Developing Designers and Design Leaders

This guide covers tools and frameworks for growing designers at every level—from individual contributors developing their craft to leaders honing their communication and coaching skills.

Why Design Leadership Matters

There are a few skills I think of when thinking about great designers: creativity, deep understanding of human behavior, and 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 just 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.

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. I now encourage other leaders to create an About Me to share with direct reports and peers.

Template Questions

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.

1:1s and Homebases

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.

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?” This builds confidence through recognition, creates habits of sharing accomplishments, helps overcome imposter syndrome, documents wins for performance reviews, and celebrates progress—not just completion.

“What are your 2-4 priorities this week?” This ensures alignment on key work, surfaces potential blockers early, creates accountability, helps manage workload, and 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): See Goal Setting.

Making 1:1s Effective

Preparation: Set the agenda, follow up on previous action items, provide any async updates.

During the Meeting: Start with a 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. The “First 1:1 Questions” section contains initial meeting and onboarding notes, derived from the excellent Resilient Management.

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

Quarterly goals provide enough time to accomplish meaningful work while remaining agile to changing business needs. Most businesses operate on quarterly cycles, making it easier to align design goals with broader company objectives. 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.

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.

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, and business metrics.

Next Quarter Planning (20 minutes): Setting 3-5 concrete goals aligned with company objectives, team needs, individual growth areas, and career development plans.

Types of Goals to Include

Craft Goals: Improving specific design skills, mastering new tools or methodologies, developing expertise in particular areas (e.g., accessibility, animation).

Impact Goals: Shipping specific features or products, improving key metrics, implementing new design systems or patterns, conducting and applying user research.

Growth Goals: Mentoring others, speaking at conferences or writing articles, leading cross-functional initiatives, building influence across the organization.

Team Goals: Contributing to team processes, improving collaboration, supporting team culture, knowledge sharing.

Goal Writing Framework

For each goal, ensure it includes a clear definition of what specifically needs to be accomplished, success metrics for how progress will be measured, resources needed (tools, support, or training), dependencies on other teams or work that could impact success, and timeline with key milestones within the quarter.

Tips for Making Goals Effective

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.

Regular Check-ins: Build check-ins into regular 1:1s, address blockers early, celebrate incremental wins, adjust goals if business needs change significantly.

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.

Be Flexible: Allow for goal adjustment when priorities shift, keep some capacity for unexpected opportunities, balance ambitious targets with achievable outcomes.

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 a 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.

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.

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.

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.

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.

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.

Strategy and Communication skills relate 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.

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 - None: 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 alongside 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.

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 and 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.”

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.

Agentic Coaching

Agentic coaching leverages Large Language Models (LLMs) as complementary tools for designer growth and development. While they can’t replace human coaching entirely, LLMs can provide valuable support for self-reflection, goal setting, and skill development through their ability to offer feedback and structured guidance.

LLMs are highly available, have a consistent structure for self-reflection, allow for risk-free space to rehearse fierce conversations, and are excellent for developing skills. The ability to have an ongoing conversation with relevant context is a key advantage.

Remember: AI is not a replacement for human coaching, and AI-generated content has limitations. The value in implementing AI-assisted coaching is in the process and reflection, not generating “answers.”

LLMs can serve as powerful tools for performance documentation when provided with detailed context, taking some of the pain out of performance review cycles. Designers can leverage LLMs to synthesize their contributions into clear, impactful narratives. AI tools excel at identifying patterns across projects, translating design work into business impact, and structuring achievements for different audiences—whether that’s for quarterly check-ins, annual reviews, or brag docs. The key is consistent documentation: when designers regularly capture their work, metrics, and feedback, LLMs can help transform this raw information into compelling stories about growth, impact, and value creation.

Example Prompts

Goal Setting

You're a design career coach. I am a designer who is working on [specific skills]. 
Provide 3-5 SMART goals for the next quarter.

Variations:
- "... working on communication, strategy, and systems thinking"
- "... focusing on user research and interaction design"
- "... developing leadership and mentoring abilities"

Project Retro

I'd like to reflect on a recent design project. Here's the context:
- Project goal: [description]
- My role: [description]
- Outcomes: [description]
- Challenges: [description]

Please help me analyze:
1. What went well
2. What could have been improved
3. Key learnings
4. How to apply these insights in future projects

Skill Assessment

As a design coach, help me assess my current level in [skill area]. 
I'll describe my experience and capabilities, and I'd like you to:

1. Evaluate my current level (novice to expert)
2. Identify specific strengths
3. Highlight growth opportunities
4. Suggest next steps for improvement

Forming Feedback

I need to give feedback on another designer's work. Here's the situation:

[describe context and work]

Help me structure feedback that:
1. Is specific and actionable
2. Balances positive and constructive points
3. Encourages growth

Communicating with Stakeholders

Help me prepare for a challenging conversation about [topic].

Context:
- Stakeholder role: [description]
- Current situation: [description]
- Desired outcome: [description]

Please provide:
1. A conversation structure
2. Key talking points
3. Potential objections and responses
4. Success metrics

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:

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 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]

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.

An Example

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:

Create definition. Define aesthetic clearly and simply so there is shared understanding around what is meant.
Resolve the implied tension. Address the aesthetic/functionality dichotomy and reframe with the definition.
Set the limit. We have a reasonable definition that is within our grasp, and know when we will overreach.
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.

Tips for Effective Talking Points

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 ad-hoc 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

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

How to Create a Conversation Model

Start with your opening question or statement
Map out 2-3 likely responses from the other person
For each response, prepare your follow-up question or statement, supporting information you might need, and potential emotional reactions to address
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, and promotion discussions.

Sample Conversation Model

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

Table of Contents

Foundations