Designing Culture

Over the weekend, I spent 3 hours with 20 strangers and friends designing an intentional community. The premise of the exercise—imagine that you pooled money together to buy 50 acres of land, how would you define how you want to live?

There were more questions than answers at the end of the session. It started off with idealistic energy: wouldn’t it be nice to escape all the madness that is the current state of the world to build a new place from scratch? A place that has all the values that we want without any of the cruft?

At the end of the experience, I started to wonder, what’s preventing us from actually creating the communities that we want? Is starting from scratch better than improving what we have now?

Some immediate questions seemed to have a bigger impact on the direction of the group:

  • How do we make money?
  • How do we sustain ourselves?
  • What kind of values do we want to have as a group?
  • What kind of commitment am I making to the group?
  • How do we prioritize the needs of the individual or the group?
  • How do we decide who to let in?
  • How do we make decisions?
  • What kind of comforts can I have or have to give up?
  • Why am I leaving what I have now to join this alternate community?

There was a need for more community, and a change in the ratio of time spent working to sustain ourselves versus spent doing what we enjoy.

The relationships we have with family, friends, and coworkers exist in curated contexts. Each relationship is different because of the assumed permanence and the implied commitments.

The yearning to start from scratch assumes that it’s an easier path than changing what we have. It assumes that some things aren’t worth the effort to try to change.

Bringing this back to reality. How can we improve the cultures that exist at home, school, or work? In our neighborhoods and cities? Are the constraints and values as immutable as we believe?

The Dynamics of Working in Public

Show Your Work

A while ago, I came across the idea of working public. Showing your work in progress as a way to find other people that are interested in the same topics and get feedback on your ideas.

The SVA Entrepreneurial Design syllabus asks students to publish their work in progress. By placing their ideas out in public, the classroom becomes a different place:

it puts all of us—the students and the instructors—on the same team. Whether the students hit their $1,000 goal is up to the world, not us. So in the course, we are their coaches and allies working with them, not grading or judging them.

As someone that is not in the classroom, publishing my ideas has other side effects:

  • More cohesive thoughts: To publish my ideas they have to be self-contained and intelligible in order to communicate to other people. Through this refinement, they become more defined for me, too.
  • Room for new ideas: Once a thought if externalized, I can continue refine it or make room for the next idea. Translating amorpheous ideas into words or images reveals new questions that still need to be considered.

Show Your Work

The book cover at the top is from Show Your Work. It’s a short read about ways to think about sharing your work. Some takeaways and nice reminders for me were:

Reminders on why we should share:

  • You can’t find your voice if you don’t use it.
  • Read the obituaries to remind ourselves of how much is possible. Similar to Steve Jobs’ commencement speech to remind us that we all have a limited amount of time here.

How to share:

  • Become a documentarian of your work.
  • Share something small every day about your work that’s useful or interesting. This reminds me of the hand lettering Raul posts on his Instagram.
  • Create a space to share. Find your medium for stock and flow content. Not being a musician, I’ve wondered how musicians can share something every day when it might take a year to produce an album.
  • Reflect on your daily posts to find recurring ideas. Turn the flow into stock.
  • Don’t hoard, attribute properly, and share what you find interesting from other’s work.
  • Don’t spam. There is a spectrum of hoarder, contributor, spammer. By sharing other people’s work, you are listening and participating in the community, rather than just waiting for your turn to talk.
  • Teach what you know.
  • Ask for support. Keep a mailing list.
  • Synonyms for work in progress that you can share: research, reference, drawings, plans, sketches, interviews, audio, photographs, pinboards, video, journals, drafts, prototypes, demos, diagrams, notes, inspiration, scrapbooks, stories, collections.

Some ideals to strive for:

  • Surround yourself with people that energize you.
  • Prioritize hearts over eyeballs.

Feedback Conversations

I’ve come across two frameworks recently that are helping me think about how I have difficult and uncomfortable conversations. They have been useful when I have to tell someone that their actions are making me or others uncomfortable, or when we are disagreeing about a decision.

Radical Candor

Kim Scott’s Radical Candor framework introduces two criterias to evaluate what we say. On one axis, how direct is your communication? On another, how much do you care about the person? When you combine these into a 2x2 chart, you can categorize your communication into four areas:

  1. Ruinous Empathy: When you care a lot, but are not very direct. This is when you hesitate to hurt someone’s feelings, so you either don’t say anything, or you say it indirectly, hoping that the other person decyphers your subtle message.
  2. Radical Candor: When you care a lot, and are very direct. This is where most of want to be more often, but we default to the first category.
  3. Manipulative: When you don’t care about the person, and you are not direct.
  4. Jerk: When you don’t care how they feel, and you are very direct.

The most useful parts of this framework helped me see how I communicate in an uncomfortable situation, and understand which direction I needed to move toward. If I am striving to be more direct, I also want to make sure that the other person knows that I do care about them and how they feel.

Difficult Converstations

The Difficult Conversations book introduced me to the different layers of conversations we have despite what both sides are be saying. When two people disagree, there are disagreements on the “what happened” layer. Did we see the same thing? Do I understand how the person experienced the situation?

There is also the feelings layer. How do both sides feel because of what they perceived to happen? Are these feelings expressed or implied during subsequent conversations? If they are not acknowledged, you have not addressed the actual issue. Or if the issue is addressed, there will still be residual, unresolved emotions associated with the incidident.

The third layer of converations are internal dialogues on indentity. How does what happened reflect on who I am or think I am?

With these layers, the conversations become less of “I am going to tell you something and you are going to receive it” into learning conversations. I need to understand you across multiple layers before making judgement calls.


Both of these frameworks have been very helpful, and I would like to spend more time understanding how they complement each other.

Difficult and awkward conversations are unpleasant, so we avoid them. There’s also the adage of not saying anything if you have nothing nice to say, which I’m starting to think is misdirected advice. If you have nothing nice to say, find a better way to say it.

How I Learn

Here’s a list of methods I’ve been using in the past couple of years to learn and grow. And a second list of new methods I would like to spend more time trying.

How I’ve been learning

  • Consulting: Working at Pivotal means that I am rotation through several projects each year. Each project has a unique set of teams, users, stakeholders, domains, constraints, timelines, goals. New challenges, mean new ways of solving them. While I’m not an expert in any business domain, I’ve helped client teams see the value of establishing and adopting new design practices.

  • Pairing: All the developers pair program at Pivotal, and designers pair design quite often. Pairing with client and Pivotal designers means I get to see different approaches to solving problems. It also allows me to learn what didn’t know I didn’t know.

  • Managing other designers: Becoming a manager recently means I am gaining additional perspective by helping others reflect on their own growth. Seeing the contrast in my reports’ goals, challenges, and working styles, I get to reflect on my own approach. Learning from what works well across reports helps me share it and apply it back to everyone.

  • Friendtorships: The conversations I have with my manager, my project team, and other designers, are invariably different. Friendtorships are peer-mentorships that create an additional space where I am able to reflect on my projects, design practice, and goals in a way that doesn’t happen in other contexts. It’s more reflective, less output driven, and the exploration reveals new paths in a way that is not pre-defined.

  • Side Projects: Creating safe spaces to practice and explore new skills are crucial for personal growth. It’s the equivalent of an R&D approach for personal growth. A place to try new ideas and fail safely and productively. It’s a sandbox of deliberate play and practice, good frustration, and tiny-but-personal victories.

  • Defining Skill Benchmarks Working with a larger design team has allowed me to see the way we define expectations for successful designers. We have a set of core values that include a set of possible behaviors/actions. Articulating the behaviors and actions allows me to see if I am doing what we say we value. To see what values and priciples a team cares about, see how they manifest themselves in the process and working relationships.

New Learning Experiences to Try

Methods I’d like to continue practicing and new ones to explore:

  • Continue managing
  • Continue old and start new friendtorships with others
  • Start mentoring designers outside of work
  • Find new formats to gather feedback and reflect on my work and myself
  • Start learning about education methods and learning styles
  • Start pairing with more designers

Design Related Podcast

I’ve been hosting a series conversations with product designers for the past year. The podcast is called Design Related, because we talk about design and the interesting tangents around it.

Subscribe to the show or listen to a single episode about:

What I’ve learned

Podcasts create new conversation spaces. The act of recording and publishing allows me to ask a lot of questions. It’s all focused on learning about the other person. This is something that would not be comfortable in a casual, non-interview, setting. Because it would be weird for me to pepper someone with questions for 45 minutes. Conversations flow back and forth, but interviews set the expectation to emphasize one person’s experiences.

It takes more effort to produce audio content than other forms of media. The process to distribute written content is streamlined, while editing and publishing audio can involve multiple workflows. All computers have a text editor, but audio editors are not first class applications. On mobile devices, creating and editing photos and videos are more accessible than audio tools. You can copy/paste a string of text easily, while copy/pasting audio only possible while you are explicitly editing sound inside certain applications.

Production quality is a biproduct of available equipment. The right recording equipment has a big impact on audio track quality. Software can only improve recordings, but it can’t save a muddled track.

Scheduling logistics aren’t fun, but the interviews make it worthwhile. Each time we conduct an interview, the steps to coordinate it take longer than expected. But when we are in a room recording, and after wrapping up an interview, there’s a sense of elation from learning so much in such a short amount of time.

It’s easier with another person. If you’re thinking of starting a show, it’s easier when you have a co-host. Especially if audio production is a new medium for you. The show would not exist without my co-host Mike McDearmon.