Leadership By Design 2026

Leadership By Design 2026

Elevate Your Leadership Skills at Leadership By Design 2026

Reframe: Leading UX Through Volatile Times

Leadership By Design 2026 centers on responsibility, authority, and the people carrying both in unsettled times. Layoffs, reorganizations, and AI mandates are rewriting how teams form, how work flows, and who has the space to make decisions.

Design leaders are being asked to absorb more change, take on broader mandates, and do it with fewer buffers and less certainty. This year we will look at what it takes to lead under those conditions: how to shape orgs, practices, and cultures where human insight, ethics, and experience remain non-negotiable, and how to grow the next generation of leaders even as today’s are stretched thin.

Join us to explore how clear responsibility and thoughtful use of authority can create space for others to do their best work. Through shared experiences, candid conversations, and practical sessions, attendees will gain concrete ways to support their teams through uncertainty, advocate for human-centered decisions in AI-driven environments, and contribute to a stronger, more resilient design community.


Leadership By Design is more than a conference; it’s a two-day journey into the heart of design leadership. This curated event brings together innovators and influencers for an immersive exploration of leadership principles and practices.

Engage in meaningful dialogues, discover proven strategies, and unlock your potential as a design leader. With inspiring speakers and interactive workshops, you’ll leave empowered and energized. Secure your seat and transform your leadership!

Leadership By Design 2026 is an online 2-day conference focused on all aspects of design leadership.

On Thursday & Friday, September 17th & 18th, from where ever you are starting at 10a Central. We’ll have 2 days of stellar keynotes and focused design leadership presentations with thoughtful Q&A that allow you to gain a lot of insightful learning. In addition, each day has an uplifting interstitial that is sure to be refreshing and reinvigorating after deep content sessions.

And we will have swag! We’re partnering with Nerditees (again!).

Event Details
Tickets
$15
Early Bird Ticket

Only 20 tickets at this price!

$26
General Admission

Only $26! An outstanding bargain!

Free
Pay What You Can

Any contribution is appreciated.

Free
Need 1, Take 1

For anyone with a need. Please join!

Speakers
Anne Cantera
Anne Cantera
Founder
Elementyl Intelligence
Anne Cantera is the founder of Elementyl Intelligence, an ethical AI consultancy, and VoiceofAI.io, a free resource helping designers upskill into AI, and also, in a recent turn of events, is now Director of Conversation and Omnimodal Design at a stealth AI startup.
Guppy Ahluwalia
Guppy Ahluwalia
Fractional Operations Executive
Guppy Ahluwalia is a fractional operations executive specializing in driving hardware and software teams to deliver strategic programs at scale.
Dan Saffer
Dan Saffer
Author, Product Design Leader, Assistant Professor
Carnegie Mellon
Dan Saffer is a product design leader and the author of four books: Designing Devices (2011), Designing Gestural Interfaces (2008), Designing for Interaction (2006, 2009) and the best-selling Microinteractions (2013).
Caitlin Steele
Caitlin Steele
Founder
Thoughtful Apes
aitlin Steele helps the people who build software get clear on what they are actually building and why.
Jessica DeMartini
Jessica DeMartini
Consultant
Jessica DeMartini is an intentionally collaborative product design leader and coach with 15+ years of experience leading cross-functional teams to use their individual strengths collectively to build innovative, cohesive product experiences.
Natalie M. Dunbar
Natalie M. Dunbar
Founder and CEO
The Content Practice Architect
Natalie Marie Dunbar is the founder and CEO of The Content Practice Architect, a consultancy focused on helping brands establish sustainable content practices. 
Christian Crumlish
Christian Crumlish
UX Leadership Consultant & Author
Design In Product
Christian Crumlish is a product and UX leadership consultant at Design in Product, where he also hosts a product/UX community.
Low-cost, high-quality events for the User Experience community.
Chicago Camps
Event Producer
Chicago Camps
Chicago Camps, LLC was formed and founded with the intention of bringing high-value, low-cost events to the User Experience community.
Speaker To Be Announced
To Be Announced
To be announced.
To be announced.
This awesome speaker is to be announced in the future.
Adam Cutler
Adam Cutler
Design Practices Director
IBM
Adam Cutler is the Design Practices Director with IBM Design and one of the first three Distinguished Designers at IBM. He is responsible for the IBM Design Studio in Austin, TX.
Schedule

We'll open the doors a little early and let folks in. Sometimes, we have surprises, sometimes, we play music, sometimes it's a little quiet. Get there a little early to be ready for kick-off!

Announcements and gratitude, schedule for the day, and general information about the event.

Defensible Space
You have probably seen the survey results by now. Design has the lowest manager ratings in tech, and you are doing the opposite of failing: holding your team together, protecting work that is being hollowed out, trying to hand down judgement fast enough that quality survives the speed. That is prevention work, done by people who are only ever handed emergencies; like forest rangers fighting fires.

In fire country, defensible space is the ground you clear in advance so that something survives. It is not the same as saving everything. It is deciding, before the season, what you are going to protect and what you are letting go.

This talk reframes what has happened to design leadership over the last two years: why the conditions changed rather than the people, what you lose when you cannot see past the end of the week, and what can still be protected from the ground you already stand on.

Caitlin Steele
Caitlin Steele helps the people who build software get clear on what they are actually building and why. She was a founding team member at MasterClass and has led design on Trello, Confluence, and lululemon. She now works with design leaders on vision and clarity through Object-Oriented UX and narrative methods. She has keynoted SwiftCraft and spoken at iOSKonf, PragmaConf, and UX Scotland. She writes at thoughtfulapes.com.

Token times: Organizational practices in a resource-constrained environment.

Re-orgs, reductions in force (RIF’s) and LLM’s are only some of the tools in our operational toolkit. Building swiftly at scale requires leaders to let go of headcount-heavy org charts and adopt enterprise -wide processes that are strategic, responsible and lightweight. This talk will discuss two case studies where teams shape-shifted their thinking to design new practices, the lessons learned plus a framework that could be extended to your team’s token optimization strategy.

Guppy Ahluwalia

Guppy Ahluwalia is a fractional operations executive specializing in driving hardware and software teams to deliver strategic programs at scale. She partners with leadership teams to turn strategy into high-impact programs, operating practices, and measurable business value. A published researcher on perception and former Head of Design & Research Operations at Dropbox, Guppy brings deep experience building the systems, governance frameworks, alignment, and decision-making structures required to scale emerging technology responsibly. She lives in the San Francisco Bay Area and is learning Italian.

Hilarious Tales of Failure: What a Year of Building With AI Taught Me

None of us feel like experts right now, and the loudest voices online are making that worse. I want to fix that for 30 minutes.

A year ago I started building an AI product-management assistant, mostly to teach myself what these tools could actually do. It's been genuinely messy: agents that confidently reported things that weren't true, a scheduled job that died silently through a server reboot, a "fix" that looked more precise and quietly made things worse. I'll walk through the real failures, not the highlight reel, and the one principle that's kept the whole thing usable through all of it: the human has to own the loop, not just be somewhere inside it.

If you've felt behind on AI, or suspicious of everyone who claims they're not, this talk is for you. Bring your hands. We're getting them dirty.

Christian Crumlish
Christian Crumlish (xian) is the founder of Design in Product, an independent consulting practice for fractional product leadership in the agentic era. He's currently building Piper Morgan, an AI product-management assistant, and Klatch, a local-first Claude conversation manager. He was previously Director of Product Management at 18F (GSA), and before that Deputy Director of Service Innovation at California's Office of Data and Innovation. Earlier in his career he was VP of Product at 7 Cups, winner of the 2016 Stanford Medicine X Prize for health systems design and the 2019 World Economic Forum Pioneer award, and Director of Product at CloudOn (acquired by Dropbox). He's the author of Product Management for UX People (Rosenfeld Media) and co-author of Designing Social Interfaces. Christian lives in Palo Alto with his wife, Briggs, and an ever-growing collection of ukuleles.

The New Design Stack: The Skills Traditional Designers Need to Add To Their Toolboxes ASAP

The New Design Stack explores the skills designers need for a world where experiences move across chat, voice, visual interfaces, agents, and human support. It shows how to design for the moment, choosing the right modality based on context, intent, and cognitive load. Designers will leave with a clearer view of what to learn next and how their role is evolving beyond the screen.

Anne Cantera

Anne Cantera is the founder of Elementyl Intelligence, an ethical AI consultancy, and VoiceofAI.io, a free resource helping designers upskill into AI, and also, in a recent turn of events, is now Director of Conversation and Omnimodal Design at a stealth AI startup. She specializes in agent orchestration, conversation design, and voice and omnimodal systems, with deep experience across telecom, legal tech, and healthcare. Her focus is on how designers move beyond static interfaces into adaptive, generative experiences without losing sight of the humans using them. Anne is a Fellow at the Conversation Design Institute and a member of the Agentics Foundation. She is also a speaker, mentor to women in AI, and host of the DESIGNathon podcast.

We'll open the doors a little early and let folks in. Sometimes, we have surprises, sometimes, we play music, sometimes it's a little quiet. Get there a little early to be ready for kick-off!

Announcements and gratitude, schedule for the day, and general information about the event.

What’s Yours to Keep: Designing alongside AI without giving up the work that made you a designer.

You think AI is coming for design. I’m not going to tell you it isn’t; I’m going to tell you what it’s coming for and what it can’t touch. These are two very different piles, and the second one has your name on it.

The artifacts go in the first pile, because a model can produce the screens, the decks, and the prototypes, fast and almost good enough. The second pile holds the judgment that picks the right one, and judgment is a muscle: when you stop using, atrophies.

This talk gives you a test you can run tomorrow for sorting your own work into those piles, then gets practical about leading a mixed team of designers and agents. An LLM is an intern with infinite confidence and stamina and no taste. Somebody still has to know good from almost good, and that somebody is a designer.

You’re Not Behind: Finding Your AI Workflow

The reality is, designers have to incorporate AI to keep a job –with no real thought behind how or why. This session is about intentions, clarity, and real stories. It isn’t another talk about prompts or trending tools. Drawing from my research with designers, it's a practical framework to integrate AI across the end-to-end product design process. It’s not a one-size-fits-all solution. We will identify our own needs, shortfalls, curiosities —and how AI can make us more fulfilled, efficient, and flexible. Bring your workflow bottlenecks, explore tangible solutions, leave with a sense of relief.

Session Takeaways

Takeaway 1: Identify where AI can make the most impact in your personal journey map, practice how to be selective, and leave with an AI-integration playbook.
Takeaway 2: Learn key emerging themes, insights, failures, & curiosities in AI integration from ongoing interviews with designers & managers across the industry.
Takeaway 3: Leave with a sense of relief: feeling that they are not as far behind as they thought, and that they can figure this out with confidence.

Jessica DeMartini

Jessica DeMartini is a design leader with over 20 years of experience creating human-centered digital and service experiences for enterprise and consumer products. She integrates AI thoughtfully into product strategy by envisioning its potential, guiding teams in effective use, and grounding design decisions in real customer context. Her expertise spans product design, service design, and UX strategy across companies such as ServiceNow, Wells Fargo, JPMorgan Chase, and Adobe. Jessica combines hypothesis-driven design with cross-functional collaboration to enable evidence-based decisions, confident iteration, and impactful solutions.

The Business of Boundaries: Maintaining a Healthy and Sustainable UX Practice

We talk about boundaries like they’re walls — keep people out, say no, protect your time. There’s a more useful way to think about it, borrowed from architecture: the purpose of a boundary isn’t primarily to block access. It’s to define what happens within a space.

That reframe changes how you build and lead a practice. A boundary isn’t a barrier; it’s a definition. It says, “this is the space where the work gets done well.” In a field where layoffs are relentless, and burnout is treated as a rite of passage, knowing what you need to protect on the inside isn’t optional. It’s the foundation of a sustainable practice and a sustainable career.

The very act of establishing a practice creates boundaries within which the work gets done, which means you’re constantly called on to help cross-functional partners understand where those boundaries sit. This talk covers what it takes to define them well: modeling intentional self-care, using vulnerability and active listening to build trust, and getting comfortable being the bottleneck rather than the burnout. It also makes the case for inclusion — that boundaries hold better when the people around you helped build them, not just when you enforce them alone.

This talk draws on Natalie’s experience building a content strategy practice, but the principles apply to any UX discipline shaped by constant demands and the pressure to say yes.

Natalie M. Dunbar

Natalie Marie Dunbar is the founder and CEO of The Content Practice Architect, a consultancy focused on helping brands establish sustainable content practices.
She has served as a content designer and strategist for leading organizations, including Anthem, Kaiser Permanente, Upwork, and Walmart, as well as federal agencies such as the FDA, USDA, and VA.

Her book, From Solo to Scaled: Building a Sustainable Content Strategy Practice, provides practical advice on scaling content operations and is a valuable resource for professionals in the field.

Six Futures

In an AI world, apps don't have a single future. They have six, and soon, a given product might occupy three or four of those positions at the same time. For companies building AI-powered products, understanding this spectrum is a strategic imperative.

We are at an inflection point where the traditional app — the thing you open, navigate, and close — is becoming just one of several ways users interact with what a product does, and in the future, possibly the least common one. Each of these futures carries a different business model, a different relationship with the user, and a different answer to the question of what makes a product defensible.

Two of these futures are already taking shape in prototyping work from my UI for AI research team at Carnegie Mellon. The first explores what happens when an operating system understands what you're working on, not just which apps are open: assembling cross-application workspaces around tasks, generating parallel approaches so users compare real outputs before committing, and preserving the exploratory thinking that current AI tools collapse into a single generated answer. The second explores ephemeral interfaces — AI that surfaces within whatever tool you're already using at the moment it's relevant, then dissolves when the work is done, earning every appearance rather than demanding permanent screen real estate. Both represent a fundamental shift from interfaces organized around applications to interfaces organized around what someone is actually trying to accomplish. This talk will show what that shift looks like in practice.

The spectrum also exposes a deeper shift in how products get built. AI is collapsing the traditional roles on product teams. When a PM can generate mockups, a designer can write working code, and an engineer can produce competent UI, the artifact is getting commoditized. What remains durable is judgment: knowing which of twenty AI-generated options actually works in context, knowing what good looks like in a domain where the consequences of getting it wrong are regulatory and reputational, and knowing which friction to preserve rather than eliminate. That last question turns out to be the central design challenge of the moment. When you remove all friction from an activity, you don't just make it efficient — you hollow it out. Automating the struggle away doesn't create value. It destroys it.

This talk draws on a year of research, prototyping, and teaching at Carnegie Mellon's Human-Computer Interaction Institute to map where AI products are headed and what it means for the people building them.

Dan Saffer
Dan Saffer is a product design leader and the author of four books: Designing Devices (2011), Designing Gestural Interfaces (2008), Designing for Interaction (2006, 2009) and the best-selling Microinteractions (2013). Since 1995, he's designed devices, apps, websites, wearables, appliances, automotive interiors, services, social networks, and robots. He’s worked at and for such companies as Twitter, Smart Design, Samsung, Jawbone, CNN, Philips, Microsoft and Flipboard. He is currently Assistant Professor of The Practice and Associate Director of Outreach at the Human-Computer Interaction Institute at Carnegie Mellon.

Tickets
$15
Early Bird Ticket

Only 20 tickets at this price!

$26
General Admission

Only $26! An outstanding bargain!

Free
Pay What You Can

Any contribution is appreciated.

Free
Need 1, Take 1

For anyone with a need. Please join!

Event Details
Sponsors
September 2026
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