People & Process

Designing, managing, and leading teams, companies, and the processes they use

Design process

A quick note on this section: process is one of the hardest topics in building products and one reason for that is that it’s so much about judgement and adaptability. It’s about what tools you have and knowing how and when to use them. No one process is right for every situation, person, product, etc. It’s something that tends to strongly correlate with experience and it’s hard to codify best practices that are widely applicable.

Principles of Product Design [EPUB] – a good reminder on best practices for design process
By Aarron Walter • Published by DesignBetter.Co by Invision

How to Present Designs
By Julie Zhuo

DesignOps Handbook [EPUB]
By by Kate Battles, Meredith Black, Dave Malouf, Collin Whitehead, and Gregg Bernstein (editor) • Published by DesignBetter.Co by InVision

Emotional intelligence

I took the course, Emotionally Fluent Leadership by Design Dept. [Course], taught by Liz and Mollie, the go-to experts to learn about understanding and managing emotions at work. Read their two books, No Hard Feelings [Book] (selected a best book of the year by NPR and Fortune) and the sequel, Big Feelings [Book]. And articles of theirs, like this one in HBR about unwritten rules in organizations [Article].

Pro tip from Liz + Mollie’s wisdom: If you work remotely, consider that the person you’re speaking to is in a different physical context, so they may bring a meaningfully different mental context to the conversation, too. Don’t forget that you’re speaking to them in their home, so you’re a sort of guest. That’s an additional layer of complexity to manage. Give yourself—and them—the space to build that skill.

Radical Candor [Book] teaches you how to be clear and kind by leading with, you guessed it, "radical candor” at work
By Kim Scott

A feelings wheel is a great tool to more clearly identify how you feel. Start in the center and work your way outward.

Therapy is incredibly valuable and everyone should do it (especially people managers) but it can be hard to know where to start. Though there are a lot of startups offering alternative formats like texting, it’s not the same as direct 1:1 time in my opinion. Alma [Product] can be a great place to find a therapist, psychologist, psychiatrist, and more.

Design thinking & sprints

Enterprise Design Sprints [EPUB + Guidebook] by Richard Banfield • Published by DesignBetter.Co by InVision

(Design) leadership & management

The Making of a Manager: What to Do When Everyone Looks to You [Book]
By Julie Zhou, formerly VP of Design at Facebook and now cofounder of Inspirit
Related: The Looking Glass

Team Structures and Operating Models
by Andrew (Andy) Warr, Sr. Staff Design Researcher at Uber  •  UX Collective
Read his other stuff, too.

The Business Impact Of Design: Five Best Practices For Measuring It  [Report, 17 pgs.]
By Gina Bhawalkar, Forrester  •  via InVision

Business Thinking for Designers
InVision

The Anatomy of a Large Experience Design Organization — 2.0
By Jesse Kaddy, Associate Director, Product Design at Wayfair

A Tactical Guide to Managing Up
First Round Review

Make a user guide to working with you with this article from First Round Review and this from Julie Zhou

Staff.design – Navigating the Individual Contributor Career Path [Website]
A fantastic project by Brian Lovin

Tips for managing a team of very senior designers [Twitter thread]
By Stan Rapp, Product Design Manager at Chan Zuckerberg Initiative

Lattice’s Library, including their collection of ebooks and templates — great resources for managers and HR pros

Cross-pollination between design teams can be a real 10xer. Try a design fika (from the Swedish coffee break), using this guide from the Webflow design team.

The Manager’s Handbook [E-Book]
By Alex MacCaw, CEO of Clearbit

Design Leadership Handbook [EPUB]
By Aarron Walter and Eli Woolery  •  Published by DesignBetter.Co by InVision

Performance Management as a New Manager, Part 1, 2, 3, 4. [Article] are incredible [Articles]
By Jasmine Christensen

The US military is one of the best researchers and teachers of leadership in the world. People significantly underestimate how much of the US military's effectiveness has depended on how they've made operational leadership a science. Wharton Business School (routinely itself ranked #1 business school) called Marine OCS some of the best leadership training on the planet. Because of the nature of the military, they love documentation (manuals), and because it's the US government, nearly all their materials are freely available in the public domain.

To name just a few. Google around—there's so much free coursework on leadership.

One caution here: the military is great at operational leadership, which is designed to achieve efficiency and order, and which benefits from strictly hierarchical, top-down leadership. Design organizations usually have very different leadership needs focused around collaboration and innovation, which benefits from a flat, egalitarian, and informal structure. Knowing both types and when to use what tool is key. Lots of friction in design leadership happens at this liminal space, between operations mindsets that hate ambiguity and creative mindsets that benefit from it. Becoming proficient in both helps you navigate both worlds and designer leaders often under-index on the operational side.

Recruiting

The art, science, and labor of recruiting by Vinod Khosla, legendary founder of Khosla Ventures

Building the Initial Team for Seed-Stage Startups
By Andrew Chen

”I’ve come to believe that the first batch of people you want on your team are going to be T-shaped, meaning they are broad in a bunch of different areas and deep in a particular one.”

How to Hire Your First 10 Employees
By Caleb Kaiser, AngelList Talent

Startup Recruiting Bootcamp

Asana’s Head of Talent on the Secrets to Finding a Great Startup Recruiter
First Round Review

Entrepreneurship

State of Startups 2019, 2018, 2017, 2016, 2015
”The industry's largest dataset on what it’s like to run a startup” from First Round

The 30 Best Pieces of Advice for Entrepreneurs in 2018
First Round Review

Everything that Paul Graham, founder of Y Combinator, has written (don’t let the 90’s website aesthetic fool you)

A great resource to find investors is Ramp’s Investor Database

Diversity & inclusion

Design Justice—”An exploration of how design might be led by marginalized communities, dismantle structural inequality, and advance collective liberation and ecological survival.” 2021 PROSE Award Winner, Engineering & Technology Category [Book]
By Sasha Costanza-Chock  •  MIT Press

Diversity and Inclusion in Tech, Part 1: Foundations, Myths, and Pitfalls and Part 2: Improving the Hiring Process
“Everything you want to know about D&I in technical hiring but are too afraid to ask.”
By Jennifer Kim and Jason Wong
Related: For startups in particular, here’s a great thread by Jennifer on Twitter on key things to know. And Inclusion at Work, too.

The Diversity & Inclusion Compendium for Designers [Google Doc collaboration]
A huge Google Doc filled with D&I resources for designers
Curated by Marissa Louie

Design Books by Womxn & People of Color
Curated by Yuan Wang

The Good Boss: 9 Ways Every Manager Can Support Women at Work
By Kate Eberle Walker

Research: How Subtle Class Cues Can Backfire on Your Resume
By Lauren Rivera + András Tilcsik • Harvard Business Review
Related: Interestingly, this seems to apply to men more than women

Research: Reducing implicit racial preferences: II. Intervention effectiveness across time
By Lai et al. • Harvard

The Art of Work presents:
Homerun’s Guide to Diversity & Inclusion [PDF]

Learn about bias in artificial intelligence with AI Explorables by Google’s People + AI Research (PAIR)

Pocket Biases [App]

Wikipedia’s Cognitive Bias Codex is a beautiful “radial dendrogram” showing 188 cognitive biases, each clickable and linked to their respective Wikipedia article. A go-to reference for learning about cognitive bias. (via Dense Discovery)

Startup finance & law

Operations startups—companies that make SaaS ops tools—obviously make it their business to write extensive thought leadership on startup operations. Check out the blogs of companies like Ramp, Mercury, Brex, Stripe, etc.—there's a gold mine of advice there—just watch out for their product placement/bias. VCs have put out tons of info as well; I particularly like First Round Review.

The Holloway Guide to Equity Compensation [E-book] is a fantastic guide to both issuing equity (if you're a founder or startup ops person) and negotiating equity offers (if you're a job candidate)

Equity for Founders [Book]
By Patrick McKenzie  •  Published by Stripe Atlas

Employment [Book]
By Patrick McKenzie  •  Published by Stripe Atlas

Stripe Atlas publishes free guides on the basics of startup operations

Structuring the design team

Ladder examples at Staff Design’s resources page, and a few linked directly here:

“Designing” a Career Ladder for Product Design
By Helena Seo, Head of Design at DoorDash

A Design Team’s Guide to Leveling
Designer Fund

Freelancing or starting an agency

Hoodzpah’s Freelance and Business and Stuff is a reasonably priced online course that tells you everything about going freelance. Includes access to a great community, including Amy and Jen Hood themselves.
"The slack channel alone is worth the price of the course." — Chris von Burske

Run Studio Run: How to operate and grow a small creative agency
By Eli Altman of A Hundred Monkeys

Graphic Artists Guild Handbook has been guiding designers for over 48 years on how to set pricing, industry ethics, legal advice, and more.