Introduction

Hi, I'm Nic Bertino. As I helped grow a design team from 18 to over 50, I took a lot of notes as we tried different approaches and faced different challenges. This includes navigating our transition to a remote (and then hybrid) environment during the pandemic. I was most recently Senior Director of User Experience at AppFolio, where our teams took the Inspired dual-track Agile approach to product development.

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, 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, focusing 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 helps you manage up, introduces new rituals to your team, and ultimately is a tool for better engagement with your work.

Design Allies

Design is hard, and leading design teams is a science. I hope this helps understand the challenges and opportunities of leading a design team.

Understanding Design Leadership

Design leadership is a multifaceted role that extends far beyond managing designers or overseeing the design process. This chapter breaks down the key responsibilities of design leadership into six fundamental areas. While the emphasis on each area may shift based on your organization's needs and maturity, these elements form the foundation of effective design leadership:

  • Vision: Setting clear direction for design's role in your organization's future
  • Strategy: Turning that vision into actionable plans and measurable outcomes
  • Culture: Creating an environment where great design and designers can thrive
  • Systems: Building the infrastructure that enables consistent, scalable design work
  • Teams and People: Developing the talent and relationships that drive success
  • Advocacy: Championing design's value and user needs across the organization

Your role might emphasize certain areas more than others depending on your organization's context, team size, and product maturity. The key is understanding how these pieces fit together so you can focus your efforts where they're most needed.

Vision

Design leaders set and communicate the future state of the product, taking words on one-pagers and Powerpoints and bringing them to life visually. They paint a picture of where design needs to go and why it matters, creating alignment between human goals and company objectives. This includes establishing design principles, quality standards, and the overall design philosophy that guides decision-making. Good vision work answers "where are we going?" and "what does good look like?"

These visions are brought to life through storyboards, lofi wireframes, physical prototypes, and other visual artifacts.

Strategy

While vision sets direction, strategy provides the framework for future actions. Design leaders develop plans that connect design work and usability to business outcomes, determine how to allocate resources, and establish how to measure success. They work closely with product and engineering leaders to ensure design strategy serves both user needs and business goals. Strategy answers "how will we get there?" and "what should we prioritize?"

Many frameworks exist to create strategies. I've found Good Strategy/Bad Strategy to be an effective and simple framework for small and large problem spaces. The framework is simple:

  1. Create a diagnosis. Define the nature of the challenge by reducing a complex problem to its simplest and most urgent form. In design, this can be a critical user challenge or pain point.
  2. Use guiding policies. Guiding policies provide guidance for overcoming the challenges you've identified in your diagnosis. In design, this is a set of principles that will inform your design approach.
  3. Create a set of coherent actions. The work to carry out the guiding policies and are a set of steps you'll take to overcome the challenge. This will help prioritize the right actions to solve the problem.

Sample Strategy

Let's say you're a designer working on a checkout flow which is underperforming, with high abandonment rates, confusion about shipping options, and low mobile conversion.

Diagnosis: Users who start checkout with high purchase intent are encountering enough friction to reconsider their decision.

Guiding Policies

We will focus on reducing cognitive load during checkout by making each step feel trustworthy. This means:

  1. Progressive disclosure of complexity
  2. Clear, immediate feedback on all actions
  3. Flexible paths that accommodate different user needs
  4. Recovery-focused error states

This approach explicitly chooses clarity over persuasion and trust over urgency. We will not:

  • Add promotional elements during checkout
  • Require account creation
  • Hide costs until final steps

Coherent Actions

Q2 2024: Foundation

Implement server-side validation to prevent failed submissions Add inline field validation with clear error recovery Create persistent cart summary that follows scroll Build mobile-first responsive layout Add progress indicator showing clear steps

Q3 2024: Payment Innovation

Integrate digital wallet options (Apple Pay, Google Pay) Implement address verification API Add card scanning capability for mobile Create payment method management system Build secure card storage solution

Q4 2024: Optimization

Launch guest checkout with post-purchase account creation Implement smart defaults based on user location Add order status tracking system Create post-purchase feedback loop Build A/B testing framework for ongoing optimization

Q1 2025: Personalization

Launch saved addresses and payment methods Add smart reordering based on purchase history Implement customized shipping recommendations Create logged-in user fast checkout Build purchase history integration

Creating Design Culture

Design leaders are architects of team culture. Their role is responsible for creating the environment where design thrives–the practice, the people, and the community.

Rituals and Practices

Culture becomes tangible through regular rituals that bring teams together and reinforce shared values. These are detailed more in the Rituals section.

Creative Exercises

Starting the week with design exercises, sharing inspiration, or collaborative sketching sessions helps teams stay creatively energized and connected. These lightweight activities build creative confidence and create natural opportunities for mentorship and knowledge sharing.

Team Celebrations

Regularly celebrating both big wins and small victories helps teams stay motivated and connected to their impact. This includes shipping celebrations, project retrospectives that highlight learnings, and recognition for strong collaboration or creative problem-solving.

Growth Opportunities

Creating formal and informal opportunities for learning keeps teams engaged and growing. This might include:

  • Lunch and learn sessions
  • Skill-sharing workshops
  • Conference attendance and speaking opportunities
  • Cross-functional collaboration projects
  • External mentor connections

Happy, healthy, and engaged

Healthy design culture requires sustainable working practices that prevent burnout and support long-term success:

Work-Life Balance

Leaders set expectations around working hours, meeting schedules, and response times that respect personal time and energy. This includes being explicit about when immediate responses aren't needed and modeling healthy boundaries.

Focus Time

Creative work requires uninterrupted time for deep thinking and exploration. Leaders protect this by establishing meeting-free blocks, managing interruptions, and creating clear priorities that allow teams to focus on what matters most.

Support Systems

Having clear support systems helps teams navigate challenges and stay healthy. This includes:

  • Regular check-ins about workload and wellbeing
  • Clear escalation paths for concerns
  • Access to mental health resources
  • Flexibility for personal needs
  • Recognition of life outside work

Remote and Hybrid Considerations

Creative energy and collaboration happens in-person, hybrid, and remotely:

Digital-First Practices

Creating inclusive experiences for remote team members through thoughtful meeting practices, digital collaboration tools, and asynchronous communication.

Connection Points

Building meaningful connections in distributed teams through regular virtual social time, occasional in-person gatherings, and structured opportunities for informal interaction.

Pulse Checks for Culture

Take an inventory of your team's rituals and practices. Are they well-attended? Are designers engaging with their peers? Do you have engagement surveys to get feedback from your team? Is the team forming new cultural norms and activities?

These are the kinds of questions that can help you identify gaps in your team's culture and opportunities for improvement.

Systems

Design leaders create, maintain, and evolve the systems that support design teams. While sometimes we think of systems as a collection of tools (or, simply, the design system), systems underpin all aspects of design work.

Tools

Design leaders ensure teams have the right tools, including:

  • Design systems
  • Design and prototyping tools (Figma, Sketch, etc.)
  • Documentation tools (Coda, Notion, etc.)
  • Research platforms (Analytics, UserTesting)
  • Collaboration and feedback tools (Slack, Miro)
  • Project management tools (Jira, Linear)
  • Asset management and version control

Processes

Design leaders establish clear, repeatable processes for:

  • Design reviews and critiques
  • Prioritization
  • Research planning and synthesis
  • Handoff and implementation
  • Quality
  • Knowledge sharing and documentation

Workflows

Design leaders create efficient workflows that:

  • Connect cross-functional partners effectively
  • Reduce friction in day-to-day work
  • Scale design impact across products
  • Enable consistent quality
  • Support rapid iteration
  • Facilitate clear communication

Support Systems

Design leaders build support structures that:

  • Guide career development
  • Enable skill growth
  • Provide mentorship opportunities
  • Foster knowledge sharing
  • Support team wellbeing
  • Enable continuous learning

Measurement

Design leaders implement systems to measure:

  • Design quality and consistency
  • Team efficiency and output
  • User satisfaction and impact
  • System adoption and effectiveness
  • Process health and bottlenecks
  • Resource utilization

Evolution

Design leaders ensure systems remain effective by:

  • Regularly assessing system health
  • Gathering feedback
  • Anticipating changing needs
  • Removing unnecessary complexity
  • Streamlining outdated processes
  • Introducing new capabilities thoughtfully

Teams and People

Design leaders develop teams that deliver impactful work while growing personally and professionally. While sometimes we focus solely on hiring and performance management, people leadership encompasses every aspect of how teams work together and develop over time.

This includes:

  • Team Structure: Organizational structure, team dynamics, and team-wide goals
  • Talent Development: Career frameworks, skill development, and growth opportunities
  • Performance Management: Feedback and coaching, goal setting, and performance reviews
  • Team Health: Monitoring workload and capacity, work-life balance, and team wellbeing
  • Hiring and Retention: Intentional and equitable hiring, onboarding, and retention strategies
  • Communication: Change management, delivering bad news, information sharing, and feedback channels
  • Culture Building: Creating shared practices, building traditions, and fostering creativity

Advocacy

Design leaders are champions of the design practice and the humans it serves. Being a design leader means advocating for design in all aspects of your organization, from hiring to product strategy to user research.

  • Building Design Influence: Connecting design decisions to business outcomes, quantifying impact through metrics, participating early in strategic planning, and demonstrating how design reduces risk while increasing efficiency.

  • Representing Users: Making user research accessible and actionable in strategic discussions, highlighting the costs of poor user experience, creating empathy through stories and demonstrations, and advocating for inclusive design practices.

  • Strategic Partnership: Contributing to product strategy and company-wide planning, connecting design solutions to business goals, building relationships with key stakeholders, and sharing industry insights and trends.

  • Education and Understanding: Making design thinking methods available to non-designers, creating shared vocabulary, demonstrating the value of user research through case studies, and making design processes transparent and accessible.

Effective design advocacy creates environments where good design is valued as a crucial driver of business success.

Rituals

Maintaining high standards with 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 crucial 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:

  • Strengthen the team's understanding of the problem to be solved
  • Ensure alignment with broader initiatives and potential integration with other products
  • Verify that the initial design direction maps to business goals and user needs

What to Review

  • Design concepts (scenarios, storyboards)
  • Preliminary navigation models and maps
  • Market and problem definition
  • Task analysis
  • Competitive evaluation

Key Questions

  • How does this concept achieve the business goals?
  • How did research help shape this concept?
  • How does this product integrate with other products?
  • What are the guiding principles that will drive the rest of the UI design?

2. Prototype Reviews

When: Mid-stage development

Purpose

  • Review interaction behaviors
  • Confirm utilization of interaction standards, best practice, and design system components
  • Ensure proper fit to the brand(s) and consistency with related products

What to Review

  • Wireframes and prototypes
  • Navigation flows with entry points
  • Task analysis and/or scenarios

Key Questions

  • How is the UI design solving key problems?
  • What interaction standards or best practices have been employed?
  • How is the interaction design consistent with the overall product experience?
  • Does this design require new components or patterns?

3. In-app Reviews

When: Late-stage development

Purpose

  • Ensure designs meet quality standards
  • Protect against usability or brand risk
  • See the product as our customers do

What to Review

  • End to end flows in-app
  • Icons, graphics, logos, artwork, emails, and other visual assets

Key Questions

  • How confident are we that this design will improve the user experience?
  • What risks or constraints are we working with? What are we leaving out right now?

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

  • Designer: Presents the design and explains rationale
  • Product Manager: Ensures alignment with product goals and user needs
  • Design Manager: Provides design oversight and guidance as a reviewer
  • Design System Representatives: Approves concept and UI design reviews
  • Optional Reviewers: May include Engineering and Product leads, UX researchers, and other stakeholders

Visual 15:5s: A visual and fun way to share progress across teams

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.

Creating Essential Journeymaps to align on core user problems

As needed

Goal: Align on a set of journeymaps that solve core needs for most 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 to improve your product

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

Frequency: Quarterly

Goal: Experience key workflows how 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 your product's 3-5 most critical user journeys.
  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.

Running retros to continuously improve design practices

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.

Critiques for fostering a collaborative and constructive environment

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

30 minutes, weekly

Goal: Inspire creativity, build team collaboration, and develop new skills through focused design exercises at the start of each week.

Format

  • 30 minute session per week
  • Large or small groups (3-5 people)
  • Facilitator for prompts and timing

Sample Prompts

Quick Exercises (10-15 min)

  • Create an icon
  • Redesign a UI
  • Explore a new Figma feature
  • Rapid wireframe exercise

Extended Projects (across sessions)

  • Create a design system component
  • Practice animation and microinteractions
  • End-to-end UI flows
  • Accessibility improvements

Collaborative Challenges

  • Pair design exercises
  • Team interface assembly

Process Guidelines

  1. Preparation

    • Facilitator prepares the prompt and any resources
    • The prompt is shared with the group at least 24 hours before

  2. Session Structure

    • 5min: Prompt explanation
    • 25min: Design time
    • (Optional) Share-out and feedback

  3. Follow-up

    • Archive exercises in shared spaces (Slack, Coda, etc)
    • Specifically call out new techniques and skills
    • Track skill development

How do know if it's effective

  1. Team participation and engagement
  2. Skill adoption and knowledge sharing
  3. Quality improvements

Product Teardowns to learn, challenge, and inspire

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:

  • App Clips in a restaurant point-of-sale app
  • A new AI digital assistant
  • The PlayStation 5 dual-sense controller

Inspiration Boards

Monthly

Goal: Creative people inspire creative people. Inspiration boards create a dedicated space for sharing creative influences, fostering team connection, and building a collective visual language.

Why Inspiration Boards Matter

Cultural Benefits

  • Builds psychological safety by sharing personal interests
  • Creates organic conversation starters
  • Helps remote teams feel more connected
  • Celebrates diversity of perspectives and influences

Design Benefits

  • Expands the team's visual vocabulary
  • Surfaces emerging trends and patterns
  • Creates a shared reference point for design discussions
  • Encourages looking outside the industry for solutions

Structure

Each month, we open a FigJam board and ask a simple question: "What's inspiring you?"

Each team member gets an dedicated area with the freedom to arrange content howerever they prefer. They can share notes or stories, and link to external content.

Anything goes: art, photography, music, family photos, or design inspiration. The goal is to create a space where everyone feels comfortable sharing their creative influences and fostering team connection.

Themed Areas

Design & UI/UX Art & Photography Music & Sound Nature & Travel Personal Projects Books & Articles Technology & Innovation

Participation

  • Make it voluntary but engaging
  • Lead by example with your own shares
  • Celebrate unique perspectives
  • Welcome non-design inspiration
  • Encourage messiness

Tools & Resources

  • FigJam or Miro for remote teams
  • Physical wall space for co-located teams
  • Shared bookmarking tools
  • Team Slack channel for ongoing sharing

Remember that inspiration boards are most effective when they're expressive. While structure helps facilitate sharing, the real value comes from creating a space where team members feel comfortable sharing what truly inspires them, design or not. This ritual helps teams see each other as whole people and builds the trust necessary for creative collaboration.

Hiring designers and scaling your team

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.

Resourcing Models

At any time, if you're given headcount, you should have a resourcing plan in place to determine how you'll resource and staff your team. As a design leader, you'll need to ensure your team shape matches the short and longterm goals of your organization. This starts with knowing how you'd allocate 1 or 10 new people at any time.

Resourcing Models

Experience Team Model

  • Ratio: 1:1 (Designer to Product Team)
  • Best for: Product development teams shipping customer-facing products
  • Key benefits:
    • Deep domain expertise development
    • Strong partnership with product and engineering
    • Clear ownership and accountability
    • Faster decision-making and iteration
  • Considerations:
    • May need additional support for platform/infrastructure teams
    • Requires strong design system to maintain consistency
    • Need mechanisms to share learnings across teams

Platform Team Model

  • Ratio: 1:5 (Designer to Platform Teams)
  • Best for: Infrastructure, API, and platform teams
  • Key benefits:
    • Efficient resource utilization
    • Consistent approach across platform teams
    • Shared learning and patterns
  • Considerations:
    • Need clear prioritization mechanisms
    • May require "office hours" or similar support models
    • Focus on developer experience and tooling

Agency Model

  • Ratio: 1:Many
  • Best for: Any team model where design workstreams are formed and handed back to development teams
  • Key benefits: Focus on delivery and speed.
  • Considerations: May not allow for discovery/dual-track, mercenaries instead of missionaries.

UX Research Team

  • Ratio: 1:10 (Researcher to Designers)
  • Structure Types:
    1. Centralized Model
      • Dedicated research team serving all product areas
      • Consistent methodology and tooling
      • Strong research practice development
    2. Embedded Model
      • Researchers assigned to specific product areas
      • Deep domain expertise
      • Closer alignment with product teams
    3. Hybrid Model
      • Core team for methodology and tooling
      • Embedded researchers for key product areas
      • Flexible resourcing for project needs

Research Focus Areas

  1. Design Research (Evaluative)

    • Works closely with product teams
    • Focuses on usability and design validation
    • Provides rapid feedback loops

  2. Foundational Research (Generative)

    • Explores future opportunities
    • Conducts market and user behavior studies
    • Informs product strategy and roadmap

  3. Research as a Service

    • Improving research practice within product development teams or models where everyone is a researcher

Design System Team

  • Ratio: 1:40 (Design System Designer to Product Designers)
  • Structure: Typically includes:
    • Visual Designer(s): Own aesthetic direction
    • Interaction Designer(s): Own component behavior
    • Frontend Developer(s): Implementation and maintenance
  • Key responsibilities:
    • Enable speed and consistency across multiple teams with shared assets and resources for designers and developers
    • Create, document, and evolve components and patterns
    • Support adoption across teams

Design Operations

  • Ratio: 1:12 (DesignOps to Designers)
  • Focus areas:
    • Process optimization
    • Tool management and governance
    • Resource planning and allocation
    • Budget management
    • Team health and engagement

Implementing a Service Layer

Design-as-a-Service Model

This approach helps teams without dedicated design resources while maintaining quality and consistency.

Key Components:

  1. Clear Request Process

    • Intake form or ticket system
    • Criteria for what constitutes a design request
    • SLA expectations

  2. Prioritization Framework

    • Impact assessment criteria
    • Urgency evaluation

  3. Delivery Models

    • Quick consultations
    • Project-based support
    • Office hours
    • Design reviews

Research-as-a-Service Model

Similar to design services, but focused on research support for teams without dedicated researchers.

Components:

  1. Research Request Framework

    • Study objectives and scope
    • Timeline and resource needs
    • Expected deliverables

  2. Research Methods Library

    • Templates for common studies
    • Self-service tools and guides
    • Best practices documentation

  3. Support Types

    • Research planning consultation
    • Methodology review
    • Data analysis support
    • Workshop facilitation

Making Resourcing Decisions

Key Questions to Consider

  1. What is the nature of the work?

    • Customer-facing vs. internal
    • Strategic vs. tactical
    • Ongoing vs. project-based
    • Research needs and timing

  2. What is the required expertise level?

    • Domain knowledge requirements
    • Technical complexity
    • Strategic importance
    • Research methodology expertise

  3. What are the collaboration needs?

    • Cross-functional dependencies
    • Geographic distribution
    • Communication requirements
    • Research and design integration

  4. What are the business constraints?

    • Budget limitations (fixed headcount vs contract)
    • Timeline requirements
    • Quality expectations
    • Research tool costs

Growing teams

As design teams grow, their resourcing needs evolve:

  • 1-30 designers: Focus on strong core team and basic processes
  • 31-50 designers: Introduce specialized roles and formal processes
  • 51-200 designers: Establish centers of excellence and shared services
  • 200+ designers: Complex matrix organization with multiple service layers

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 energy and consideration.

Rubrics

Hiring designers is one of the most consequential responsibilities of design leadership. While intuition plays a role, the goal is to gather objective information about a candidate's potential for success. This comes primarily from evaluating their experience with similar work in similar contexts, and when that's not available, understanding their problem-solving frameworks and approaches.

Why Rubrics Matter

Rubrics create consistency across interviewers and candidates while reducing (but not eliminating) the impact of unconscious bias. They help teams focus on relevant skills and experiences rather than arbitrary preferences or pattern matching.

A well-designed rubric transforms subjective impressions into measurable observations. Instead of vague feelings about a candidate being "not quite senior enough" or having "great potential," rubrics push us to identify specific behaviors and capabilities that indicate readiness for the role.

Crafting Effective Rubrics

Start by defining what success looks like in the role. For a senior product designer, this might include leading complex projects independently, mentoring associate designers, track record of launching products, and influencing product strategy. The rubric should reflect these key responsibilities through concrete, observable behaviors.

For each interview question or evaluation area, document three levels of responses:

Needs Development "I would solve this by making it look nicer" indicates a surface-level understanding of design's role in problem-solving. The candidate focuses solely on aesthetics without considering user needs or business context.

Meets Expectations "First, I'd validate the problem through user research and metrics. Then I'd explore solutions through rapid prototyping, getting feedback from users and stakeholders throughout the process." The candidate demonstrates a structured approach incorporating both user needs and business goals.

Exceeds Expectations "Based on my experience with similar challenges, I'd start by analyzing our metrics to size the opportunity. I'd then conduct targeted research to understand user pain points, while working with engineering to understand technical constraints. This would inform a design strategy that balances user needs, business goals, and technical feasibility." The candidate shows strategic thinking, draws from relevant experience, and considers multiple stakeholder perspectives.

Implementing Rubrics Effectively

Share the rubric with your entire hiring panel before beginning interviews. This ensures everyone understands what good looks like and helps calibrate expectations across different interviewers. Regular calibration sessions using real examples (anonymized) help maintain consistency over time.

Create space in your rubric for capturing specific examples and quotes. These concrete details prove invaluable during hiring discussions and help combat recency bias. They also provide excellent material for constructive feedback to candidates who aren't selected.

Remember that rubrics are guides, not checklists. A candidate might show exceptional ability in unexpected ways that your rubric didn't anticipate. Build in flexibility to capture these insights while maintaining the structure that makes rubrics valuable.

Learning and Iteration

Treat your rubrics as living documents. After each hiring cycle, gather feedback from interviewers about questions that worked well or needed clarity. Look for patterns in candidate responses that might suggest adjustments to your evaluation criteria.

Work closely with your recruiting partners and UX researchers to refine your approach. Researchers bring valuable expertise in structured evaluation and reducing bias. Recruiters can help identify which criteria might unnecessarily limit your candidate pool.

Beyond Individual Interviews

Extend your rubric thinking to other aspects of the hiring process, including other activities like case studies. This comprehensive approach helps ensure you're evaluating candidates fairly at every stage.

Consider sharing portions of your rubric with candidates, particularly for case studies. This transparency helps candidates understand your expectations and prepare effectively, leading to better signal in your evaluation process.

The ultimate goal isn't perfect prediction of success—some uncertainty is inevitable in hiring. Instead, rubrics help you make more informed decisions based on relevant evidence rather than implicit bias or incomplete evaluation. When used thoughtfully, they make your hiring process fairer, more consistent, and more likely to identify candidates who will thrive on your team.

Remember that rubrics serve your evaluation process; they shouldn't constrain it. The best rubrics create structure while leaving room for the human elements of hiring—the spark of potential, the unexpected strength, or the unique perspective that could transform your team.

Phone screens

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: An imperfect but better approach to portfolio presentations

Credit: The UX leadership team at AppFolio brought this to life - specifically Carlisle Sargent with visualizing this early on and helping us find a format that works across design, leadership, and research.

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 balances 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:

  • No free work or labor that a candidate can't reuse.
  • We structure the case study session to allow candidates to showcase their personality and design philosophy, not just their work.
  • We involve cross-functional partners to give candidates a realistic preview of the collaborative environment they'll be working in.

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 ensure you see the right examples in their work history.

After the Case Study

  • Provide timely feedback to candidates, whether moving forward or not.
  • If not moving forward, offer constructive feedback that the candidate can apply in future interviews.

Developing People

Use Homebases for Better 1:1s

Regular one-on-one meetings are crucial touchpoints between design leaders and their teams. While the format may vary, having a consistent structure and shared space—what I've called a homebase—helps make these conversations more effective and meaningful.

What is a Homebase?

Credit: Elizabeth Kang for the original Homebase template we used, developed in Coda.

A homebase is a dedicated space that serves as the single source of truth for your relationship with each direct report. It includes:

Essential Documentation

  • Meeting agendas and notes
  • Career development plans
  • Quarterly and annual goals
  • Growth areas and progress
  • Wins, accomplishments, and brag docs
  • Project updates and challenges
  • Preferences and working styles

Regular Check-in Structure

  • Weekly priorities and progress
  • Wellbeing check-ins
  • Feedback and support
  • Blockers and needs

Types of 1:1 Conversations

Weekly Check-ins (30-45 minutes)

Two essential questions form the foundation:

"What's something that went great last week?"

  • Builds confidence through recognition
  • Creates habits of sharing accomplishments
  • Helps overcome imposter syndrome
  • Documents wins for performance reviews
  • Celebrates progress, not just completion

"What are your 2-4 priorities this week?"

  • Ensures alignment on key work
  • Surfaces potential blockers early
  • Creates accountability
  • Helps manage workload
  • Identifies needed support

Monthly Development Discussions (60 minutes)

  • Review progress on goals, growth plans, skill assessments, and other action plans

Quarterly Goals Reviews (60 minutes)

Making 1:1s Effective

Preparation

  • Set the agenda
  • Follow up on previous action items
  • Provide any async updates

During the Meeting

  • Start with wellbeing check (we cringingly called this "the vibe check")
  • Focus on the person, not just the work
  • Listen more than you speak
  • Take clear notes in the homebase
  • Set specific next steps

Follow-up

  • Update notes
  • Close out any open action items or questions

Homebase Structure

├── About this Homebase
├── First 1:1 Questions
├── Weekly Notes
│   └── Meeting Notes [by date]
├── Growth and Performance
│   ├── Goals
│   ├── Skill Assessment
│   └── Quarterly Check-ins
├── Resources and Templates
│   ├── Agenda Template
│   ├── Brag Doc Template
│   ├── Quarterly Check-in Template
│   └── Continuing Education Resources

This structure keeps everything organized and accessible:

  • About: Overview and how to use this space
  • First 1:1 Questions: Initial meeting and onboarding notes, derived from the excellent Resilient Management.
  • Weekly Notes: Ongoing meeting documentation
  • Growth and Performance: Development plans and progress
  • Resources: Templates and references for key activities - these may be provided by your HR team.

Be sure not to over-design the homebase. Work with your direct reports to adapt it to what works best for them.

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.

Why Quarterly Goals Work Best

  1. Just the right amount of time: Quarterly goals provide enough time to accomplish meaningful work while remaining agile to changing business needs
  2. Natural Alignment: Most businesses operate on quarterly cycles, making it easier to align design goals with broader company objectives
  3. Regular Check-ins: The cadence allows for meaningful progress tracking without becoming overwhelming

Structure of Quarterly Goal Sessions

During the last week of the quarter, I spend about an hour with each direct report in a dedicated goal-setting session. Here's the recommended format:

  1. Review Previous Quarter (20 minutes)

    • Assessment of progress on each goal
    • Discussion of what worked and what didn't
    • Identification of patterns in successful goal completion
    • Review of unexpected challenges or pivots, as well as any new opportunities arising during the quarter

  2. Impact Discussion (20 minutes)

    • Designer's self-assessment of their impact
    • Leader's perspective on impact and growth
    • Discussion of how completed goals influenced:
      • Team success
      • Product outcomes
      • Personal growth
      • Business metrics

  3. Next Quarter Planning (20 minutes)

    • Setting 3-5 concrete goals aligned with:
      • Company objectives
      • Team needs
      • Individual growth areas
      • Career development plans

Types of Goals to Include

Balance your team's quarterly goals across these categories:

  1. Craft Goals

    • Improving specific design skills
    • Mastering new tools or methodologies
    • Developing expertise in particular areas (e.g., accessibility, animation)

  2. Impact Goals

    • Shipping specific features or products
    • Improving key metrics
    • Implementing new design systems or patterns
    • Conducting and applying user research

  3. Growth Goals

Anything related to career development or personal growth, including:

  • Mentoring others
  • Speaking at conferences or writing articles
  • Leading cross-functional initiatives
  • Building influence across the organization
  1. Team Goals
    • Contributing to team processes
    • Improving collaboration
    • Supporting team culture
    • Knowledge sharing

Goal Writing Framework

For each goal, ensure it includes:

  1. Clear Definition: What specifically needs to be accomplished
  2. Success Metrics: How progress will be measured
  3. Resources Needed: Tools, support, or training required
  4. Dependencies: Other teams or work that could impact success
  5. Timeline: Key milestones within the quarter

Tips for Making Goals Effective

  1. Document Everything

    • Keep written records of goals and progress in a shared space like a 1:1 homebase
    • Track changes and adjustments throughout the quarter

  2. Regular Check-ins

    • Build check-ins into regular 1:1s (again, use that homebase)
    • Address blockers early
    • Celebrate incremental wins
    • Adjust goals if business needs change significantly

  3. Connect to Career Growth

    • Align quarterly goals with longer-term career aspirations
    • Use goals to build portfolio-worthy projects
    • Create opportunities for visibility and impact

  4. Be Flexible

    • Allow for goal adjustment when priorities shift
    • Keep some capacity for unexpected opportunities
    • Balance ambitious targets with achievable outcomes

Providing situational support with 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:

  • Increase skills and knowledge in 2-4 areas (see Skill Assessments)
  • Provide timely support in the team context
  • Set growth goals for the near term to continue improving skills and building on existing strengths.

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 serve as a coaching tool for designers at every stage of their career. Through structured evaluation and discussion, these assessments create clarity around current capabilities and future growth opportunities. They provide starting point for career conversations and help both managers and designers align on development priorities.

The Assessment Framework

The assessment framework measures competency across seven core areas of design.

  1. User Research sits at the foundation, focusing on both qualitative and quantitative methodologies. This includes everything from conducting user interviews and usability studies to analyzing metrics and creating research plans. A designer's mastery in this area directly impacts their ability to make informed design decisions.

  2. Context and mental models form the second pillar, encompassing how users interact with interfaces across different devices and situations. This includes deep knowledge of information architecture, understanding of various user contexts (mobile, desktop, assistive technologies), and ability to design for different user states and scenarios.

  3. Interaction design centers on the dynamic aspects of user interfaces. Designers with this strength excel at designing for state changes, status indicators, and progress communication. They create interfaces that feel natural and intuitive by aligning with users' mental models and maintaining consistency across application components.

  4. Aesthetic covers the visual craft of design. This includes mastery of UI best practices, typography, visual hierarchy, and use of space. Strong aesthetic sense manifests in designs that are both beautiful and functional, where every visual element serves a purpose.

  5. Prototyping skills reflect a designer's ability to bring ideas to life quickly and effectively. Beyond tool proficiency in platforms like Figma, this area measures how well designers can communicate concepts through appropriate fidelity levels and create interactive experiences that demonstrate their design intent.

  6. Strategy and communication skills are related to long-term vision and collaboration. This encompasses storytelling, writing clear UX copy, managing stakeholder relationships, and articulating design decisions. Strong strategic thinkers can plan and execute design work that aligns with 1-3 year product horizons.

  7. Leadership rounds out the framework, focusing on vision-setting, people development, and organizational influence. This includes hiring, mentoring, conflict resolution, and the ability to drive design culture across teams.

Assessing Mastery

The assessment uses a 0-5 scale that maps to clear mastery levels:

  • 0 - I don't understand this competence, or it is non-existent
  • 1 - Novice: I have a basic understanding of this competence
  • 2 - Intermediate: I can demonstrate this competence with help or supervision
  • 3 - Competent: I can demonstrate this competence independently
  • 4 - Proficient: I can supervise other people in this competence
  • 5 - Expert: I develop new ways of applying this competence

This scale allows for nuanced discussion about growth. A designer might be proficient (level 4) in interaction design but intermediate (level 2) in research methodologies. These variations help identify focused areas for development and celebrate existing strengths.

Implementation Strategy

Effective skill assessments begin with self-evaluation. Ask designers to rate themselves across each competency, providing specific examples to support their ratings. This creates a foundation for meaningful discussion about their perceived strengths and areas for growth.

As a manager, conduct your own evaluation before meeting. Document specific examples that support your ratings, focusing on observable behaviors and outcomes rather than subjective impressions. This preparation ensures feedback is specific and actionable.

During the assessment discussion, focus on areas of alignment and difference. Where ratings differ significantly, explore the reasons why. Often, these discussions reveal important insights about job expectations or assessment criteria that benefit both manager and designer.

Use the assessment outcomes to create targeted development plans, focusing on 2-3 areas for short-term improvement. While it is important to work on gaps, ensure you're also focusing on strengths.

Integration with Career Development

The skill assessment framework should align closely with your organization's career ladder and job level descriptions. Regular gap analyses help ensure designers are growing in ways that support both their personal career goals and organizational needs.

Consider conducting formal assessments quarterly, with informal check-ins with other goal conversations. This cadence allows enough time for meaningful progress while maintaining momentum. Document each assessment to track growth over time and identify patterns in development.

Remember that the goal isn't perfect scores across all dimensions, but rather intentional growth in areas that matter most to the designer's career aspirations and your team's needs. Use the framework as a guide while remaining flexible to individual circumstances and opportunities.

Growing Design Leaders

Why design leadership matters

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

  • Creativity
  • Deep understanding of human behavior
  • Storytelling

These powerful skills are honed through the trials of taking messy, complex problems and turning them into simple, elegant solutions. These skills make for fantastic leaders because we still serve 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.

1:1s with People Leaders

Many of the same principles from effective 1:1s apply to 1:1s with people leaders.

A few key additions to leader 1:1s:

  • I always schedule 45 minutes. This generally gives us the whole hour if needed, which is helpful especially for senior people leaders.
  • We always have a "how's your team doing?" question for line-of-sight and tactical support if needed.

Writing a leader 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.

  • Who are you?

    • Who's your supporting cast?
    • Where can we find you outside of the 9-5?
    • What was your path? What's the weirdest job you've ever had?
    • What's your art?
    • What's the day-to-day of your role?

  • Principles

    • What's important to you in design? What is good design? What's your favorite design principle or design pet peeve?
    • What's important to you as a leader? How do you define your leadership philosophy or identity?
    • What's important to you as a creative leader?
    • What's your BICEPS letter?

  • What can I, the reader, expect?

    • What's the best way to engage you? What are your preferred communication norms? How do you like to receive feedback?
    • What makes a good 1:1?

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.

You need a communication plan

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:

  • A document that outlines the communication plan where leaders can collaborate and align on messaging and audience.
  • The who, what, when, where, and why: what are the key elements of the communication and why, who is impacted, where will each impacted person find out, and when will they be informed?
  • A table that shows the cascade of communications: who is responsible for communicating what message, and when? Who has been informed, and who needs to be informed?

Simplified Communications Plan Template

Initiative: [Name of Initiative]

Key Elements

  • What: [Brief description of the key message or change]
  • Why: [Reason for the communication or change]

Audience and Impact

Who (Audience)How ImpactedWhere They'll Be InformedWhen They'll Be Informed
[Group 1][Impact][Channel][Date/Time]
[Group 2][Impact][Channel][Date/Time]
[Group 3][Impact][Channel][Date/Time]

Communication Cascade

CommunicatorMessageAudienceChannelDate/TimeStatus
[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]

Talking Points

Ad-hoc communications can be painful. Memory is unreliable, and as humans, we need as many shortcuts as we can get to reduce the amount of thinking (and spontaneous speech) we have to do, especially when we're on the spot with large audiences. Developing a communication framework to share with leaders brings consistency and clarity to messaging. It creates a unified front when presenting information and making decisions, fostering trust and credibility with teams and stakeholders. It also gives other leaders a foundation to craft their own messages, avoiding misunderstandings while creating shared ownership of the messaging.

During a team townhall, I was asked about the role of aesthetic in design and how we can balance aesthetic with functionality. Our team recently declared our intention to elevate the aesthetic of our product, and with it, some questions came up around what that means from a day-to-day product development practice. I began crafting a bulleted answer:

  • Aesthetic means we are focusing on harmony, symmetry, hierarchy, order, and rhythm in our designs. We use design to make complex interfaces feel less heavy.
  • Aesthetic and functionality do not have to be at odds: the humans we are designing for deserve a beautifully functional experience.
  • We do not aspire to be decorative or vogue, and we stand by our principles for good visual design.
  • Our product is chaotic and stressful because we've tolerated an unfocused and distracting experience. Until now.

I try to be as clear and definitive (read: not handwavy or overly broad) in communications as possible. In async and sync communications, I try to develop as many supporting points as is necessary to balance conciseness and clarity, and outlining is something I now do automatically. In the previous example, I wanted to guide the answer through a few key messages:

  1. Create definition. Define aesthetic clearly and simply so there is shared understanding around what is meant.
  2. Resolve the implied tension. Address the aesthetic/functionality dichotomy and reframe with the definition.
  3. Set the limit. We have a reasonable definition that is within our grasp, and know when we will overreach.
  4. Status quo. Where are we now and how did we get here?

While I've crafted these short notes, there is great power in socializing with other leaders and key stakeholders across the organization. Collaborating with others builds a shared responsibility for the communication, building cohesion in the messaging. I started practicing sharing many of my notes with others (especially senior leaders within my organization) so we have an FAQ-style approach to communications that helps create a shared narrative. Other leaders can then rebound off of the key points and cascade communications to their audience in a way that fits their personal style.

Some tips I wish someone told me:

  • Don't YOLO talking points. Share frameworks and talking points early and often.
  • Encourage collaboration. Create shared ownership of messaging and unification.
  • Follow up on ad-hoc answers. If you are giving ad-hoc comms, make sure to follow up with leaders and key stakeholders on your talking points.
  • Definition helps, but leave room for style. There are key definitions to have shared alignment on, but let leaders craft messages that work for their style or audience that can support shared goals and outcomes. Don't be overly definitive or scripted.

As I write this, it seems painfully obvious that this is a good practice. Communication plans have saved me from myself many times in my leadership career, and I'm a big proponent of not YOLOing the comms plan. In addition to having talking points crafted for different audiences, comms plans usually have a cascading element which doesn't apply for adhoc questions or rollouts of larger initiatives. These communication frameworks and shared artifacts are extremely helpful for executing communications across multiple speakers and audiences.

Conversation Modeling

Conversation modeling (sometimes called conversation mapping or dialog planning) is a helpful activity for navigating potentially challenging discussions, particularly around sensitive topics like performance, promotions, or organizational changes.

What It Is:

  • A structured approach to mapping out how a conversation might unfold
  • A question-and-answer tree that starts with an opening question and branches based on anticipated responses
  • A tool for preparing thoughtful, empathetic responses to different scenarios
  • A method for staying focused when emotions run high

Key Benefits:

  1. Reduces anxiety by helping you prepare for multiple scenarios
  2. Ensures you talking points ready for different conversation paths
  3. Helps maintain calm during difficult discussions
  4. Allows you to anticipate potential pitfalls or triggers before they arise
  5. Creates space for empathy by forcing you to deeply consider the other person's perspective

How to Create a Conversation Model:

  1. Start with your opening question or statement
  2. Map out 2-3 likely responses from the other person
  3. For each response, prepare:
    • Your follow-up question or statement
    • Supporting information you might need
    • Potential emotional reactions to address
  4. Continue branching until you reach logical conclusions, including your desired conclusion

Best Practices:

  • Use different colors for your questions versus anticipated responses
  • Include "pivot points" where you might need to redirect the conversation
  • Note specific examples or data you'll need for each path
  • Include reminders about emotional regulation (e.g., "pause here if needed")
  • Remember it's a guide, not a script
  • Practice with a trusted colleague

Tools:

  • Physical: Sticky notes on a wall (two colors)
  • Digital: FigJam, Miro, or similar collaborative tools

This technique is helpful for any conversation, but it is particularly valuable for:

  • Performance feedback
  • Conflict resolution
  • Salary negotiations
  • Promotion discussions

Sample Conversation Model

Here's an example on Mermaid.js for a conversation model with a direct report that's expecting a promotion.

Brag Docs

Julia Evans' 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."