Designy

Designing on Purpose—Getting UX Feedback That’s Actionable

Darrell Estabrook

Principle UX Product Designer & Founder at Designy

Design leadership starts with asking the right questions to get the right answers.

Unlock the mystery of getting design-strengthening feedback

You’ll be able to field ”I don’t like it” comments with ease, no matter who says it, and guide them to dig deeper.

Turn endless meetings into objective feedback and buy-in

You’ll be able to focus any size group to contribute: whether it’s a design team, product team, stakeholders, or users.

Conduct (and even teach) your team to think on purpose

You’ll be able to conduct your first design review meeting with actionable feedback today, tomorrow, or later this week.

Start using this core process  immediately

At Airbnb, I experienced the magic that happens when business leaders truly understand Design. What if your stakeholders understood the value of design and empowered you to do the best work of your career? Describing the ROI of Design gives you tools to break through to business leaders. Through frameworks, lessons, and tactics taught in top business schools, you will develop the skills to articulate and demonstrate the value of your work in a way that resonates with non-designers across all levels of your organization. As one design leader put it: "The way I talk since your course has completely changed and I’m being heard by everyone! I’m a little bit pleased about winning arguments and creating visibility and understanding of all the awesome work my team and I are doing." If you want more room to do great work, want leaders to listen to your design rationale, want to be more involved in the product development process, or want to drive more impact as a designer in your organization, this course is for you.

Learn business school tactics to gain influence & drive impactful design work

Course syllabus

2x live sessions introduce actionable tactics and frameworks.

Live sessions

Optional Q&amp;A session immediately after class while lessons are fresh

Post-session Q&A

Optional exercises, lessons, and resources to expand your learning

Self-paced exercises

Course schedule

Experienced UX designers who want to unlock more strategic and impactful product design work for themselves and others

Design leaders &amp; managers who must collaborate with and persuade founders, executives, and other cross-functional leaders

Designers who work in Product or Eng-led environments where good Design must be strongly (and carefully) advocated for

Designers interested in business, but don't want to take on the huge cost of business school to learn key skills

Who this course is for

What you will get out of this course

Through five proprietary frameworks developed by Ryan from his experience getting C-suite execs bought into major initiatives, expand how you think about the business value of your work so you can effectively communicate it to others

A new business perspective on your design work’s value

Lectures pull the most valuable lessons from 11 MBA courses—including Entrepreneurship, Statistics, Finance, Negotiation, Marketing, Economics &amp; more—to help you speak the same language as business stakeholders.

A communication style that resonates with business leaders

Through exercises and Q&amp;A, get feedback, advice, and tactics from Ryan to ensure course content is immediately applicable to your specific situation

Personalized 1:1 guidance

The course attracts Senior Product Designers to VPs of Design. Through small, live cohorts, get feedback and advice from fellow designers from around the world

Access to an engaged group of international expert designers

Can't make every live session? Never miss a beat with recordings sent immediately after each lesson. With lifetime access, refer back to every framework, tactic, and "ah-ha" moment for the rest of your career.

Lifetime access to recordings from every session

Articulate & demonstrate the value of your Design work in a way that business stakeholders understand, appreciate, and reward.

Ryan Scott

Learn business from a designer with real-world business expertise

August 2025

September 2025

Product, UX &amp; Content Design folks seeking to grow and enhance their leadership practice, welcome home! This course, community and live coaching sessions are your guide to stepping into the Leader you aspire to be. Leading teams is a "what got you here" (craft, leading the work) "won't get you there" (leading through others, business results, visionary leadership) moment for many – especially as you scale. It's my mission to demystify what is needed to be seen as a business leader and be known for excellence in craft AND in leadership. From imposter syndrome → confidenceFrom overwhelmed → organized focusFrom tactical work → strategic influenceFrom feeling stuck → career plan Shift from feeling isolated and overwhelmed, to feeling confident and centered in this supportive environment led by sought after coach Alison Gretz. The course lasts 8 weeks, with one self-paced module and a live cohort call weekly. We'll will dig into the 4 common sticking points that hold Design Leaders back as they step up to management and then evolve to Director+. It's by building key muscles and overcoming these sticking points, while also grounding in your own authentic leadership style that will further you as a leader.

Unblock your Growth in Design Leadership

You can go at your own pace and jump into topics that are most relevant to your growth ahead of the cohort.

Self-paced videos & workbook

Each week, Alison will host a live cohort coaching call where we'll dig into REAL WORLD scenarios and transformation.

Weekly Group Coaching

Alison will host an intimate community where we can tackle more Q&amp;A, weekly AMA topics, and peer mentorship.

Community Q&A

Flexible Course schedule

I'm ready to scale up to Director, but I'm feeling stuck and blocked from receiving the opportunities to promote up. How do I grow?

I'm a Director of Content Design, but I'm feeling out of my depth and need to up-level my soft skills expertise.

I want to lead in Design with authenticity and impact – is this possible while still being a respected boss?

I'm struggling with imposter syndrome, and my tough stakeholder relationships are causing burnout.

Does this sound familiar?

Walk away with the soft skills needed to grow in Design Leadership

Direct and frequent access to accredited coach + executive Design Leader Alison Gretz alongside a supportive peer group.

Coaching and advice on your leadership journey

Learn about common pitfalls to avoid, in a space where you can ask questions and identify key blockers or bumps that are in your way.

Ability to overcome the top 4 pitfalls of design leadership

Define and explore how you will show up as a human-centered leader.

Leading in alignment to your values

Each week, Alison will share a value-packed workbook and video/audio recording. Since you get life-time access, many students utilize our frameworks for months and years!

Expand your Toolkit with Workbooks, Frameworks & Tools

You'll leave the course with a clear path forward, broken down into actionable steps.

Design Your Next roadmapping and goals

Rise in your Design Career: Build your confidence & skills, then create your path from craft leader to business leader.

Alison Gretz

Cohort 8

Cohort 10

You're talented. Your designs solve real problems. So why does leadership treat you like the "Figma person"? Because you're not translating your design work into terms your business understands. Your stakeholders don't see the connection between your thoughtful design decisions and the business outcomes they care about. When you present user research findings, they're trying to figure out how to make multi-million dollar decisions around it. When you present design recommendations, they want to know why it's worth the time and resources. It's not that your design work doesn't create business value. It's that you're not measuring and communicating that value in terms your audience understands. Without this ability:You'll stay excluded from strategic decisions: You'll watch as others make bad user decisions while you're forced to execute on bad ideas.Your best ideas will get dismissed: Because stakeholders don't see the business impact until it's too lateYou'll remain the "Figma person": When you're seen as tactical rather than strategic, you get treated (and paid) like a commodityYour expertise gets undervalued: As leadership questions the ROI of design work and whether you can be replaced by AI The solution isn't working harder. It's learning to work with the data your business already has. Every other department leader collects data to measure progress, quantify outcomes, and justify their value. That's how they're seen as a strategic partner instead of a commodity. Why not you? As multiple Design Leaders have told me, "The difference between okay and great designers is that great ones bring data and a package that helps sell the idea they've created." This course is how you create that package. When you master Data-Informed Design, you'll:Get invited to strategy meetings: because you bring measurable insights about how design impacts business outcomesGain immediate credibility: Using data from tools your company already has to generate actionable business insightsBecome a strategic partner: by proving your designs drive business results with rapid hypothesis validationEarn the recognition you deserve: as someone who understands both design and business, and can leverage AI to communicate value at the speed leadership expects You don't need an MBA or advanced analytics training. You need a systematic framework to measure design impact, validate your hypotheses from multiple stakeholder perspectives, and translate it all into compelling business narratives. This 4-week program transforms overlooked designers into data-informed strategic partners:Week 1: Align design with Product Goals and Track the Value of Design WorkWeek 2: Define the current problem that matters to audiences, and turn it into a Data VisualizationWeek 3: Validate your proposed Design Solution from UX and PM perspectives using AI Week 4: Package everything into persuasive 5-minute business presentations Limited to 15 students for personalized 1:1 coaching. ﻿Training Your Team? Email kai@datainformeddesign.online for bulk pricing and personalized cohorts.

Tired of your design work being seen as just 'making things pretty'?

I will have live lectures with Q&amp;A, reviewing this week's lessons. These will also be where I review student's exercise and provide live feedback

Mondays and Thursday

In these lectures, I'll dive into the specifics around Data, Narrative, Visuals, and more. This will be a more detailed videos on the stuff I cover live on Mondays and Fridays

Pre-recorded lectures

These exercises, paired with the lecture, will help you practice the concepts you learn from lectures

Weekly projects and exercises

Designers who want to use data to bypass office politics and prove their value immediately

Designers tired of watching 'strategic' roles like PMs get promoted while their insights are ignored

Designers in low-UX maturity environments where relationship-building isn't enough

Mid-level designers whose great ideas get dismissed by skeptical executives

Who is this course for

What you'll walk away with 

Have clear frameworks to immediately show your design impact in meetings, presentations, performance reviews, and interviews.

Data-Informed frameworks that make even skeptical stakeholders approve your designs

Stop talking in hypotheticals and opinions. Show experiments that prove your design value in business outcomes

ROI experiments that prove your design value in business outcomes, not opinions

Not sure how to talk about your design work in an effective way? You'll get templates that provide you with step-by-step instructions

Templates to turn any design project into a compelling business case study

Not sure what to say when talking with decision-makers or executives? You'll get scripts to help you in crucial situations

Scripts to present user research that gets immediate executive buy-in

You won't just learn theoretical concepts. You'll learn how to apply it to your work with 1:1 coaching with a Data-Informed Design expert.

60 minutes of 1:1 Data-Informed Design coaching

Stop being the 'Figma person.' Learn to measure design impact, translate design into business value, and become a strategic partner.

Christopher Kai Wong

Top Design Writer on Medium (325+ design articles). Data-Informed Design Expert.

Private Cohort

September Cohort

But most teams are still designing like it’s 2015. AI is transforming industries and changing the very foundation of how products work. Companies are moving fast to integrate large language models, agents, and adaptive systems into their products. But as model complexity grows, the user experience often gets left behind. Powerful algorithms can now predict, generate, and decide but without thoughtful design, they often confuse users, introduce risk, or fail to earn trust. The challenge? Designing for AI isn’t like designing for traditional software. It’s not just about usability or polish anymore. It’s about system behavior, adaptation, and collaboration between humans and machines. If you’ve ever launched an AI feature only to see users abandon it because they didn’t understand what it was doing or if you’ve been asked to “design the AI experience” but weren’t sure where to begin → this course is for you. The Role of the Designer Is ChangingUntil recently, designers focused on interfaces and flows. Today, the frontier is different. OpenAI recently posted a job for a Model Designer, a new kind of design role focused on shaping how models behave. And it signals a broader shift across the industry: Designers aren’t just styling outputs anymore. They’re architecting how intelligent systems learn, adapt, and interact. In AI-powered products, design happens upstream, at the level of:- Data inputs and how users shape them- Model decisions and how they’re surfaced or corrected- Feedback loops that guide learning- System behavior that evolves over time To adapt to this new environment, designers must understand how models work, not to become ML engineers, but to ensure what the system learns, shows, or hides aligns with human expectations and values. Real Challenges This Course Prepares You For You launch an AI-powered feature and maybe it recommends content, summarizes input, or automates a task. But users are confused or drop off quickly. They can’t tell why the AI did what it did, or how to influence it. The model works, technically. The experience doesn’t.→ Learn to design transparency, feedback, and control into intelligent systems before trust is broken. Your CTO asks you to “design the AI experience.” There’s no interface yet, just a prototype from the ML team and a prompt to “make it usable.” You’re left staring at system outputs, unclear where to start, or how much of the system behavior is even within your control.→ Gain the tools and frameworks to work upstream, shaping behavior, not just UI. You’re in a meeting where the team is debating whether to launch a model with 72% accuracy. Product wants speed. ML is confident the model will improve post-launch. But no one’s talking about the UX cost of being wrong nearly 1 in 3 times or how the system will recover from those mistakes.→ Learn how to design for failure, uncertainty, and system correction from day one. A personalization feature goes live. But user feedback is harsh: “This feels random.” You realize the issue wasn’t the model, it was the lack of communication and guidance. There’s no explanation, no context, and no way for users to improve the output.→ Understand how to design model feedback loops and trust-building interactions. You inherit a half-built AI assistant. It occasionally interrupts users at the wrong time, answers inconsistently, and disappears when needed most. The UI looks fine but the behavior feels off. You realize this isn’t a layout problem, it’s a systems design problem.→ Move from UI design to shaping system behavior, flows, and agent logic. You will bring your own real-life project scenarios, and we’ll coach you through how to solve them—using frameworks, feedback, and hands-on critiques.

The AI Tech Revolution Is Redefining Design

Class will meet once a week for live lectures and project discussions.

Weekly Live Sessions

Plan to work on a capstone project to apply your learning to a capstone project

Weekly assignments

Get weekly 1-1 office hours for personalized feedback on your capstone project

1-1 Coaching 

Senior UX &amp; Product Designers: Deepen your systems thinking skills and learn to design around model behavior

Design Leads &amp; Heads of UX: Guide teams, shape AI product strategy, and lead with system-level thinking and trust design.

AI-Aware PMs &amp; Researchers: Collaborate better with design, align model goals with UX, and support ethical, adaptive systems.

What you’ll get out of this course

Learn how to speak the language of models, data pipelines, and evaluation metrics—so you can contribute meaningfully from early scoping to final delivery. You’ll practice framing use cases, defining handoffs, and aligning design with system capabilities.

Collaborate effectively with ML and Product teams

Instead of just designing around the model, you’ll explore how interaction design can shape what the model learns, retains, or ignores. You’ll build UX patterns that create useful training signals, structured inputs, and adaptive guidance.

Shape model behavior through smart UX architecture

You’ll create flows that help users understand, question, or override the model’s decisions—like confidence indicators, correction mechanisms, and recovery paths for failure scenarios.

Design interactions that support user trust, control, and adaptation

Learn to design feedback loops where user actions (like corrections, inputs, skips, or feedback) help the model adapt. You’ll map those flows and create testable patterns that help close the loop between model performance and user value.

Build systems that improve over time—with users in the loop

Whether you’re dealing with ranking systems, generation models, or multi-step agents—you’ll practice mapping decision logic, designing trust dashboards, and identifying failure points. You’ll learn how to advocate for UX in model evaluation and behavior design conversations.

Lightning Lessons

Designing on Purpose—Getting UX Feedback That’s Actionable