Tyler Quackenbush shares her journey from UX design to project management, offering insights on how designers can expand their roles and thrive in Agile environments. She’ll discuss the real-world challenges of integrating design into Agile workflows, the practical strategies that help teams move beyond outdated waterfall processes, and how to keep creativity alive in fast-paced iterations.
This conversation will highlight how a design mindset can enhance project management, improve cross-functional collaboration, and create more effective workflows. Tyler will share actionable techniques UX teams can use to balance iteration with deadlines, structure design backlogs, and ensure design remains a driving force in Agile teams. Whether you’re looking to refine your team’s process or rethink your role, this session will provide ideas you can put into practice right away.
Session Notes
Session Overview
In this Tent Talks session, Heidi Trost dives deep into the evolving relationship between AI, privacy, and the future of UX. She introduces a helpful mental model involving three key players in the cybersecurity ecosystem: Alice (the user), the threat actor (the adversary), and Charlie (the design of the system). Through this lens, Heidi explores how invisible interfaces and AI agents are shifting the landscape of privacy and security, often creating tension and confusion for users like Alice.
Heidi emphasizes that while AI can enhance usability and offer powerful new capabilities, it also opens up major risks—especially when users are unaware of how their data is being used or what rights they have. She calls for UX designers to become advocates for Alice, learning enough about the underlying technology to design responsibly and communicate clearly. Throughout, she stresses the importance of trust, transparency, and cross-functional collaboration to build safer, more user-friendly systems.
How do less visible interfaces change perceptions of privacy and security?
- Introduced a model with three roles: Alice (user), threat actor, and Charlie (system design).
- AI-powered tools like transcription at a doctor’s visit or smart glasses can provide value but also raise privacy concerns.
- Users often don’t know what rights they have or how their data is being used.
- Trust is key—users behave differently based on how much they trust the system, even when that trust is misplaced.
- Invisible interfaces make it harder to know when data is being collected, creating new security and ethical concerns.
What are the biggest risks with AI agents acting on users’ behalf?
- AI agents can access email, financial accounts, and more—making life easier for users but also for threat actors.
- The broader the access, the bigger the attack surface.
- Onboarding and setup must balance ease of use with friction that promotes awareness.
- Advocates for “secure by default” settings—like Firefox’s built-in safe browsing—as best practice.
- Good UX needs to clearly explain choices and risks specific to users’ context, which security often fails to do.
Can AI help users understand privacy, or does it create false security?
- Answer is both—it depends on how Charlie (system design) shows up.
- Currently, Charlie is like an annoying coworker who interrupts Alice with jargon and unclear warnings.
- AI has potential to become a helpful sidekick, like Daniel Miessler’s concept of a digital perimeter protector.
- Danger lies in over-reliance; users might trust AI too much and stop questioning or verifying.
Advice for UX designers building AI-driven experiences:
- Learn the dynamics of Alice, Charlie, and threat actors—security is a constant game of reaction and adjustment.
- Understand enough about the tech to ask the right questions and push back on bad decisions.
- Don’t gather or store more data than needed—reduce risk at the source.
- Prepare for multimodal experiences: voice, gestures, facial expressions, and text.
- Communicate clearly what the system is doing and why, without overwhelming users.
- Make system limitations visible—users need to know what AI can and can’t do.
- Allow for reversibility: let users undo mistakes the AI makes.
- Embrace cross-functional collaboration—design alone can’t solve this, but it must lead the way.
Notable Quotes
- “You can’t lose data that you don’t gather—or don’t keep.”
- “Charlie is the security UX—and UX people, you are in charge of Charlie.”
- “Trust changes how Alice behaves—even if the trust is misplaced.”
- “The holy grail is building in security and privacy so Alice doesn’t have to think about it.”
- “Help Charlie help Alice.”
- “The Venn diagram of engineering, design, security, law, and product—that’s where the magic happens.”
Reference Materials
- Human-Centered Security by Heidi Trost
- Daniel Miessler – Security researcher and writer (danielmiessler.com)
- Firefox – Example of secure defaults in UX design
Session Transcript
[00:00:35] Chicago Camps: Can you share how your journey from UX design into project management unfolded? What challenges did you face making that transition, and how has your UX background shaped your approach to managing projects?
[00:00:49] Tyler Quackenbush: My journey from UX design to project management unfolded semi-organically. I stepped into the role when our previous PM left, but even before that, I was already learning about Agile.
I was asking questions about Scrum and getting certifications. I was getting curious about what project management actually looked like in practice, and I’d been paying close attention to the way that our PM worked and how she handled relationships and how she ran meetings and the timing just lined up.
So when the opportunity opened up, it felt like a natural next step, both for me and for the team. At that point, I had already built strong relationships. I was deep in the work, so I was able to step in and keep momentum going. That said, there were definitely challenges, some communication gaps, a little bit of friction between teams, and I had to learn that while helping the team navigate through those transitions… it was a lot, but it was a lot of really valuable learning opportunity and time
And the way I worked day to day, I carried that design mindset with me constantly. I still think like a designer because I still am a designer, so I listen. I ask questions, I look for patterns, and that helps me approach the project work with focus on clarity and alignment. I’m also thinking about how to support a good flow, so what’s clear and what’s not, and what’s getting into team’s way.
One of the biggest lessons I’ve learned and one of the biggest lessons that I keep learning is that I don’t have to have all the answers. So I’ve taught myself more than once overcomplicating something or trying to solve it solo, when what I actually really need is to pause and zoom out and bring others in. And that’s when I lean back into the design mindset. So break things down, simplify what can be simplified, and stay focused on what we actually need to achieve together.
Project management, it’s about creating the conditions for collaboration and momentum. It’s not about controlling a group of people, it’s about making space for the team to do great work together, and that’s why it lines up perfectly with ux.
[00:02:50] Chicago Camps: Agile can sometimes feel more suited for development teams. What practical steps can design teams take to better integrate into agile workflows without sacrificing that creativity or quality?
[00:03:03] Tyler Quackenbush: I’ve been lucky to be on a team where design was approached in a really agile way from the beginning. So
Instead of feeling like we were the ones trying to fit in a dev first process, we actually often found ourselves encouraging our developers to do work in a little bit more agile way than they might’ve been used to.
One of the core principles that we practice is “sharing before we’re ready,” and it’s a huge part of how we work. Even if something isn’t polished or finished or fully thought through, we still put it in front of each other, and that gives the whole team context, so it opens the door for early feedback and creates these moments where we can either course correct really quickly or give someone kudos for having the courage to share something raw. And that kind of vulnerability is a strength, and I think it’s one of the biggest things that makes our design process feel truly iterative.
Beyond that, we’ve made a habit of being involved early, participating in sprint planning and backlog refinement, all the key conversations where the work is being shaped. So we’re not designing in isolation. We’re contributing to the direction that the team’s moving in, which helps everyone stay aligned.
And we also tend to work just a little bit ahead of development. So while Dev is building one thing, design is exploring what might come next. And that overlap gives us a little bit of room to test ideas and make more thoughtful decisions without slowing down the spring cadence.
So if I were gonna give advice to another team, trying to integrate design into Agile, I’d say start by involving design earlier. Build in space to share before things are done and normalize feedback is part of the process, not something that comes at the end. Because at the end of the day, integrating design into Agile isn’t a doable thing. It’s a necessary thing. It’s what keeps the team aligned and keeps the goals focused, and it helps everyone deliver without spinning their wheel on work that doesn’t need to happen.
[00:04:48] Chicago Camps: And that’s how our team works and it’s made a huge difference.
Many design teams still struggle to break out of traditional waterfall processes. What strategies have you seen work to help teams shift into a more iterative and agile mindset?
[00:05:02] Tyler Quackenbush: I think what’s helped our team move away from Waterfall the most is that we just made iteration and non-negotiable part of how we work. The way we share early, and I mentioned this in the last question, it naturally breaks the habit of waiting until everything’s finalized or fully thought through.
When you share before something’s polished, you have to be okay with it changing. And once you build that muscle as a team, you start to expect change and you start to welcome change. And that’s a big mindset shift from the more traditional “handoff-and-hope-it’s-right” model.
Another thing that’s been really effective is anchoring our work to the small wins. Instead of aiming for one big reveal; we’re looking for regular check-ins and small validations and little course corrections. And that pace of feedback actually keeps momentum up and makes room for learning without the pressure of getting it perfect the first time.
I’ve also noticed that working this way invites more collaboration across design, devs, PMs, everyone on any team that you’re working with because when you’re iterating out loud, you’re opening the door for more people to contribute, and that shared ownership helps move everyone out of their silos.
I think if a team wants to move away from Waterfall, the key isn’t overhauling the whole process overnight. It’s practicing. All of those small, intentional behaviors that reinforce flexibility and collaboration, and over time that starts to shift how the team thinks and works together.
[00:06:26] Chicago Camps: How do you ensure that creativity and innovation don’t get lost in the speed of Agile iterations? Are there specific practices you recommend to balance speed and thoughtful design?
[00:06:36] Tyler Quackenbush: I immediately think about one person or one small team of designers and how we protect their creativity in the middle of everything moving so fast.
But the truth is, the answer isn’t about how one person or team stays creative all the time because that’s not realistic. What actually works is building a culture where creativity is shared. So on our team, we lean on each other and spark ideas through feedback and quick unexpected working sessions. One person might share something that’s not fully baked and suddenly we’re workshopping six different ways to solve the problem together.
And what’s cool is that the best ideas don’t always have to come from the design team. Sometimes it’s a developer or a data scientist or a PM someone who brings a totally different perspective. When everyone’s engaged in the process and has that shared context, that creative lift doesn’t fall on just one person’s shoulders or a team of designers shoulders, and that’s what keeps creativity alive even when we’re moving fast.
We don’t treat creativity as something to protect in isolation. We treat it as something that thrives in a collaborative and transparent environment. And when that’s in place, creativity isn’t something we have to slow down for. It’s actually what keeps us moving forward.
[00:07:50] Chicago Camps: How does bringing a design mindset into project management change the way teams work together? Are there specific techniques or approaches from UX that you found especially useful in leading cross-functional teams?
[00:08:03] Tyler Quackenbush: Bringing a design mindset into project management really changes the way I show up as a leader.
So as a designer, I’m used to listening and asking questions and simplifying complexity, and I carry all of that into how I manage projects. It’s not just about tracking tasks or timelines, it’s about designing the conditions for good work to happen.
So I’m always paying attention to where things feel off. When something’s unclear or disconnected or just heavier than it should be, I’m asking, how can we make this feel easier? How do we get back to shared understanding?
And sometimes I realize I’m the part of the problems, and that’s been a big learning curve for me, is recognizing, like I said before, I don’t have to have all the answers. And if I’m overcomplicating something for myself, I’m probably overcomplicating it for my team as well.
So I’ll take a step back and use the same mindset I would as a designer. And ask what the actual problem that we’re trying to solve is. What’s the clearest way to move forward? I’m not trying to oversimplify anything, but I’m trying to just remove the noise and if I had to name the two core principles that I try to lead by as a PM, we’ve talked about it during this whole interview.
The first thing is the share before we’re ready, principle that fosters that vulnerability and that collaboration that helps us move faster and iterate better. The second is the belief that everyone on the team, regardless of title, has a role in getting us to the right solution. Feedback, clarity, alignment, everything falls apart if people are working from different versions of what they think the goal is.
So for me, being a design minded PM is being someone who helps uncover the real problem and creates that shared understanding around it to help build the space for the team to solve that problem together.
The idea of being a designer and being a good PM is at its core, you just make the problem simple and then solve the simple problem.
