About

Design Outcomes is the working notebook of a Design Executive in practice. I'm Leonardo De La Rocha, and this site is where I publish the actual work of running a design organization, in real time, in two formats.

Articles run long: full-length pieces on the decisions, the frameworks that held up once a live team leaned on them, and the tradeoffs that turned out harder than they looked on paper. This is the work I want to think through carefully and put on the record.

Field Notes run short: annotated reads on the tactics other teams are getting right, with notes on what makes them worth studying, the kind of entry you'd find scribbled in the margin of a paper notebook.

The goal is to share the practice as it happens, before it gets polished, with no sponsors and no popovers between you and the work.

Want the career overview first? The executive summary lays out each role and the scope of the work behind it, or you can jump straight into selected projects.

The design itself is meant to be read too, so here's a quick tour.

The Design Outcomes mark that sits above the articles tips its hat to Ben Barry, designer and co-founder of the Facebook Analog Research Lab, whose blackletter mark for that team set a bar for what a design org's flag could look like. Mine borrows the spirit of that work.

Hero illustrations are drawn in a Risograph style: two inks on cream paper, with all the registration drift, edge wear, and pinhole specks the medium asks for. Each one is bespoke to the article it announces, and the cover should argue for the piece rather than decorate it.

The articles carousel cycles through them the way a Riso ticks through prints, one sheet at a time.

Field Notes (the section) borrows its name from Field Notes (the notebook). Each card is a pocket notebook, kraft band and all, the kind of object that ends up creased in a back pocket and weirdly indispensable.

The cream background is the paper, the italic serif headlines come from editorial print, and the all-caps sans labels come from broadsheets and gig posters, letterpress thinking rendered in pixels.

I'm an engineer turned designer turned design executive, roughly 25 years in, starting with graffiti and lettering in Denver and winding through Yahoo, Facebook, Intuit, Spotify, and now SimplePractice, where I'm VP of Product Design.

At SimplePractice, I lead a 30-person design organization building the EHR (electronic health record) platform that over 250,000 independent behavioral health clinicians use to run their practices. The work spans clinical care, revenue cycle, mobile, and an emerging AI practice. The clinicians we serve are mostly solo or small-group, which keeps the bar high: their software has to be the kind of thing one person can run a business on.

Before this, I led design for Spotify Advertising, a 64-person organization across product design, research, content design, and program management. Before that, Intuit's design system and accessibility work across TurboTax, QuickBooks, ProConnect, and Mint. And at Facebook, Creative Director for Studio X (the in-house creative team for business products) and Product Design Manager for the ads platform. The ads team was called Outcomes, and I liked the name enough to carry it over to this publication.

A few principles have followed me across every role: help people grow rather than just finish tasks, save time without losing sight of what people are using the tool for, bring clarity to complex tools without flattening them, and be reliable in the way organizations need, which mostly means predictable enough to plan around.

Outside the day job, I take freelance branding and illustration work to keep a hand in the craft, mentor on ADPList, and speak on design leadership and AI's impact on design orgs. Most recently I keynoted Upscale Conf on how new AI input modalities are changing the way design teams work.

I believe design is a form of tuned awareness, that leadership is posture more than title, and that the surest way to build trust with a team is to show your work. This site is me showing mine.