David Hoang — Writing — career

Career reboot

Mon, 21 Apr 2025 00:00:00 GMT

Every April I seem to take an unplanned creative spring break. It’s not a sabbatical or a formal PTO strategy—just a self-imposed ritual to step away from the chaos of work and reconnect with what inspires me. I’ve learned that if you’re not in a full-time IC role, making things—especially design—becomes a form of recovery from meeting fatigue and managerial overhead.

This year’s reboot took me to San Diego and Palm Springs, where I spent the week writing, vibe coding, updating my personal site, and binging content—not passively, but actively, taking notes like a student of inspiration. It’s a reminder that creative recovery isn’t idle time; it’s compost for what comes next.

One of the shows I caught up on was Daredevil: Born Again—a reboot of one of my all-time favorite comic book characters. After finishing it, I fell into one of my favorite internet rituals: watching YouTube breakdowns from New Rockstars, Screen Crush, Heavy Spoilers. The algorithm did its thing, and suddenly I was watching clips from the original Daredevil series that aired on Netflix in 2015. Ten years ago. I was living in Capitol Hill, Seattle, designing mobile apps at Black Pixel, deep in my craft.

Pandora’s Box was open. From there, it spiraled into Secret Wars theory videos and MCU reboot rumors. It’s no secret that Marvel is plotting a reset. Though my heart still belongs to the 1984 Secret Wars, the upcoming cinematic version borrows heavily from Jonathan Hickman’s 2015 arc—the one where the multiverse collapses, Doctor Doom ascends, and the patchwork world of Battleworld emerges from the ruins.

As the Marvel multiverse collapses from a series of catastrophic incursions, Doctor Doom seizes godlike power and creates a new patchwork world called Battleworld, where fragments of destroyed realities are stitched together under his rule. Avengers: Secret Wars is set to release in 2027, which is fifteen years after the original Avengers film.

The AI incursion

I was sitting on our couch in Palm Springs, flipping through YouTube clips between the two Coachella weekends—an event I once flew across the country to attend (yes, I was there for Hologram 2Pac). Now, the bands that once headlined my youth are soundtracking ads for minivans and insurance, targeting geriatric millennials like me. I’m 41. Bryan Johnson might argue I’m not getting old, just aging. But let’s be honest—I’m definitely losing my edge. (For the record, the GRS Club cover of that LCD Soundsystem track is still my favorite.)

The hardest part of aging isn’t the number—it’s the creeping sense of irrelevance. That quiet panic when you realize you’re no longer fluent in the tools or jokes shaping the next era. For many of us, the AI incursion feels like that moment. Unlike past hype cycles—remember NFTs?—this one feels different. Real. Fast. Disruptive. Existential.

We’re not just navigating a new wave of tech; we’re dealing with two systemic shocks at once. The AI acceleration is colliding with what feels like the second Great Recession. Around 2023, tech hit a hard reset—blitzscaling gave way to layoffs, cautious capital, and a culture shift. And from that rubble, a new archetype emerged: the vibe coders. A term Andrej Karpathy used to describe the new generation building apps with generative AI—no traditional coding required, just vibes, vision, and a good prompt.

Using generative AI, I had ChatGPT write a satire of Losing My Edge about vibe coders and a millennial trying to keep up with the Gen Z kids:

I’m losing my edge…to the kids with ring lights and one-shot prompts, the ones who ship from Discord DMs and sleep in Notion.

I remember when we wrote our own auth, when you had to beg Heroku for more dynos.

I remember debugging IE6 in Starbucks on airport Wi-Fi.

I remember when product specs were PDFs, when A/B tests took weeks and no one said “vibes.”

I’m losing my edge…to the locked-in Gen Zs with Arc tabs like trading desks, shipping AI agents at 3AM while I’m still writing the brief.

Tech incursions equalize

Millennials, we’re losing our edge. The experience we once relied on—the war stories of scaling, shipping, and staying late to debug—no longer guarantees relevance. The Ruby on Rails apps we built with Twitter Bootstrap and deployed on Heroku? They can now be replicated in a single-shot prompt with generative AI. Even Reid Hoffman, the founder of LinkedIn, used Replit to spin up a clone of the platform he originally built. Just because you can mimic something doesn’t mean you’ve matched its scale or impact—but using that as a reason to dismiss what’s happening is a mistake.

As General Eric Shinseki once said: “If you don’t like change, you’re going to like irrelevance even less.”

The upside of these tech incursions is that they act as great equalizers. They flatten the hierarchy. They don’t care how senior you are or how many portfolio pieces you’ve amassed—they care how quickly you can adapt. Whether you’re just starting out or decades into your career, everyone is trying to figure out how to design with AI while designing for AI.

I’ve seen this pattern before. In my 20s, during the mobile incursion, no one had experience designing for a piece of glass you touched with your fingers. I managed to break into tech because I had mastered Photoshop and could craft rich, skeuomorphic interfaces. In a landscape with no established veterans, everyone was new—and that opened doors.

It’s tempting to push back by saying, “But I have decades of experience.” And sure, experience matters. But relevant experience matters more. I remember a graphic design professor from college—someone who had written books, spoken at conferences, and built a career in print. He refused to teach web design, dismissing it as a fad. That mindset didn’t age well.

There are still strengths that tech incursions can’t displace—understanding customers, navigating complexity, leading teams across disciplines. But we can’t ignore how the craft itself is changing. And if you’re a design leader, your job isn’t just to set direction—it’s to stay close enough to the work to guide your team through the shifts. Because when the ground moves, they’ll need you to be steady and skilled.

Career reboot

As my spring break wraps up, I’m not walking away feeling old—I’m walking away with a sense of clarity: it’s time for a career reboot. Two years ago, I called the tech factory reset. Now, I’m giving myself permission to do the same. A reboot doesn’t mean discarding everything. The valuable experiences, the hard-earned instincts—they reinstall quickly. What I am letting go of are the dependencies and assumptions that no longer serve me. The ones that keep you comfortable but slowly make you obsolete.

I don’t need to be recast as the lead in someone else’s Marvel reboot. I want to play a different role: the bridge between generations, helping to pass the torch—not by clinging to the past, but by staying grounded in it while reaching toward what’s next.

To do that, I’m making a few commitments:

Stay healthy and well. Don’t let burnout rob you of clarity or connection. Take care of your mind, body, and the people who matter.
Keep the craft blade sharp. Return to your roots. Lead through craft. Understand the material of this new era—especially AI. As Nikunj Kothari put it: stop bookmarking, start building.
Invest in the next generation. Mentor. Share your playbook. Let their perspective reshape yours, too.

I was an IC running my own studio when The Avengers hit theaters. Now, fifteen years later, I’m an operator and investor as Secret Wars looms. My 20s were shaped by the Mobile Incursion in Seattle. My 30s, the Blitzscaling Era in San Francisco. And now, in my 40s, I’m back in SF, navigating the AI Incursion.

This isn’t the end of an era. It’s the beginning of another. I don’t feel irrelevant—I feel rebooted. And I’m working on the most relevant things of my career.

Let’s get back to work.

Operator Mode

Sun, 15 Sep 2024 00:00:00 GMT

I love Paul Graham’s writing. Hackers and Painters is one of my favorite books of all time. Graham’s thoughts on art and science resonate with me as a designer who studied fine art. The internet broke when the long-time Silicon Valley investor wrote about Founder Mode. There’s been a shift in tech’s factory reset moment during the past few years. The professional management class is getting slashed with the reduction in workforce and the advancement of AI capabilities. Graham’s essay references a talk by Airbnb CEO Brian Chesky about Founder Mode vs. Manager Mode.

As always, the internet had a lot of opinions that obviously have to be binary and polarizing towards one direction; classic Silicon Valley hopping on bandwagons. My critique is not Graham’s writing. In fact, he’s right. What’s wild to me is management somehow got conflated to professional management consulting. More accurately, it’s BCG Mode, not Manager Mode. Instead of picking sides, I’m going to propose a different mode.

Operator Mode.

While we talk about founders and C-suite professional managers, the majority of people working at companies are operators. Tech loves adopting words from the military. An operator is someone who…well, operates—plans and executes. Above all else, I consider myself a company operator (who comes from a design background). In this issue, I’ll share how I think of my role helping founders in running their companies.

Operators that add value

In my experience, there are two primary regrets founders have. The first is raising too much money that results in higher demands from the board. After that, it’s building a leadership team from a professional management class. Both result in the founder losing control and getting tucked in a corner as a Chief Strategy Officer or an honorary title.

It sucks to see that happen. Instead, founders are better equipped to find operators that add value to their needs. There are three core areas I believe are most valuable for founders: managers with strong craft, expansive experience, and scaling the mission.

1) Craft-oriented managers

The concept of professional managers is the biggest mistake. A professional manager is perceived as someone who is hands off, focuses on administration of management, and a master bullshitter. Trust me, these people exist and it's true. Let me ask you a question. As a designer, how would you feel if the person that has authority over your job has a degree in Design Management but has never been a designer? Imagine an army general who has never seen combat, only studying philosophy and tactics. In my opinion, that's not management.

Most direct reports don't expect their manager to be the best designer on the team, but they need to know that at one point they were in their career. In order to grow in your craft—one of the top performance indicators in every career ladder—you need someone who knows the craft to elevate yours.

Founders don't need professional managers. They need strong craftspeople who know how to manage. From first-line manager to executive, the best managers are the ones who are in the role to scale the craft, not something self-serving.

Whether it's being the founding designer or needing to fill gaps with team churn, the craft-oriented manager has no problem rolling up their sleeves.

2) Expansive experience for the company

An operator brings their experience to expand what the startup is capable of. That is the value of bringing someone in. It might be hiring a sales leader to build out a team as the startup expands into the enterprise. Perhaps the company is about to IPO and needs a CFO who has repeated experience in this. The one thing an experienced operator cannot do when joining a startup is live through the past experience of the company’s existence. This is why expansive experience is the biggest value add for startups growing: helping the founder get to where they want to be.

3) Scales the culture

The last one might be the most important. Operator Mode is scaling the culture of the company, not destroying it. When I decide to join a company, I make sure I’m aligned with the culture and values of the company. It’s impossible to align 100%, but I understand it’s part of my job to scale the culture, so I better be on board with it.

When good operators join companies, they transform the culture for the positive. I only join companies where the culture and mission resonates with me deeply because I feel it's my responsibility to help grow it. I'll never have the same influence as the founder, and that's precisely the point. What's important is for them to have other people they trust to scale the culture, not constantly combat it.

My belief is this doesn't mean to blindly execute without question. In fact, the best mission-driven operators will challenge founders on the hardest parts and hold them accountable.

Leading while in Operator Mode

The goal of an experienced operator is to not be a professional manager. The purpose is to help the founder achieve the vision, hopefully with a desired outcome for everyone at the company. It's difficult to achieve both, but that should be the motivation. Let me share three areas I focus on to help founders and why I think they want me in the first place.

Filling founder gaps

Operator Mode is about filling the gaps of the founder, not replacing them. I remember talking to a former colleague at Replit. One of the main reasons we joined was to work with an inspiring founder like Amjad; give him the amplification (but also counter-balance) to be the best founder possible. The goal is not to silence founders but make them better.

The responsibility in Operator Mode is to find areas you can take over for the founder to be more effective. Most pure founders don’t love managing, and they need managers they can entrust to look over the things they care about. I find the duty of an experienced operator to a founder as a crucial one. Founders have been grinding and putting their heart and soul into their company, and now they entrust you with it.

Scaling the entrepreneurial spirit

When it comes to entrepreneurship at scale, there is nobody who personifies that more than Claire Vo. The CPO of LaunchDarkly's philosophy is that she joins companies to help inject innovation. She reminds teams how to work like a startup and not to be a bureaucratic professional management machine. Vo is in the weeds by reviewing designs, getting into the work, and even building Chat PRD on her own time. Having a leader who builds and stays close to the craft is the only way they can help you grow. I still design, craft prototypes, and conduct research. The only difference is they serve a different purpose: to guide, invoke ideas, and stay sharp with the tools.

Operator Mode is leading in executing your craft

Whether a founder, operator, or executive, the goal is leading towards shared outcomes; fulfilling the mission while leading a great exit. Your craft may come in many forms. It might be design or engineering. It might be business growth or recruiting. Good managers know how to right-size process and scaling. Despite their abundant experience, they’ll start with first principles to devise what’s needed, not blindly run a playbook. The balance of craft and management is why I continue loving Operator Mode.

Originally posted on Proof of Concept

The fog of war of company onboarding

Sun, 21 Jul 2024 00:00:00 GMT

When you start at a new company, onboarding is a crucial phase to get right. The previous three times I’ve onboarded to a new company have been in a leadership role at a company already established. Onboarding is not simply following the artifact your new employer gives you. It’s a two-way street. The higher the role you enter at a new company, the more important it is to onboard to the company well, because you only have one first impression with your new employer and colleagues.

The Fog of War

I describe onboarding as navigating the Fog of War—a game concept. The "Fog of War" in Real-Time Strategy (RTS) games is a game mechanic that conceals portions of the game map from the player until their units explore those areas. This creates an element of uncertainty and strategic depth, as players must scout and gather information about enemy positions and terrain. The concept was first introduced in the game Herzog Zwei, released in 1989. Notable examples of RTS games that have incorporated this mechanic include the Warcraft series, Starcraft, Age of Empires, and my favorite of all-time, Command & Conquer. These games use the Fog of War to enhance the strategic complexity by requiring players to balance exploration, defense, and offense without having complete information about their opponents' actions.

The Fog of War is my metaphor for onboarding to a new company. You start at an empty point, and the onboarding document the company gives you is the game instruction manual. It’s a great resource, but it doesn’t have to be the only one you use to play the game. The natural action might be to clear out the entire Fog of War first to get a full landscape of the map. Just because you haven’t uncovered the Fog of War doesn’t mean things aren’t happening. You have to quickly bridge the gap between expanding what you know and anticipating what might happen.

Capturing all the historical context is an impossible task

It’s important to build context as you join a new company. I advise you to do the traditional listening tours, intro 1:1s, and scout the Fog of War to gain as much insight from the people who lived them directly. However, one mistake I see people make is trying to capture the historical context of the company before taking action. One of the reasons you were brought in is the ability to act quickly with precision.

You are unproven regardless of your experience

Regardless of the experience you bring, you’ll remain unproven until you gain your new team’s trust. Whether it’s a new sailor on a fishing vessel, a free agent joining a new football club, or a squad member in the military, current teams already have a way of working and prior experience working together. Being the new factor on the team means it’s key to find ways to provide value and execute with the team.

My onboarding plan for every company

Even though most companies provide an onboarding doc when you join, you should come up with your own. It’s not because of lack of confidence that the company can do it, but based on your experience, there are likely things you know you want to learn.

First, my onboarding starts at the first interview. Interviewing at companies is not only a way for them to interview you for the role, but for you to interview if they are a good fit. From the first call with the recruiter and hiring manager, I’m already asking questions about the challenges and opportunities coming in. My favorite question is, “What am I getting myself into?” It’s good for both sides to have honest conversations and it results in better satisfaction on both ends. If a company doesn’t disclose any problems, I’m skeptical of why they need me to join.

Conduct desk research about the company. I will be explicit that I don’t like to reach out to people directly in respect of their time. You can learn quite a bit from online research about the company to map out where you might be impactful. A few examples of what you might research are:

Looking up the backgrounds of the people you’d be working with (don’t be a creeper)
Watch YouTube videos of recent company announcements, and my favorite, creators reviewing the product
Sign up for the product and begin understanding the landscape; develop a POV of where it should go. It’s a red flag for me when interviewers don’t even try the product during their candidacy.

Once you join the company, speed run the Fog of War. Get a good sense of what’s important to learn without having it consume your first several weeks. It’s important to onboard well, but equally as important to make an impact. I often tell my team that I start with a lot of assumptions, which are not decisions, but a method to move quickly. However, I’ll refine the assumptions based on the context I learn, including chatting with them. As a new team member, it’s important to share with them what you’re thinking about or what your point of view is, even if you don’t have a definitive determination yet. You can always update your assumptions based on new information.

To understand the boundaries quickly, I navigate the most important parts of the Fog of War seeking:

The biggest areas of risk that need to be acted on immediately.
People and stakeholders not on the onboarding doc handed to you to be familiar with.
Meeting with people who understand the state of the business. Going directly to the CEO, founders, or execs might not be possible due to their schedule. Seek the data scientists, finance folks, and operations.
Advocates and skeptics of your org and what you might need to address

There is likely a reason you were hired and it’s important to emphasize your external value immediately. We might feel cognizant of not wanting to step on toes and assimilate to the new company. However, you were hired to bring your external skill and perspective. Don’t forget that. Since it’s impossible to turn yourself into a tenured employee of the new company, you gain wins by bringing your external value to them immediately. This might be the institutional knowledge you have in an industry or craft. It could be your skill in building teams. Identify that and push hard in those areas.

Successful onboarding is the company’s onboarding + yours

To be abundantly clear, the onboarding your company provides is extremely valuable. Remember to think of it as the game instruction manual. Bring your own knowledge and experience to the table and onboard yourself. For certain roles or company types, the ability to onboard fast and act is key. To recap, my onboarding method is:

Begin onboarding during the interview process
Speed run the Fog of War to build momentum
Be loud and clear about what external value you bring

You only onboard once (YOOO?). The next time you join a company, design your own onboarding to navigate the Fog of War.

Originally posted on Proof of Concept

Choosing a company

Sun, 05 Nov 2023 00:00:00 GMT

This April, I made a big life change and switched companies after nearly four years at the previous one. Every time I say I’m taking a sabbatical, it never happens. One day, I’ll make sure it happens. I took about a week off before advising with Replit, then ultimately joining the company. Many people ask what made me choose the software creation platform over other opportunities I had, and I’ll share with you my framework for choosing.

"What are you optimizing for?" I've asked this question to every person I've interviewed as a hiring manager for the past seven years. "What are you optimizing for?" helps candidates think bigger about what’s important to them in their next opportunity. Though title and comp are important factors, there are more underlying motivations, sometimes not realized by the candidate in conversations. Recruiters or hiring managers should understand candidate needs and work backwards from there.

Answers from candidates may be surprising. It might be a Software Engineer wanting to move into a Technical Product Manager (TPM) or a Product Designer with the desire to make impact in a different industry. Perhaps it is looking for a different pace/cadence in their work life. Take a look at my own notes of my optimization list.

Early stage company building Design/dev tools, Marketplaces, or Creator Economy This might be my last job as an operator. Make it count. Here’s the kicker—I wrote this list before I joined Webflow, not after I left. My optimization list is something I’ve had clarity for several years and not only after I decided to leave. This artifact helps you guide what you’re looking for. What you optimize for doesn’t show up in job descriptions or aggregators. They emerge in conversation. Once you know what you're optimizing for, stack rank priorities.

The three P's

On the Design MBA Podcast, Lattice SVP of Design Jared Erondu spoke about the decision to join Lattice as a founding designer after doing High Resolution. He mentioned three P's for him: People, Purpose, and Pay. Inspired by Erondu (which we all are), I reflected on my own of what a post-Webflow world looked like for me. My stack ranked three P's were Purpose, Product, and People.

Purpose Kimber Lockhart, my first manager and the person who hired me at One Medical, wrote, "Don't create a sense of urgency, foster a sense of purpose." This mantra stuck with me everywhere else I’ve gone. For me, purpose is your life version of being mission-driven.

Work is a big aspect of my life, and it’s the best environment for me to contribute to something meaningful. Purpose in the workplace can be multi-fold. It could be helping build a product that has a positive impact on the world, helping the company scale effectively, or growing humans on the team. My hope is what I contribute to exceeds my own lifetime.

Product If I can’t be excited about the product, I won’t join the company. The product is the artifact that delivers purpose. Regardless of title, compensation, or any other incentives, I will never work at a company where I don't believe in the product or can’t be enthused by developing it. I have no interest in being a Chief Design Officer at a place where material change can’t be made and the product is shitty. I care more about the product and what can be achieved vs. the notoriety of design leadership royalty.

People At first glance, this may be surprising for some that People is the last one in this stack rank. It doesn’t mean I don’t care about people, but if Purpose and Product aren’t right, it doesn’t matter who I work with. There are many people in my career I’d love to work with again or start something with friends, but if it’s not the right company, it doesn’t matter. That said, it’s usually the case I’m working with people at multiple companies that check all three P’s.

I optimize work for working, not making friends. I’m not looking for a family at the workplace; I’m there to achieve something with a team. Through that, many friendships are formed organically; not optimizing for it, but they happen.

Understanding the signals and anti-goals As you have conversations, identify what signals might tell you if a role is a good fit for you. Signals aren’t red flags—they’re factors to help you consider making a decision. One person’s red flag might be another person’s green flag. It all depends on what each person is optimizing for. For example, something I optimize for is working at a company where I know it’s a multi-year effort, not because I want to rest and vest, but because I know it’s going to be a long-term investment. In one of the interviews I had, I mentioned this. The person’s answer was, “Oh, you could be here a year.” That’s when I knew it wasn’t the right fit for me. Again, the opportunity was great and I didn’t view it as a red flag but had the utmost clarity in what I was seeking.

Anti-goals come before signals and are a strong filter before conversations. These aren’t essential, but they help in creating constraints to guide you along the way. A few of the anti-goals I established were:

I do not care about title whatsoever. I’m in a privileged point in my career where it’s no longer important Org size: I’ve led teams 30-40 people before. I knew in a market decimated by layoffs and the rise of AI, orgs would look different and number of people on the team wouldn’t be a measure of success No repeating of “the same job.” I wanted to make sure wherever I ended up presented a new challenge and opportunity for me to grow as a person. Recap Don't spend all your time career planning, but have an idea of what makes sense for you. Like all the good things in life, they happen organically when you’re not trying too hard to make it happen.

Identify what you're optimizing for Establish a priority framework (Note: they don't have to start with the letter P) Understand signals and anti-goals The reflection I ask people who are considering a job change is, "Are you running towards an opportunity or running away from one?" If the place you work at is a dumpster fire and you need to get a new job immediately, then GTFO. However, if what you're running towards isn't clear and the current role you're at is meeting your needs, then create more time. Having this rubric already established made it obvious what the right choice would be.

Originally posted on Proof of Concept

Crafting a leadership portfolio

Sun, 08 Jan 2023 00:00:00 GMT

One of the top questions I get asked is what a portfolio for a manager should look like. Unsurprisingly, the answer is like any design answer: it depends. The ultimate output of a portfolio looks different based on so many factors: whether you're in brand or product, the type of management role, and what you're optimizing for. In this post, we'll look at the goals of a manager’s portfolio, what you are optimizing for, and the core elements of a portfolio. There are a few common artifacts you'll have as a manager: résumé/CV, portfolio deck, and website. The last two might be the combo of your portfolio.

Setting clear portfolio goals

The truth is at some point in your management career you will not need a portfolio! You will be reached out to by recruiters or apply based on your experience and credibility, which is a much harder thing to maintain than a portfolio! You might be optimizing your portfolio for different reasons than looking for a new career opportunity. For example, you might want to get into public speaking at meetups and conferences. The content you show there is going to be much different than what you show in a career portfolio.

A leadership portfolio might not be optimized for looking for work.

What type of role am I looking for?
What size team do I want to take on?
What type of industry/product do I want to work on?
Who do I want to report to?

Questions to ask:

Who is the audience for my portfolio? Is this to attract a potential new role, increase speaking engagements, or network?
What type of leader are you? Do you want to emphasize certain skills? Do you want to eventually lead larger teams? Do you want to stay close to the product and lead that way?

Differences between a portfolio for managers and individual contributors

Depending on the level or the role, you may or may not show the work you directly contributed to. For example, if you're interviewing for a product design manager role at an early startup or at an agency, it's very possible that part of your responsibilities is doing the work. If you're interviewing for a VP of Design role, you won't be showing any pixels you pushed (at least I'd hope not!)

Similarities

Learning about what you're like as a person and working with you
You’ll still have case studies that show business and customer impact

Differences

Your case studies will be more focused on what you put in place to enable teams to do the work
You’ll showcase tools you’ve created, such as 1:1 docs, frameworks, and others
Visualize your process of how you got work done
Though it’s good to show business outcomes as an IC, as a manager, this will be expected in your portfolio

Capturing the content for your portfolio

Building a portfolio takes a lot of time, but you can start capturing data of what you'll put in it as you go along. As a manager, the type of impact you make looks different than when you were an individual contributor (IC). Your IC portfolio is more around your work, process, and craft, and the management portfolio focuses on how you manage towards outcomes leading a group of humans. Keep an Infinite Slide Deck to track your work.

Keep a management journal

Journal your experiences as you’re doing the work. It’ll help you keep track of data and moments you want to share later. Trust me, it’s hard to remember later on. As you keep your journal, capture key metrics you’ll need to remember to tell the story.

Career Management Doc by Jessica Ivins
Hype Doc by David Hoang (inspired by CMD)

Constructing the portfolio

My portfolio is a Keynote deck. You can use anything that can be exported as a PDF you can share. I also highly recommend building a website that will be your digital portfolio. The website can serve as general content and the portfolio deck can be more detailed. You may not want to disclose every single detail of your portfolio online, and that's where a website might serve better to speak to things at a high level. It's common for design managers to have absolutely no portfolio published online.

Platform

I recommend having a website and a presentation deck ready to go. The content does not have to match 1:1 but it’s nice to have a website where you can have a general overview and a deep dive slide portfolio.

Elements of your portfolio

About / your leadership story
Career history
Management philosophy

Management approach and frameworks

A few images and slides on your approach to management. This might include your leadership philosophy, what methodologies you subscribe to, etc.

Work

Company and role overview

Summary of your role (Ex: Head of Product Design at Company A, leading growth, product design, and content design.)

Hierarchy of portfolio

Company-level
Initiative level
Project level

Include

Visuals of early ideation, decision points, and final outcome (credit who worked on it)
Company goal
Core metrics

Case studies are different for managers. Though you’ll show project work (presumably what you did leading your team), the story you tell is slightly different. The core elements are:

Executive summary: What were the business goal and customer opportunities? What processes and frameworks do you put in place to drive outcomes for your team?
How did you manage towards outcomes?
Success metrics you put in place for your team
What did people on your team do?

Build a web presence

This can be a complement to your slide deck. I recommend managers have a website. Elements to include:

About

The section that includes details about you:

Bio: A manager should have a quick bio to give an overview of a career summary. Keep it about two or three paragraphs
Resume or CV: This can be a downloadable PDF
Philosophy and leadership principles: A nice section to share a bit about your approach and philosophy to leadership. This isn't essential though very nice to have

Writing

I recommend that managers have a blog, whether on their personal website, or Medium. Writing articulates what it’d be like to have you as a manager or your philosophy. A few examples of good ones:

https://nlevin.medium.com/inside-figma-the-product-design-teams-process-3897332d8565

Featured

Work: Case studies and portfolio pieces you might want to include online. Be mindful of the company metrics you share publicly in case it's confidential

When you're done building your portfolio, you'll have your about page and at least one case study of a project you led.

Best practices and tips

There is no one-size-fits-all approach for a leadership portfolio. However, here are some tips to keep in mind as you build your portfolio.

Focus on outcomes and impact

Focus on outcomes and impact; present your work at a level higher than you might be used to. Your portfolio will look more like case studies of your time at the company and with your teams vs. individual projects.

Tell the story of the product you impacted during your tenure: what difference did you make in the customer’s journey with that product? Who did it impact? At what scale?
Tell the story of how you impacted the business during your tenure: did you launch a new product? A new business line? Impact revenue or go-to-market?
Tell the story of how you impacted people during your tenure: did your team grow? Did you branch out to hire new disciplines? Did you set up a career ladder and promote? Who were your successes?
Tell the story of how you influenced cross-functional team members -- both at your peer level and up/down. Did you help them understand the customer better? How did design impact their roles and outcomes?

Show what your team did and give them credit

It’s okay to show the work of your team. In fact, you should. However, make sure you give them credit.

Display your IC work somewhere to de-risk

Even as a manager, people want to know you used to be a good designer! I recommend including a few pieces of content around your work when you were an IC. No need to go in detail and include this as part of your overview.

Share what you learned

Part of what people will expect from leadership portfolios is the lessons you learned along the way. It will be more authentic if you talk about the lessons and address the “What would you have done differently?”

Example narratives you can tell

Organizational excellence: example of how you identified a gap in how your team worked and solved it
Leading through changes: How you led and kept your team resilient during challenging times
Creating effective processes
Teams you’ve built
Initiatives that you led
How you evaluate work
How you ensure design quality at scale

Website examples

Mastery for generalists

Sun, 19 Jun 2022 00:00:00 GMT

When I was on the Product team at One Medical, our clinical and Ops teams were critical partners in how we shipped work. It was common to visit the offices to observe (going to gemba). During my four years at the health tech company, I learned about the various roles on clinical teams: primary care providers, registered nurses, care navigators, specialists, phlebotomists, and many more. In my research work, I spent the majority of the time with primary care providers (generalists).

"Why did you decide to be a generalist instead of a specialist?", I'd ask each provider. What compelled them to pursue general care vs. being a specialist? Primary care physicians experience more burnout and specialists make more money. The truth is you make more money as a specialist, so what would compel someone to pursue general care? The answer was consistent: to have a broader range in which to care for their patients' health.

The path for specialists is more clear than generalists. If one chooses the generalist path, what does mastery look like? The notion of mastery as a generalist sounds oxymoronic. Let's challenge that and identify how to grow in your craft in a generalist role. In order to master being a generalist, let's reflect on how to know if you are a generalist, the impact they make, and leveling up as generalist practitioners.

You might be a generalist...

If you grew up in the 90s and are experiencing lower back pain, you may remember comedian Jeff Foxworthy's "You might be a redneck" routine: "If you've been on the television more than five times describing what the tornado sounds like, you might be a redneck." We can remix that and play it back with being a generalist:

If you can't decide if you want to be a product manager, designer, or engineer, you might be a generalist
If you find yourself always wanting to learn new things outside of what you do, you might be a generalist
If you highly enjoy collaborating with every department, you might be a generalist
If you get excited about trying out emerging technology and tools, you might be a generalist
If you get bored by doing one thing, you might be a generalist
If you're comfortable hiring people better than you at everything, you might be a generalist

Generalists are people who love variety, connecting the dots, and are curious. In contrast, specialists usually focus and go deeper on a certain practice. I use the clinical metaphor above a lot when describing generalists and specialists. A brain surgeon could conduct a physical if needed the same way a primary care provider could do certain operations in the case of an emergency. However, based on the level of skill and precision, a specialist is more effective. Every designer can contribute to a design system and having a specialist in design systems will merit in more effective outcomes.

Why be a generalist?

"Jack of all trades, master of none" can sound negative—almost implying one isn't good at anything. Do you ever feel like you don't fit into a specialty? Being a generalist allows flexibility and has broader range in what you can do. This is a great skill for early stage startups when wearing multiple hats is common. As the company grows, it'll specialize at scale, and it makes sense. You don't want your generalist co-founder to continue being responsible for people experience or finance and bring in the specialists. What happens to people when they relinquish the said hats? You're able to freelance and move around more. There might be a new initiative that needs to get spun up. If you're interested in management, many people managers are generalists.

Generalists spark alchemy

In the article "Generalists CEOs Not Specialists Spur Innovation," there is a great excerpt on how generalists spark innovation:

"Under generalist CEOs, companies tend to engage in more 'exploitative' innovation, which involves improving or refining something that already exists, and also more 'exploratory' innovation — that is, engaging in a risky search for radical and transformative innovation. However, the difference between specialist CEOs and generalists is especially pronounced in exploratory innovation."

You don't see many specialist CEOs unless the business does something specific to it. A generalist can start an important initiative and collaborate with specialists to drastically improve it.

Building mastery as a generalist

"Mastery as a generalist" is an oxymoron, but let's embrace the duality. How does one become a better generalist? Great teams need a blend of generalists and specialists.

Be an expert at learning

If there's one specialty a generalist has, it's learning to learn. Build familiarity in a discipline enough to understand the mechanics, develop experience, and when it scales, find a specialist. If you've ever had a manager who understands what you do because they've done it before, they can build more advocacy for the effort of your work. A designer understanding how the software development cycle works can anticipate questions that come up.

Understand every role

Whether as UI Designer, Information Architect, Marketing Designer, Motion Designer, Researcher, or Product Designer, I've worked in dozens of roles. Understanding everyone's roles and responsibilities helps you influence at a higher scale since you have a sense of what everyone is doing. It allows you to give better input and direction.

Build connective skills

Understand how every org works and connecting the dots across them. One of the services I was most passionate about at One Medical was pediatrics and family practice. Whenever I had a coffee break or free time, I'd make time to connect with people who were passionate about that program and ways to support it. Learn how to synthesize, storytell, and connect to the big picture.

Mastering the generalist path means everyone will be better than you at something, but you're better than everyone at every little thing.

Originally posted on Proof of Concept

Being a generalist does not mean the work is shallow. It's right sizing the amount of upskill needed to get the job done. If the path of a generalist resonates with you, continue diversifying your skill portfolio and extend your range.

Keeping an advisory close

Sun, 12 Jun 2022 00:00:00 GMT

Originally posted on Proof of Concept

The investor update is a crucial email sent by startup founders. Every month or quarter (or whatever cadence), founders send a note to all investors to give them updates on metrics, product roadmap, burn rate, etc. I’ve found them exceptionally informative and they also bring a lot of joy in hearing people’s successes. When it comes to your career or life ambitions, I’m a proponent of assembling a personal board of directors—trusted individuals who can give you guidance as you need. For the last few years, I’ve made an effort to keep them informed and updated on my progress—career advisor updates.

I send an annual update to this group to keep them in the loop. Here's how I think about who belongs on your advisory board, why these updates matter, and what to include when you write one.

The advisory roster

Mentors and advisors are crucial supporting characters in your career journey. As you continue moving forward, it’s natural you won’t communicate with them as much as you did. You no longer work with them and people are busy. However, it’s important to foster these relationships along the way. Some ideas of people who might be on your group of advisors:

A former manager
An investor in the startup you worked at
The former colleague you used to work with who you’d like to work with again
Instructors or teachers who made a big impact on your life
Friends who hold you accountable and tell you like it is

The value of sending updates

The best updates are relationship-based vs. not transactional. We've all experienced that icky feeling when someone comes out of the woodwork, wanting to catch up, only to reveal they need a favor from you. This doesn’t feel great. My rule-of-thumb is continually fostering relationships and if there is an ask, it naturally arises.

Email updates to your advisors invoke serendipitous moments. People I’ve managed from years ago on occasion send updates to me when they’re looking for a change. Their message sparks more intention for me to be on the lookout to point them in a direction they might be interested in.

Crafting an update

Let's brainstorm a few places to start if you feel stuck on where to begin.

Start with a personal intro

Start with a human intro and let your advisors know how things are going personally before jumping into business. Update on how life is going and how you’re doing.

Professional wins and challenges from the past year

This is the bulk of the update—a recap you'd give to stakeholders. This advisory group knows you very well and can give you guidance other people cannot. When I write about something I'm struggling with professionally, they tend to come back with a lot of advice that is useful because they know my strengths, weaknesses, and ambitions.

Any requests or asks

They've helped you through your career and likely will continue to do so. For me, it's usually an FYI of something I'm interested in doing and asking them to keep an eye out if there is any serendipitous opportunity. Perhaps it's launching a side project or looking to get into advising.

Share your gratitude

Finally, end it with gratitude—for yourself and them. They've been your backers and don't expect you to thank them. However, it's important to remind them what a spark they've been in your journey. A lot has changed since they were highly involved in your life and it's nice to share where you're developing. I like to mention that I grew in a certain area and how they helped me grow.

A few tips

Though some advisors have become friends, I keep it professional. Here are a few tips and considerations.

Keep it brief: I try to keep my updates to about three paragraphs to keep people in the loop
Don’t spam: You're not growth hacking your advisors. If you're sending from your personal email, BCC everyone to keep it confidential.
Personalize it: There may be instances where you want to add additional context for certain people.

Write a quick update It takes 10 to 15 minutes to draft an email update, select the contacts, and send it. People are busy, and you might not get a reply from your recipients. I guarantee you that they'll read it, and hearing from you will put a smile on their face.

This action to send an update to your advisors might seem obvious to do, but it's often the obvious things we forget to prioritize in life. Send a quick update.