🤯 Imagine that — 2000 people with 800 projects running. It doesn’t take a math genius to work out that this is not a sustainable balance.

Within two weeks, Josh had to kill 60% of these 800 projects — 480 of them, to be exact. The most painful one was Etsy Studio — 150 full-time employees, 18 months of work. Gone.

And if you were one of those 150 people, you’d probably spend the rest of the week doing that quiet, awful maths in your head. Was the work not good enough? Was I not good enough? Eighteen months of my life…for what?

Now, let’s flip the role. 👉🏽 You’re the CEO Josh Silverman. You are responsible for the survival of this company and all of its customers. When you stand in front of a wall of 800 projects deciding what lives and what has to go — hard decisions have to be made.

So why am I sharing this story?

Over the past decade, I’ve used a handful of storytelling frameworks to help raise millions in funding. Not one dollar of it came from a better prototype, a slicker deck, or more technical polish.

It came from knowing how to build and tell the story in the room.

Business storytelling skill becomes even more prominent in the age of AI, building the thing is the easy part.

Anyone can generate a prototype, a deck, a plan. What still decides whether your work gets funded, prioritised, and shipped is one skill — how you communicate it.

What’s cooking in this blog:

• How to understand what executives care about

• How to craft messages that win their attention

The uncomfortable truth for designers

A pitch that doesn't hit the right point at the right time doesn't just fail to get buy-in. It quietly costs you credibility. And this isn't a big-company problem. I've watched it happen in a 12-person startup AND in a 30,000-person enterprise, and the shape is identical.

We’re too close to the craft.

The design process.

The research, the tension in the tradeoffs, the moment the flow finally clicks. That’s genuinely where the joy is. But somewhere along the way, most of us picked up a quiet belief that if the work is good enough, the work will speak for itself.

I’m sorry to say, good work is never enough. You’ve gotta know how to deliver it, at the right time when it matters.

Building the case for the work is not the annoying admin at the end of the real job.

It is the job.

While craft and design decisions are key to product success, the problem is that it’s chronically “under valued” in the rooms where money moves, and “under-translated” into the language those rooms think in.

How do we fix that? Let’s start by understanding how executive think:

What executive leaders want to hear besides your design decisions

I used to work with a CEO who sat next to me through a run of designer pitches.

And almost every time, the presentation would be a tour of design decisions. Why this pattern, why not that one, how we got from version three to version seven.

He’d ask the same thing after most presentations:

Why are they telling me all of these? None of it is on the top of my radar right now.

After a few rounds of those, he stopped turning up to the design pitches.

✋🏽Hold on, before you roll your eyes. He wasn’t being dismissive. He was being honest about a constraint the designers couldn’t see.

What this CEO was actually saying:

I think about that every time I coach someone to prepare a big presentation. Because it reframes the whole thing.

Breaking down the layers that lead to strategic storytelling.

1. Being brilliant at your craft is the entry ticket to the idea.

2. The art of connecting that craft to the business is the next layer.

3. And how you structure and deliver that connection in the room — that’s the make-or-break of whether the idea lives.

Most designers are never trained beyond the first layer.

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The two questions every exec runs in their mind to filter ideas

In this order:

1. Why this? Is the problem real, specific, and costly right now?

2. Why now? Is the window closing? Is the cost compounding while we sit here?

The key is to answer BOTH in your pitch.

Most people spend 90% of their time on question one — evidence, research, prototypes, competitors, ideas — and run out of runway before they ever touch question two. 🥱

Think again:

Silverman didn’t kill 480 projects because the work was bad. Plenty of it was excellent. He killed the ones that couldn’t answer why this, why now.

A pitch that answers “why this” but not “why now” often gets a “maybe we’ll look at it next quarter”. And that means you’ve already lost the room.

Andy Grove, Intel’s former CEO, said it best:

☝🏽☝🏽☝🏽 Your job in that room is to show them which moment they’re standing in.

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How to draft your message to win the room: “Why Now” — not later

“Why now” is the funding lever. Pull it in your first three sentences.

Before:

❌ We redesigned the insurance claims flow. Here are the screens. We’ve tested with users. What do you think?

After:

✅

We’re losing around 4,000 new members a quarter at claims submission. 36% abandon partway through, and the ones who never complete a first claim churn at 5.4x the rate of those who do. Every week we wait, another cohort hits it and never comes back.

Here’s the plan to make the shift..

The first version asks for approval. The second makes inaction feel expensive. 💸

That’s the whole shift. You’re not asking someone to say yes to you. You’re showing them what doing nothing costs the business — and everyone should be worried about it.

Here’s your exercise today:

Pick one initiative you’re working on about fixing money leaks. Write your one sentence pitch in this shape:

Consider these 3 crucial rules

Real — this is a real issue, not a hypothesis.

Be Specific — not “improve the experience,” but “36% skip this step.”

Costly — not “it could be better,” but “5.4x higher churn.”

If the data is missing — that’s an indication of the actual gap in your business case, and a calling to investigate and answer these questions as a strategic decision maker, before you bring a half-baked case in front of a round of executives who are extremely time poor.

Remember — wasting time in high-stakes meetings will contribute to loosing reputation. If you get to showcase your judgement 3 times a year, make them count.

Somewhere in those 480 killed Etsy projects could have been a piece of work as good as yours. The difference wasn’t quality. It was whether anyone in that room could say why it mattered — and why it mattered right now

👏🎬

And then there’s the part nobody plans for

Structure provides clarity to your idea.

The art of delivery gets your idea remembered.

That’s Part 2 — in the next newsletter, I’ll cover how to deliver the actual pitch and build influence in ways you never thought of.

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And if you’d rather go through the frameworks with me live, I run a free 45-minute session on the techniques behind building a winning business case.

In this session I’ll break down the exact pitch structure, how to read the room and techniques to turn listeners into supporters.

👉 Save your spot: Business Storytelling — How to Influence What Gets Funded

Thanks for reading. Jac ✌️

How I can help you:

After 18+ years as a strategic business designer running two successful companies and helped companies raise millions in fundings, I now help designers unlock their strategic thinking skills and become irreplaceable business partners.

This 4-week live cohort “AI Powered Strategic Design Accelerator.” covers strategic business acumen, strategy visioning, strategic communication, connecting design to business impacts.

Alumni reflected +67% more confidence in making strategic decisions and connecting design to business.

Next Intake: OCT(3 spots left)
Price will increase after Jan 2027
Your educational expenses should be fully tax deductible for the financial year (please check with your accountant)

🎉 Self paced course launching soon! stay tuned.

5/5 reviews ⭐️ from Recent cohort:

We watched the group of them started to crawl towards the moss house, surround the sweets. They would crawl around there for hours. Like they’ve got sent a spell. My sister and I would leave the park feeling satisfied, like we’ve successfully commanded a group of ants to do exactly what we want them to do. And they obeyed. It’s quite a new feeling as a kid gaining a new set of power and pride.

Fast forward years later, someone shared a video and it completely blew my mind about the behaviour of “ants”. In the video, someone took a pen, drew a circle around a crawling ant, and just like that, suddenly, the ant obeyed to the spell, only crawl within the circle. 🤯

I get you asking:

Well Jac, What does this ant story have to do with Career Growth?

A lot actually …

The Ant Trap Mentality

Imagine someone goes to work, gets briefed what to do, they do the job within the brief. And that’s all there is, nothing more. Like the ants crawling within the circle drawn for them.

A closer to home example for the designers here:

PM asked: Build a new feature (✍️draws the circle)

Designer: Builds the feature, and that’s it. (🐜 plays within the circle)
(even when the project goal shifted slightly beyond the original ask, they were still stuck at the “original feature build”

The question worth asking is:

What might have gotten them into this situation of just…doing?

Wake up, go on with their day, sit back and wait to be assigned the task, do the task and clocks off.

Nothing wrong with that, until the same pattern goes by days, weeks, months and years.

They find themselves within the trap they’ve drawn for themselves, and by that point, it’s extremely challenging to leap forward and upwards.

They’ve built the comfort zone to enable that to happen. The problem solving muscles and critical thinking ability had weakened, no longer built for the ever changing industry landscape.

Escape the Trap

A high performing operator is able to make the unlikely connections to the impact of this one job to multiple connections beyond what they do. They find the gaps within the initial circle, crawl beyond the drawn lines, and see beyond their work through multiple layers.

Beyond what was told about the feature, they are able to connect this task with other parts of the product within their Team,

They are able to connect what they do with how it impacts other products within the org.

They are able to draw the connections and patterns towards how the industry trend and movement impacts the decision they make with this one single feature.

Daily system set the ceiling before your willpower gets a say

Behaviour precedes belief, change your behavior and your thinking will start to follow, not the other way around.

Proactively step into the “new” is the opportunity to expand the growth of your behaviour and agile problem solving ability.

James Clear phrased it perfectly in his best selling book Atomic Habits -

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In order to do that, these behaviour traits are required:

1. Agency

2. Velocity

3. Pattern recognition

4. Curiosity

Agency - the willingness to identify opportunities, and proactively go explore them.

☝🏽 Agency is driven by “Curiosity”

Pattern Recognition - The ability to acknowledge patterns and impact within the team, beyond the product, collected amongst trends and industry. A thing happened once, the brain collects it, and is able to bring it up where relevant to make the unobvious connection. AI can’t do that for you.

☝🏽 Driven by observant, analytical and critical thinking skills

Velocity - Able to quickly draw the hypothesis on: When to do what (timing), How to do it (knowledge), What does good look like (standard), How to do it well (breakdown into actions)

☝🏽 Velocity excels with confidence, and it’s driven by mastery experience, craft, knowledge, working with people that inspire you to rise above yesterday - Everyday!

Curiosity - Proactively lean towards the unknown. Question what’s outside of the ‘designated remit’, push beyond roles and descriptions with measure.

☝🏽 None of these would exist - if you don’t have the passion behind what you do.

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Rise above

There’s an everyday-ness to excellence.

And if you currently feel like you’re operating within the Ant Trap - whether it’s within the project you’ve assigned, team, company, marriage, friendship, the culture, the environment around you.

Just know that, almost everyone is operating within some sort of hypothetical ‘boundaries’ like the circle drawn for the ant.

And congratulations, if you are observant enough to acknowledge it - you’ve ticked the awareness step. ✔️

Next, things will get a little harder, you’d need to work out some muscles to push beyond the circle you’re in. By seeing, to draw a new circle, perhaps a second circle, and finally gained the confidence to keep pushing.

At that stage, it’s a constant uphill climb. But once you get to the next circle, it’s like the feeling of hiking 2 hrs and standing on top of a mountain - “Wow, This is amazing”. That sense of achievement makes you want to do it again and again. That’s the rep! That’s the new habit and the sentiment loop to keep your gears sharp towards new heights.

Along the way you’re going to experience: Pain, Judgement, Shame, Breakthrough, Confidence in a mixed bag.

That’s it for today. Thanks for reading.

Talk soon,

Jac ✌️

How I can help you:

After 18+ years as a strategic business designer running two successful companies and helped companies raise millions in fundings, I now help designers unlock their strategic thinking skills and become irreplaceable business partners.

This 4-week live cohort “AI Powered Strategic Design Accelerator.” covers strategic business acumen, strategy visioning, strategic communication, connecting design to business impacts.

Alumni reflected +67% more confidence in making strategic decisions and connecting design to business.

Next Intake: OCT(50% SOLD OUT)
Your educational expenses should be fully tax deductible for the financial year (please check with your accountant)

🎉 Self paced course coming soon!! stay tuned.

5/5 reviews ⭐️ from Recent cohort:

The reason why I love what I do. 🫶🏾

And there’s a pattern.

I’ve started calling them Multi-Level Operators. Once you see it, you can’t unsee it — and it shows up in every interaction, especially the way people communicate. There are three levels. Most people live and die on level one. A few make it to level two. The rare ones — the people who consistently create the best outcome for everyone in the room — are operating on level three.

Let me break down the art of influence through the lens of “Multi-Level Operators”

Level one: “Here’s what I want.”

Level one is all about self-expression. My idea. My product. My ask. What’s important to me.

Picture someone presenting at a company all-hands. The level-one presenter turns up to report what the team did — the whole story framed around their own work. Within minutes, half the room has quietly drifted back to their inboxes.

Why?

Because they never made the leap from self-expression — “here’s what I shipped” — to the only question that earns attention: “why should anyone else care?”

They ticked the box (“I did this”) but planted no seed about what it means for other teams, or what anyone in the room could actually take away.

It shows up in my inbox, quite often too. I get cold emails from complete strangers that open with: “Hey, would love to grab a coffee and pick your brain.”

Wait, why the hell would I do that? Firstly, That person didn’t even bothered to call me by my first name. Think about this from the receiver end.

My immediate reaction: I don’t know you — and you want me to set aside time, get changed, get in a car, and drive 30 minutes — for what, exactly? It lands with a thud, because it’s built entirely around what you want, with nothing in it for me.

Level two: “Let’s do this together.”

Level two adds a second layer: impact on the other person.

If I say this, how will they react? What’s in it for them?

This is where communication stops being a broadcast and starts being an invitation. Instead of “here’s my idea,” it becomes “this might improve your sales funnel — I’d love your take.”

I see this with designers all the time. A good one spots that their work has ripple effects on another team, and instead of charging ahead, they proactively pull those people in — gracefully — so the idea gets shaped with them, not at them.

Level two operators understand that being right isn’t enough. You have to make room for the other person in the story.

Take a pause to think about that for a second!

Level three: “Let’s get to the best outcome — together.”

Level three is a different game entirely. These operators aren’t trying to win — they’re trying to create the best outcome for everyone. And, counter-intuitively, that’s exactly how they end up where they wanted to go.

They can run through all three levels of analysis in an instant — input, likely reaction, outcome — and choose the move that speaks so directly to your needs that, without any prompting, you arrive at the same idea. It isn’t manipulation; it’s the opposite. It only works when the goal and mission is crystal clear.

What sets them apart:

• They are system thinkers - instantly see the variations of a single input, and pick the one that does the most good and the least harm.

• They go the extra mile on rigorous thinking, so by the time they put anything forward, it’s already a well-rounded direction that serves the bigger picture.

• They play the long game. They can hold the full arc — now, next, and future — and they’re genuinely okay if the win isn’t theirs today, as long as everyone moves toward the goal.

The mental model underneath it looks like this:

Input → reaction → outcome → behaviour change → long-term impact.

Level one stops at input. Level three is already thinking about long-term impact.

And notice where the real work happens: before a word is said, shared, or presented. Level three isn’t quick wit in the moment — it’s rigorous thinking, done up front.

Here’s a perfect story about Level Three Player Moves 👇🏽

Keep your eyes on the prize - The ultimate level three move

My partner Toby once told me a story that stuck with me.

Toby was working with a young hotshot — the kind of person who’s convinced they already know everything and that you know nothing. One of their emails was openly dismissive of Toby’s suggestion.

The level-one move is obvious: fire back, prove them wrong, win the exchange. 🫨 But the result could be - fractured work relationship, takes longer to rebuild.

Toby did the opposite. He sat with it. He drafted the next reply slowly, designing it to do three things at once:

1. Make it clear the goal was a shared goal — that he was there to help, not to compete.

2. Plant just enough evidence that he’d actually done this before and knew what he was talking about.

3. Drop the seeds of the ideal idea that could get to the goal together — quietly — so the kid could pick up the hint and “come up with it” themselves.

The kid felt like the smart one at that moment. But here’s what Toby was really doing: turning the kid’s self-interest into a shared one — quietly moving him from “me versus you” to “we’re both here for the same goal, and you are the one with the great idea, congratulations”.

You can imagine life after that email makes working relationship much easier to deal with, not the opposite had you played the “Level one - shot back” card.

Yes, it’s about playing the long game. Because the lesson was never about who came up with the idea, or who won. It was about getting everyone to the best outcome — together.

So when you’re in a negotiation and someone needs to vent, let them. You don’t have to agree. You just have to tame the reactive animal in your head, let them talk, and show them you heard it. Then adjust.

Spending a little longer planning the conversation at the start can completely reshape where it ends up.

Comms Queen - Taylor Swift

Turn the people around you into your distribution channel

There’s one more level-three move worth naming: the best operators don’t just win the room, they turn the room into their megaphone.

No one does this better than Taylor Swift. She’s the ultimate example of turning fans into a distribution community — going direct to her audience, routing around the middlemen, and giving people something to belong to.

Her fans decode her clues, defend her online, and sell out stadiums before she spends a dollar on advertising. She doesn’t market to them; she hands them a story and an identity worth sharing, and they do the marketing for her.

The mechanism is simple but ruthless: give people an incentive they genuinely care about, and behaviour changes on its own.

Colleagues, partners, clients — same principle. When you make the mission genuinely theirs, they carry it for you.

So where do you operate?

Most of us default to level one under pressure. It’s faster, it feels safer, and it’s all about us.

But level three isn’t about being more clever. It’s about training your mind to be a multi-level thinker — to swiftly read the incentives other people actually value, and shape the narrative so everyone is rowing toward the same shore. It’s more generous, more patient, and, over time, far more powerful.

And here’s the part I love: this isn’t a gift you’re born with. It’s a muscle. Every conversation is a rep. Every all-hands, every tense email, every negotiation is a chance to pause and ask one quiet question before you speak

“What does the other person need to feel, so that what I want becomes what we want?”

Get good at that, and your influence will shift with lasting impact. You begin to pushing your ideas less and start pulling people toward a shared one. You start moving people towards a shared direction. And the outcomes you reach together grow bigger than anything you could have reached alone.

Level three is where true leaders operate.

Thanks for reading, til next time.

Jac 🫶🏾

How I can help you:

If you’re curious about how to uplift your communication game to a Level three operator, I built “AI Powered Strategic Design Accelerator.” to achieve exactly that.

Use this code to take $100 off as a subscriber: DoYourThing
Price will increase after JAN 2027

This 4-week live cohort “AI Powered Strategic Design Accelerator.” has been taken by 200+ designers (Alumni from top companies: Anthropic, Google, Linkedin, Doordash, Superhuman, Microsoft). Rated Top 7th Design Course in Maven.

Course syllabus covers strategic business acumen, strategy visioning, strategic communication, connecting design to business impacts.

Next Intake: OCT 2026 (50% SOLD OUT)
Educational expenses should be fully tax deductible for the financial year (check with your accountant)

Birds. Sunshine. My little plant corner. A laptop.

It took me a while to figure out that this one small moment in the morning is what fills my cup.

I believe in taking proactive steps to build the environments to enable the best version of myself - if the energy takes me to a different country, I would make the move.

Speaking of good energy, I went to the Miro Canvas event in Sydney this week. What a vibe. I’ve been a Miro user since day one, and if you know me, you know blank canvas is where all great things start. We designers have always lived in the messy middle. Idea dumps, wild connections, organised chaos. Miro just makes it feel more human.

They gave me my personalised emoji stickers at the event - and I was like a kid in a candy store!! 🤩 Needless to say - this is one of my favourite new features from the upcoming Miro AI releases (YESS, you can soon create your on digital stickers).

One of the key reminder for the event 👇🏽

“Keep things weird and fun.”

In a world that’s sprinting toward efficiency, that reminder is actually a creative lifeline. Weird and fun is where innovation lives.
And innovation, as we all know, is what creates real business differentiation.

OK.. Today’s post is all about BUILDING and BREAKING TRUST

I’ve been thinking about it a lot lately. I’ve broken trust. I’ve met people who made me feel immediately safe and seen. And I’ve worked alongside people for years where something invisible always sat between us.

Trust is the invisible architecture of every relationship, every career, every team.

These are some of the personal stories and reflections - I hope these inspire you to build and find trust in your own circles.

The time when I thought I was building trust...

I wasn't.

Years ago, I landed a role building a design function from the ground up at a startup. I was passionate. I was ready. I had the whole plan.

30 days: establish the foundation.

60 days: the team hits momentum.

90 days: we launch.

I thought this was leadership. I thought the clarity of the plan showed vision. What I didn’t see was that I had walked into a room where everyone was swimming in their own lane, at their own pace, in water I hadn’t spent any time in yet.

I pushed my agenda. I moved fast. My intention was to do good work for the company.

But I created anxiety in the process.

And slowly, quietly, I lost trust along the way. Not because people didn’t like me. Not because the work was wrong. Because I had inherited my past into an environment that wasn’t ready for it. I forgot to stop and ask: what does this team actually need right now?

It took a longer road to rebuild. One relationship at a time.

Then one day I came across Bruce Lee’s words. 🧘🏽‍♀️

Water shapes itself to a waterfall. It flows through rock. It rests in a lake. One element, infinite forms.

That hit me somewhere deep. I had been showing up as a battering ram when what the situation needed was flow.

The shell I’d built around myself: “the high achiever, the one who delivers, had made me rigid.” Underneath it, I still had water. I just had to let it flow and be adaptable to the surroundings.

What breaks TRUST:

A collaborator who taught me what integrity costs.

A few years back, I was deep into a business collaboration on a complex project. We both showed up passionate in week one. By month two, something had shifted. Meetings got cancelled last minute. Messages left unanswered until I followed up. Then followed up again.

The project became exhausting. Not because of the work, but because of the weight of uncertainty and the emotional labour of chasing. I had to called it off - despite how much hard work had already gone in.

That experience sharpened something in me. I have what I call a personal branding promise: I will always deliver early. I never miss a deadline. If it’s a collaboration, I am proactive, always moving the needle, never waiting for the last minute to become someone else’s problem.

Your work integrity is your personal brand: Find them. Name them.

And these becomes how people talk about you when you’re not in the room.

Great work + being invisible = still not trusted.

I managed a designer once who was genuinely talented.

Every time he showed up, it was perfect. Perfectly finished deck. Precise product delivery But he didn’t communicate between deliveries. He’d finish a project without telling me so that I can reevaluate his work capacity. He’d join team calls with camera off half the time. I was always the one reaching out to ask where things stood.

I gave him feedback. Nothing shifted.

He kept delivering. But trust never grew. And promotions stayed distant.

Visibility also builds your personal brand!

Visibility isn’t vanity. It’s how trust accumulates.

"They hired me, so they trust me" is a trap.

Earlier in my career I genuinely believed that being hired meant being trusted.

Wrong.

Trust isn’t transferred with a contract. It’s earned in micro-moments. In the things you notice, the things you make room for, the way you show up before anyone asks you to.

Here’s what I’ve learned: everyone has their own definition of what good looks like.

A CEO worried about headcount productivity needs you to read that and bring your work close to that concern.

A PM focused on go-to-market traction needs you to connect what you’re building to those stakes.

Here’s the question I ask designers when they tell me a stakeholder doesn’t understand their work:

“Have you taken the time to understand them first?”

Lay the bricks for others. That’s how others eventually lay them for you.

Read the room. Enter their sandbox.

Someone who earn real trust aren’t always the best at their tools. They’re the ones who understand what the people around them actually care about, and bring their work close to that.

They pave the way for others to work better. Before justifying their own value.

That’s the shift from execution to partnership.

What I’d say to the version of me on that rooftop ten years ago.

She was good. She was passionate. She meant well.

But she was so focused on what she wanted to build that she forgot to ask who she was building with.

Trust isn’t something you announce or plan into a 90-day deck. It’s something you earn in the daily fabric of how you work. How you show up when no one’s watching. How you talk about your colleagues when they’re not in the room. How you hold your word when it would be easier to let something slip.

And if you’re reading this and thinking about a relationship, a team, a stakeholder, a collaboration that feels a little distant right now...

Maybe ask yourself:

what does trust look like to the person on the other side?

A few questions to sit with:

💬 Who in your work life do you most want to build trust with right now?

💬 What does “good” look like to them, not to you?

💬 And what’s one thing you could do this week to define your integrity value - so that you can define a trustful personal brand.

🫶🏾

I hope this post spark some lights and reflections for your day.

Hit reply if this resonates.

I read everything.

Jac ✌️

How I can help you:

After 18+ years as a strategic business designer running two successful companies and helped companies raise millions in fundings, I now help designers unlock their strategic thinking skills and become irreplaceable business partners.

This 4-week live cohort “AI Powered Strategic Design Accelerator.” covers strategic business acumen, strategy visioning, strategic communication, connecting design to business impacts.

Alumni reflected +67% more confidence in making strategic decisions and connecting design to business.

Next Intake: JULY (SOLD OUT) // OCT(50% SOLD OUT)
If you’re in Australia - All of your educational expenses is fully tax deductible for the financial year

💬 What alumni say from previous cohorts:

Two exciting things happened in the last two weeks I want to share before we get into the main piece.

🦹🏼‍♀️ First highlight: I showed up as a guest mentor at Design Table in Sydney - given feedback to 4 very brave designers presented their work about how design moved business. No Figma. No slides. Just them, their story, and 10 other designers as audience.

My friend Aniruddha runs these small gatherings, often between 6-15 people, where designers gather to have closer conversations in person. Compare to big name meet ups - These events generates different level of energy - with opportunity to dive deeper into closer/ real conversations.

We worked through how to structure a pitch, which metric to highlight for which audience, how your voice and your body language either earn trust or undermine it before you’ve said anything important, and how to close in a way that creates a lasting impact to your message.

The biggest thing I kept coming back to all night: Your audience’s time and attention is sacred. Make it worthwhile for them.

I have lots of respect for those to carve out time to do the ‘uncomfortable’.

Because hoping to get noticed by doing good work quietly is not a strategy. The strategy is getting out there, showing the work, taking the feedback, and getting better at it.

🎊 Second highlight: I just wrapped two weeks with the latest cohort “Claude Code AI Product and Design Velocity”. And I’ve had butterflies ever since last Monday.

Every time students shares their results on the final demo day, I feel it. This time especially.

The cohort between Pms and Designers both shown the perfectly balanced business case pitch output and an on brand Prototype built with Claude.

This amazed me because we often presume in a world where PMs don’t have the ‘visual in their story’ and Designers don’t have enough ‘Business in their presentation’. Now with AI, business acumen and the right skills, it’s achievable for both.

👑 I was blown away. Two weeks. That’s what it took.

The cohort walked out more confident, more able to hold the business conversation they’d always wanted to have, less likely to shrink when the numbers come up.

This is exactly why I do this.

Okay. Let’s get into the newsletter!

In this issue, it’s the insights from a candid conversation with the legendary David Wang:

• The skill gap that’s quietly making senior people unemployable (it’s not what you think)

• What really happens to your role when the handoff model dissolves

• Why distribution is still the game, especially when everyone can build

Where AI product building is going (and what it means for your career)

I’ve been sitting with a few conversations from the past few weeks, one in particular that I keep returning to, about where AI product building is actually going and what it means if you’re a senior designer watching the landscape shift.

Not the hype version. The practical version. What skills matter. What changes in how teams work. And what to do if your handoff model is already starting to feel a little... wobbly.

We had a fireside chat inside the cohort with David Wang. Group PM, ex-Linktree, ex-Kajabi, now based in Seattle with a very close view of the US hiring market. He also teaches PMs and has spent years coaching people through product career transitions.

We put 3 hot topics on the table - aiming for sharp, direct, no filler reality checks:

1. With AI tools levelling the playing field on execution, what skills are companies actually paying a premium for right now?

2. Does “everyone can build” make PMs and designers more valuable or less?

3. How should someone think about their role when the traditional handoff model starts to dissolve?

Here’s what landed. 👇🏽

The two skills that actually matter right now

The highest leverage skills in the market right now are AI skills and business thinking.

But the AI skills part is way more specific than it sounds. It’s not “how do you prompt AI” - It’s which level you’re operating at with AI in your process.

There are three:

Level 1 is using AI daily. Prompting. LLMs. The baseline. No excuse not to be here at this point.

Level 2 is building. Taking an idea from concept to design to prototype to production. And ideally, integrating AI functionality into what you build, not just using AI to help you build it. There’s a meaningful difference.

Level 3 is the agentic layer. Understanding how to chain agents together, create systems that run without your constant input, orchestrate multiple specialised agents to do the work of a whole function.

Most people are at Level 1. Some are at Level 2. Level 3 is where the conversation is happening, especially for senior and leadership roles.

The good news is you don’t need to be all all 3 levels. But you do need to know where you are and which gap to fill.

The business thinking piece connects to all of this. It’s not a separate skill. It’s the lens that makes the AI work meaningful. Because everyone is building stuff. The question is whether you’re building toward something that matters.

Building to the right direction. That’s the thing.

Not just: what did I make?

But: what problem does it solve, what metric does it move, and why does that matter to the business?

That gap, between what you built and what it changed, is still where most people stuck at.

✏️ Your takeaway: Map yourself against the three levels honestly. Where are you? What’s the gap? Level 2 is learnable - Start there before you worry about Level 3.

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What happens to roles when everyone can ship

This is the one question I hear most from senior designers. And it’s a fair question.

When everyone can push to production, what does that mean for how teams work? For the handoff process? For what your role actually plays?

Here’s the honest version.

Engineers aren’t writing code anymore, they’re building infrastructure. Deployment reliability, security, scalability. The work evolved, not disappeared.

For PMs, the PRD isn’t the job anymore. But accountability for what ships is. Talking to customers is. Owning the metric is. Asking why someone didn’t sign up is.

For designers, the shift is the same. We can’t lead with what the design looks like. We lead with what moved because of the design. Designers (Senior level) are now expected to identify business opportunities and at some level, shipping directly to prod without the former “handing off” process.

The title confusion, “Am I a designer, a PM, a builder, what does this mean for my job?” is common. But it’s an inward question - it’s time we break those title boundaries.

From outside the product teams, the people making resourcing decisions aren’t asking about your title. They’re asking: Are you shipping good stuff?

And at senior levels especially, a new and uncomfortable question is being added: what have you personally delivered?

When hiring managers asked “what have you delivered?” The answer that don’t show direct business impact sounds like: “I built the culture.”

Every role now has to point to something towards the outcome. Not what they oversaw a team or process - but produced outcome that moved business!

✏️ Your takeaway: Be less attached to the title. More attached to being able to answer that question clearly.

Audit how you talk about your own work. Are you describing the thing you made? Or are you describing what changed because of what you made? That’s the gap. Start closing it now, not at your next performance review.

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When is an organisation actually ready for AI?

Spoiler: waiting for “ready” is usually how you end up behind.

Here’s the reality at board and C-suite level right now. Every executive team has an AI adoption mandate. Teams adopting faster create pressure on teams that aren’t. That’s the current dynamic.

Whether that’s the right move is a separate conversation. But it’s the operating reality.

The smarter frame isn’t “are we ready?”
It’s “what opportunities are we creating for people to experiment, and are we actually holding people accountable for doing something with them?”

Change happens in small increments. Early experimenters. Early majority. Then it becomes expected. The companies that wait for a clean moment to go all-in usually don’t find one.

And here’s a cautionary tale that stuck with me. One large tech team built a very sophisticated AI rollout dashboard. They tracked one thing really carefully: how many tokens were burned per month.

Not problems solved. Not outcomes delivered. Just tokens burned.

That’s a vanity metric. And it’s just a matter of time before a vanity metric produces a disaster. And it did.

They’re now tracking something more useful: Revenue per token per employee.- What is our ROI applied to AI spend.

That framing might sound cold. But it’s actually just business thinking. Which loops back to where we started.

It’s not about whether you use AI. It’s whether you’re using it toward something that matters.

Every time you reach for a tool, it’s worth asking: is this helping the outcome, or am I just burning tokens?

✏️ Your takeaway: The org-readiness question is really a habit question. What’s one thing your team could experiment with this week that directly connects to a metric you care about? Start there. Not with the roadmap. With the experiment.

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Distribution is still the game

AI didn’t change this. It just made it more visible and harder to ignore.

Now that everyone can build, the product is no longer the scarce thing. Getting it to the right people, in the right way, with the right pricing, at the right moment?

That’s where the gap opens up between a good business and an average one.

When I first started my fashion business, I ignored sales and marketing for the first full year. Entirely focused on making the thing better. Struggled to understand why the sales doesn’t pick up even with products well crafted.

The second year, I redirected 50% of revenue into distribution. That’s when the market opened up, revenue tripled 💰. Over the course of 7 years in business, it’s the mix of good product, strategic distribution channels, and business model pivoting to make the scale exponentially.

Product quality is the ticket to play. Distribution is the game to win.

As designers, we spend so much energy on making things right. So little on how the right thing reaches the right people.

That’s not a craft failure. It’s a training gap. Nobody taught us that part. With AI now becoming a key business player - It’s becoming more prominent that designers need to consider broader spectrums within the business landscape than staying safe at the Product level.

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If closing that gap, from great work to actual business impact, is what you’re working on right now, that’s exactly what I focus on in my course - it’s designed for practical shift from “here’s what I built” to “here’s what it moved.” You can learn more here.

Hit reply. I read everything.

Talk soon, Jac ✌️

PS — If you want to work through business acumen , powered with AI operation in a structured way without spending 2 years on a dated MBA, learning with a group of people who inspire each other to improve, Take USD $100 Off here: maven.com/jacalin-ding/ai-powered-strategic-design-accelerator

After 18+ years as a strategic business designer running two successful companies and helped companies raise millions in fundings, I now help designers unlock their strategic thinking skills and become irreplaceable business partners.

This 4-week live cohort “AI Powered Strategic Design Accelerator.” covers strategic business acumen, strategy visioning, strategic communication, connecting design to business impacts.

Alumni reflected +67% more confidence in making strategic decisions and connecting design to business.

Next Cohort Kicks Off in JULY (timezone: AEST / PDT / EDT ) - If you’re in Australia - All of your educational expenses is fully tax deductible if enrolled by JUN 30th.

💬 What alumni say from March (Sold Out) cohort:

A quick life update before we get into it.

I’ve been heads down teaching the Claude Code AI Product & Design Velocity course.

I also celebrated my friend Vida’s book launch. Soft Power. A room full of brilliant people, a couch, and me telling an unscripted story about Bruce Lee and learning to be like water. More on that another time. But go get the book.

And quietly, in the background, I’ve been sitting with a calling: Title jail.

The idea that most of us wrap our entire identity around what we do and what we’re called. Senior / Lead / Head of X …The moment the title disappears, so does the sense of self.

I’ve been training myself to escape it.

True freedom, I’m realising, is when you no longer need to hold on to what others see you as.

But that’s a longer letter for another day.

Today I want to talk about something that connects to all of this.

The skill nobody taught us in design school.

Something I’ve noticed teaching over 200 designers through my courses

They are brilliant.

Thoughtful. Strategic. Deeply skilled.

They came to the course because they’ve noticed how important it is to talk about their work in a way that makes executives care.

Not because they’re bad communicators.

Because nobody ever taught them the translation.

The structural problem nobody names

The reason designers work gets backlogged first isn’t because design isn’t valuable.

It’s because of where we sit in the org.

A salesperson closes a deal. The money hits the account. The link is direct. A marketing campaign runs. Downloads go up. Clear cause and effect.

Design ships a feature.

Something improves. Maybe conversion. Maybe retention. Maybe nothing measurable yet.

But who gets credit? The PM who owned the strategy. Who gets cut when budgets tighten? The designer.

It’s not personal. It’s structural.

The further you are from a clear financial outcome, the harder your value is to defend.

Design sits 4 steps from the C-suite conversation. User researchers sit further.

And when a CFO has to choose between cutting the sales team or cutting design? That math is brutally simple for them.

The 4 steps most designers skip

There are 4 steps between your design work and the thing the business actually cares about.

→ What you built → How it changed customer behavior → What that did to the business metrics → How that moved the financial outcome

Most designers nail step 1.

“We built a design system.”

Cool. And?

Almost nobody connects all the way through. And that’s exactly where the PM steps in and takes the narrative. Not because they did more work. Because they speak that language fluently and we don’t.

The mistake I kept making

Early in my career I thought making myself smaller would work.

If my ask is small enough, maybe they’ll say yes.

“It’s just a small usability issue. Low effort.”

“Can we just tighten the navigation? Nothing major.”

“Can we just clean up the empty states before we launch?”

Every time. Deprioritised. Ignored. Not right now.

Here’s what I learned the hard way.

Small asks don’t feel safe to executives. They feel forgettable.

If the benefit isn’t obvious, the cost always wins.

The designers who get resourced, get heard, get their work shipped. They don’t make themselves smaller. They make the value impossible to ignore.

The language problem

“The redesign reduced cognitive load.”

Crickets in the boardroom.

Not because the work wasn’t good. Because nobody at that table knows what to do with that sentence.

Design has a language problem, not a value problem.

We were trained to talk about craft. Hierarchy. Flow. Friction. Clarity.

The C-suite was trained to talk about money. Revenue. Retention. Cost. Growth.

Neither side is wrong.

But only one of them is in the minority. And it’s us.

“This flow change increased checkout completion by 14%.”

Same work. Different sentence. Completely different conversation.

One thing to do this week

Take a project you’re currently working on.

Walk it through the 4 steps out loud.

You don’t need perfect data. A clear hypothesis is enough to start.

That’s the translation.

And once you learn it, you can’t unlearn it.

Until next time,

Jac x

🥁 How can I help you:
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- Paulina Galindo 🇺🇸 Principal Product Designer @Meta | ex-DoorDash | Ex-Linkedin

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“This course was definitely an eye opening learning for me as a mid level designer. With tactics to communicate your design value and connecting this with the business strategies, I feel so much more confident about advocating myself.”

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“This course was a game-changer. It shifted how I see my role as a designer - from executing great work to driving meaningful impact. I learned how to connect design to business goals, manage stakeholders with clarity”

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• Every week there’s a new tool and somehow everyone else has already “integrated it into their workflow”.

• The process you know is now being pulled under your feet — research, ideation, prototyping, handoff… all of it.

• Job titles feel… wobbly. Like the ground rules changed and nobody sent the memo.

• You’re trying to learn fast enough while still doing your actual job (lol).

• And the noise is relentless. Demos, hot takes, doom posts, “10x designer” threads, LinkedIn victory laps.

And underneath all of that is the same quiet question:

Am I about to get better at my craft… or get left behind by it?

If that’s you right now — hi. I see you. I feel you 🫶🏾 That was me too.

If you’re reading this and thinking “I’m already behind”, I want you to know:

Fast forward 12 months, and the panic has mostly gone, and now replaced with EMPOWERMENT!

Not because the internet chilled out (it got louder). Not because I suddenly became a “tools person”. But because I stopped treating AI like a threat and started treating it like what it actually is: a supplement. 💊

It doesn’t replace the craft. It makes you slightly superhuman at the slow parts — drafts, variations, scaffolding, first passes — so you can spend your energy on the parts only you can do: taste, judgement, trade-offs.

And once I stopped spiralling and started building, I ended up shipping a bunch of real things with AI:

• a teaching assistant that runs my course prep

• a personal net worth tracker

• an investment property finance app that shows all outgoing and incoming from last 13 years

• a demo meal planning product (full prototype)

• a content strategy planning agent

• a grocery shopping site with authentication gateways

• an industry news + insight scout agent

• …more on the pipeline every few weeks

None of these required an engineering team. None of them required me to “learn to code”. (The first one was rough. The second was less rough. By the sixth, it was… weirdly normal.)

So if you’re still dabbling, still unsure, still wondering if you’re already behind: this one’s for you.

Recently I ran a little experiment: could I build a real, on-brand product in two weeks — no engineering team, no dev handoff — something I’d actually feel comfortable showing a product team?

Turns out, yes.

Before I get into the three key takeaways with you, if ai is fresh to you.
I got ya. I’ve pulled out one of the video from my course about here’s a quick 7-minute intro video on “How to work with AI effectively” - don’t mind me pulling it straight from the course 👇🏽 This is all of the foundations you need to know.

👏

Okay. now you know the foundations - Let’s get into the insights - these will make more sense now.

1) Diagnose “why this now” is the key

Here’s the trap: AI makes building so fast that you can accidentally ship something that’s beautifully made… and completely irrelevant.

The building is the easy part.

Knowing what to build is where everyone gets stuck.

So I started using a three-question sniff test before I let myself touch anything:

1. What does the data say? Is the problem real, not just a hunch?

2. What number moves if you fix it? If you can’t name the number, the problem isn’t clear enough yet.

3. How does your solution change the behaviour? Not “improve the experience” — what specifically changes for the product?

   And when you’re feeding AI “data” to help you find opportunities, don’t overthink it. Start with the same inputs you’d use in a normal discovery sweep:

• Funnel + drop-off points: where people abandon (signup, activation, checkout, key feature)

• Support tickets + verbatims: the exact words people use when they’re confused/angry/stuck

• Search terms (in-app + help centre): what people are trying to do but can’t find

• Qual notes / call snippets: “I expected…” / “I tried…” / “I gave up because…”

• Usage patterns: what power users do vs what new users never reach

• Churn reasons / win-loss notes: the honest “why now / why not”

And if you don’t have access to product analytics (very normal), you can still do this from design-native signals:

• Usability test notes: where people hesitate, misclick, or ask “wait, what does this do?”

• Research repo themes: repeated pain points across studies

• Design QA / bug bash notes: the papercuts that keep coming back

• Stakeholder friction: “this keeps coming up in every review” is a signal

• Rework patterns: the flows you keep redesigning because the underlying problem isn’t clear

🎓 In the course: Week 1 is all about turning real company inputs (tickets, drop-offs, market signals) into an opportunity to create. You leave with a crisp “why this, why now” and a build plan — not a vague idea.

2) Building with AI is layering, not prompting.

Everyone wants the “one perfect prompt”.

AI doesn’t work like that.

Expecting a single prompt to produce a brilliant output is like expecting a contractor to build your house from a text message that says “make it modern and nice.”

What actually works is “context layering” — giving the model a stack of things it can build inside, so it stops guessing:

• Layer 1: Product context — what you’re building, for who, and why.

• Layer 2: Design system — colours, typography, spacing, voice. (A design.md is basically “how our product should look + feel”, written so AI can follow it. Reference/spec here: https://github.com/google-labs-code/design.md)

• Layer 3: Skill files — reusable playbooks that encode your judgment (“how I decide”, not just “what I want”).

Try this today: create a tiny context.md with three lines — what the product is, who it’s for, what problem it solves — and paste it into your AI chat before you ask for anything. Watch how quickly the output stops being generic.

Then keep going: add a second file that’s basically “how we build around here”:

• product principles (what we optimise for)

• constraints (what we won’t do)

• UX patterns + component boundaries

• voice + tone rules

• examples of “good” and “bad”

This is the difference between “AI can generate” and “AI can generate in your lane.”

🎓 In the course: Through out the course we build your context stack properly — product context, design system specs, figma brief specs, product evaluations — so your project compounds instead of resetting every time you go through the same workflow

3) You can teach AI taste. Seriously.

AI’s default output is usually… politely generic.

Which is fine. Until you’re trying to ship work that actually feels like you.

That’s not a model problem — it’s a context problem.

The moment you hand it a design.md with your brand’s personality — the hex codes, the font pairings, the spacing philosophy, the voice — the output shifts.

It stops being “AI-ish” and starts looking like something you’d actually put your name on.

But there’s a second layer most people miss: taste training.

Designers don’t become “good” because they read one style guide. They get good by collecting references, noticing patterns, and building a mental library of what works.

Do the same for your AI.

Create a lightweight “taste” file inside your project — call it taste.md — and fill it with:

• screenshots/links of work you love (and why)

• a few “hard no” examples (and why)

• your favourite interface patterns

• microcopy examples you’d happily ship

• a short list of “this is what good feels like for us”

Then reference that file any time you ask AI to generate UI or copy. Over time, you’re not just prompting — you’re training your system to consistently hit your bar.

🎓 In the course: We turn “taste” from a vague intuition into something you can hand to AI — design system + taste references + review standards — so the output gets better and on brand at every iteration.

What if you build a real product in two weeks?

Everything you just read in this newsletter is basically the starter pack:

How to find better problems, how to stop prompting and start layering context, and how to teach AI what “good” looks like.

If you got value from that, imagine what happens when you do it with a structure, support, and a real business case to build with.

The goal isn’t “learn AI tools”.

The goal is to build something that stands up in a real product conversation.

and that’s exactly why Simon Hilton and I built Claude Code AI - Product & Design Velocity

It’s a 2-week live cohort where we take you from “I’m not even sure where to start” to building a real product with AI — even if you know nothing about it today.

Expect you can achieve these in two weeks:

• A product opportunity backed by evidence (not vibes)

• An on-brand prototype (HTML or Figma)

• Making sharper decisions about what to build and why

• An evaluation loop (so you’re not just shipping pretty screens)

• A business case + pitch deck that makes sense to decision-makers

• Reusable AI “skills” you can keep using (so your work compounds)

• Story-telling techniques shifts the value for every idea you put forward

No coding experience required. .

First cohort kicks off this Saturday — and because you’re a subscriber, there’s a One time offer - 50% off for the first cohort.

Talk soon,

Jac ✌️

They’re synthesising research at 3x speed. Generating a dozen concept directions before lunch. Shipping working prototypes that used to take a week.

And then they write a portfolio case study that mentions none of it.

The AI layer is invisible. Buried. Or worse — dressed up as a footnote: “I used AI tools to support ideation.”

That’s not the portfolio that gets you hired right now. That’s the portfolio that gets politely declined.

But here’s what nobody’s saying out loud: this isn’t really about AI. It never was.

Great designers are adaptable. They think in systems. They’re builders with the agency to solve problems — not people who sit around waiting for the right prompt. They’re enablers. AI just made that more visible.

So let’s talk about four moves that actually land with hiring managers at the companies you want to work for.

1. Show the Workflow Story, Not the Tool List

Nobody cares that you used Midjourney or ChatGPT. Sorry. I don’t make the rules.

What hiring managers actually want to see is how AI changed the shape of your process. Not that you used it — how it changed the order of operations, what you attempted that wasn’t possible before, and what you did with the time you got back.

Figma’s hiring data backs this up:

85% of designers and developers say learning to work with AI is essential to their future success. 58% of hiring managers still say visual polish matters, and more than 45% point to collaboration, systems thinking, and product strategy as top skills.

“When anyone can make things, teams need designers who will raise the bar higher.” — Figma

The AI isn’t the story. What it unlocked is.

Try framing it in three layers:

• What AI accelerated — the production tasks: synthesis, first drafts, image exploration

• What AI enabled — things you couldn’t do before, like testing 15 directions instead of 3

• What you still owned — the judgment calls, the direction, what you rejected even when the output was technically fine

That third layer is what separates a senior designer from a prompt operator.

✏️

2. Show Your Judgment — Especially When You Said No

This is where senior designers separate from everyone else. And honestly, it’s the part that makes me sit up straight when I’m reviewing portfolios.

Knowing when not to use AI — or how to constrain it — is a judgment skill that can’t be automated. And it’s rarely shown in portfolios.

Stripe’s design team operates in a world of developer trust, financial infrastructure, and regulated complexity. Their hiring bar reflects it:

Designers who thrive there innovate within constraints like latency, token budgets, and model confidence — adapting UX flows to the realities of AI systems while maintaining usability and trust.

Beautiful screens with no evidence of how the system behaves when AI fails? That’s a red flag.

Or take Lovable’s perspective. They’re building at the frontier of AI-assisted product development, and their hiring philosophy is blunt:

“AI is a junior practitioner with infinite speed but zero judgment. We want someone with the flight hours to spot errors, validate solutions, and steer the tool toward outcomes aligned with business goals.”

A candidate who can prompt but can’t critique? Not senior.

Every company you’d want to work for has constraints — regulatory requirements, brand voice rules, accessibility standards, data privacy policies. AI doesn’t know your government client can’t surface probabilistic outputs without a confidence disclosure. You do. That’s the design work.

✏️

Your takeaway: For every case study, show one moment where you built the guardrails before you touched the tool.

• What were the business goals?

• What were the brand constraints?

• What outcome were you driving towards?

Beyond AI fluency, this is the strategic design layer — knowing why this, why now, and what’s at stake if you get it wrong.

3. Lead With Outcomes, Not Your Process Diagram

I need to say this with love: the Double Diamond is dead as a portfolio format. Nobody needs to see your sticky notes again. You following a framework thats given to you without your own critical thinking is the biggest red flag. It’s time to let those go.

The new case study structure is scannable, strategic, and outcome-oriented:

1. What was the measurable result?

2. What was the precise problem?

3. What constraints and trade-offs did you navigate?

Netflix’s design team thinks at scale — recommendation algorithms, content artwork personalisation, emotional pacing. Their hiring managers want to see measurable outcomes:

“At 0–3 seconds, we scan your opening case study title and the first visual. If it doesn’t immediately signal business impact, we’re already mentally moving on.”

Three seconds. That’s what you’ve got.

And Airbnb’s perspective adds another layer. They’re not looking for “cool AI apps” with slick mockups. They want to see how you navigated the messy, probabilistic, unpredictable part of the product and made it legible to a real human being. The trust design — how you made an uncertain output feel reliable — that’s what matters.

If you don’t have hard metrics, make the inference explicit: “We estimated X based on Y.” That still signals analytical thinking.

✏️

Subscribe now

4. Build Something Weird and Ship It

This is the wild card. And honestly? It might be the single highest-signal move available to a mid-to-senior designer right now.

Not a concept. Not a prototype sitting in Figma. A working experiment. Something that lived in the world for a week, got tested, and taught you something real.

Hiring managers at places like OpenAI, Notion, Anthropic, and Figma are looking for portfolios that scream “I know how to design with AI in mind.” A personal experiment — messy, honest, and real — can make you unforgettable.

But the experiment itself is only half the signal. The other half is what it took to get there.

• You noticed something worth solving. That’s observation — a muscle most people never bother to train.

• You cared enough to do something about it instead of just tweeting your hot take. That’s heart.

• You moved your arse on a weekend to learn and actually built the thing. That’s agency.

No course teaches that. No prompt generates it. No manager can assign it to you.

That combination — the eye to spot the problem, the drive to care, the guts to act — is what every hiring manager is actually screening for when they say they want “self-starters.” They just can’t put it into words that cleanly. Your side project does it for them.

It could be a book club community app you built for your parents group, shared with the community to get real feedback. A personal finance bookkeeping flow you prototyped in a weekend. A rough research assistant you hacked together to help your team run faster synthesis sprints.

Document it simply:

1. What I noticed

2. Why it mattered

3. How I built it

4. What actually happened

5. What I’d do differently

✏️

Speaking of going from “Designer to Builder” mode — if you want to go from idea to shipped AI product in days instead of months, I’m running a live cohort on exactly that. Claude Code for AI Product & Design Velocity teaches builders how to make outcome-driven, business-driven decisions with AI and build an on brand product — so whatever you build answers the “why this, why now” question before you write a single line of code. Use Substack only 50% Off code: 50BETA

The Honest Summary

The AI layer isn’t a section you tack onto the end of your case study. It’s the lens through which you tell the whole story.

The designers getting hired right now aren’t the ones with the fanciest AI tool stack. They’re the ones who can make the AI layer visible, specific, and unmistakably human. They show the workflow. They show the judgment. They show the guardrails. They show what they built.

And here’s the uncomfortable stat:

Design roles requiring AI skills grew 225% since 2024 — but only 5.8% of applicants are actually qualified. That’s not a skills gap. That’s an open door for anyone willing to walk through it.

Great designers have always been adaptable systems thinkers who build things and enable others. AI didn’t change that. It just raised the stakes.

Be the designer who sounds like they’ve actually done the work.

Because you have.

🥁 How can I help you:
–
Future-Proof Your Design Career With Business Acumen:
AI-Powered Strategic Design Accelerator (4 weeks)
Top 7th Design Course on Maven.
Alumni from: Anthropic, Google, Linkedin, Doordash, Canva
Take $100 Off: DoYourThing
—
NEW - Claude Code AI - Product & Design Velocity (2 weeks)
Build faster. Decide smarter. Ship with intent.
From finding the right opportunity to building an on-brand product to defending your decisions under real pressure.
50% Kick Off Cohort Code: 50BETA

Designers shipping production code. Learning Swift. Pushing features directly into the app.

And everyone’s asking the same question: do I need to learn to code now too?

I want to offer you a different question entirely.

Because I read the same article.

And I don’t think code is the point.

Do you think shipping the thing is more important than knowing what to ship?

Sit with that for a second.

Because here’s what nobody’s talking about:

AI hasn’t just made building faster. It’s made shipping the wrong thing faster too.

When building was slow and expensive, bad decisions had a natural speed limit. You’d catch the mistake somewhere in the process. Now? You can build, ship, and scale the wrong thing in a week. AI is so accessible that the cost of a bad decision has never been higher, and it compounds faster than ever.

Shipping the wrong thing, or shipping many of them without clarity, burns more resource than it ever did before.

But knowing what to build?

That’s an entirely different conversation.

That’s the skill that sits at the front of every decision, before a single line of code gets written, before a single frame gets designed. It’s product sense. It’s judgment. It’s knowing which bet is worth making for this business, right now.

Everyone’s racing to learn the next AI tool. New titles every quarter.

If you see through the noise👀…
the people thriving right now, not freaking out, aren’t the ones building fastest.

They’re the ones who can walk into a room and explain:
what to build, what it’s worth, and why it had to be this.

Here’s where the industry is actually heading:

The roles are shifting right in front of our eyes:

💼 PM → to build

🎨 Designer → to decide

⚙️ Engineer → to evaluate

🚀 Founders → to make it happen

The question isn’t what’s your title? anymore.

It’s “can you own the full decision cycle?”.

So what did Ruolan actually build?👀

She didn’t learn Swift to replace engineers.

She learned it to close the gap between her design intent and what actually shipped. To see the full chain. To develop the judgment that only comes from following a decision all the way through.

That’s the blueprint. Not the code.

The judgment.

And here’s the part I want you to sit with:

AI can now do most of the building. The execution, the code, the iterations, all of it is increasingly within reach without deep technical expertise.

So if the building is being handled, what’s left for you?

The decision about what to build in the first place. Whether it’s the right call for this business. Whether the output in front of you is actually worth shipping.

That judgment is yours to own.

AI can guide you through developing it, step by step.

The two designers in every room right now

Same title. Often the same years of experience.

One is worried about their job. One is getting promoted.

The difference isn’t talent. It’s which skills they’ve invested in.

The designer who built their identity around making things — producing screens, generating options, building specs — is watching AI absorb that work in real time. The craft was real. The years were real. But the market value of that execution is dropping fast.

The skills that compound in this era:

• Strategic framing: knowing which problem is worth solving before anyone asks

• Business fluency: connecting design decisions to outcomes the business is measured on

• Output judgment: knowing when the thing in front of you is actually right, regardless of how it was made

None of these are taught in design school. Almost nobody is teaching them anywhere.

But they’re learnable. And with AI as your guide, it’s more accessible than you might think.

Come jam on this topic with us 🫶🏾

I’ve been bugged by this for a while. And I know a lot of you feel the same way.

Simon Hilton (Executive AI Leader @MYOB) and I are running a free 45-minute session on exactly this, with open Q&A:

🥁 FREE LIGHTIN’n SESH: What to Build and Why: The Only Skill That Survives AI

In this session we’ll cover:

1. Why business acumen compounds while tool skills commoditise

2. How to identify what’s actually worth building before you build it

3. The skill stack that lets you scale yourself regardless of your title

4. Behind-the-scenes processes we use to cut through the noise

Can’t make it live? Add your email and we’ll send you the recording.

Join Free Workshop

Bring a friend who needs to hear this.

See you there.

Jac

Source: DoorDash Design — Darren Delaye & Ruolan Xia — https://medium.com/design-doordash/how-designers-at-doordash-are-becoming-builders-c08386315b92

🥁 How can I help you:
–
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AI-Powered Strategic Design Accelerator (4 weeks)
Top 7th Design Course on Maven
Take $100 Off: DoYourThing
—
NEW - Claude Code AI - Product & Design Velocity (2 weeks)
Build faster. Decide smarter. Ship with intent.
From finding the right opportunity to an on-brand product to defending your decisions under real pressure.
collaboration with Simon Hilton (AI Product Executive @MYOB)
50% Kick Off Cohort Code: 50BETA

It has been… a minute. Three months into 2026 and I’m only now resurfacing in your inbox. If you’ve been wondering where I disappeared to — fair. Let me catch you up.

January was a hospital month. 🏥 My partner had a bad accident and broke both elbows. Both. At the same time. If you’re wondering how someone eats, sleeps, or does literally anything with two broken elbows — the answer is: they don’t. You do it for them. So January through February was a blur of emergency rooms, surgeries, and me becoming a very average but very dedicated full-time carer and grown an unbeatable layer of new strength.

He’s now in rehab and already back to light work, which honestly feels like a miracle. We’re getting there.

Meanwhile, in the background, things kept moving. Because apparently I don’t know how to sit still even when life is falling apart:

• I updated about 70% of my course curriculum — and the March cohort sold out. (Cue quiet fist pump 🤜🏼🤛🏽 from the hospital waiting room.)

• A design leader from Anthropic joined the course. Yes, that Anthropic. I may have screamed into a pillow.

• I built my own AI teaching assistant in two hours. It’s live. It works. It answers student questions better than I do at 11pm. (That’s not a high bar, but still.)

• New heights for AI Powered Strategic Design Course - all 5/5 reviews. I think my Ikigai lives right here.

• Two exciting B2B collaborations are in the works. Can’t say too much yet, but here’s a hint: every organisation wants to invest in shifting their designers into business decision-makers. And they’re coming to us to help make that happen. 👀

• I’m collaborating with a AI Product Lead to create a Claude Code for Product and Design Velocity Course - more on this at the end.

So yeah. It’s been a lot. But I’m back.

And I have tones of insights I’ve been wanting to write about for months!! I’ll be sure to slow drip them so you won’t get overwhelmed.

Get your cup of tea ready and let’s get into it.

Because oh boy… hasn’t the industry changed so much since we last spoke?!

Thought Partners, Not Decorators

How designers who encode their thinking will become the most influential people in the room

I want to start with something uncomfortable.

A few weeks ago, in one of my sessions, a designer said:

“I’m tired of being boxed into pixel pushers.”

“I’m tired of QA-ing with engineers to update a few pixels.”

This is still a familiar scene for many designers. You know it. The back-and-forth over spacing that no user will ever notice. The redlines.
Years of proving your value to people who think your job is just “surface level”.

If you’re a designer, you’ve probably felt this. Maybe you’ve said it yourself.

Here’s the thing: this isn’t new. But the stakes is shifting. 😎

I want to emphasis that the goal of this piece to help you see more value you can provide and the time to shift our mindsets is now and it’s exciting!

Everyone can build now. So what do you actually bring?

The execution layer has been democratised. Your PM is prototyping. Your engineer is designing screens. Your CEO is experimenting with vibe coding and proudly showing off something that looks… surprisingly decent.

I watched it happen in real time. A market manager — no design background whatsoever — shipped a working app. His business team loved it. A designer who had spent years doing things “the right way” watched it get celebrated. 🫨

That moment is happening in companies everywhere right now.

So the question that’s been uncomfortable for years is now unavoidable: if everyone can execute, what does a designer actually bring?

This is not doom. This is clarity.

Because the answer was always the same. It was NEVER the Figma file.

It was the hierarchy read that saves three rounds of user research. The cognitive load catch your PM missed because they were reading the feature list, not the screen. The accessibility flag. The “we’re solving the wrong problem” call. The “we’re building too much” instinct.

That kind of thinking is rare. That kind of thinking is the value.

One of my students put it perfectly:

“Thought partners, not decorators.”

Yes. Exactly. But here’s the problem — and it’s a big one.

Your judgment has a scaling problem

Right now, all of that strategic thinking lives in one place: your head. It travels with you. It’s available when you’re in the room, in the review, in the meeting.

And when you’re not?

“Your judgment travels with you. When you leave, so does it.”

This is what I’ve started calling the augmentation problem. Not “will AI replace designers” — that’s the wrong question and frankly, I’m bored of it. The real question is:

How do you make your expertise available beyond your own presence?

How do you be in five places at once without burning out or becoming the bottleneck everyone resents but can’t work without?

The answer is not working harder. It’s not attending more meetings. (Please, not more meetings.)

It’s encoding.

“Encode your thinking.”

This is what augmentation actually means in practice. Not replacing yourself. Multiplying yourself. Your principles, your review criteria, your “things I always check” list — moved from your head into a system that runs without you.

I see three directions this can go:

1. Orchestrator of systems. You stop executing every output and start directing the systems that produce them. AI is your team. You are the creative director.

2. 10x your expertise into an organisational asset. Your taste, your judgment, your business fluency — encoded, scaled, made accessible. Not a bottleneck. Infrastructure.

3. Business operator specialised in design quality. You set the quality bar. You make the trade-off calls. You connect the design to the outcome. That is not replaceable.

What this looks like when it actually works

I don’t want this to stay theoretical. Let me tell you about three designers who did this recently.

The one-hour review that now takes minutes.

A designer in one of my sessions had spent an hour manually reviewing a vibe-coded prototype against her design principles. Cognitive load. Information hierarchy. Accessibility. All the things she knew mattered. She also knew she’d have to keep doing this as more people in her company started building their own prototypes.

So she built an AI skill instead. Spoke her principles out loud. Let Claude organise them. Fifteen minutes later, the skill runs her review on every prototype. She doesn’t need to be in the room anymore.

Her standards are.

The full-day task that now takes ten minutes.

Another designer built a user research synthesis skill live in a session. She uploaded her interview transcripts and the skill produced colour-coded affinity clusters organised by theme and sub-problem.

Her reaction:

“This is insane. It used to take a full day.”

Ten minutes. That’s not a typo. And the day she just got back? That’s now available for the thinking that actually matters — not the sorting and organising.

The career strategy that compounds.

A third designer built something I didn’t expect: a personal career strategy skill. She runs it monthly. It researches industry signals, assesses whether her career bets are proving true, identifies blind spots, and surfaces what she might regret not doing.

Six months of outputs, then a quarterly pattern summary. Her strategic intelligence, compounding over time. Honestly? I’m a little jealous of this one.

The part nobody talks about: augmentation is a political move

This is the section most articles skip, but it might be the most important.

Augmentation is not just a personal productivity strategy. It’s a team influence strategy.

Design leaders have a structural problem: they know what good looks like, but enforcing it means being in every meeting, reviewing every output, becoming the gatekeeper everyone avoids eye contact with. That’s not influence. That’s a bottleneck with a title.

When everyone runs the same design check before a prototype goes forward, something shifts. It’s not the design leader’s opinion anymore. It’s the standard. Nobody’s the bad guy. The skill is.

“You don’t want to be a spoke in the wheel. But you can definitely influence how they’re doing it.”

Here’s a real example: five teams at one company are each building separate AI chatbots. None of them are talking to each other. All inconsistent. A designer trying to insert herself into every project? Exhausting and unscalable.

But a design component skill that every team deploys? That sidesteps the politics entirely. Her judgment runs on every build. Her name doesn’t need to be on every meeting invite.

That’s influence at scale. No drama required.

Where this is heading

The designers with the most influence in the next two years won’t be the ones who fought hardest for a seat in every meeting. They’ll be the ones whose thinking became unavoidable. Embedded in the system. Running on every build. Scaling without them.

That’s not a threat to designers. That’s the job description finally catching up to what the best designers have always done.

They were never just making things look good. They were making sure the right things got built, for the right reasons, in the right way.

Now there’s a way to make that thinking travel further than one person ever could.

Encode your thinking. That’s where it starts and lands.

🫶🏾 If this resonated, I’d love to hear from you. Hit reply — I read everything.

PS. if you’re keen to go from AI novice to AI native - launching a new Claude Code AI Product & Design Velocity course (50% off for readers) kick off on May 17 with Simon Hilton (VP of AI Product from MYOB)

While every other course is teaching you to blindly produce AI outputs, this one teach you to evaluate, measure, defend and build product that drives business outcome.

Talk soon,

Jac ✌️

Talented. Solid portfolio. Couldn’t land interviews to save her life.

I dived deeper with her and realised that there’re three blindsides she’s made.

These matters ALMOST more than design work at the interview stage.

Yet, most designers don’t even realise they’re making these mistakes.

It’s portfolio prepping and self reflection season (the holidays), I want to take this blog opportunity to address these three things: Time management. Preparation. Articulation.

Hot off the press.

⏰ Read time: 4 mins

Subscribe now

Before we begin. Let me put this out there: Didn’t pass an interview doesn’t mean it’s always on you. It could be unpredictable shifts that’s out of your control: Financial decision shift, hiring priority shifts at the company.

But it’s on you, if you did any of these three things:

👇🏽👇🏽👇🏽

Interview blindside #1:

Too much details. Not enough time management. 🫣

Here’s what happens:

You get 30 minutes for your case study presentation.

You dive deep. Every research finding, every iteration, every stakeholder conversation.

25 minutes later, you’re still talking.

The interviewer is checking their watch.

By this point, it’s already too late.

You’ve left zero time for the actual interview: the conversation where they assess whether you can share just enough context with good time management.

It doesn’t matter how complex your project is, the crucial part is: Your decision on how much to share to get enough context across - This separates the strategic thinkers and the talkers.

Do this next time:

Consider the 30mins interviews in 4 chunks: 5-15-5-5

First 5 mins to get to know you and the company.

15 minutes max for your case study. That’s it.

5-10 minutes for the interviewers to ask you questions

and the remaining 5 mins for you: Come prepared with 1-2 thoughtful questions to ask them.

—

Interview blindside #2:

You skipped the research 🧐

“It’s just a small startup. I don’t need to research them deeply.”

Wrong.

Your lack of preparation shows the second you start speaking.

When you haven’t researched their business, product, and team...

You give generic answers.

They want tailored solutions.

They’re looking for designers who think strategically and understand their specific context because businesses would be taking a risk to hire one type of designer for all types of needs.

So, before every interview:

• Study their product, business models

• Read recent announcements

• Understand company maturity and market position

• Research who you’re meeting - if you have 5 rounds of interviews, do the research every single round.

Then draw parallels in your case study presentation.

Show how your approach adapts to their technology capabilities and company stage.

Make it about them, not you.

—

Interview blindside #3:

The Data Excuse (the biggest killer) 😭

“The previous company didn’t track data, so I don’t have metrics.”

I hear this constantly.

Here’s what that tells interviewers:

1. You don’t know how to measure impact.

2. You don’t know if the solution going out the door is wasting everyone’s time.

Your previous company’s lack of data maturity doesn’t mean you lack the knowledge.

You can still show them that you know:

• What metric the project impacted

• The minimum validation you did (even getting validations from internal colleagues or social listening)

• How you knew it worked or didn’t work after it rolls out

So what can you do when you don’t have enough data for your project?

The surprising truth for many is: You don’t need the perfect data.

But you must learn how to articulate your thinking:

1. Can you explain what success looked like?

2. Do you have user frustration data, industry trends, decision rationale?

3. Did this project generated impacts beyond product?

4. When you come across blockers and challenges, what did you do to overcome?

5. What would you have done differently?

Show your decision-making process, not rigid frameworks. (Frameworks are there to help you think - your audience is more interested to know what you got out as a result)

Connect your design work to business benefits: beyond product, users, revenue. Think operation, time to market, team culture.

—

Many designers came to my course struggle with these:

“I don’t know how to connect design to business outcomes.”

“I am not confident to validate design opportunities.”

“I can’t articulate the business benefits of my work.”

This are the exact pain points I help with in Strategic Design Career Accelerator

With the growth of AI replacing repetitive craft skills, now it’s the time to become the strategic creative orchestrator every organisation needs.

• Master business strategy decision making as a designer.

• Learn to connect designs to measurable business outcomes.

• Apply proven frameworks for compelling interview storytelling.

You have so much more to offer than being another designer with a nice looking portfolio.

Next cohort: February 2026.
Take 25% OFF - One week only Nov 17-24
Code: FAST25

ENROL NOW

FYI:

My teaching styles are:

Straight up. Never just share slides. Hands on practise is key. Unlimited 1-1s. Humour and optimistic. Sometimes overshare.

😍 Here are some solid outcomes from Oct cohort:

If you’re not sure if this course will suit your growth, feel free to book a call with me.

Book a call with Jac

More honest.

And infinitely more useful.

You see, most PM-Designer partnerships aren't just "challenging" - they're organisational disasters waiting to happen.

😵‍💫Teams burning weeks in revision cycles.

😵‍💫 Products shipping with zero soul.

😵‍💫 Revenue opportunities vanishing because nobody speaks the same strategic language.

We ended up recorded 5 episodes about this topic 🔥🔥🔥🔥🔥 (ON FIRE)

Here's what Teresa and I discovered: 90% of design-product collaboration fails because both sides are playing completely different games.

And honestly? We've both been guilty of this.

You can go ahead to YT and watch episodes roll out week by week

👇🏼

But if you can’t wait that long,… stick around:

In this blog, I want to give you a heads up to few hot takes from this epic series.

Three Stories Under the Cover

1 - "I Need More Time to Design" Drama (And Why It Makes PMs Want to Scream)

The PM (aka Teresa): "My biggest pet peeve is when a designer says 'I need more time to design' but can't articulate what they're actually designing. Well… how am I able to justify the time you’d need if it isn’t communicated in value terms?"

She's absolutely right.

I've been there. We all have.

Designers craves more space to think, to iterate, to “get it right” - but you can't explain WHY without sounding like you're chasing perfection for perfection's sake.

Because design process is messy, we’ve been told not to jump into solutions, so may reasons behind that.

Here's what I've learned from countless designers hitting this exact same wall: Designers are terrible at translating our process into “Business Values”.

• Is there any risk that require longer time to investigate

• Will there be design, tech debts if it isn’t done right?

• Can you roll out a “test version” and propose for iteration in the future? Because you understand “Time is money” when it comes down to product competing in the market.

What designers can do:

Think like a consultant!

Present few options with clear time-quality trade-offs.

No business partners want just one option, help them make that decision to choose the right path forward.

What PM can do to get designers going?

Use the word 'experiment'!! Yes, this word motivates designers to steer away from 'final delivery,' they're immediately less stressed. They know it's not permanent and they can iterate quickly."

That single word: experiment could eliminates the perfectionist pressure that kills velocity.

1 - Designers’ Drama: The Executive Meeting You'll Never Be Invited To

I told Teresa about something that's haunted designers for years: "Business execs don't think designers need to know business goals or strategic context. We're always designing in the dark." aka - designers wants a “seat at the table”

OK… this one i’m going to point you directly to the video - It’s good!
I also shared how I break through from a craft designer into the strategic involvement.

Hint: It takes two to tangle.

3 - The High-Fidelity Trap ( ‘Perfect Ideations” Kill Collaboration)

Teresa dropped this truth bomb: "When I see high-fidelity designs early, I think 'you spent way too much time perfecting corners. Any change I ask will be such a hurdle of an argument.'"

This hit me hard because I've been that designer. The one who jumps straight to polished mockups because it FEELS like progress.

It's not.

You know what is? The best designers sketch on napkins during briefings. They draft flows while the PM is talking, creating collaborative artefacts in real-time.

Teresa walks away from those meetings confident the designer actually gets what she's saying. No anxiety. No translation gaps. Just immediate strategic alignment.

So here, I have a message to Design Leaders out there who’s ‘drafting’ in high fidelity: If you're modelling high-fidelity-first behaviour, you're creating a shadow that makes everyone think that's faster. But AI will replace drag-and-drop design system work. Your value lays in strategic thinking and alignment connecting, not pixel perfection.

Finally, the magic.

Leadership Style (Discovered Over Many Mistakes)

Through all our conversation mishaps and breakthrough moments, Teresa and I uncovered what great leaders always do to ensure the “dramas” are minimised:

70% Functional Expertise + 30% Strategic Vision

The best leaders knows how things are done, they know when to deliver JUST ENOUGH so that the needles are moving.

They ensure that the vision story is front and centre in everything the team is focusing on.

They tell the story that’s so moving, that becomes the battery the team needs to feel inspired to delivery velocity.

This is the motivator that drives sustainable partnerships between every discipline in the product teams.

Stuff you can do from today:

For designers craving PM respect:

• Lead with business impact: "This design decision reduces checkout friction, which should improve conversion by addressing the trust barrier we identified in user research."

• Connect every aesthetic choice to user behaviour and revenue potential

• Demand the bigger strategic map - you can't think architecturally without it

For PMs wanting design excellence:

• Frame problems emotionally: Users don't just complete tasks, they experience emotional journeys that drive retention

• Use experiment language to encourage rapid iteration over pixel perfection (but make sure reflections and iterations are in place.

• Share the roadmap, the long term vision because context creates velocity

Here's What I Know Now

Most collaboration advice treats PM-Designer tension like a communication problem.

It's not.

It's a strategic intelligence problem.

The high performing team succeed effortlessly because they build better collaboration systems that turn cross-functional friction into competitive advantage.

Teresa and I both learned this the hard way:

When designers understand business impact and PMs understand emotional value, magic happens.

You see, the real collaboration killer isn't personality clashes or competing priorities.

It's leaders on both sides who haven't created the culture for strategic partnership to flourish.

Here's what I know for sure: 👇🏼

The question isn't whether you're good at your job.

The question is whether you're good at helping other people be good at theirs.

That's where the real magic happens.

But mostly? Start having these honest conversations with your PM or designer counterpart.

The messy ones. The vulnerable ones.

The ones that actually change how you work together.

Jac x

The conversation with Teresa reminded me why I love this work: Real change happens when smart people get honest about what's actually broken. Want more unfiltered insights on design-business alignment? Follow along for the stories nobody else is telling.

Subscribe now

Meet the special guest - Teresa Huang

Teresa is a product leader that is based in Melbourne, Australia, who love to share actionable strategies and practical tools to continuously grow in your career - Subscribe to her channels below

Youtube: Teresa Huang & Linkedin: Teresa Huang

If you like this blog, this is how I can help you 👇🏼

After 18+ years as a strategic business designer running successful companies and helped companies raise millions in fundings, I now help designers unlock their strategic thinking skills and become irreplaceable business partners.

This 4-week live cohort "Strategic Design Career Accelerator." covers strategic business acumen, strategy visioning, strategic communication, connecting design to business impacts.

Alumni reflected +67% more confidence in making strategic decisions and connecting design to business.

Next Cohort Kicks Off in OCTOBER👇🏼 (timezone: AEST / PDT / EDT )

Join now and take $100 Off

(OR 20% off for 2+ ppl) Code: DoYourThing

💬 What alumni students say about the course:

“This is by far, one of the best courses I've taken about combining business and design.”
- Paulina Galindo 🇺🇸 Principal Product Designer @Meta | ex-DoorDash | Ex-Linkedin

—

This course was definitely an eye opening learning for me as a mid level designer. With tactics to communicate your design value and connecting this with the business strategies, I feel so much more confident about advocating myself.
- Taejin 🇦🇺 Product Designer@REA Group

—

“This course was a game-changer. It shifted how I see my role as a designer - from executing great work to driving meaningful impact. I learned how to connect design to business goals, manage stakeholders with clarity”
- ChengChang 🇺🇸 Staff product designer @ServiceNOW / ex-Linkedin

One reflected: "So long designers".

The other: "So long PM".

PMs can now generate fast concepts with a decent business requirement description.

Also, Designers can now "build" a live product without engineer.

If you flip the coin and think deeper, The PM who built the working product concept, is it good enough? Does it work?

The Designer who built a live product without an engineer, how do we know if the quality of the code is good? What else is missing?

That is the space in between - those decision points between prompt and final product where human judgment becomes absolutely critical.

Where AI Falls Short (And Why That Matters)

AI systems still struggle with:

• Understanding human emotions and cultural context

• Providing empathy essential in healthcare or customer service

• Grasping subtle market nuances

Recent studies show 85% of AI projects fail due to poor data quality or lack of sufficient data. (VisionX) That's not an AI problem-that's a human judgment problem.

Here's what's fascinating: AI excels at the 80% of innovation that's incremental—tweaking and recombining existing things. But the other 20% that represents "radical innovation" requires developing something completely new. (Wharton Knowledge)

And that's where human expertise becomes irreplaceable.

The Real-World Test

Few weeks ago, I attempted to build a property rental app for international students in Australia.

AI generated something functional. But it wasn’t able to think beyond basic ‘features’, lack considerations into what ‘success’ product could do for this particular audience:

• The cultural implications that differ from local renters?

• Language barriers these students face?

• Currency conversion anxieties?

• Visa documentation requirements?

• Financial history and rental background check

• The fear of being scammed in a foreign country?

• That these students often need to secure housing before arriving?

Here's the thing - I can spot these gaps immediately because I've been a landlord for overseas students for 4 years. I know what they care about inside out.

Without that background knowledge, I’d be essentially asking AI to fill in blanks it can't see.

AI generates. Humans evaluate. And evaluation requires experience. (for now)

The Master's Eye

Here's what separates masters from prompters in each stage:

IDEA Stage:

• Observation skills: Spotting trends others miss

• Cultural intelligence: Understanding different user contexts

• Customer empathy: Knowing pain points intimately

• Market reflection: Connecting dots between demand and opportunity

DESCRIBE Stage:

• Requirements translation: Turning fuzzy ideas into clear specifications

• Technical feasibility: Knowing risks and scalability

• Experience design: Understanding user journeys beyond features

• Constraint definition: Setting the right boundaries

BUILD Stage:

• Quality assessment: Recognising quality code vs. working code

• Performance evaluation: Knowing what "fast enough" means

• Security awareness: Spotting vulnerabilities AI might miss

• Feedback loops: Observing, communicating, re-evaluating

SELL Stage:

• Market positioning: Understanding competitive channels

• Pricing psychology: Knowing what value means to customers

• Risk assessment: Identifying legal and business implications

• Go-to-market: Connecting product to distribution channels

These are knowledge that marks the difference between generic AI output and scalable business impact.

Top performers aren't just good at prompting. They're exceptional at evaluation.

Back to my rental app example 👉🏽 AI might build me a functional prototype in hours. But without my landlord experience, I wouldn't know to question:

• Why isn't there a "virtual inspection" feature?

• The bond protection explanation isn’t done in different languages?

• How do students verify their income from overseas?

The expertise makes the AI valuable, not the other way around.

Hi I'm Jac. I'm a Product Design Leader and a self-proclaimed mis-fit. I create content to help you amplify your knowledge scope and discover your superpower in this rapidly changing world. ☺️ Subscribe to keep growing together.

Building Your Space Navigation Skills

So how do you develop this kind of discernment?

Hint 😉: It's not a weekend workshop situation.!

Get obsessed with excellence:

• Study the best in your field

• Notice what separates good from great

• Expand your observation skills

• Get back to the basics, do it yourself first to know if it's actually "Good"

Build cross-functional fluency:

• PMs need "a blend of technical understanding, design taste developing to match their business acumen"(Innerview)

• Designers need "a blend of business acumen, financial literacy to support their product success"

• Speak the language of different disciplines

Stay close to your customers:

• Understand the human stories

• Spend time in the trenches where your product lives

• Test assumptions with real people, not personas

Keep building

I remember my lecturer at uni once said:”Never become a consumer. Always be a builder”.
Builders can invent, iterate and shift movements.

• Try out any tools, one small step at a time. Do this to observe and learn, not to stay on top of trends.

The Future Belongs to the Bridge Builders

While AI enhances efficiency, the quality of results is deeply tied to the quality of your interaction with it.

And that interaction quality? It comes from understanding not just how to prompt, but what to look for in the response.

The professionals thriving in the AI age aren't competing with machines. They're conducting them like orchestra leaders, knowing:

• When to let AI run

• When to step in with human judgment

• What deserves amplifying

They understand that AI is a phenomenal amplifier—but only when you know what deserves amplifying.

Bottom Line

I can get AI to do A thing - and it goes ahead and did it like an enthusiastic intern.

I check the intern's output, prompt it to update and adjust, over and over until it's on point.

The intern does what I asked - it completes one step as I requested.

I am the one who's pointing out the missing pieces and the blind spots - And that took me years or decade of experience to get there.

I hope you don’t think and operate at the depth of one step at a time level, because that's what AI does. Be an operator that thinks three steps ahead by filling your knowledge gaps in the spaces in between, own the agency to act, towards the value you want to contribute.

Develop the judgment, and strategic thinking that turns AI output into business impact. Owning the agency to make decisions that create real value.

Think about those two product people from the beginning. Both created functional prototypes. But ONLY themselves with years of industry experience could answer the follow-up questions:

• Is this solving the right problem?

• Will customers actually pay for this?

• What happens when we scale this?

• Have we considered the risks?

That's the space in between. That's where value lives.

And in a world where everyone can generate, those who can truly evaluate become invaluable.

How I can help you 👇🏼

After 18+ years as a strategic business designer running successful companies and helped companies raise millions in fundings, I now help designers unlock their strategic thinking skills and become irreplaceable business partners.

This 4-week live cohort "Strategic Design Career Accelerator." (Top 7th Design course on Maven) covers strategic business acumen, strategy visioning, strategic communication, connecting design to business impacts.

Alumni reflected +67% more confidence in making strategic decisions and connecting design to business.

Next Cohort Kicks Off in OCTOBER👇🏼 (timezone: AEST / PDT / EDT )

https://maven.com/jacalin-ding/strategic-design-career-accelerator

👉🏽 Enrol now and take $100 off as a subscriber (OR 20% off for 2+ ppl) Code: DoYourThing

💬 What alumni students say about the course:

“This is by far, one of the best courses I've taken about combining business and design.”
- Paulina Galindo 🇺🇸 Principal Product Designer @Meta | ex-DoorDash | Ex-Linkedin

This course was definitely an eye opening learning for me as a mid level designer. With tactics to communicate your design value and connecting this with the business strategies, I feel so much more confident about advocating myself.
- Taejin 🇦🇺 Product Designer@REA Group

“This course was a game-changer. It shifted how I see my role as a designer - from executing great work to driving meaningful impact. I learned how to connect design to business goals, manage stakeholders with clarity”
- ChengChang 🇺🇸 Staff product designer @ServiceNOW / ex-Linkedin

During our one-on-one meeting, she raised this question with that mix of frustration and vulnerability I've seen too many times: "In meetings where there are a lot of voices, everyone sharing strong opinions... how do I feel comfortable to speak up? How do I pick the moment to share my thoughts?"

I'm not an introvert myself, well I consider myself a bit of both extrovert and introvert depending on the situation. But her question hit me hard because I've watched brilliant people struggle with this exact challenge. Talented designers, strategic thinkers, problem-solvers who have incredible insights but can't seem to get heard in the chaos of modern workplace meetings.

That's what inspired me to reach out to Tim Yeo, author of "The Quiet Achiever" and former Design Director at IBM.

We tried something new this time, a limited invite only attendees list, unrecorded fireside chat. This turned into a value packed session and I can’t wait to share with you some gold nuggets to super charge your way of working!

Before we dive into strategies, we need to clear up the biggest myth about introversion.

"For a long time I had different ideas of what introversion actually meant," Tim shared with our group.

Here's the real difference: Introversion is about how you respond to stimulation and where you get your energy.

Tim painted this picture perfectly: "The last thing that I want to do is to go to a pub and meet somebody new for the first time, and then go around the room in a networking event. If I can have a nice cup of tea or a glass of wine watching Netflix and chilling at home. That's exactly what I want to do, because I spend the whole day peopling. And I cannot people anymore."

I realised how many people had never heard it explained this clearly.

The Superpower Hidden in Plain Sight

Tim described his approach to meetings, and I could see the lightbulb moments happening in our chat:

"When people are speaking, I don't often feel like I'm in a hurry to respond. Listening comes very naturally to me... I find myself just happy to listen to what they are saying, not in my head thinking about what I'm going to say in response, but really simply taking in and listening."

I had to jump in here because I've observed this exact phenomenon in my teams: "The difference I see is that as extroverts think about ideas, they communicate the thinking process out loud. But I observe that introvert colleagues take a lot more deeper consideration into how they can consolidate all of their thinking into clear messages

There’s nothing right or wrong to either approach. While others are rushing to respond, you're actually processing. We’re just like different operation machines, each functioning in our own OS model.

Be proactive: Organise the agenda

"One of the biggest things that's still happening in this day and age," Tim said, "is oftentimes you go to a meeting, you show up, and there's no agenda sent out beforehand. You show up to find out what the meeting is about."

I couldn’t agree more. Setting up an agenda is so basic yet many still don’t implement this into their work habit.

I've heard from a friend where she gets a 2-hour meeting in her agenda with no agenda, no goals, no discussion points. Also, there’re 20 people on the invite list. This was shocking to me. Meetings like that are time wasting, It doesn’t enable everyone to show up fully. Not to mention how expensive it becomes.

When you set up the agenda, you are in control of how the meeting is run!

"All of the introverts that I've spent time with and coached, they have been amazing preppers," Tim says, "If you give them the agenda, they're going to come with a bullet point of 3, 4, 5 things they want to talk about."

Instead of waiting for others to set the scene, proactively pick it up and do it already. This isn't just good for introverts, it's good for everyone. That’s what high performers do.

Allow yourself to share ideas early

Gives you self the permission to contribute, even when your thoughts aren't fully formed:

"This is the first idea that came to mind. It's not fully formed yet, but maybe I can share it with the group, and you guys can tell me what you think."

"This little prefix that you say before you say the thing," Tim explained, "it kind of gives you permission and license to speak up because you already told them it's not perfect, it's not fully formed, so they're not supposed to judge you."

The genius here? You're acknowledging imperfection while still contributing value.

The pressure's off, and your voice is heard.

The Strategic Side Conversation

Many designers I’ve coached often ask this same question:”How do I get buy in? How to share my ideas more effectively”.

Firstly, we’ve gotta learn how our decisions impact multiple aspects of the business before you can get your leaders to hear you out. Focus on expanding adjacent skills besides design (that’s what my course is about). Knowledge is power, so actively build those up to gain the knowledge confidence.

Besides that, is how you get the message across:

Here’s Tim’s take, and I couldn’t agree more.

"If you want to change their thinking and influence the direction you want to implement," he said, "you want to be influencing early, and not every one of those opportunities are going to be big, large group meetings. You want to be able to do that one on one."

That's exactly what I do as well.

Sideline conversations are so powerful, they give you space to hear everyone out, write down what everyone cares about. You become a quiet facilitator. By the time you present that idea evolution, it's got a piece of everybody's ideas in it, so it becomes even more influential."

Don’t be afraid to reach out and get quick feedbacks, while hearing others out. You don't make dramatic course corrections in public. You make small, strategic adjustments over time, in the right conversations, with the right people.

Build your knowledge to understand when to utilise what strategic tool is exactly what’s in my course “Strategic Design Career Accelerator” (⭐️9.7/10 rating)

The next cohort starts in OCT 17th. This 4-week live cohort covers strategic business acumen, strategy visioning, ROI of design, strategic communication, connecting design to business impacts.

Alumni reflected +67% more confidence in making strategic decisions and connecting design to business. 👉🏽 Join now and take $100 off as a subscriber (OR 20% off for 2+ ppl) Code: DoYourThing

Join now and take $100 OFF

Power move: Let others know how to best work with you

Communicating your energy rhythms can be the strategic move that benefits everyone you work with.

Become a master at managing your own agenda: If you're facilitating a 2-hour workshop, do not organise a one-on-one with your direct report right after, because you're going to have no energy at all. Make sure that you got buffer time in between.

As a manager with direct reports, I actually love it when my direct reports tell me, 'I'd like to have this time on Wednesday afternoon as my focus time.' If they set the boundary, it helps me to better support them.

Audience Q&A:

Q: "As a designer who does their best thinking independently, how can I increase my visibility in team meetings where I tend to be quieter?"

Tim: "Everything doesn't have to be a meeting. Most companies have some kind of chat platform like Slack... You can always record a short video of yourself talking about your design. When you do those things, make sure that you have that close juxtaposition of you talking about the work and the work itself, so that people can see you made that work."

I loved this reframe—visibility isn't just about speaking up in meetings. It's about choosing the right medium for your message.

Q: "What's a mistake introverts often make when they're trying to be visible, and what's a better approach?"

Tim: "Don't assume that meetings are the only place for you to be visible. Think about the content and the stuff that you share in 3 sizes—small, medium, and large. Nobody has time to write a very thoughtful blog post all the time, but if you're more visible, you're sharing snippets, even simple things like sharing funny memes that relate to something you're working on."

Q: "Was there a turning point in your career when being an introvert became your superpower?"

Tim: "I think it was when I realized that I was a very good facilitator. I always hated when meetings went over, hated sitting in meetings that were run poorly... So I started running those meetings myself. You don't need to have all the answers. You are like a bus driver—your only job is to make sure that you get everyone to the destination on time and on agenda."

Watching Tim explain this, I could see why facilitation works so well for introverts. You're not competing for airtime—you're orchestrating the conversation.

You don't need to become an extrovert to be successful. You need to become a confident introvert.

Start small.

Pick one technique from this conversation and try it this week.

Maybe it's asking for a meeting agenda.

Maybe it's scheduling that one-on-one you've been putting off.

Maybe it's simply giving yourself permission to share an unformed idea.

Your perspective matters. The question isn't whether you're qualified to share it, it's whether you're ready to let it be heard.

Different doesn't mean deficient - the same qualities that make you different are exactly what today's workplace needs more of.

I hope you enjoy today’s read.

Feel free to send me feedbacks and let me know what you’d like to hear more of next

Jac

x

How I can help you 👇🏼

After 18+ years as a strategic business designer running successful companies and helped companies raise millions in fundings, I now help designers build strategic thinking and communication skills.

This 4-week live cohort "Strategic Design Career Accelerator." covers strategic business acumen, strategy visioning, strategic communication, connecting design to business impacts.

Alumni reflected +67% more confidence in making strategic decisions and connecting design to business.

Next Cohort Kicks Off mid OCTOBER👇🏼 (timezone: AEST / PDT / EDT )

https://maven.com/jacalin-ding/strategic-design-career-accelerator

👉🏽 Join now and take $100 off as a subscriber (OR 20% off for 2+ ppl)
Code: DoYourThing

Strategic Design Career Accelerator

💬 What alumni students say about the course:

“This is by far, one of the best courses I've taken about combining business and design.”
- Paulina Galindo 🇺🇸 Principal Product Designer @Meta | ex-DoorDash | Ex-Linkedin

This course was definitely an eye opening learning for me as a mid level designer. With tactics to communicate your design value and connecting this with the business strategies, I feel so much more confident about advocating myself.
- Taejin 🇦🇺 Product Designer@REA Group

“This course was a game-changer. It shifted how I see my role as a designer - from executing great work to driving meaningful impact. I learned how to connect design to business goals, manage stakeholders with clarity”
- ChengChang 🇺🇸 Staff product designer @ServiceNOW / ex-Linkedin

It's the same playbook as ever:

• Find a great learning opportunity

• Block the time in my calendar

• Pay the fee (gulp 🤑)

• Immerse myself completely

• Return inspired!

I try to to this every quarter. Yup, 4 times a year.

🛫 Fly to my parent’s where I get mental space and time back in my calendar, and dive deep into being a student again. 👇🏼

The first time I paid that much from my own pocket for self development (probably from 7 years ago), it felt like I was "spending" so much money. But afterwards, it quickly became clear that it wasn't an expense—it was an investment.

It's hard to underestimate the importance of continuous learning, especially if, like many designers, you work in isolation in a squad, in a high velocity environment or in small teams. Those situation made it too easy to forget about your own growth path.

If the question you're asking is: "What's the hard ROI on learning?" ...then you won't get any good answers.

But I like to see it as an A/B comparison of my day to day.

💬 Which version of your career do you think performs best?

A) The version where you churn out the same work day in, day out, collecting your pay check and delivering ok results to make the company profitable?

or

B) The version where you constantly push your boundaries, learn new methodologies, connect with other designers, question your assumptions, get exposed to different perspectives, occasionally feel completely lost before having that breakthrough moment, and return to your projects with fresh eyes and renewed energy?

The delta between these two paths isn't just incremental - it's exponential over time.

A designer on path B might not just be 10% more valuable than one on path A.

They might be 10x more valuable after a decade. (Almost certainly!)

Think I'm exaggerating? Consider the designers who learned only print design and resisted digital transitions. Or those who mastered Photoshop but afraid to switch to Sketch or dismissed Figma as unnecessary. Or those who perfected visual UI but never developed strategic thinking skills.

Version A - Their skills stagnated. The gap widened.

And just like any product, lack of growth means lack of competitive edge.

The industry moves on, with or without you.

The most resilient designers I know aren't necessarily the most naturally talented - they're the most adaptable learners.

Some designers refuses to pay for learn themselves because their company didn’t set aside budget to grow their people. "I’ll wait until they approve" they say.

What they’ve put on the line isn’t money, it’s their own growth. It’s the opportunity cost!

And yes, absolutely leverage whatever learning budget your company offers. But tying your growth exclusively to your employer's budget is like limiting your fitness to whatever exercise equipment your office provides.

If you're still not convinced by the performance argument...

Well then, how about career longevity?

Do you think you might avoid burnout longer when you have meaningful growth and feel truly engaged with your craft?

What value do you place on sustaining a creative career for decades rather than burning out after five years?

Have you thought about the immense personal cost when your skills become outdated, or the price you pay when your portfolio shows the same thinking year after year?

I know designers who have been evolving and thriving in this industry for 20+ years.

The one they they did - they challenge themselves to evolve. EVERY. SINGLE. DAY.

And I can't even begin to tell you how much their work inspires me, irrespective of the "value" to their bank accounts.

For those who seek to learn, opportunities naturally seeks them.

Let’s say…

On a $100k salary, if you get a 10% increase, that's a pretty good return.

Now, I'll agree that the high cost only starts to make sense from a certain level.

If you're making $40k as a junior designer, then spending $10k on workshops and conferences doesn't make sense.

But if you can invest in your learning for, say, 5% of your annual income, then it's an absolute no-brainer.

But, to be honest, I don't really think much about ROI on this.

For me it's about long term investment- and it’s both qualitative and quantitative of my career

I'm the constantly-curious, step-outside-your-bubble, question-your-assumptions, against-stagnation, enjoy-growth-while-you-can type of person.

And what this says for me is:

I don't want to live a innovative designer life where I don't get to grow.

And I won’t leave it in someone else’s hands. Do you? 🫠

Before my first major investment in learning, I'm not sure I would have seen the value, especially given the cost.

But having done it for many years in a row now, taken workshops in different countries, stepped away from my desk, gotten to know so many brilliant designers, had all kinds of breakthroughs, some failures, periods of doubt and moments of clarity...

I just wouldn't want it any other way.

Every $5,000-10,000 I've spent annually on personal development has led to flourishing in ways I couldn't have predicted:

• ✔️ Built courage to speak out and align business and design decisions

• ✔️ Learned new techniques that immediately differentiated my work

• ✔️ Discovered capabilities I never knew I had, helped companies raised millions in funding

• ✔️ New personal insights to share with my team, my students and clients

• ✔️ Connections that turned into collaborations and business opportunities

All of these shows the learning investments I’ve made had been pivotal to my growth.

Not to mentioned, it’s the key contributor to 5x my annual income since 7 years ago.

Here's what I've learned: just getting paid to do what you do is not enough.

The greatest designers I know use their time wisely to learn, adopt, connect, and reflect. They work on self-awareness as diligently as they work on their craft.

Stay comfort is one of the biggest risk in anyone’s career.

I’d like to encourage you to take it into your own hands:

• When was the last time you stepped outside your design bubble?

• What are you doing next month to invest in your growth?

• How might your future self thank you for the learning you do today?

So my challenge to you is simple:

1. Every quarter, select one skill area. It could be "Communication," "Craft," "Strategy," or "Facilitation.".. pick your own.

2. Break down exactly 2-3 sub-areas for your chosen skill.

3. Then list out what activities you'll be doing to practice that skill.

4. Then finally, and this is the most important part, communicate to your manager about your intent to grow. 👈🏼By doing so, you're showing up as someone who's eager to learn, with an open growth mindset. Better yet, your company might pay for your self-development ventures.

Your ROI might not be immediate. But it will be immeasurable.

Most importantly, start action on it!

Or Subscribe to this blog:

Subscribe now

How I can help you 👇🏼

After 18+ years as a strategic business designer running successful companies and helped companies raised millions in fundings, I now help designers unlock their strategic thinking skills and become irreplaceable business partners.

This 4-week live cohort "Strategic Design Career Accelerator." covers business acumen, strategy visioning, business communication, connecting design to business impacts.

This course is selected as the TOP Design course on Maven across two categories:
Design Leadership + Designer Career Growth.

Over 100+ designers have taken the course with incredible transformations:
Alumni reflected +67% more confidence in making strategic decisions and connecting design to business.

My next two cohort are:
🌎 OCT - AEST / PDT / EDT.
🌎 FEB - EU / APAC / UAE / AEST

Use code for 20% OFF this week only: MAVEN100 (Code will apply to the first 10 enrolments only)

ENROL NOW (limited seats left)

💬 What alumni students say about the course:

“This is by far, one of the best courses I've taken about combining business and design.”
- Paulina Galindo 🇺🇸 Principal Product Designer @Meta | ex-DoorDash | Ex-Linkedin

This course was definitely an eye opening learning for me as a mid level designer. With tactics to communicate your design value and connecting this with the business strategies, I feel so much more confident about advocating myself.
- Taejin 🇦🇺 Product Designer@REA Group

“This course was a game-changer. It shifted how I see my role as a designer - from executing great work to driving meaningful impact. I learned how to connect design to business goals, manage stakeholders with clarity”
- ChengChang 🇺🇸 Staff product designer @ServiceNOW / ex-Linkedin

Let’s get straight into it few of them…

THE POWER SHIFT IS HAPPENING

The business of tech is a shark eats shark world. Figma isn't playing the nice anymore. Introducing “Buzz” and “Draw”, they're aggressively moving to eliminate Canva and Adobe from designer’s multi touch point workflow. This!! is Figma’s strategic move to provide value to multi tool creators - all in one place.

The days of justifying subscriptions to three different design tools are soon to be over. Figma intend to become an all-in-one platform that will separate the traditional designer from multi platform system thinkers.

My take #1:

Tomorrow's designers will be end-to-end value creators, not specialised contributors.

What's truly revolutionary about this year's product launches is the clear focus on transforming designers into one-person product and business orchestrators. The vision is comprehensive: designers can now create unique branding, generate on-brand marketing materials that drive immediate leads, and rapidly build high-quality websites - all within a single ecosystem.

This means..(drum roll 🥁🥁) 👉🏽 the nature of design role expansion.

Figma is betting that the future belongs to designers who can independently drive business outcomes without depending on specialised teams for each stage of the product journey.

This shift empowers you, the designers to take control of your creative destiny. Imagine bringing your complete vision to life without compromise, without waiting for others to catch up to your thinking. This isn't about doing more work -it's about having more impact with the work you're already passionate about.

Doing more with less. I’m all in.

FIGMA “SITES” & “MAKE”: THE REVOLUTION WE ALL SAW COMING

I’m sure we could all see the “Publish” button was coming, though few understand the business implications of this feature. It’s the elimination of the designer-developer handoff buffer time that has crippled innovation cycles for decades.

It’s still early days for this feature. I still can’t simply copy the code it generated and build a custom Kajabi site (a project that’s on my radar for sometime now) - I still need to hire an engineer to do it.

My take #2:

The future rewards designers who can move product ideas into reality with speed.

The competitive advantage for founders and product teams will be astronomical. Tomorrow's designers will be responsible for delivering them to market with unprecedented speed and autonomy.

This is your invitation to move at the speed of inspiration. When your brilliant ideas no longer sit in implementation queues, you get to experience the pure joy of seeing your vision materialise in real time.

THE BUSINESS DESIGNER ADVANTAGE IS GROWING

The most valuable insight from Config wasn't on any main stage - it was hidden in those talks about building one-person products and founding businesses. The design role is rapidly expanding beyond traditional boundaries and into strategic decision-making territories previously reserved for business leaders.

My journey of building two businesses as a founder serves as a powerful reminder of this evolution. This experience hasn't just made me a better practitioner - it's fundamentally transformed how I approach design problems by layering in systems thinking and business strategy. It forces me to consider multiple business hats with every design decision.

My take #3:

Business fluency will become the defining skill for tomorrow's design leaders.

What we're seeing is the emergence of a new breed of designer: one who doesn't just create based on user needs but re-shapes business models and drives organisational outcomes.

This expansion of the designer's role represents an incredible opportunity for creative minds to gain unprecedented influence. When you can make decisions that impacts business outcomes and drives key market competitiveness, you transform from a service provider to a strategic partner whose voice matters in the most important conversations.

And it’s possible. Designers gotta stop blaming how the game is being played, but start planning the game instead!

So what does this all mean!! Design is evolving faster than ever right in front of our eyes.

Don’t fear, lean in.

Adjusting your skills to adapt as design evolves:

And I’ll be working towards these in my growth pillar to ensure my skill to market readiness.

1. Become the End-to-End Value Creator Tomorrow's designers won't be specialised contributors but comprehensive value creators who can independently take ideas from concept to market without handoffs or dependencies. This is your moment to step into your full creative power and deliver complete solutions that showcase the full spectrum of your talents.

2. Implementation Timeline Collapse: The most valuable designers will be those who can dramatically compress time-to-market through mastery of tools that eliminate traditional development cycles and handoffs.

3. Business Fluency as the Ultimate Skill: Design expertise alone won't be enough. The designers who thrive will be those who can speak the language of business, connect their work directly to revenue outcomes, and make strategic decisions efficiently. And we’re lucky to be in a time with tools that enable us to achieve this.

Config topics this year signal a fundamental shift that places designer at the center of value creation. It’s clear that the walls between disciplines are coming down, the lines are blurred.

I am excited to see designers are now equipped to be the key drivers to products we build for the future we want to shape.

I think next year a CONFIG watch party might be in order. Who’s in? 👇🏼👇🏼👇🏼

Join this newsletter as I share more thoughts after I watch the rest of 82 CONFIG talks … 😅

New designer joins a company/team.

Before you know it, the company spends 4-6 weeks onboarding this designer.

They inject all existing systems, boundaries, constraints, and frameworks into the designer's creative brain.

They set boundaries so the designer becomes part of the factory.

The new hire blends into the familiar process.

Is there another way to utilise a new hire?

What if... The first thing for a new designer to do is completely reimagine how the product works?

At this point, they're a perfect candidate to provide fresh perspectives.

Go wild. Go without restrictions. Forget about design systems. Forget about budget restrictions. 🤩 What could be some possible outcomes from this experiment?

Systems and processes are implemented as baseline foundations.

When systems are overused, innovation gets capped.

👇🏼

Thanks to a rule breaker, cancer patients today can access radiation therapy

In 1898, Marie Curie emerged at a time when women were barred from higher education.

She overcame gender discrimination, poverty, and worked in primitive lab conditions with dangerous radioactive materials.

Along with her husband Pierre, she discovered the elements polonium and radium.

Marie Curie became the first woman to win Nobel prizes in two different scientific fields.

Her work paved the way for the development of radiation therapy for cancer treatment as we know it today.

Thanks to a norm challenger, people worldwide now have powerful computers in their pockets

In 2007, Steve Jobs unveiled the iPhone when mobile phones were defined by physical keyboards and limited functionality.

Along with his team at Apple, he created a revolutionary touchscreen device that transformed personal computing.

He combined phone, internet, music, and digital ecosystem all in our pocket – a concept that was otherworldly at the time.

This was possible because Steve Jobs had the courage to question existing behaviour patterns and technology boundaries.

He envisioned a future relationship between humans and technology that was so believable, it took the whole Apple team on this journey.

Because of that, Apple fundamentally triumphed as the innovative leader other competitive brands look up to.

My point is:

Innovation is the key to building competitive advantage!

Companies need innovation to get ahead of competition!

And you, the designer, have the power to influence innovation!

But how? I'm glad you asked, read on 👇🏼

Designers barrier to innovation

In my opinion: “Fall in love with the problem, Not the solution.” is an overrated statement in our industry.

Spend 80% of the time finding the right problem - Sure. I won't deny the importance of solving the right problem.

But if you vaguely rush through the solution, you limit the possibility to innovate.

Designers get trained to identify problems, but when creating solutions, most follow what's already been done.

They do this because it's already a design pattern. Because it's "safe."

Most design schools lack "innovative thinking" instructors to guide students.

They over-index on solving the right problem but lack innovative practices for create outside the box.

Innovative thinking is a muscle. Without pushing boundaries, it affects our ability to see the right problems, create innovative solutions, generating a dull cycle.

It's about seeing beyond existing problems, well into the future.

Just like Steve Jobs – he didn't follow market research or incremental improvements. He used provocative thinking that questioned existing assumptions.

💬 This makes me question:

Why are so many designers "afraid" to push boundaries or question existing patterns?

disclaimer: I'm not sure "afraid" is the right word to describe it yet. (if you can think of a better word please comment below to let me know)

After working with companies operating with 10-150 designer teams, My observation tells me this:

Those fear to challenge generally associated with these factors:

1. Being the change engine is scary! - no one wants to be the black sheep

2. Design culture doesn’t focus on “innovative thinking” - we’re expected to get in the weeds and roll out features in a rush.

3. Power dynamic - Unless the design lead is advocating for it, it’s too hard.

If you’re in that environment, ask yourself:

What is the purpose of the “designer”,

if we don’t have the space to innovate?

What is the purpose of a “designer”,

if we don’t get the opportunity to challenge the norm?

What is the purpose of a “designer”,

if we continue to “fall in love” with existing problems, but not brave enough to experiment bold solutions?

What you can do today?

Keep in mind any change needs time.

You're planting small seeds that might not show immediate growth.

Eventually, they could become a forest.

Add innovative ingredients to your design culture.

In every single organisation I worked at,

this is what I do to slowly implement innovative culture.

1 - Lead and inspire the team like a futurist

Become the voice of the future in your company.

Invest time to read about future behavior shifts and trends.

Use your spare time to build small showcase projects.

Inspire your company that innovation is key to excel in competitive markets.

Share how trends and market predictions might impact your industry.

This will encourage conversation and attract stakeholders who support building innovative thinking culture.

2 - Create space for provocative ideation.

Ideation techniques aren't utilized enough in many design teams.

I encourage you to introduce brave "Provocation" ideation frameworks.

Most Fortune 500 companies have structured innovation processes that include provocative thinking:

• Apple is famous for their "think different" approach – asking questions against the norm like "what if we remove all buttons?" led to the iPhone design.

• Google uses "10x thinking" where they focus on solutions 10 times better than existing ones, not just incremental improvements.

• IBM uses "Radical thinking" workshops where conventional assumptions are deliberately challenged.

As the design lead - you’re in the perfect position to implement innovation conversation and culture activities.

As an IC designer - you can start by introduce at least one of these new way of work to influence your team and broader company stakeholders.

Whatever you choose to do: Make it fun. Make it memorable. Make it relatable.

All impactful change started with the passion within, I encourage you to create opportunities for yourself to push boundaries.

👩‍🏫 How can I help you?

I’ve turned 15 years of strategic designer experience into practical learning materials to help senior IC designers become Indispensable Strategic Business Partners.

This 4-week live cohort "Strategic Design Career Accelerator." covers strategic business acumen, strategy visioning, strategic communication, connecting design to business impacts.

Alumni reflected +67% more confidence in making strategic decisions and connecting design to business.

Next Cohort Kicks Off in JUNE - Join us!

Enrol Now

The pressure to show hockey stick growth to investors was palpable in every decision.

The roll out speed escalated.

We need to add feature after feature.

We need to sell!

🤔 umm… have we talked about feature quality?

💬 "We'll fix it later."

🤔 Wait, we need to validate this with user research?

💬 "No time for that now."

We’ve all been there. 🫠

Business metrics matter - they keep the lights on.

But when they become the only language spoken,

everything else gets tossed into the 'trade-off' bucket.

User experience suffers.

Long-term risks accumulate.

“User experience” is just one of the many side effects,

The long term risks is what designers can talk about to help business stakeholders make better decisions.

It’s never about winning an argument.

It’s about helping them seeing the full picture.

And!! You’d want to pick the right time to communicate this.

“Every business metric needs to balance with a design metric.”

This realisation was when I stopped fighting business priorities and started translating them and connecting them instead.

Here's what worked for me:

1. Pair Every Business Metric with a Customer Impact Measure 🤝

When the business team celebrates a 20% increase in free-to-paid conversions, bring data on what happened to user retention 60 days later. Create these pairings proactively:

• Conversion rate 👉🏽 Customer satisfaction score

• Revenue per user 👉🏽 Long-term retention rate

• Acquisition cost 👉🏽 Net promoter score

What does it mean for business stakeholders:

By balancing the metrics, you're helping them see the long-term impact without dictating that user experience is non-negotiable.

2. Calculate the debts 📈

Mindlessly rolling out features creates design and tech debt. This reduces future scalability and increases time to market.

Why business partners should care about this:

Design and tech debt means scalable risks in the future, they’ll need to factor in resources and investment to resolve down the road, so that they’re well informed about their trade-off options.

Work with your team to keep track on potential investment, time required and the risks. (i.e. Lack of design system will cause inconsistency → impact NPS. Slow deployment → impact operation. Cost of rebuild)

Present a win-win: “A take two step forward, one step back option without loosing significant momentum”.

3. Visualise the impact 📊

Humans process visuals faster than spreadsheets.

And you and I are designers, we are equiped with this super power - Visualise the problem to help others see clearer.

Create simple diagrams showing:

• Short-term gains alongside projected long-term impacts

• Before/after comparisons of experience quality versus business metrics

I once created a dashboard showing how our "optimised" onboarding flow increased signups by 30% but decreased engagement by 40% by week 6.

That visual told the complete story numbers alone couldn't.

Why this matters:

You’re making it easy for everyone to see the long term impact by visualising it and creating more clarity. This is designers’ superpower, use it wisely.

4. Reframe risks as business concerns 🔗

❌ Stop saying: "This change will frustrate users"

👉🏽Start saying: "This approach risks increasing churn by 5% over two months due to feature complexity. With a 4% growth rate, that translates to reduced annual revenue of $X.”

Translate every customer concern into the business impact language leadership already values.

By that, I mean you need to know who are in the decision seats, and what does success mean to them. Understand their motivation and their success metrics is essential to reframe and reposition your story.

5. Offer the win win balanced solution ⚖️

❌ Never arrive with just problems.

👉🏽 Business decision makers always want options.

Develop options that address both immediate business needs and sustainable customer experiences.

For example:

"Version A might increase conversion by 25% but risks 20% higher churn. Version B could deliver 18% higher conversion with minimal impact on retention.

Here's how we test both..."

Your role as a strategic design partner

As designers, yes – our job is creating delightful experiences.

How would you feel if you can become 10x more impactful when you’re able to help stakeholders understand the full decision-making landscape?

That’s a completely different game to play than an average IC designer.

As a designer, you are uniquely positioned to help business connect the dots.

The first step, is to learn what the different point of views looks like.

High performing strategic designers expand the organisational view to include both immediate metrics and long-term success indicators.

They connect business to design, vice versa, and educate their stakeholders along the way.

This is the most important thing to remember👇🏼

❌ Your job isn't about fighting business metrics vs customer metrics.

👉🏽 Your job is to help sharing the full picture to ensure everyone is on the same page, and well informed to make the best decision forward.

Great businesses need both growth and sustainability.

Be the bridge that connects them. You’ve got this.

—

My ask:

🤩Let me know what you want to hear more of?

It’s the greatest motivation to know that I’m able to provide value to support you on this journey.

👩‍🏫 How can I help you?

I’ve turned 15 years of strategic designer experience into practical learning materials to help senior IC designers become Indispensable Strategic Business Partners.

This 4-week live cohort "Strategic Design Career Accelerator." covers strategic business acumen, strategy visioning, strategic communication, connecting design to business impacts.

Alumni reflected +67% more confidence in making strategic decisions and +62% more confident in connecting design to business.

Next Cohort Kicks Off in JUNE 2025

https://maven.com/jacalin-ding/strategic-design-career-accelerator

💬 What students said from the last cohort:

“This course has been one of the best investments in my career.” - Oliyanka, Senior Designer @Randstad

”This course was more than I could have asked for.”-Sophie, Product Designer at Atlassian

⏳ If you prefer flexible learning at your own pace, self paced course is launching soon!

A lighter version of “Strategic Business Acumen for Designer” is launching in Q1.

Join waiting list today

In our quest to stay relevant and competitive, many have fallen into a pattern of consuming information at an unsustainable pace.

"Learn UX design in 7 days!"

"Speed-read that business book in 30 minutes!"

"Master stakeholder management with this 2-hour course!"

🫠

We're consuming information like we're drinking from a fire hose – gulping down podcasts during our commute, skimming books on lunch breaks, and sitting through course slides while multitasking.

I know the challenges of information overload, because I've lived them.

For years, I prided myself on how many books I could get through in a year,

how many courses I could complete,

how many certificates I could collect.

But here's the uncomfortable truth I had to face:

I wasn't growing. I was just consuming.

We all want to learn. We all want to become better.

But “speed learning” does the opposite to effective growth.

A different approach I've started to apply has transformed how I learn, and I want to share that with you.

⏰ Read time: 4 mins

The Slow Learning Revolution

Last year, I made a radical shift in how I approach learning.

I call it "Slow Learning" – and it's been nothing short of transformational.

True growth results come with time and actively putting new knowledge into practice.

Slow burn yields long-lasting results.

This new way of learning, has been the 360° shift in how I absorb new knowledge.

I'm not overwhelmed anymore.

I'm not suffocated with information.

Best of all, I'm actually applying what I learn.

Let me break down what this new set of habits looks like:

1. Don't just read the book, slow reflect the book

I used to set an annual goal of how many books I wanted to complete in a year.

It would take me a weekend to wrap up a non-fiction book. I'd race through pages, highlight occasionally, and feel accomplished when I hit that final page.

I did that for years until I realised – all these books I've read, I didn't properly apply what I learned. Not even close.

It's not about the number of books. It's the quality of integration.

Since last year, I've changed the game.

For every book I read, I:

1. Highlight parts that resonate (nothing new here)

2. Take handwritten notes – yes, this old-school method helps information stick because you're forcing your brain to process and synthesise

3. Leave the book for a week, then return to my notes to identify actionable insights

One of the most recent books I've applied this to is "Your Next Five Moves Master the Art of Business Strategy" – and the insights I've extracted are directly being applied into my business.

2. Don't just listen to the podcast, slow listen to the podcast

I used to turn on podcasts every time I was on the move: gardening, commuting, grocery shopping, having solo lunch. You name a solo activity, and there'd be a podcast episode playing in the background.

Sometimes I'd go through 5 podcasts in a single day. 😵

Then I'd stop and think: "Wait, what were the key takeaways?"

NADA.

I was rolling through these podcasts without truly paying attention because I was preoccupied with everything else.

So I changed my podcast learning habit.

Every Sunday morning, I go for a quiet walk in nature. I put on ONE podcast and give it 100% of my attention.

During this process, when insights or inspiring moments pop up:

I stop.

I open my Notion app and start taking reflection notes.

This act of writing and reflecting continues to give me new ideas every single week. I then transform these ideas into resources and content that support my design community.

3. Don't just turn up to a course, participate, connect, and do the work!

I used to sign up for course after course – especially those fast and furious ones promising mastery in days.

But thousands of dollars later, I still walked away with half-understood concepts.

Frankly, I don't ever believe that turning up to a PowerPoint slide showcase is going to be as effective as actually creating spaces to apply learnings through practice.

Learning new knowledge is one thing.

Knowing how to do it in practise is one thing.

Doing it well is a whole other thing.

Now, I rarely sign up for learning materials that are just instructor presentations.

A good learning experience includes:

• Easy-to-understand content with examples and walkthroughs

• Peer collaborations

• Applied learning with practices

• Repetition until it becomes second nature

There's no shortcut to this.

New knowledge won't stick unless you put the work in.

So what do I do with all these notes and reflections collected?

Each point resonates with me in a different way.

I sort them in my Notion workspace into three categories:

1. Fast-Track Adoption - Things I can apply tomorrow

   Action: Seek professional opportunities to put new learning into practice immediately

2. Curiosity Deepening - Things I want to learn more about

   Action: Seek deep-dive learning resources on these topics

3. Value Creation - Things that I can share to inspire others

   Action: Create useful resources to support designers and growth learners

Counter-Intuitive Truth

Here's the thing that will mess with your productivity-obsessed mind:

By slowing down my learning, I've actually accelerated my growth.

Because I'm not just collecting knowledge – I'm integrating it. I'm not just aware of concepts – I'm applying them. I'm not just learning – I'm transforming.

"Slow Learning" has changed the way I value my own time.

More importantly, I can feel, see, and read my own growth path with a lot more breathing room.

Your Turn to Slow Down

If you're feeling overwhelmed by the constant pressure to consume more information faster, try this "Slow Learn, Fast Adopt" approach:

1. Choose Quality Over Quantity - Better to deeply understand one book than to skim ten

2. Create Space for Integration - Schedule dedicated time for reflection, not just consumption

3. Apply Immediately - Knowledge without application is just mental clutter.

4. Document Your Journey - Track not just what you learn, track your growth in particular areas. Get feedbacks, Share your learnings.

In a world obsessed with speed, the real competitive advantage might just be your ability to slow down and actually absorb what matters.

The journey to becoming a better designer happens one thoughtful step at a time.

I encourage you to find a learning rhythm that works for you. When you do, you'll not only feel more fulfilled in your learning journey, but you'll see the tangible results in your work and career.

That’s all for today.

If you found this post helpful, please share to your network.

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👩‍🏫 How can I help you?

1. Join our next "Strategic Design Career Accelerator." This 4-week live cohort program covers strategic business acumen, strategy visioning, strategic storytelling, connect design to business impacts, and strategic career impact planning.
   (runs 3 times a year)

   Join the next cohort starts in JUNE
   

💬 What students said from the last cohort:

“This course has been one of the best investments in my career.” - Oliyanka, Senior Designer @Randstad

”This course was more than I could have asked for.”-Sophie, Product Designer at Atlassian

2. If you prefer flexible learning at your own pace, self paced course is launching soon!

“Strategic Business Acumen for Designer” Join waiting list today

As I advanced into higher positions, with more responsibilities and a broader view, I've learned overly invested emotions were doing more harm than good.

I became hyper focused, "emotions" blurred my view to look at the bigger picture.

The key is: Balance with logic and macro view.

Few things I do now to consciously remove access emotions:

• Acknowledge my own bias - ask "What if the opposite is true"

• Put extra efforts to research and understand the opposite

• Look at every project through the lens of a good journalist.

Read time: 4mins

The emotional bias cost

Let me introduce you to Liam (name changed).

Liam is the kind of designer who would drop everything to pick up lunch for a colleague, the most considerate soul you'd ever meet.

With over 15 years of design experience, he carried a heart so big it sometimes overwhelmed his professional perspective.

We were working on a critical project - restructuring a website navigation system that impacts millions. Liam's passion ran deep, especially around sensitive topics like domestic violence and aged care.

His intentions were pure gold - he wanted to ensure support resources prioritised front and centre.

But here's where emotions began to cloud logical judgment:

The website's metrics were screaming for help:

• a 55% churn rate affecting 2.5 million visitors - daily! 😱 That’s 1.3 million users turned away due to unintuitive navigation system.

• We were sitting at a 15% conversion rate, that’s 195,000 daily users that could have could have turned into leads!

While Liam was fixated on surfacing needs for a selective user segment, he was missing the larger operational context. His emotional bias is creating tunnel vision for his work.

Business leaders operate with a macro view - they're balancing outcomes, trade-offs, roadmap actions, and financial impacts. We ended up spending more efforts to show Liam the “blind spots” and the trade offs he wasn’t able to see, just so we can get the project through to next steps with urgency.

This isn't about diminishing empathy for a group of users.

It's about expanding designer’s perspectives.

Balancing emotion and intelligence

I've learned to consciously check my emotional temperature. Here are my personal strategies:

1. Acknowledge Your Bias: Ask yourself, "What if the opposite is true?"

2. Curiosity: Put extra effort into understanding perspectives different from your own

3. Adopt a Journalist's Lens: Observe without immediate emotional attachment. Catch yourself doing the “over empathy” thing, and actively seek broader perspectives. This part, requires high level of self-awareness. Did I mention that’s a super skill for high performers?

What Liam could have done

Strategic Repositioning

Approaching the project with a macro lens, Imagine Liam understands that solving a design challenge isn’t just for certain users, but it could unlock multiple opportunities for discovery and the business.

There’s opportunity for Liam to help business partners broaden considerations with multiple potentials to broaden his influence.

Example action points could be:

• Soft launch of targeted support navigation: Less risk, high impact for millions of site visitors

• Phased approach: Reducing implementation risk without loosing growth opportunities

• Suggest measurable incremental improvements: Identify targeted data points to set milestones to move the project forward

• Layout risk, trade offs, quick wins and long term impact across the lead generation pipeline: Sales, Marketing, Customer metrics, Conversion rates..etc (And he works closely with multiple teams to get their perspectives)

Impact at scale:

As Liam escapes his own “empathy tunnel”, he's doing something revolutionary:

• Demonstrating multiple business considerations as a strategic partner

• Showing risk management skills

• Proving he thinks beyond his design silo

This is the opportunity for Liam to up-level his influence from a "nice-to-have" designer to a critical strategic partner.

Influence: the day to day “personal brand”

What Liam is achieving with the above actions is building his “personal brand” as a strategic thinker. Yes, the personal brand thing applies to work environment too: He’s selling his expertise as the “go-to system-thinking” designer.

He's showing that:

• Empathy can coexist with strategic thinking

• Passion becomes powerful when channeled selectively

• Design is a business solution, it’s empathy problem solving with the bigger picture in sight

Leap to leadership

Expanding your horizon is the leap you need to master towards leadership (and it isn’t an optional skill)

This is the zone to demonstrate a Senior IC’s ability to lead, the ability to identify opportunities beyond your immediate emotional response and understanding the intricate dance of business, user needs, and strategic movements at a macro scale.

Being intelligence means creating space between your emotional reaction and your professional response.

So next time you feel that surge of emotion threatening to hijack your professional judgment, take a breath.

Step back. Look wider.

Your most intelligent design might just be the scale perspective you create.

😇 If you like this topic. Please share or give it a 👍.

Here’re other ways I help designers level up their career:

Strategic Design Career Accelerator. (Top Maven Course - 9.7/10⭐️)
This 4-week live cohort program covers strategic business acumen, strategy visioning, business storytelling, connect design to business impacts, and career impact planning.

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Watch Free Webinar: Level Up Your Design Career Beyond Senior
Great design skills equals a great career. In reality, the game-changers are strategic thinking, system thinking, influence expansion and communication skills outside the realm of design execution. These are critical tools for unlocking the next level in your design career to become a strategic super IC or people leader.

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If you prefer flexible learning at your own pace, an affordable and value packed self paced course is launching soon!🤩 Join the waiting list now👇🏼

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📚 Any topic you’d like to hear more of, please let me know. I’m all ears.