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How I supercharge my work journal with Notion AI
I began a work journal for my Netflix projects one day after starting the job. I update the journal semi-regularly, documenting everything from daily activities, achievements, feedback, and ideas, to priorities, challenges, and visuals such as prototypes or design critiques. The journal has been valuable for documenting my work and reflecting on my experiences and growth. But the integration of Notion AI has taken my work journal to new heights, magnifying its value tenfold. Before I get into details, I'll briefly address the critics and naysayers: Is a work journal in Notion, paired with Notion AI, really all that valuable? Yes. It has exceeded what I imagined possible and helped me summarize my work, generate insights into my behaviors, identify trends, create a strong outline for a future case study, and much more. I use Notion AI in my journal to analyze sentiment across projects, extract themes, highlight frequently mentioned projects, and compile blog posts and case studies. Notion AI has been beneficial in generating insights for self-assessment. Asking the app to "Highlight what strengths the author seems to have, then highlight the areas for improvement" offers an interesting perspective on my work. The natural language processing capabilities of Notion AI enable time-boxed queries and interpretations, making it easier to assess and identify valuable insights. For example, running a prompt like "Summarize the most impactful things I did this year" provides fantastic results. Setting goals for upcoming quarters has become more effective, and summarizing specific work periods, like "the last quarter," saves time while providing a unique way to reflect on past work. At the end of each month, I now ask Notion AI to "Summarize the past month of work entries" for a quick and easy overview of the month's work. Additionally, the AI-generated design case studies based on my journal entries are incredibly accurate and can be enhanced by adding a personal perspective. Asking the AI to "Generate a design focused case study of the most recent project in this journal" returns incredible results. However, asking the AI to then "Make the case study more personal and reflective" amplifies the case study to an exceptional level. While I can't share specific examples due to confidentiality, I wholeheartedly recommend starting a work journal in Notion. After a few months of logging your experiences, thoughts, concerns, ideas, etc., take advantage of the built-in AI. Notion AI can seriously help make sense of your work journal, identify themes, summarize your experience, generate case study outlines, set goals for future projects, and much more.
Using a work journal to create design case studies
Testing
Systems thinking is what makes designers great
I used to believe that what made great designers so great was their craft; their ability to add polish and style to whatever they touched. Now I see that what makes exceptional designers so incredible is not only their attention to detail, but their ability to think holistically about their work. Long ago, I would spend time browsing Dribbble or Behance and admiring the beautiful aesthetics and animations I saw there. I'd look at portfolios of the most stylish, trendy work for everything from logos and websites to app designs and character illustrations. Whenever I encountered something that seemed highly polished, I'd think: "This is great design!" It's easy to view design as making things pretty, as though the presentation of the work is all that matters because that's the thing we can see. For those outside the design world, this is a similar perspective to that of art. We tend to celebrate art for its appearance. Apple famously makes beautiful objects and proudly shows them off as such under the veil of "great design." At some level, this notion that good design is polished craft is true—craft (a delicate process of detail) and visual polish matter significantly in design. But what I've learned over time is that the best designers can think holistic about the work, not just its presentation. They have a keen ability to think and imagine beyond just the design on the screen or canvas. Inexperienced designers tend to think only within the boundaries of what they're making. They've heard that building a deep understanding of what they're making will strengthen it but often narrow their focus, so they fail to understand how putting their work out into the world might break it apart. The design these inexperienced designers create fails to stand up when it encounters someone with a disability or is taken out of context or distorted by size or time. Poor design meets one need while creating a dozen others. Good design resolves problems without negatively affecting anything else in its ecosystem. We call this lens of thinking "systems thinking." It tends to separate the genuinely great designers from the pretty-great ones. The designers who do tremendous work know that what they're creating does not exist within a bubble. They understand that the context of what they're making plays a vital role in how the team should build it. They know how what they create affects everything it touches, particularly the people. The design is intentional. Trade-offs are known, weighted, and decided on. Not only in the immediate problem space but in the surrounding spaces too. If you want to be an average designer: focus on a narrow perspective around whatever you're making. Don't worry about how what you make will affect the industry or the people who use or encounter it in different capacities. Don't worry about those who will have to evolve the design or those who might come after you to tweak it. On the other hand, if you want to be a designer whose impact is beyond a narrow scope: constantly hone your process to consider the range of what—and who—your design work will impact. You can do this in many ways, some of which have been documented in-depth across the Internet. Build out extremes of your work, the most straightforward and complex versions. Not to say you've done it, but to get a feel for what those extremes look or feel like in context. Build always with the intent of sharing your work (even if that's not going to happen). Sharing work early and often might mean leaving ample notes or comments in your working documents if you're on a team. If you're working independently, leave the comments anyway. You never know when you'll have to return to some old work and how quickly statements and well-structured documents can help you reconnect and understand the work. Invite others to provide feedback as often as possible and engage them with questions and curiosities about how their work shapes their perspective of your work. Look at the larger ecosystem your designs need to exist in, and you'll build things that look better (due to consistency and familiarity) and function better. And that's what makes someone a phenomenal designer.
The bridge to Head of Design
Illustration by Raul Gil for this article. Nobody warned me how challenging being the Head of Design at an early-stage startup would be. Then again, nobody warned me how much I would love the challenge. How did I get to this point? The journey started for me over a year ago. I had spent a small part of my earlier career managing a team and after a number of years I found myself longing to get back to that. I wanted to feel again what it’s like to not only design products but also business groups, organizations, and the processes around each. There is no more significant design task than getting a group of people to work together toward a shared objective, growing and evolving as they go. Additionally, I found myself wanting to be in a position much closer to the core business of the work I was doing. I wanted to not only and continue to see design's impact on customers and products, but also get close to the metal and manage how the function of design impacts and influences a business's bottom line. What is the bridge to head of design? As a creator, I feared moving into management would mean missing out on time spent actually designing things. For many designers, moving into management means exactly that: the end of making. Managers tend to miss out on being close to the craft and instead must dedicate their time to helping manage and lead the team. Meetings, managing calendars, presenting work and representing the team, negotiating with executives... I wasn't sure all of that was what I wanted to do with my time as I started exploring my next career move. Then Nick Bushak, CTO and co-founder at Gem, reached out for coffee, and through conversation with him I had a revelation. As a Head of Design I could spend a good year or two in a player-coach position before having to decide which path I'd like to take more long-term. Being Head of Design at an early stage startup often means building and managing a design team from the ground up while also doing the work expected of a very senior individual contributor. You have to do both because both are needed at the early stage and small size of a series b company. As the company grows, the need to balance both managing and designing subsides as new members join the team, eventually pushing the Head of Design into either a senior designer role or focusing on management as a Director of Design. Moving into the role of Head of Design meant I would be tasked with identifying headcount, hiring, defining what the team's purpose is and how we’ll operate, what parts of the product development process design is responsible for, and creating a vision for how we would grow. It also meant I'd have ample opportunities to get my hands into the work because the design team would be small early on, but the work required of us would be plentiful. I'd be not only a coach for the team but a player too. Of course, a Head of Anything in a startup faces obstacles and issues you don't get if you are only an individual contributor or a manager. At the bridge between both manager and individual contributor roles, you face challenges at both ends. If you’re acting as both manager and designer, how do you know when to focus on team building and processes as opposed to focusing on the craft itself? How do you show up to lead and manage the team when you're also spending a reasonable amount of time showing up as a designer too? Where do you draw the line at being a partner to your team and their manager? Possibly most important: how do you help others on the team (the design team and the leadership team) understand what to expect of you if you're constantly doing both leading and designing? To answer these questions I did three things immediately upon joining the team at gem: Set out to define what matters most to me as a leader Sought to understand what matters to the company in a leader Sat down for 30 minutes with every single person in the company to learn of their perspective on design, the most pressing needs as they saw it, and what they wish design would tackle first As part of a Stanford class on leadership, I outlined my leadership values (what my team and peers can expect from me as someone guiding a function in the company) before starting the role. I then created an outline of how I see the design team role functioning, based on early conversations with other design leaders I had developed connections with over the past few years. Alongside guidance from my manager, Nick, I was able to identify where I should spend my time and draw lines between the tasks ahead of me as a new Head of Design. (I also found this article from McKinsey to be very helpful.) Each of these things helped set expectations around the role for both myself and the broader company. Crossing means expanding and refining skills Moving across the chasm between individual contributor (or IC) design and management meant facing many skills and problem areas I never had to think really, truly, deeply about before. Things like: How should a design team be structured? What roles does the team need inside the company to be most effective? What's the right time to bring in specialists vs. hiring for generalists? How do finance and talent teams play a part in the planning of a team? How do you negotiate the importance of a role on the team? How do you find and source high-quality design candidates to join the team this early in its formation? (Product plug here, because Gem is making this process a little easier!) What work is most pressing for design, and what work can wait? What will help the business achieve its immediate goals, and how will that work be prioritized against more long-term investments in user experience? As a result of some of these questions, I started the job at Gem by focusing my time on two core areas: 1. Capitalizing on immediate design wins Immediate wins for the company were easy enough to tackle as a former IC designer. I spent a few weeks up-front auditing the entire product, talking with every member of the company, and working directly with customers to understand what design work needed to be done right away. I asked: what could help demonstrate the value of design to the company while getting me familiar with the product, customers, and culture? Within a few weeks, I had shipped minor but readily apparent changes to the product and begun shaping processes around the role of design as a function. 2. Preparing design to scale and create business influence Scaling a design team was a new space for me to work in. I never had to think about building and scaling a design team as an IC. As such, I relied on external resources and help from other design leaders in the industry to spotlight the skills I would either need to improve in or learn for the firs time. Amongst the skills I identified: Business strategy: How does our product solve real needs in the market, how are we growing our presence in the industry, what are our strengths and areas of opportunity as a business? How do we establish ourselves as leaders and convert that presence to dollars? What is design's responsibility for each of these things? Organization building: How do we get the most benefit from a team of people? How do we align business objectives with team structure and career planning for individuals? How do you hire designers for a rapidly growing company? Communication, negotiation and product strategy: Three skills not only belonging to managers, but skills I hadn't needed to become truly an expert in previously (as my peers in engineering, product management, and design leadership could fill in my gaps for me as an IC). Most helpful for me during this time of identifying skill gaps was having a personal "board of directors" I could reach out to. Whenever I encountered a challenging situation or whenever I'm unclear about something as it relates to my role, having this close group of people I can seek guidance from has been rewarding. Being in a Head role can be overwhelming and leave you feeling like you're on the verge of failing at any moment. There’s so much to be done and only one you. Having a small group of peers who have done the role successfully before can be all the support and inspiration you need to stay afloat. First brought up for me during the DesignX State of Leadership panel. The idea is simple enough: Find people in the industry who have successfully done what you're doing now Build a close connection with them Regularly meet with them to glean insights from their experience Surprisingly, not a single design leader I have reached out to over the past year has declined time to chat. Many of those conversations have grown into regularly recurring catch-up calls. Without this personal board of directors, I'm not sure I could survive the dynamic world of a fast-paced startup, let alone the role of attempting to cross between management with designing at the same time. What it means to grow a design practice As many of the people the design team works with at Gem haven't worked with a product designer one-on-one before, I found it essential to live our company value of transparency and make the design process as straightforward and clear as possible to everyone in the company. This emphasis on working transparently is great because it aligns with my personal values as a creator and leader. Early on at the company I started hosting weekly, hour long, Design Reviews on Fridays, inviting everyone in the company to attend and see a bit of my work process. The company at this stage was very interested in the topic, and I found upwards of 90% of the company would regularly attend these virtual meetings to see what this new “design” function was all about. Over time as the design team has grown, I've pushed for us to continue this practice of transparency in other ways. As a design team, we share work daily in Slack. We host Design Reviews each month for discussion with anyone in the company who wants to attend. We also host weekly Open Office Hours for anyone in the company to ask questions and work with us collaboratively—in real-time—on problems. These things have helped connect design to the business and demonstrate how our function does much more than just turn an ugly screen into something pretty. Scaling the team and lessons learned thus far One of the biggest focus areas in my role is thinking about how the design team will scale inside the company. Kristin Skinner and Peter Merholz wrote a book on designing the design organization in a company, in which they outline a time-tested process for building and scaling a team. The book, aptly titled Org Design for Design Orgs, is an excellent reference and helpful guide for any organizational leader who needs to understand how design might scale in their company. Though the book is a good reference, it's also relatively generic and requires deep thinking into what your specific company might need as it scales. For Gem, this meant looking at the company size, product-market fit, and investment in the product itself. As I thought about building the team, I landed on hiring strong design generalists first, then scaling to include specialists (across design functions like writing, research, motion, and interaction design) later. By focusing on generalists out of the gate, our small team could work in a scrappy way to accomplish whatever needs to get done quickly. The outputs of this small group’s work may not be ideal or perfect, but when it comes to a startup, done really is better than perfect. If you’re not moving quickly—producing work, snuffing out fires, and focusing on scaling—the competition is always there in the wings waiting for their chance in the spotlight. Design generalists are exceptional at moving quickly, no matter the task. During the first few months at the company, I also learned just how difficult hiring can be. I've participated in interviews before, but have never been responsible for defining an open role, writing the job post, creating a rubric for evaluating designers, and putting together an interview guide. When it comes to hiring, that's not all: during the first few months of looking to hire designers, I had to actively reach out to potentially strong candidates and show them why joining a small, early team like Gem design was a good move, even though externally it can seem very risky as a career move. It’s a hard sell for many designers who cherish stability and certainty over the potential reward of being an early leader at a growing company. General wisdom when it comes to hiring is to go with who you know. Close connections—the people you have worked with before—are easier to hire for and more reliable in the long-term but also introduce a ton of bias. I knew from the start I wanted to build a diverse team of designers from many different backgrounds and expertise areas, not just from my network of former colleagues at big tech companies like Facebook and Lyft. So, after countless months of talking with designers, reviewing portfolios, calibrating the hiring team, making offers only to have them declined for various reasons, we landed two incredible designers within my first eight months on the job. Melinda Kilner and Wandi Liu joined the team, and each has contributed heavily to the overall makeup of how we work and what it means to be a team. I could not be more thrilled with both of these designers and the work we’re doing together to build the foundations of what will inevitably be a truly world-class design team. If you’re hiring designers you can’t be afraid to hire from smaller companies than the big FAANG ones. You should look for designers with strong processes, adaptability, creativity, and grit. You may be surprised what you find when you give a conversation a chance. Of course, having such great designers on the team has meant my perspective of leading them has evolved as we continue working together and scaling the team. When we say "head" of the team, I now view that as helping to gently nudge decisions, demonstrate practices and processes, and provoking meaningful discourse and debate for both the team and individuals on it. I've learned an incredible amount in this role already. I've learned about startups and how to both show up and not show up as a leader (those messages you send on Slack intended to be witty and humorous, for example, tend to have a different punch when you’re a leader). I've learned about the way design can subtly influence decisions inside and outside the company (a vision workshop can be helpful for driving vision, but only if it’s regularly referenced). More than anything: I've learned I made the right decision bridging the gap between IC and manager. Because in this role, I've discovered my passion for getting to know the individuals I work with so closely daily. I've uncovered just how incredible (and incredibly hard) it can be to get people aligned and doing great work. I’ve learned from my team, and I’ve seen the mistakes I’ve made in the past as an IC designer. I’ve grown a lot, partially out of ambition but probably more so out of necessity. I now wake up every day both excited and anxious for what the day holds for me in this role. Where will I fall short? What new obstacle will I uncover and have to maneuver around? Am I making the right decisions for my team and the company? Am I contributing in a way that is helping move the bottom line? Is this road going to be one I want to stay on for a long while? Only time will tell. For now, I'm loving it all. The challenges and opportunities.
What to do about ambiguous design problems
Illustration by Simina Popescu for this article. How do you approach a problem that has no definition, not even a hypothesis? How do you walk into a room of talented and experienced cross-functional peers—engineers, product managers, customer success managers—and guide them through problem identification and solution brainstorming… when you yourself have no idea of what’s to come? As product designers grow in their careers we are tasked with taking on more complexity and ambiguous problems. We find ourselves in situations where our job is to help others envision and explore a complex and often poorly defined landscape. If you’re just starting out in your career as a designer, you will likely be tasked with feature-level or already clearly defined problems: improving the information hierarchy of a screen or finding a way to grow interactions on a particular button. As you progress in your design career—improving skills and understanding of how design plays a part in digital products getting made as well as how they become successful—you may be tasked with more ambitious and ambiguous challenges: researching and synthesizing ideas around expanding the business, leading a organization-wide usability effort, or dramatically improving the usability of several broad feature areas of the product (or the entire product itself). At some point a senior designer may decide to continue and work on the product side of things or they might decide to transition to a new type of problem: managing and leading a team. Team problems are very much like ambiguous, multi-faceted product problems: in that they consist of many moving parts that you, as a leader, need to figure out how to help work effectively together. In either case, the challenges ahead will be fraught with ambiguity and uncertainty. Others on the team will be looking to you, as the designer, to help lead them forward. Progressing to a point in your career where you have the trust and skills necessary to be held accountable for, know how to approach, and successfully navigate, very large, ambiguous problems (team or product related) can be stressful and often frightening. Particularly if you’ve never done that type of work before. I’ve talked with quite a few designers over the course of my career who find the challenge of growing through ambiguous problems almost overwhelming. How do you approach ambiguous problems? You start. With what you have now, however you can. When faced with uncertainty and ambiguity, starting is a powerful way of creating definition. A step in any direction is a step forward. Even if you come to learn the direction you’re heading in is the wrong one, you’ll have learned something tangible. That learning is far more valuable than not moving and not learning. As Lewis Carroll famously wrote in Alice’s Adventures in Wonderland: "If you don't know where you are going, any road will get you there." Of course, the alternative is to wait, to research, to plan before you start off in a direction. That’s a direction worth considering, often worth taking. But the way to even do that is to first set off in a direction, to take a chance on some question, some idea, some hypothesis. Movement is what matters most at the start of any endeavor. Often we fear that if we make a wrong choice—if we ask the wrong questions or head off in the wrong direction—we’ll be viewed as a failure. But most decisions can be turned around. Most directions can be informative, even when they turn out to be wrong. As designers, we’re often best suited for rapid adaptation, keen awareness of user needs and problems, and ideating through solutions. When others around us are paralyzed by uncertainty, we can take it on ourselves to take that first step, wrong or right, and help guide our team forward. Define a list of what you know and what you don’t know, create a document of questions and hypotheses, audit competitors, start a conversation with any customers who will make time for you, drawing out low-fidelity maps of existing experiences... When faced with an ambiguous design problem, the best thing you can do is anything. There is no right or best way to move forward, there is only action and inaction.
Defining your own career path
Illustration by Mariah Barnaby-Norris for this article. "If you want to be a better contributor to the human condition, you have to understand that the most powerful thing you can be is yourself.” — James Victore At some point in your career as a designer you might find yourself asking some hard-to-answer questions. Questions along the lines of: "should I learn to code?” and "even if I wanted to learn to code, what language should I focus on between Python, Swift, Kotlin, Java, Javascript, TypeScript, Ruby, C, or something else?” You'll probably end up asking questions about industry and craft too, questions like: "Should I focus my work in blockchain or self-driving cars or virtual reality?” Or "Should I focus on visual design or interaction? Should I host my portfolio on Instagram or Behance or Dribbble or a custom hosted website? Should I start a YouTube channel to grow my reputation? Should I be using TikTok for growing my network? Should I be concerned with neumorphism… is that even a real thing?” For all the questions we find ourselves asking over the span of our careers I have come to learn the only truly appropriate response to each is: it depends. Experienced designers love to use "it depends” as a response to questions because the reality of the world we live in is there is no definitive answer to anything. There are only appropriate answers to questions as dependent on things like context, needs, constraints, and resources. To quote Albert Camus from his essay The Myth of Sisyphus: "There are truths but no truth.” Because the answer to any of the career questions we face is inevitably "it depends” we are then led to ask ourselves what our personal, individual answer would, in-fact, depend on. And in my experience there is really only one dependency to keep in mind when it comes to the work you do and how you do it: who is it you want to be? That's it. That's the top of the hierarchy of career questions in terms of what's going get you the most return on investment. Who do you want to be? Such a critical question often leaves those it's asked of paralyzed with indecision. Unless you already have a clear vision of who it is you want to be, how do you even begin to conceptualize who it is you could be? Faced with this existential mirror of defining who we want to be, we turn to the world outside ourselves in hopes of uncovering inspiration. We convince ourselves that anything that might help us answer the most important question about ourselves is de-facto "good.” We look to others in places like Instagram, YouTube, Twitter, and Dribbble, for inspiration. Each corner of the Internet rife with small nudges of who we might possibly want to become in our career. Yet what we see through these channels are not realistic versions of anyone or any career; they're each meticulously curated feeds of idealized realities, not reality itself. The work posted by designers to Dribbble is rarely, if ever, real work. Instagram is famously where people go to share altered images of their otherwise imperfect lives and careers. The thing about looking to the Internet for inspiration is that it's all just carefully curated, manipulated, and intelligently selected thoughts and images of a fake world nobody lives in. So here we find ourselves in pursuit of the unrealistic, overly trendy, and ultimately foolish. Many who go down this route often end up being unhappy with themselves and their decisions. And, again, it's no wonder why: when we look to the Internet for inspiration for our careers what we're really doing is looking at a made-up reality nobody could ever live in. We inevitably end back right where we started: uncertain of who it is we want to be. The reality is that in listening to these digital sirens we not only betray ourselves and who we really are, we deprive the world of something it greatly needs: our true selves. By trying to pursue interests that are not our own—but instead belong to the algorithms and celebrities of the digital realm—we deprive the world of our real, true selves. Our authentic, wacky and weird, sometimes broken, often afraid, selves. This is a hard lesson to learn, but it's true. It's taken me a good decade to come to the realization that I'm valued not because I follow some trends or because I work in a specific industry. I'm valued in my work because I'm wholly, authentically, weirdly, me. If you find yourself pursuing trends, you're going to be disappointed when they fall short of expectations or otherwise don't pan out. If you're pursuing the career path someone else has taken, you're going to be frustrated when you don't get the same opportunities they did. If you want to define a life that makes you excited to wake up every morning, that challenges you and propels you to stand out from others, that gives you a long-lasting and fulfilling life of work, the way to do that is to focus not on externalities, but to focus inward on yourself. The solution to defining your career is to create it for yourself. Through experimentation, play, and yes: failure. Do not worry what others will say or think or whether you'll get more likes on your Instagram story one way or the other. Discover who you are, who you really are, by experimenting, by making things (including mistakes, as long as their mistakes on your own terms and not somebody else's). Start side projects, not because they'll turn into a billion dollar business but because you are curious about how to to do the work. Go to local events in industries you're curious about, not because they're trendy but because you have a passion for what goes on there. Design in the styles and with the foundations you grok best, because that's what's going to set you up for success down the road. In discovering and embracing your true self you will find some people won't like that version of you. Some people will be afraid, will talk down to you, or even blatantly reject you. That's ok. The world is an extremely big place and thanks to the Internet we're more connected than ever before. If you be who you really are what you'll find is others like you will inevitably connect with you. Then all the haters simply won't matter any more. Worry more about moving and less about where to place your feet. That's how you create value for the world and happiness for yourself.
