Bio
Matthew Holloway is a design executive with more than 25 years of experience leading cross-functional teams to create products, services, and systems that solve complex problems and deliver meaningful business impact. He views design both as a verb—a disciplined, iterative process grounded in customer and market research, systems thinking, and prototyping—and as a noun—the tangible expression of value, whether through the resulting product, service, or policy that creates clarity, value, and competitive advantage.


Summary
In this conversation, Matthew and Matthew discuss the challenges and opportunities in technology, particularly focusing on enterprise software, generative AI, and the importance of user experience and empathy in business. They explore the hesitancy in investment, the role of automation, and the need for a balance between technology and human agency. The discussion also touches on the significance of understanding user needs and the impact of AI on human interaction.


Takeaways
Technology can often be a source of frustration.
Investment in enterprise software is currently hesitant.
Generative AI has potential in business process automation.
Data security remains a top concern for companies.
User trust is essential for AI systems to succeed.
Empathy plays a crucial role in understanding customer needs.
Automation should not eliminate human agency.
Design should align with business outcomes.
Experimentation is key in technology adoption.
Understanding the context of use is vital for effective solutions.


Keywords
technology, enterprise software, generative AI, business process automation, data security, user experience, empathy, automation, design, AI impact

Bio
Ali Maaxa is a weird optimist (in the best way) and the Chief Behavioral Scientist at Maaxa Labs. She leverages her deep experience in global innovation and product discovery to provide strategic insights for product innovation, market fit, organizational change, AI/ML & Cloud Innovation, CX & UX. With over two decades in the field, she has worked with a host of organizations, from AT&T's global cloud transformation team to local recycling companies, to understand teams and customers, test solutions, and strategize & deploy change.

Summary
In this engaging conversation, Matthew and Ali Maaxa explore the multifaceted nature of identity, the implications of technology and AI, and the importance of empathy in UX design. They discuss the cultural contexts of technology use, the limitations of AI in understanding human experiences, and the need for responsible governance in AI implementation. The dialogue also touches on the challenges faced by startups, the impact of technology on society, and personal reflections on values and aspirations.

Takeaways
This is a conversation between people that just happens to be recorded.
AI doesn't understand how hormones affect cognition.
Empathy leads to the impulse to attune and understand user needs.
If the user can't find it, the feature doesn't exist.
We need to do some R&D before implementing new technologies.
Take your sweet time with technology adoption.
We are definitely in our getting burned phase of AI adoption.
I wish people cared more about kids and their needs.
It's important to keep talking about the implications of technology.
Living the dream is complicated by real-life challenges.

Chapters
00:00 Cold (awkward!) Open
00:51 Buy My Books?
07:16 The Taco Revolution is Coming
13:03 AI Adoption and Governance
18:55 The Importance of Meaningful Work
24:26 Reflections on Time and Value Systems
26:31 The Future of AI and Human Interaction
38:05 Matthew Stumbles Across Thin Ice
50:24 Navigating the Challenges of Technology
59:21 7 +/- 2 Questions
59:35 What is something that you did recently that went really well?
01:00:23 What do you wish people cared more about?
01:01:10 What's your go-to dish?
01:03:03 What's the business value of empathy?
01:07:23 Waving at flaggers, yes or no?
01:09:23 What do you hope to not be carrying anymore?


Keywords
AI, UX, technology, empathy, startups, governance, cultural studies, innovation, human experience, responsible AI

Bio
Chaos wrangler, community builder, storyteller, turning burnout into wisdom and neurodivergence into gold. One eye on justice, one hand on the mic, the other holding a gluten-free snack. Portland forever. @camikaos

Summary
Matthew interviews Cami Kaos, exploring themes of neurodiversity, childhood experiences, and the challenges faced by individuals with ADHD and Autism. They discuss coping mechanisms, the impact of diagnosis on relationships, and the importance of advocacy in tech. The dialogue also delves into the nuances of calling in versus calling out in social interactions, emphasizing the need for understanding and allyship in professional spaces. In this conversation, Cami Kaos and Matthew explore various themes surrounding communication challenges, burnout, the complexities of autism, social interactions, and the role of empathy in both personal and professional contexts. Cami shares her experiences with burnout and autistic burnout, emphasizing the importance of understanding and respecting personal boundaries in social situations. They discuss the impact of alcohol as a social lubricant and the perceived versus actual value of empathy in business. The conversation also touches on leadership dynamics, self-worth, and aspirations for the future, culminating in a reflection on the weight of unemployment and the desire for personal growth.

​Takeaways
Childhood experiences shape adult coping mechanisms.
Diagnosis can provide clarity and understanding of oneself.
Advocacy in tech is crucial for neurodiverse individuals.
The importance of calling in rather than calling out.
Coping strategies can include routines and medication.
Navigating systems can be challenging for neurodiverse individuals.
Personal growth often involves reflecting on past relationships.
The tech industry is often designed by neurotypical individuals.
Understanding and empathy are key in professional interactions. Cami emphasizes the importance of clear communication in professional settings.
Burnout can manifest in various forms, including autistic burnout.
Understanding autism involves recognizing the complexities of masking and social interactions.
Setting personal boundaries is crucial for mental health and wellbeing.
Alcohol often serves as a social lubricant, but its role can be problematic.
Empathy is a vital component of successful business practices.
Leadership often comes with the challenge of lacking authority to make necessary changes.
Self-worth is tied to the ability to prioritize one's own wellbeing.
Social interactions can be exhausting for those with autism, leading to the need for personal space.
Future aspirations include overcoming the weight of unemployment.

Chapters
00:00​ Open, No Cold
05:27​ Coping Mechanisms and Self-Discovery
24:26​ Surviving In Tech, Neurospicy-style
30:12​ The Importance of Perspectives
34:43​ Calling In vs. Calling Out
43:03​ Burnout and Its Implications
01:03:59​ Authenticity and Adaptability in Work
01:15:22​ 7 +/- 2 Questions
01:15:38​ What is something that went really well for you recently?
01:16:25​ What do you wish people cared more about?
01:16:41​ What's your go-to dish?
01:21:22​ What is the business value of empathy?
01:22:27​ Waving at flaggers, yes or no?
01:24:26​ What do you hope to not be carrying anymore?

​Keywords
podcast, neurodiversity, ADHD, Autism, coping mechanisms, childhood experiences, advocacy, calling in, calling out, personal growth, communication, burnout, autism, social interactions, empathy, leadership, personal boundaries, alcohol, self-worth, wellbeing

Bio
Jasmine Isaac is a self-proclaimed "people person" who's turned her knack for connection into a career as a UX Researcher and Product Strategist in the CPG and Healthcare worlds. She's passionate about helping others find that sweet spot where personal goals and professional expectations meet. Outside of work, you’ll likely find her on long walks with her 3-year-old Bernedoodle, Pablo, finding her zen at a Maven hot vinyasa yoga class, battling it out on the tennis court in a doubles match, or trying to be the next barefoot contessa with a recipe from the NYT Baking section!

Summary
In this conversation, Jasmine and Matthew explore the complexities of leadership, the importance of empathy in business, and the evolving nature of research in understanding consumer behavior. They reflect on past events, discuss the dichotomy of work and personal life, and emphasize the need for leaders to acknowledge the emotional landscape of their teams. The conversation also delves into the role of researchers in organizations, the balance between stakeholder and participant needs, and the art of conducting meaningful research that drives business strategy.

Takeaways
Real conversations are essential for authentic connections.
The impact of past events shapes our current perspectives.
Leaders must acknowledge the emotional landscape of their teams.
Empathy is crucial for maintaining relationships in business.
Understanding user needs is vital for effective research.
The role of researchers is to bridge the gap between consumers and organizations.
Curiosity drives better research outcomes.
Empathy leads to sustainable business practices.
Balancing stakeholder needs with participant insights is key.
Research should inform and drive product roadmaps.

Chapters
00:00 That's Cold Open
00:21 Reflections on Leadership and Team Dynamics
09:59 The Dichotomy of Business Decisions and Human Experience
34:15 The Researcher's Role in Business
49:35 Transparency and Participant Engagement
01:01:28 Understanding Stakeholder Relationships
01:05:41 7 +/- 2 Questions
01:06:17 What is something you did recently that went really well?
01:07:27 What do you wish people cared more about?
01:11:19 What's your go-to dish when you are going to share food with people that you make?
01:13:55 What is the business value of empathy?
01:15:26 Waving at flaggers, yes or no?
01:16:11 What do you hope to not be carrying anymore?
01:17:32 byeeeee

Keywords
leadership, empathy, research, consumer behavior, organizational culture, personal growth, business strategy, qualitative research, stakeholder management, emotional intelligence

In this conversation, Matthew and Cornelius Rachieru explore various themes including the current state of global instability and the (possible) importance of systems thinking in design. They discuss the role of empathy in business, the challenges of service redesign, and the cultural differences in communication and acknowledgment. The conversation culminates in reflections on personal and professional growth, emphasizing the need for understanding and collaboration in complex environments.

Takeaways
Designing systems is about understanding and addressing complex behaviors.
Empathy in business enhances collaboration and outcomes.
Cultural differences shape our perspectives on acknowledgment and gratitude.
Service design should focus on asking questions rather than providing answers.
The complexity of systems makes redesign challenging but necessary.
Being a decent ancestor to future generations is crucial for sustainability.
Personal growth often comes from stepping outside of comfort zones.
Understanding the nuances of design can lead to better outcomes.

Sound Bites
"We are living in the stupidest of times."
"I want to understand the problem."
"Canada broke me."

Chapters
00:00 Cold Elbows Up Open
02:41 Jumping right off. In. Both.
09:07 Understanding Systemic Change
18:17 Design Questions — Design Solutions
27:18 The Future of Design Practice
32:04 Shift in Focus
39:27 Understanding Organizational Dynamics
51:51 Matthew has an epifanny
58:33 7 +/- 2 Questions
59:36 What's something that you did recently that went really well?
01:03:44 What do you wish people cared more about?
01:06:09 What's your go-to dish that you like to share with people?
01:15:22 What is the business value of empathy?
01:18:16 Waving at Flaggers: ¿Sí o No?
01:21:00 What do you hope to not be carrying anymore?

keywords
Service Design, Instability, Systems Thinking, Design, Empathy, Business, Culture

Bio
Jeffrey Zeldman is partly responsible for how you do your job, if you work on the web. You should say “thanks”. Or “curse you”. Depending on how you feel about working on the web. Check out his site which has been around since 1995. https://zeldman.com/about/

Also: “I sobered up the same time New York did” is the first line in the novel Jeffrey should write. Right? Who’s with me!

Summary
In this conversation, Jeffrey Zeldman and Matthew discuss a range of topics including the treatment of military veterans, the impact of news on mental health, personal boundaries in social situations, experiences with travel and events, health and safety protocols, the importance of codes of conduct in communities, the challenges of writing and personal narratives, and the process of collaborative storytelling. They reflect on their own experiences and the complexities of navigating social interactions in a post-pandemic world.

Takeaways
Technology can create unexpected family dynamics.
Nostalgia plays a significant role in our attachment to devices.
Communication styles vary based on audience and context.
Honesty in conversations can sometimes lead to misunderstandings.
Writing for different audiences requires adaptability.
The emotional impact of current events is profound.
There is a need for new perspectives in UX research.
Writing a book on UX can be a daunting task.
Political discourse often reveals shared human experiences.
Understanding different viewpoints is crucial in today's society.
The treatment of military veterans is a critical issue.
Avoiding news can help manage emotional overload.
Social interactions can be overwhelming for some individuals.
Travel experiences can be both exciting and exhausting.
Health and safety protocols are essential in social settings.
Codes of conduct help create safer community environments.
Writing personal narratives can be challenging due to privacy concerns.
Self-doubt can hinder creative expression.
Collaborative storytelling can enhance character development.
Personal experiences shape our perspectives on various topics.

Chapters
00:00 Quick N' Cold Open
02:02 Welcome to Two Old Dudes With ADHD. Likely.

Keywords
technology, communication, writing, UX research, personal conversations, honesty, emotions, politics, nostalgia, family dynamics, military, veterans, news, emotional health, social interactions, travel, health safety, code of conduct, writing, creativity

Summary
In this conversation, Matthew and Alex discuss the challenges of navigating job loss in the tech industry, the struggles of job searching, and the importance of content in UX design. They explore the impact of AI on the industry, the significance of personal integrity, and the need for community and connection among professionals. The discussion also touches on the challenges of speaking up in corporate environments, the search for meaningful work, and the journey of writing and creativity.

Bio
Alexandra Carson is a versatile writer and strategist with over 15 years of experience in various creative fields, including acting, screenwriting, makeup artistry, and events. After years of juggling multiple jobs to support her artistic career, she discovered the world of UX research in 2018, thanks to a friend who recognized her potential in the field.

Simultaneously, as Alexandra embarked on her UX journey, she gained a deeper understanding of complex PTSD (CPTSD). This newfound knowledge highlighted the harmful experiences people encounter in various aspects of life, ranging from exclusion due to identity and accessibility issues to digital tools being misused for abuse.

In a conversation with a trusted advisor, Alexandra questioned why trauma-informed design was not a more widely discussed topic. Her advisor's response, "Why don’t you?" inspired her to take action.
Driven by a desire to create experiences that make everyone feel seen, heard, and safe, Alexandra is now an advocate for trauma-informed design. She combines her passion for UX research with her commitment to inclusivity and accessibility, striving to contribute positively to people's lives through innovative and empathetic design solutions.


Takeaways
Job loss can lead to existential dread and shame.
Tech salaries can create golden handcuffs.
Content is often undervalued in UX design.
AI is changing the landscape of job opportunities.
Personal integrity is crucial in professional life.
Building community can help navigate challenges.
Speaking up can have both risks and rewards.
Finding meaningful work is a common struggle.
Visibility and advocacy are important for change.
Creative writing can be a fulfilling outlet.


Chapters
00:00 Jump right in...
07:18 Understanding Roles and Responsibilities in UX
13:25 Integrity and Ethics in the Tech Industry
22:10 The Future of Work and Personal Values
31:20 Visibility and Modeling Behavior
38:02 Navigating Change in a Capitalistic World
49:09 The Challenges of Honesty in Corporate Culture
01:01:31 7 +/- 2 Questions
01:01:51 What's one thing that you would change about your profession?
01:03:10 What do you wish people cared more about?
01:04:06 What is the best meal you've ever had?
01:05:42 What do you wish you'd done differently?
01:07:29 What do you hope to not be carrying anymore?


Keywords
job loss, tech industry, UX design, content strategy, AI impact, personal integrity, community building, professional advocacy, meaningful work, creative writing

Summary
In this conversation, Peter Russo and Matthew explore the complexities of finding purpose in work, especially in chaotic and dysfunctional environments. They discuss the importance of community, creativity, and personal fulfillment, while also addressing the challenges posed by organizational dynamics and the ambiguity of purpose. Through a series of rapid-fire questions, they reflect on their experiences and insights regarding career paths, communication, and the desire for meaningful work.

Bio
Peter Russo has been tech-ing it up since before it was classy to wear an onion on your belt. He’s worked as a UX designer and researcher in health care, fintech, and education—and he's built some pretty great teams.

He lives in Portland, Oregon with his wife and no dogs. He is passionate about....things. Probably. And stuff. Also, his wife is driving like a maniac rn, pardon any typos.

Takeaways
Finding purpose is a constant journey, not a destination.
Community plays a crucial role in personal and professional fulfillment.
Ambiguity in purpose can lead to burnout and confusion.
Organizational dynamics can hinder personal purpose and growth.
Creativity is essential for personal satisfaction in work.
Navigating change requires adaptability and resilience.
Effective communication is key to overcoming expertise blindness.
Understanding team dynamics is vital for a healthy work environment.
Personal fulfillment often comes from helping others and creating.
It's important to reflect on past experiences to inform future decisions.

Chapters
00:00 Hiding From the Cold Open
03:02 Community and Purpose
03:24 On Finding Purpose
08:12 The Complexity of Purpose
18:12 Breaking Down Silos: The Challenge of Community Boundaries
25:27 Creative Pursuits: Finding Purpose in Art and Work
46:01 Purpose in Adversity: Learning from Challenging Situations
01:03:48 What's one thing you would change about your profession?
01:04:29 What do you wish people cared more about?
01:05:16 What's the best meal you've ever had?
01:07:15 What do you wish you'd done differently?
01:08:08 What would you do for a living if you stopped doing what you're doing now?
01:09:45 What do you hope to not be carrying anymore?

Keywords
purpose, work, organizational dynamics, creativity, community, career, UX design, personal fulfillment, change management, collaboration