Product design is organizational health on display

Lately I'm experimenting with this thing they call "business development," where you intentionally reach out to people and companies who may have a need for your services and let them know you exist.

Shocking, I know! I started my career at Apple in an era where social media was verboten and we lived as warrior poets, unseen except as through our work. As a design studio owner I am required to unlearn that, so this past week I built new workflows to make this "business development" as easy as possible.

Window-opening and copy-pasting has been replaced by chaining together AI services. Whenever a company is hiring senior design leadership I get an assessment of whether they'd be a studio client candidate, a draft in Gmail of a message to the CEO or CPO based on examples I've already written, and outreach tasks in Linear for me to prioritize and complete. I get to focus on what I love as an extrovert: seeking a real, true connection through personal edits, human-to-human writing, and care.

So imagine my delight when one day into this new process, I received an email back from a founder and executive chairman of a company that's in the same space as a prior studio client, who's hiring a head of experience design and a conversational designer.

For the earlier client, ———, I'd been operating as an interim design executive to guide consumer AI features. My work on Siri was literally as one of the first conversational interface designers. So, lots of overlap. Love it.

The email I got back:

——— has pretty atrocious experience, tbh

That was it. As someone who loves things written by humans, I loved it even more.


First, I love how human it is to absolutely hate your competitors. Every flaw impossible to look away from, the rage inescapable as you try to figure out how they're getting away with this.

It's a lot like how designers in an unhealthy organization look at their own company's products. An engineering team is rushed to ship something that didn't undergo pixel-by-pixel QA, undermining design intent and product cohesion, while product managers seek their flowers for the up-and-to-the-right. How are they getting away with this? Don't they see we'll have to solve that later in a harder way? seethe designers, wincing every time they see the feature live onscreen. Why do we need designers? They just want to slow us down and keep us from being great, seem to conclude their product managers.

On one studio project, the team I worked with was incensed to discover that a product manager went rogue and shipped a "painted door experiment" claiming the company had invented an incredible new AI feature, and you could tap right there to use it immediately. When tapped, a message appeared instead — You'll be first to know when we release this feature! They intentionally left their engineering and design lead partners out of the Slack channel where they commanded a small set of engineers to build it, so as to avoid any prioritization, copywriting, design, or project brief debate or oversight.

The product manager was delighted to share that of the 10% of product users that saw the button, 60% tapped it, and therefore proudly interpreted the results as signal that users would trust the company to ship that kind of feature. Their management was thrilled, extolling the quick turnaround to the company as signal that product managers should go rogue more often. The design and engineering partners they'd hidden the project from were livid at both interpretations. Don't you know that you've just taken the cohort that self-identified as people who would trust us to build that feature, and proved ourselves untrustworthy? And everyone who worked on this, thinking it was approved, is ashamed?


The second thing that I love — this founder has a point. The competitor's product has a great brand and great revenue narrative. They also had, until they left in droves after one year of vesting, a great product design team. In the story above, the design and engineering partners left out of the Slack channel by the product manager were not left out of the conversation by their own bosses. Those designers and engineers first learned about the shipped experiment when their peers and management chain saw it in the wild, and reached out by phone, DMs, and at-replies in public threads to hold them accountable for an ugly, discordant, misrepresentative experience plopped in the middle of a primary page.

Companies typically hire designers and design leadership for a few reasons. These include wanting to build trust with consumers, satisfy or raise money from from unimpressed investors, partner with a certain kind of company or individual, broaden the reach of their public profile, differentiate from competitors, increase engineering throughput without reduced quality, create an attractive work culture of innovation and excellence, and maybe sometimes, from personal taste and love of design in the founder or executive team. The last one is something Bob Baxley talks about — a belief that people want to be proud of the things they make, and that a design culture comes from the essential beliefs and taste at the top.

But companies also need certain things to survive, and those depend on the operating structure of the company and the presiding market culture. The type of company and metrics that were fundable in the 2010s became un-fundable after the pandemic in 2020. What is fundable in 2026 is very different than what was in 2025. I will never forget a critical dinner where the founder realized for the first time that the board wasn't joking about how future investment would be evaluated on a path to profitability, not innovation and happy users. Market forces and major leadership shifts drove big changes in what design was accountable for, how they had to hold the line on the experience, and whether and when they even should.


So when I look at a company's design quality, I don't assume I'm looking at the capability of the designers that work there. I'm looking at the company's priorities and I'm looking at the company's organizational health amid market conditions. That's a big part of why I like working with companies as an outside studio partner — I can assess these things honestly with leaders, identify the unique leverage that design can and should be delivering in their situations, and lead design in a way that does it. I get to identify whatever is happening in their organization that prevents design from unlocking their wants and needs successfully, and often I get more latitude to help unfuck it than those on the inside.

Having both worked at Apple for 5 years and a single startup for 5 years, I do absolutely love long-term planning and helping a company envision many futures. I also love shipping fast, while abhorring work that ships below the quality that its creators and its consumers deserve. I love doing everything in my power to make the work that ships go out at high-craft and high-delight. And if a company's priorities and organizational health limit the overall impact of design, I love getting to focus on where we can drive value regardless and then get out — with companies having spent a very efficient dollar and my team's health intact.

Which leads me to my response to that founder this morning:

Haha! I’m sure you can appreciate the opportunities that they have better than most. Consumer AI focus was a fun studio project, but as you know, their product covers a lot of ground beyond that.

Glad to share a perspective on what kinds of organizations make the most of their design team. Your company has a great opportunity in these hires, and to your point, it’s not just about bringing in great designers.

Happy to chat.

All the best,

Lia

In the name of business development, that offer to chat extends to you reading this, too — not just to founders who start their mornings shadowboxing their competitors.

Here's a link to our design studio. Tell your friends.

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