Design Leadership Recipes

Chapters

Introduction

I’ve been designing applications and leading teams for a long time. I view leading teams as an exercise in systems thinking: understanding events, patterns, structures, and mental models that drive successful and engaged design teams. In practice, this means I’m constantly evaluating new rituals, resources, and tools to help design teams be more effective and efficient. This is a collection of my thoughts and experiences on design leadership, with a focus on the role of design leadership in the design process.

I do not claim these as my own, and I’ve drawn influence from many people and sources, which I’ve tried to acknowledge along the way. I hope this material can help you as others have helped me.

Who is this for?

Design Leaders

Whether you’re new to management or a seasoned leader, I hope these resources can help you continue to grow and improve your skills (or those of your team).

Designers

A great way to be self-determining is to understand what your manager (or their manager) uses as their source of truth. For designers, I hope this is helpful in managing up, introducing new rituals to your team, and ultimately a tool for better engagement with your work.

Design Allies

Design is hard, and leading design teams is a science. I hope this is helpful in understanding the challenges and opportunities of leading a design team.

Rituals

Design Reviews

Frequency: As needed throughout the development process

Goal: Ensure alignment, quality standards, and diligence throughout the product development lifecycle, from initial concept to final implementation.

Design Reviews are a crucial mechanism for maintaining high standards, ensuring alignment with business goals and user needs, and promoting diligence throughout the product design process.

Types of Design Reviews

There are three main types of design reviews, each corresponding to a different stage of development:

1. Concept Review

When: Early discovery stages

Purpose:

What to Review

Key Questions

2. Prototype Reviews

When: Mid-stage development

Purpose

What to Review

Key Questions

3. In-app Reviews

When: Late-stage development

Purpose

What to Review

Key Questions

Review Process

  1. Schedule the Review: Set up the review at the appropriate development stage.
  2. Prepare Materials: Create a brief to share with reviewers, including the design, any relevant research, and any key questions.
  3. Conduct the Review: Present the design, discuss key questions, and gather feedback.
  4. Document Feedback: Record all comments, suggestions, and decisions.
  5. Approve, Revise, Stop: Determine if the design is approved as-is, needs revisions, or presents significant risks and needs to be revised before moving to the next stage.
  6. Follow Up: Implement approved changes and schedule any necessary follow-up reviews.

Roles and Responsibilities

Visual 15:5

Every two weeks

Goal: Provide a summary of your team’s accomplishments, work in progress, and opportunities that anyone in our organization can read in 5 minutes or less.

Visual 15:5 derives from a practice created by Yvon Chouinard, of Patagonia fame, and draws inspiration from Scrum's standup formats.

Getting a line of sight on work-in-progress for large teams can be challenging. At AppFolio, we tried several formats: Google Slides, Coda/Notion, and Trello. The implementation mostly looked the same: a description of what each designer completed in the last week and a visual artifact to help those who were unfamiliar.

We remixed Figma’s weekly team update FigJam. Every two weeks, we open a copy of this template for each team to fill out. The board “closes” toward the end of the week, and the design manager is responsible for synthesizing updates and providing a summary, which goes to their manager. At the end of the week, a large FigJam with all of the week’s updates is shared with the team, along with the written summary by the senior-most leader.

At the end of each quarter, we have the design leadership create a “UX Hall of Fame” to recognize and celebrate each designer’s most impactful contributions.

Essential Journeymaps

As needed

Goal: Align on a set of journeymaps that solve core needs for the majority of your users.

Essential Journeymaps are simplified, high-level representations of the most critical paths users take through your product. They focus on the key steps, touchpoints, and potential pain points in core user workflows.

Components of an Essential Journeymap

  1. User Goal: The primary objective the user wants to achieve.
  2. Key Steps: The main actions or pages the user goes through, both inside and outside of the product.
  3. Touchpoints: Specific interactions within each step.
  4. Potential Pain Points: Areas where users might struggle or get frustrated.
  5. Success Metrics: How you measure if the journey is successful.

Note: I’ll have a sample Essential Journeymap for E-commerce checkouts in FigJam soon.

Walking the Store

Credit: Katie Dill, Head of Design at Stripe. She also talks about essential journeymaps.

Frequency: Quarterly

Goal: Experience key workflows the way your customers do, identifying pain points and opportunities for improvement in your digital product.

“Walking the Store” is a practice borrowed from visual merchandising and brick-and-mortar retailers. In the digital world, it means systematically going through your product’s key user journeys to assess the user experience, functionality, and overall product quality.

Preparing to Walk the Store

  1. Identify Essential Journeys: Determine the 3-5 most critical user journeys in your product.
  2. Create Essential Journeymaps: Develop simplified maps for each journey.
  3. Assign Owners: Each journey should have a designated owner responsible for its quality.
  4. Conduct the Walk: Regularly go through each journey, experiencing it as a user would.
  5. Log Issues: Document any problems, inconsistencies, or areas for improvement.
  6. Prioritize and Fix: Address the identified issues, prioritizing based on impact and effort.

The walk

When walking the store:

  1. Go through the entire journey as a user would.
  2. Try variations: returning user, mobile device, different payment methods.
  3. Attempt common error scenarios: invalid discount code, expired credit card.
  4. Note any confusing language, unclear instructions, or visual inconsistencies.
  5. Check that all success metrics can be properly tracked.
  6. Log any issues or improvements to a UX Debt board.

Retro

Quarterly

Goal: Improve practices, increase engagement, shape culture, and identify challenges.

Like many collaborative sessions, UX retros generally follow typical team retro formats: Generating ideas in categories like start/stop/continue, synthesizing and grouping themes, and voting on 3-4 areas. Time for discussing the identified themes.

Retro’s value is in generating quick actions, such as stopping an ineffective practice, trying a new ceremony, or reinforcing something that works well.

Weekly Critiques

Weekly

Goal: Foster a constructive, collaborative environment that drives design quality and team growth.

There are many different formats for weekly critiques, but here is a non-comprehensive list of best practices:

  1. Structure and Preparation

    • Set a consistent schedule and time limit
    • Have a clear process for designers to submit work for review in advance
    • Ensure all participants have access to the work before the session

  2. Set the Tone

    • Establish ground rules for the session by reiterating the purpose of the critique
    • Incorporate your design principles and values to create a shared language for feedback
    • Designate a facilitator or lead to keep the session on track and ensure all participants are heard

  3. Facilitate the Session

    • Balance context with actual design work
    • Experiment with different formats for generating feedback, such as generating sticky notes or questions for 5 minutes and having each participant share their feedback.
    • Make sure questions are open-ended and allow the presenter to discuss their perspective and defend decisions.

  4. Provide Actionable Feedback

    • Offer specific, constructive feedback rather than vague opinions
    • Balance positive feedback with areas for improvement
    • Tie feedback to user needs, business goals, and design principles

  5. For leaders

    • Allocate time fairly among presenters
    • Keep discussions on track, parking lengthy debates for follow-up sessions if necessary
    • Demonstrate how to give and receive feedback constructively
    • Show vulnerability by presenting their own work for critique occasionally
    • Recap key points and action items at the end of each critique
    • Ensure there’s a system for tracking feedback and improvements
    • Hold designers accountable for sharing their work and feedback regularly

  6. For teams

    • Regularly seek feedback on the critique process itself
    • Adjust the format as needed to keep it effective and engaging

Design Warm Up

Weekly

Goal: Design warm-up is a time to exercise creativity and learning to start the week.

Design warm-ups are generally the first meeting of the week and include a prompt or challenge for the design team:

If working in Figma, use huddles to share ideas and collaborate. The goal is to create a dedicated time for creativity and exploration.

Product Teardowns

Monthly

Goal: Reverse engineer physical and digital products to critique, learn, and inspire.

Each month, a designer chooses a product to analyze in depth and presents their findings to the larger team or organization. They work with product and engineering counterparts to consider usability, feasibility, and viability details and provide context on why decisions may have been made.

Examples include:

Inspiration Boards

Monthly

Goal: Creative people inspire creative people.

Each month, we open a FigJam board and ask a simple question: what’s inspiring you?

Think of inspiration boards as a shared mood board where everyone can show designs, products, art, photography, family photos, or music that inspires them. It’s a fun and low-stakes way to include whole people at work and an excellent opportunity to build camaraderie amongst your team.

Hiring Designers

You’ll be responsible for growing and maintaining a high-performing team as a leader. Starting with hiring, I’ll discuss my approach to equitable hiring processes and tools for evaluating designers.

Be kind

If you take one thing away from this chapter about hiring, I hope it’s this: be kind.

If you’ve interviewed before, you know how much energy and anxiety is driven by the interviewing process, from pre-interview nerves to anxiously awaiting to hear whether you’re moving forward. As an interviewer, you benefit from an incredible amount of asymmetrical power. You are, after all, driving a decision that can permanently alter someone’s career and future.

So, when you’re interviewing, make it your priority to review a candidate’s materials. Read your recruiter’s notes (if you have one). Take the time to write questions that will give you the most information about whether they’ll succeed in their role. Be on time and prepared to be in the interview and nowhere else. Lastly, express gratitude for their consideration.

Role of Rubrics

The goal of hiring is to gain as much objective information about how successful someone will be in a role based on their experience doing similar work in similar contexts. Without this direct experience, discovering what frameworks they’d employ in certain situations can help determine how successful they can be. Ultimately, not everything can be known, and every hiring decision creates some risk.

Rubrics can help align hiring managers and hiring teams on what “similar work in similar contexts” looks like and what types of frameworks would help them be successful. Thanks to the wonderful UX Researchers I’ve worked with, whenever I ask an interview question, I try to model the potential responses to pressure-test the question and its effectiveness. This can be as simple as documenting what a poor answer looks like versus satisfactory or excellent.

Hiring Manager Screening

Once you have some alignment on the product team context, you’re prepared to start speaking to candidates on the phone or via video. Thirty minutes is generally the amount of time these screens require. My agenda is:

  1. Introduction to me, the interviewer, including my role, how long I’ve been with the company, and my current location
  2. Information about the role, the larger business, product, or team context, and the size of the organization
  3. Role-specific questions informed by the rubric
  4. 5 minutes minimum for any candidate questions or clarifications

Thirty minutes goes quickly, so this is an opportunity to assess the candidate’s experience, verbal communication, and storytelling skills and ensure they match their goals. These go well when you can review each role-specific question and have preliminary data on their experience working in similar contexts.

Keeping in mind the massive power disparity and physiological stress response, I like to let candidates settle in with an icebreaker that is highly effective in setting the tone of the conversation:

“What, to you, is good design?”

I will usually dig deeper using whatever they answered with. For example, if they respond, “Good design is simple,” I might ask why they feel like so many products are so complex. I will also ask for products or companies that exemplify their definition of good design to understand how they examine other products and designs.

Case studies

Case studies are a common and often contentious practice in design hiring. While they can provide valuable insights into a candidate’s abilities, they also come with challenges and potential drawbacks. This guide aims to strike a balance between gaining meaningful information about candidates and creating a positive, respectful candidate experience.

The Purpose of Case Studies

My approach to case studies is designed to assess:

  1. Storytelling ability
  2. Visual design skills
  3. Comfort in presenting and discussing their own work
  4. Understanding of different work contexts
  5. Collaboration and communication skills with cross-functional partners

Acknowledging Candidate Experience

We recognize that case studies can create anxiety and additional labor for candidates. To mitigate this:

Case Study Format

Our case study sessions follow this format:

  1. Personal Introduction (5 minutes)

    • Candidate shares about themselves, including interests outside of work.
    • This helps ease nerves and reminds us all that candidates are more than their professional personas.

  2. Design Philosophy (10minutes)

    • Candidate discusses their design process and philosophy.
    • They share a product they admire and suggest one thing they’d add to improve it, explaining their reasoning.

  3. Case Study Presentation (20-30 minutes)

    • Candidate presents their chosen case study.
    • They should focus on their role, decision-making process, and outcomes.

  4. Q&A (15 minutes)

    • Panel asks clarifying questions about the presented work.
    • Candidate has the opportunity to ask questions to the entire team.

Rubric for Case Studies

Use this rubric to assess candidates consistently across different interviewers and roles. Rate each area on a scale of 1-5, where 1 is “Needs Significant Improvement” and 5 is “Exceptional”.

  1. Storytelling and Communication

    • Clarity of presentation
    • Logical flow of information
    • Engagement with the audience

  2. Visual Design Skills

    • Quality of visual artifacts presented
    • Understanding of visual design principles
    • Appropriateness of design choices for the problem at hand

  3. Problem-Solving and Process

    • Clear articulation of the problem being solved
    • Logical approach to solving the problem
    • Consideration of constraints and trade-offs

  4. User-Centered Approach

    • Evidence of user research or consideration of user needs
    • Application of user insights in the design process
    • Ability to advocate for the user

  5. Cross-Functional Collaboration

    • Examples of working with other disciplines (e.g., product, engineering)
    • Understanding of technical constraints and business goals
    • Ability to communicate design decisions to non-designers

  6. Impact and Results

    • Clear articulation of the project’s impact
    • Quantitative or qualitative results, if available
    • Lessons learned and applied to future work

  7. Design Philosophy and Critical Thinking

    • Articulation of personal design philosophy
    • Thoughtful critique of admired product
    • Ability to suggest meaningful improvements

  8. Adaptability and Growth

    • Examples of overcoming challenges or setbacks
    • Openness to feedback and alternative viewpoints
    • Evidence of personal or professional growth through the project

Remember, this rubric is a guide, not a strict scorecard. Use it to structure your thoughts and ensure consistent evaluation across candidates, but also trust your instincts and consider the specific needs of your team and role. You can also share your rubric with candidates to make sure you’re seeing the right examples in their work history.

After the Case Study

Developing People

Goal setting

I have tried every form of goal setting, from OKRs to SMART to Scorecards. While goal setting should be in line with your company’s chosen framework, I have found that quarterly goals are the most successful and consistent way to track performance.

During the last week of the quarter, I spend about an hour with each direct report reviewing:

  1. Previous quarter’s goals and progress
  2. A narrative of the impact of hitting/missing their goals (they provide their view, and I offer mine)
  3. The next quarter’s goals

Shadowing

If you lead designers embedded in product development teams, you’ll balance empowering your team to solve problems and deliver while having a line of sight into their day-to-day work. Having the right level of visibility can help with growth planning and support; in instances of underperformance, it can set up better scaffolding and accountability.

The best way to calibrate this is to sit with product development teams for at least two weeks. Shadowing allows for fast feedback in the team context. The goals of shadowing are:

Shadowing starts with a conversation with your mentee or direct report, during which you create a contract outlining where you’ll focus during the shadowing period. Ideally, this is documented, and you agree on your focus. During the two weeks, you pair with your designer in team spaces and frequently meet to debrief and review feedback in real-time.

At the end of the two weeks, you’ll meet to review the self-assessment and strengths/areas for growth. You can then develop (or tweak) your growth plan for the coming months.

Skill Assessments

Skill assessments are a coaching tool for designers of all levels. They identify strengths and areas for improvement and help create growth plans and set intentional goals.

For UXers, here are some suggested skill areas:

The self-rating scale is defined from 0-5 and is derived from mastery scales:

This should match your org’s ladder or job descriptions, and you should regularly conduct “gap assessments” to align with your direct report on how they perceive their skills and any deltas you may recognize.

Growing Design Leaders

Why design leadership matters

There are a few skills I think of when thinking about great designers:

These are powerful skills honed through the trials of taking messy, complex problems and turning them into simple and elegant solutions. These skills make for fantastic leaders because we’re still serving the same user: people. Whether it be a team, an individual designer, a peer, or the CEO, the same toolkit matters. I’ve found creativity to be the ultimate superpower of design leaders, and their toolkit for expressing creativity is invaluable in leadership spaces.

I also philosophically believe that it’s design leadership, not leadership. A false binary exists where moving into management means you must somehow give up hands-on design work, but I believe this is an antipattern. By giving up hands-on design work, you’re giving up the ability to create and communicate design solutions.

About Me

Leaders with About Me documents always gave me pause until a direct report encouraged me to put my own spin on it (check out my about me). I now encourage other leaders to create an About Me to share with direct reports and peers.

I’ve created a quick questionnaire as a template for an about me.

Sharing the answers to these questions helps others understand your point of view, what you care about, and your whole person inside and outside of work. It can help to set expectations and build connections. An About Me isn’t a shortcut to developing deep relationships with others; it’s a starting point for future conversations and interactions.

I share my information publicly in interviews so future teammates know a little about me and what to expect, so I’ve adopted Google Slides. I’ve also adjusted my About Me often, adding and removing sections as I’ve grown and developed new perspectives.

Talking Points

See my blog post on the importance of shared comunications.

Communication Plans

Comms plans are one of the most important tools for executive communication and ensuring the right message gets delivered to the right people.

This includes:

Simplified Communications Plan Template

Initiative: [Name of Initiative]

Key Elements

Audience and Impact

Who (Audience) How Impacted Where They’ll Be Informed When They’ll Be Informed
[Group 1] [Impact] [Channel] [Date/Time]
[Group 2] [Impact] [Channel] [Date/Time]
[Group 3] [Impact] [Channel] [Date/Time]

Communication Cascade

Communicator Message Audience Channel Date/Time Status
[Name/Role] [Brief] [Group] [Email] [Date] [Sent/Pending]
[Name/Role] [Brief] [Group] [Meeting] [Date] [Sent/Pending]
[Name/Role] [Brief] [Group] [Slack] [Date] [Sent/Pending]
Collaboration Notes

[Use this space for leaders to align on messaging, discuss audience concerns, or note any important considerations]

Conversation Modeling

Conversation modeling is a technique I use to guide conversations that may be charged or contentious. The conversation model is essentially a question-and-answer tree, starting with an opening question and anticipating the other party’s response or answer. From there, the tree continues by modeling responses or questions to those responses until an agreement or goal is reached. Think of it like a flow chart for a conversation.

This works best for me in physical form, using sticky notes (two colors, one for my questions and another for anticipated responses). The simple modeling exercise can strengthen or defuse an argument and ensure you are prepared with resources or information that might help resolve tension when the stakes are high.

When conversations are spirited, the model is helpful when combatting physiological outposts and responses when fight or flight kicks in.

Here’s an example on Mermaid.js for a conversation model with a direct report that’s expecting a promotion. Figjam is a great tool for these as you can use sticky notes for questions/responses and move them around as needed.

Effective 1:1s with Homebases

Having a consistent time and agenda is critical to successful 1:1s. Asking your direct reports what makes 1:1s effective for them while sharing what you’re looking for from your time together is the best wayto ensure your time is well-spent. Homebases are a great tool for this.

A homebase is a hub for weekly notes, agendas, first 1:1 questions, weekly notes, and links to personnel docs such as goals, growth plans, and more.

There are two questions in every 1:1 that I ask:

What’s something that went great in the last week?

The goal of this question is to celebrate a minor or significant accomplishment in the last week and develop an expectation that your direct reports are comfortable speaking about their work and results; this can help overcome imposter syndrome, get recognition (especially in remote environments), and build confidence.

What are your 2-4 priorities for this week?

This question is meant to ensure alignment on the most important work. It’s a great way to set expectations and clarify priorities.

This should leave plenty of time for any other questions or topics that need to be discussed.

Brag Docs

Julia Evan’s blog post on Brag Docs is an excellent primer for why Brag Docs are essential, especially for remote teams. Opening a shared space with your direct report to list accomplishments and impact makes quarterly/yearly check-ins significantly more accessible and allows people to take ownership of their contributions.

I also set the expectation that I would place things in my direct report’s brag docs–praise received from peers, for example, would go into the brag doc.

The title “brag doc” causes some consternation related to the stigma around celebrating your accomplishments and owning your impact. Some alternatives might help: hype doc, atta boys, or go full corporate with “performance review self-assessment.”

Coming Soon

Benchmarking, Single Usability Metric, and quantitative to qualitative loops

Single Usability Metric

Quantitative to qualitative loops

Craft

Setting visions and strategy

Design as Strategy (not service)

Mastery of Tools (Figma)

Implementing research (and Researchers)

Collaboration

Speed

Implementing lofi

Co-design

Design systems