🤿 ugly design systems

What does it look like to advance your career in the age of AI?

That’s what this week’s episode with Dan Winer (Director of Product Design at Kit) is all about.

And he’s the perfect person to teach the topic because he has one of the most popular courses on Maven (Strategy and Influence for Product Designers).

So if you want to learn how to go from pixel pusher to strategic partner then this is the episode for you 💪

Some highlights:

• Dan’s strategies for effective storytelling

• How to shine a light on the value of your work

• Tactics for building alignment across key stakeholders

• The 8 skills that Dan is evaluating in the hiring process

• Why design systems are becoming more important than ever

• Harsh truths designers don’t want to hear about their portfolio

• What to do if you don’t have data to prove the impact of your work

• + a lot more

Listen on YouTube, Spotify, Apple, or wherever you get your podcasts 👇

🤝 WITH GRANOLA

By now you probably know how much I love Granola…

So I’m gonna toss it to one of my favorite designers James McDonald to share his experience 👇

I couldn’t agree more 💪

I simply cannot imagine life without Granola at this point. So if you’re a designer, you shouldn’t be having a conversation about your work without running Granola.

They’re offering 3 months free for you and anyone on your team all you have to do is click the link 👇

🔑 KEY TAKEAWAYS

3 Portfolio strategies

1 — Understand what hiring managers are evaluating first

Dan recently hired 2 designers out of 1,000+ applicants.

When I asked what he looks for first, he admitted that you might not like the answer:

He compared it to getting your driver’s license: you have to pass the theory portion before you get an opportunity to demonstrate that you drive.

Same goes for portfolios. If the basics aren’t there (white space, hierarchy, typography, contrast), no one’s sticking around to read your case study.

And if your instinct is “well that’s subjective”… that’s a signal you don’t yet understand the craft. The foundations of visual design are actually quite measurable, and people hiring for the best teams can spot them in seconds.

2 — Don’t let ugly design systems block you

I hear this pushback all the time. Which is why I loved Dan’s take 👇

If a designer told me they re-designed their product for their portfolio just to show their visual skills, that’d be a huge +1 in my book.

And yet I’ve never seen anyone actually do it 🤔

Don’t let an ugly design system keep you from demonstrating your craft.

3 — Capture testimonials early

I’ve shared a lot of portfolio advice over the years (like these 6 tips to make your portfolio stand out) but you can boil them all down to one idea:

👉 Design your portfolio like you’re selling a product (aka you).

This mindset changes everything:

• the way you think about layout

• what goes on your home page

• the copy you put into your headings

• and especially the importance of social proof

Good product pages feature compelling testimonials. Portfolios rarely do.

Every once in a while I see a Linkedin endorsement about the designer as a person, but I can’t remember a time I saw a sharp customer quote about something a designer shipped. And yet, it’s always more powerful when someone else speaks to the value you created.

That’s why Dan recommends proactively capturing testimonials:

After something ships, take the time to gather the evidence (ex: customer quotes, support feedback, research data, ec.) Save it somewhere before you need it.

Because when it’s time to update your portfolio, those receipts are gold.

There’s a lot more in the full episode. Tbh I started out thinking this portfolio piece was going to be a single takeaway but it was too dense 😅 So you’ll have to learn about the onion metaphor for storytelling and the new value of design systems in the full episode 👇

Meet the Dive partners 

I made a list of my favorite products and asked them to come on as sponsors of the newsletter/podcast. They said yes 🥹

The #1 way to support Dive Club is to check them out👇

Framer​ → How I build my websites

Genway → How I do research

Granola → How I take notes during CRIT

Jitter​ → How I animate my designs

Lovable → How I build my ideas in code

Mobbin → How I find design inspiration

Paper → How I design like a creative

Raycast ​ → How I stay in flow while I work

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