much more diluted response than capturing someone at that moment at the end of their week.

Project follow-ups

To take another example, the other day I had a call with someone from my team to talk through a complex project that was coming up. I made a point during the call to ask for some specific dates when the next steps were planned. After the call, I jumped immediately into Slack (with the conversation fresh in my head) and began to type a future check-in message.

It went something like this:

[Project name]
Hey — good morning. I set up this little reminder after our chat on Tuesday. You mentioned that you should be finishing up with [stage X] yesterday.

As a recap, we discussed two key things to start looking at today:

• [Thing 1]

• [Thing 2]

Did you manage to complete [blocking task]?

Let me know if I can help with anything and let's aim to review the work in progress at the end of this week.

I realised one thing writing this in Slack vs capturing it as a to-do made it feel like I was writing to that person. This immediately adds a level of writing standard that is all too easy to ignore when capturing tasks for yourself. It was far more articulate and relevant as I captured the key context immediately after our discussion.

In task form, it would have looked something like: “Catch up with [person] on [thing]”. Once that day rolled around I would likely look at that task and wondered what the hell we spoke about and maybe fail to follow up as a result.

Learning the “killer” move

If you would like to use automated reminders and queue up conversations like a robot, but with the goal of being more human and staying connected even if you are absent, here’s how to get started:

1. Simply draft your message to someone when it’s relevant and you have the context

2. Do a quick proof-read and make sure you don’t land your future self in trouble

3. Click the schedule button

4. Choose an appropriate time for the Slack spirit version of you to reappear 👻

   

Powering this week’s thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to.

It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week.

Last week, I took a break away for the long Easter weekend and instead of sharing chocolate eggs, I bring you another type of treat — in the shape of Figma plugins.

After working closely with the team on a significant refactor of our Figma files and the Design System behind it, I’ve found these three plugins to be a massive help throughout the process. So without further ado, let’s check them out.

1. Style Organiser

Check out the plug-in

Whether you are migrating from one design system to another, creating one from scratch, or would just simply like to do some spring cleaning on your styles, this little gem will save you a tonne of time.

2. Able (accessibility)

Check out the plug-in

Accessibility can often be seen as a luxury and a nice-to-have but with tools like Able, there really is no excuse for not making your products more accessible. Check it out and help to improve the accessibility of your products today.

3. Themer

Check out the plug-in

Last but not least, this little doozy of a plugin has been a great help as we move towards a cleaned-up version of our dark mode. With minimal set-up, this little floating box can quickly flip the switch on your UI. Lights on. Lights off. Lights on...you get the picture.

All of these plugins have been a great help during the process of cleaning up both our light and dark themes for our Design System. As we reach the end of the roll-out I’ll share some further feedback on what we learned along the way.

If you have any specific thoughts you’d like covered in that future article, feel free to drop a comment below 👇

Powering this week’s thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to.

It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week.

When I stumble across articles or books on design systems a surprising amount of focus is put on starting with audits—that document which shows a shameful array of button styles and components using 50 shades of grey.

This is absolutely a necessary step in building a Design System but the real need starts way before that.

It’s a product — used by humans

The word system, and its inherent technical implications, can make it easy to forget that a Design System at the end of the day is simply another “Product” which is used by humans. The majority of the time, this will be your colleagues and peers across your product, design and engineering teams.

The first place to start is by discussing with those folks what challenges they face and how a Design System can respond to those challenges.

In previous companies, I have been fortunate enough to build systems from the ground up. Working closely in small teams gave me a clear sense of the problem as all the folks affected by the lack of a Design System were in regular discussions in the small teams that we head.

In my current company, we are a tech org of almost 300 people and I joined the company when they were already 6 years old.

In that situation, one of the most beneficial stages in building the design system was to throw all assumptions out of the window and interview a large group of designers and engineers.

One of my first questions was to understand what level of experience they had in building a design system. Once known, you can tailor the message and your approach to building this new Design System product.

Why do we need one?

If the answer to this question is not clear, you need to go back to step one and continue with those interviews. Like any product, launching without a product-market fit is a great way to secure failure.

There can be many reasons for needing a design system but the most common needs will fall somewhere within these:

• The need to work more efficiently

• The need to align with brand

• The need to easily iterate on and update the brand over time

• The need to improve overall product quality

• The need to improve collaboration between design and engineering

Playing back people’s needs throughout the early stages can be a key driver of success. Remind folks of the pain points and how building out a Design System will alleviate those pains.

For example, I discovered that many teams were using many different “Design Systems”. Each team believed they were working in the best way using libraries and frameworks to help get the job done.

The problem was that there was no alignment and in some cases, different libraries were used. This of course means that many products start to look, feel, and behave differently.

It means if someone switches teams or needs to work on another product it’s not easy as easy to just dive in and get working, as there is a need to learn a new way of doing things.

All of this compounds into high inefficiencies across teams and sub-standard products. Rather than building on top of each other’s work and amounting to something magnificent like the Pyramids of Giza teams were all building in parallel, resulting in a few garden walls, all built from different stone.

Repetition is key

As you transition your team from a world without a Design System to one that does, or if you are taking them from an immature system to a mature system, one thing stays true: repetition is key.

Repetition of the problem that you are solving. Repetition of the need for this Design System. Repetition of key concepts and terminology. Repetition, repetition, repetition. You get the idea.

The reason is that depending on how you build and maintain your system, some folks may only be exposed to it on occasion, and some may be working on it every day. In any case, it’s unlikely your users are “in it” every waking hour.

The Design System solves a problem for them. It’s a product. Just like you use a weather app to check the weather for the day, a designer or an engineer will reach for the design system to help build that next feature.

Once it has solved that job to be done, it will be set aside while the person gets back to what they were doing. This is where the long-term repetition of key messages can help instil a culture and a vision of this Design System.

Wrapping up

Like any good product, this one will need iterations too based on strong feedback loops with its customers. There are few shortcuts to building a solid design system that is widely adopted — it’s a long game.

So, next time you are working on yours or making use of one, remember to connect the human part and ensure that as a product it is solving your, or your customers, needs.

If you have any thoughts on this topic or would like to continue the conversation, feel free to connect on Linkedin.

Powering this week’s thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to.

It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week.

Start strong

As the organiser of a meeting, whether in person or virtual, you are expected to lead the session. There’s nothing worse than walking into a room or connecting to a call when the organiser is just as confused as everyone else as to why we are here.

When attending a recent workshop, I observed three key ingredients to the intro that set it up for great success:

• It was stated what will be covered

• It confirmed what will not be covered

• What was needed from the audience

Being very clear and very explicit on these points immediately sets the expectation of those in the meeting and gives you a reference to point back to and say “remember, we are not covering X in this session”.

Starting strong commands the attention of people and aligns them with the purpose of the meeting, leading to more fruitful outcomes.

Being very explicit from the start about what will not be covered helps to proactively remove any derailing discussions and helps to keep folks focused on the goal. Even if this is all laid out in your agenda, be sure to repeat it.

Use effective tools

In this particular session, the organiser created a matrix to review the roadmap topics that were up for discussion.

This could have been a list of items or a typical roadmap visualisation. What helped here was that there were some hard trade-offs to make. When you drop topics on a matrix, alongside other items, it allows you to more objectively reason which is more important.

In this instance, the axes plotted impact and effort and it was amazing to see how quickly decisions could be made when viewing topics through these lenses. In other contexts, this could have easily led to derailed conversations based on subjectivity.

Find the narrative

We’ve all seen those movies where halfway through a connection is made between characters that leave you mind-blown. Can you create that same a-ha moment with your audience?

It’s very rare that the work we do exists in a vacuum yet many of us will come to meetings or workshops only to see the world through our lens. The reality is though that great ideas are ones which connect the needs of different teams, and customers. Look for ways to help others see the bigger picture and look for that change in mindset.

We could all benefit from thinking more broadly at times and telling stories is a great way to achieve this.

Hi, my name is…

Apologies if I just got Eminem stuck in your head for the rest of the day, but if it helps to land the message, maybe it’s worth it.

Remember, those first impressions that we know are so important should not be limited to new encounters.

Next time you are going to lead any type of discussion, be mindful of your introduction and the first impressions that you are creating. Whether it be that next meeting, that workshop, an interview with a candidate or your 1:1. The way you choose to start that conversation can make more of a difference than you think.

Powering this week’s thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this weeks:

Feedback is something that we experience in early life. As a child, as soon as we start to become aware of our surroundings and begin to understand language we begin to hear phrases like: “don’t do that”, “you made your sister upset”, and “go and think about what you’ve done”.

Those examples sadly tell what kind of a kid I was — sorry mum!

Speaking of my mum, I’ll never forget the time she recounted a story of when I was in primary school back in Scotland. You see, I was often getting told off for being disruptive in class and for misbehaving. I had just accepted that I was a bad kid.

When my mum went to school to meet with the teachers, she was told of all the terrible things that I had been doing in class.

“Is he doing the work?” My mum had asked. To which the teacher confirmed.

”And, what does he do when he finishes his work?”

“He disrupts the class, so I have to move him around to different tables.”

“He’s bored” my mum exclaimed, offering a conclusion that the teacher had not come to herself.

I had been receiving feedback loops in class that I was a bad kid — that I was disruptive and disliked by my teacher. For years after I was convinced that was the truth. But hearing my mum recount the story from her perspective and how she interpreted and challenged the feedback, completely changed my perspective.

Catching the ball

After attending some training at work last year, a concept regarding feedback was shared that has stuck with me since. The idea was that feedback is like a ball that is thrown towards you. It’s an object that you can catch, and in doing so, it’s something that you can dissect and examine.

When it comes to actual sports, at least ones with rules and stuff, I am pretty bad. In that reality, the ball would likely hurtle towards me and strike me across the face leaving me dazed and confused. And this is what feedback can sometimes feel like.

At work, we have recently wrapped up our end-of-year reviews where a lot of feedback has been gathered and shared. Some good, and some not so good. But negative feedback that is constructive is a good thing. It’s a chance to learn.

Instead of letting that ball come at you and knock you sideways, take a moment to catch it in flight. Hold it in front of you and rotate it. Look at it from different angles, from other people’s perspectives.

Why might people have this feedback for you? What did you do, or not do, to elicit the feedback in the first place?

Instead of acting like a squirming mess in the middle of a dodgeball court, instead, act like a world-class goalkeeper. Catching each and every piece of feedback and deliberating over the underlying message. Reflect on your accountability and then decide how best to proceed.

It’s on you

My mum could have taken that feedback about her misbehaving son at face value and returned home to ground me for that evening. But she didn’t. She chose to pause and reflect. To ask questions, and to try and understand the bigger picture.

In doing so, she encouraged the teacher to offer an alternative to simply punishing me. She offered her feedback and suggested viewing my disruption from another angle — boredom.

She captured the ball, rotated it around, and passed it back. This exchange went on until they were both clear on what was happening and what needed to change.

The end result was that I simply needed to be fed more work, and be given activities to keep me busy. This ended up being a win for everyone.

(Most) People aren’t bad

So, next time you receive feedback, whether it’s personal to you or to the work that you are doing, understand that a pause, seeing things from different angles and some follow-up questions can often lead to some interesting outcomes.

Most people who offer feedback are simply trying to share their perspective on something that has meaning to them. When we can see that the intentions are clear, and crave the need to understand each other, we can take bigger leaps in receiving and working with all types of feedback.

So next time you are given some feedback, say “thank you for the gift”.

Powering this week’s thoughts

Music plays such an important role when I am thinking, working, and reflecting. I also find it interesting to see what others are listening to. It's a gateway into an aspect of their personality. That's why I'd like to share, with each article, an artist or playlist that I have been listening to that week. Here's this weeks: