Ride of a Lifetime is an excellent book by Bob Iger, who led Disney for fifteen years. I heard about the book from Bill Gate's <a href="https://www.gatesnotes.com/About-Bill-Gates/Summer-Books-2020">2020 reading list</a>, where Gates called it "one of the best business books I've read in several years."
The book touches on culture, personal relationships, and organizational design through an unusual lens of mergers and acquisitions. Disney's purchase and subsequent integration of Pixar is regarded as the gold standard for not killing culture during an acquisition. If you're interested in other book recommendations, check out my <a href="/reading-list">reading list</a>.
In this post, I want to focus on my favorite passage in the book around giving feedback to creatives.
<h3>Don't Start Negative and Don't Start Small</h3>
<blockquote>
Don't start negatively and don't start small. People will often focus on little details as a way of masking a lack of any clear, coherent, big thoughts. If you start petty, you seem petty.
</blockquote>
Don't start negative. When giving feedback on a project, Iger reminds us to be mindful of how much someone has poured themselves into the project and how much is at stake for them. Project leads are fully committed to a project, and their current impact, recognition, and career growth are all attached to this single contribution. This level of investment makes negative drive-by comments from leadership exceedingly unproductive. These remarks leave the recipients deflated (flight) or frustrated (fight) and overall unmotivated to do their best work.
Don't start small. This is the most common feedback trap I see. Small feedback takes little effort and feels useful even when it's only minimally so. The number of times I've seen code reviews and design walk-throughs suffer from small feedback is countless, and as is the number of times I authored that feedback. Iger points out that small feedback is so prevalent because big feedback requires work and thoughtfulness. It takes effort to consider the whole, identify its merit and gaps, and package that feedback in a clear and coherent form. This approach to feedback goes beyond changing our communication and instead invites us to participate more deeply in this aspect of our work. Coherent communication comes from clear thinking, and clear thinking comes from thorough consideration.
<h3>Conclusion</h3>
To put Iger's quote another way: Start positive and start big. Don't focus on the little detail but instead come up with big thoughts that are clear and coherent. If you start thoughtful, you'll seem thoughtful.
<hr>
No post about feedback and criticism is complete without including this <a href="http://www.youtube.com/watch?v=Ih6jcKd7VwU">wisdom from Ego</a>.
<img src="/images/bookCovers/ride-of-a-lifetime.jpeg" alt="Figma">

Feedback advice from Disney's CEO Bob Iger

Bob Iger's Feedback Advice

I was recently asked to share my perspective on missional work with a candidate, and this is what I wrote. The content was lightly edited for blog format.
<hr>
I also wanted to share some of my thoughts on doing missional work since this is a strong consideration for you. I've spent significant time in the past ten years thinking about technology and how it intersects with social &#x26; civic good. I've worked at a civic startup, chatted with several ed-tech and health-tech companies, and have volunteered significant time at local and international NGOs. I don't say these things as proof that I'm an expert but just to show that it's been an area of interest for me.
I will start by saying this: if there's a missional company or organization out there doing effective work in a specific area you've been passionate about, then you should join them! Life is short, and our professional years are even shorter, and these opportunities don't come up often. However, I've come to find that fit is essential and that often it's not there. Sometimes the company was in a missional space but not be very missional themselves. Or they weren't very effective at bringing about the change desired. Or my own passions were only adjacently related to what the company was doing (e.g., I might have cared about making healthcare more affordable, and the company was helping patients find better experts).
In these cases, I've found that simply working at these companies wouldn't be very fulfilling. In fact, sometimes, it was downright frustrating. I've had many conversations with people who were disappointed after joining a missional company only to find out that the company was more worried about growth, engagement, and revenue (as companies do). They felt deceived by recruiters and leaders who touted the mission to close the candidate but never mentioned it again once they started working there. The disappointment was especially acute when joining these companies came at the cost of other opportunities that had higher compensation or career growth.
So what does that mean? Is there no opportunity to do work that feels meaningful and impactful? I think there is and that this type of work exists in more places than we expect. For me, it came down to: unambiguous positive impact, long-term thinking, and making a positive difference on those around me.
Unambiguous positive impact: Impact can be unambiguously positive even if the work isn't in a recognized missional field. This is what draws me to building tools. Building great products that help others create, craft, and produce is a great outcome.
Long-term thinking: My goal is to maximize my overall impact over my lifetime. Which is different than maximizing my impact at any given time. Sometimes it's worth taking on an opportunity where I might have a less immediate impact but will get a chance to grow my skill set. This can prepare me to take on a more significant role with higher impact once the right opportunity presents itself.
Make a positive difference in those around me: "if you want to help other people, be a manager. If done well, management is among the most noble of professions. You are in a position where you have eight or ten hours every day from every person who works for you. You have the opportunity to frame each person's work so that, at the end of every day, your employees will go home...living a life filled with motivators." This is an excerpt from Clay Christensen's How Will You Measure Your Life (checkout my <a href="/reading-list">reading list</a>). I very much believe in this principle. It has often guided me towards companies where the culture, values, and people encourage me towards this mindset and challenge me to do better every day!
This is a personal evolving perspective that changes year by year. I wanted to share its current state in case it was helpful to you. Deep consideration of the impact of our work on this world has been one of the most rewarding areas of my career and led me to meet some great people who shared similar questions. I would love to hear your perspective if you're open to sharing!

Personal thoughts on how to think about missional work and impact

On Missional Work

I’ve been meaning to write this post for the past year and a half. It’s taken this long in part due to 2020 but also because I wanted to wait until the rose-tinted glasses of starting at a new job faded to a more objective hue. Though company fit is personal, I want to share why I joined Figma, hoping it will resonate with some readers and help them make their own decisions.
<h2>Build a great product</h2>
Some companies are successful because of their product, and others are successful despite their products. I was definitely looking for the former.
In the past, you would hear people criticize browser-based applications by cheekily asking: What about Photoshop? No one could imagine an application as complex and resource-intensive as Photoshop running well on a browser. And then ta-da! Figma happened.
As I learned more about Figma through the interview process, it became clear that the company was obsessed with building a great product. They thought deeply about the user’s problems and came up with elegant solutions. They weren’t afraid to sweat the details and pushed the boundaries of performance.
The results speak for themselves. It’s unreal how many designer friends told me how much they liked the product and how I “just had to go work at Figma.” I can’t think of any other widely used tool that still retains such a high level of fandom.
However, building a great product isn’t enough. I was also looking for one…
<h2>… that’s differentiated on its technology</h2>
I’ve been in countless conversations with engineers who loved their team and the product they were building. Overall, they were happy with their work situation except for a deal-breaker: there was no growth opportunity.
Many of these engineers switched to platform teams because product engineering work can often be repetitive and shallow. Many products are at their heart CRUD applications, and there’s nothing wrong with that. Still, it can leave ambitious developers frustrated that their impact doesn’t translate into personal growth.
I believe that the most effective way to minimize this phenomenon is to work on technical products. These products are differentiated on their technical implementation, and therefore more of the product development involves overcoming technical challenges.
Even though Figma (the company) builds design tools, both founders were developers, and that is no accident. The two most recognizable things about the Figma editor are that it supports concurrent editing and runs in the browser, and these are both technical challenges. Figma engineering frequently tackles complex problems around graphics, browser performance, event synchronization, and data format. It makes for a non-boring <a href="https://www.figma.com/blog/section/engineering/">engineering blog</a>.
Personally, I’ve gotten the opportunity to help optimize <a href="https://www.figma.com/blog/improving-scrolling-comments-in-figma/">React to 60fps</a> and build <a href="https://twitter.com/figmadesign/status/1447964299570393088">branching &#x26; merging</a> for design files from scratch.
Figma’s trajectory reminds me of the Innovator’s Dilemma by Clay Christensen:
<blockquote>
Disruptive technologies bring to a market a very different value proposition than had been available previously. Generally, disruptive technologies underperform established products in mainstream markets. But they have other features that a few fringe (and generally new) customers value. Products based on disruptive technologies are typically cheaper, simpler, smaller, and, frequently, more convenient to use.
</blockquote>
Though initially, a browser-based design editor underperformed compared to native solutions, its innovative technical approach meant that it was lighter-weight, more accessible, and easier to use. It could also support collaboration flows that were virtually impossible to do for a native application. As Figma started to get more and more parity to the incumbents in functionality and performance, it became the tool of choice for even the power users at the largest tech companies. This is how Figma disrupted the design tool space so completely.
However, there was one more thing I was looking for in addition to building a great product that was technically differentiated. That is to build it…
<h2>… with great people</h2>
Much has been said about how impactful our work environment is on our own personal satisfaction. We often spend more hours talking with our coworkers than we do with some of our closest friends. So it’s crucial to find a great group of people who inspire you and spark joy.
More specifically, I’ve found that some of the best engineering teams with the brightest people trend towards cynicism. Engineers are by nature skeptics, and engineering orgs can inadvertently foster a culture that is quick to criticize new ideas. This ultimately leads to an unsafe work environment where people gossip behind each other’s back and question abilities, motives, and intentions.
Figma has a distinctively warm culture that is biased towards support and empathy. It’s vibrant and energetic and sometimes a <a href="https://www.youtube.com/watch?v=iQFDDbRkUaA">little quirky</a>, and it brings together a diverse set of people of all backgrounds and interests. It does it all while maintaining a fiercely competitive spirit and incredible execution.
<h2>In Conclusion</h2>
Build a great product… that’s differentiated on its technology…with great people.
<a href="https://www.figma.com/careers/">If you're interested...</a>
<img src="/images/posts/figma.png" alt="Figma">

A post on why I chose to join Figma engineering and why you should too!

Work Somewhere Great: Why I Joined Figma Engineering

Since you graduated college, you’ve been on a steep growth trajectory, getting promoted every couple of years. However, in the last few years, things have taken a turn for the worse. You don’t feel like you’re learning as much, and no one will spell out what you need to do to get your next promotion. You tried to switch your team, manager, and company, but it didn’t help. Your team and peers seem to like and respect you. Even though you’re not the best person in this role, you would put yourself in the top 5%. What’s wrong with your career?
I’ve been versions of the paragraph above a few times in my career. I found myself in a place where I wasn’t necessarily failing, but I wasn’t growing either, and I didn’t know how to get unstuck. In this post, we’ll be going over <a href="https://sfelc.com/speaker/wade-chambers">Wade Chamber’s</a> talk on <a href="https://sfelc.com/videos/debugging-your-career-how-to-increase-your-ability-to-win-as-a-manager-by-wade-chambers">Debugging Your Career</a> that he gave at ELC Summit 2020.
Wade guides us through how to go from the oblivious state of unconscious incompetence to the mastery state of unconscious competence.
<img src="/images/posts/competence.jpeg" alt="Competence">
<h2>Oblivious: The Peter principle and why people fail</h2>
<blockquote>
Peter Principle: People in a hierarchy tend to rise to their “level of incompetence
</blockquote>
We start our journey in unconscious incompetence. In this phase, not only do we not have the skills required to be successful at our role, but we’re often not even aware of it. Our significant blind spots lead us to have an overly inflated assessment of our own work.
A study done at two bay area tech companies found that about 37% of software engineers rated themselves in the top 5% of skill and quality of work in the company. That’s right, almost one-third of the engineering team thought they were crushing it and were likely confused by why they weren’t getting recognized for it.
These blind spots are partly due to the Peter Principle, which states that people in a hierarchy tend to rise to their “level of incompetence.” The Peter Principle often gets brought up in gossipy discussions about senior leadership, but that misses its most significant implication: most people in a hierarchy are at their “level of incompetence.” This phenomenon is not limited to senior leadership, and it likely also includes you.
This doesn’t mean that you’re a failure and undeserving of the position that you currently hold. It’s usually quite the opposite. You likely had a track record of success which led someone to bet on you and entrust you with even more responsibility. But at some point, your new role required behaviors and competencies that you didn’t have; and even worse, you couldn’t see that you needed them.
I asked Wade to walk us through common challenges faced by engineers and managers at different career milestones.
<h3>senior -> staff engineers</h3>
Assuming that their technical chops will carry them to the next level: Most engineers arrived at the senior role by solving technical problems of increasing size and complexity. However, larger problems are more likely to span multiple teams or organizations. These projects end up stalling due to a lack of momentum or organizational buy-in. The senior engineer will double down on flexing their technical muscle, oblivious to the fact that interpersonal skills are the hindering factor.
Overly reliant on pattern matching: Another failure mode for senior engineers is not thinking critically enough about the problem. They shortcut to using associate thinking to get to default answers. This type of thinking was enough when they were only expected to contribute to technical conversations, but it’s not sufficient when they are on the hook to get to the best solution.
<h3>first-line managers → second-line managers</h3>
Not starting from desired outcome: First-line managers are great at building individual connections and growing people. That skill allows them to create a high-performing team with high output that generates value for the company (team → output → value).
However, second-line managers need to flip the direction of that thinking. They should start with what the company needs and work backward towards what outcome the team needs to generate and have that dictate what team or individual changes need to happen (value → output → team).
<h2>Struggling: Identifying the gaps that are holding you back</h2>
<blockquote>
It’s impossible for a person to begin to learn what they think they already know.
<ul>
<li>Epictetus</li>
</ul>
</blockquote>
We’ve gone over unconscious incompetence and why it’s so common for people to be oblivious to why they aren’t growing. The next step is to arrive at conscious incompetence, where we still have a lot of gaps in our skillset, but we’re at least aware of what they are.
It’s tempting to skip this step because you feel like you know what you’re not good at. But not all gaps are created equal, and focusing on the wrong ones will see most of your efforts wasted. 
Why do we fail to identify the correct gaps? Most of us employ a passive strategy of gap identification. We wait for a failed project or critical feedback to hit us in the face, and then we go: “Aha! This is what I’ll work on!” However, this reactive approach to self-improvement rarely leads to focus on the essential things (just the loudest ones), and its shortcomings become more acute the more senior you are.
I fell into this trap the first time someone gave me their two-week notice. A manager always remembers their first churn, and mine happened during a walking one on one. The notice came with a long list of things that I could have personally done better to retain this individual. I immediately swarmed the problem and spent the new few weeks investing in and successfully improving each person’s relationships and engagement in my team. To my surprise, when my manager found out, he thought I was wasting my time. From his perspective, the team’s engagement had always been excellent; instead, I needed to focus on reducing the regressions going out with every release.
It wasn’t that the team’s engagement wasn’t important (it was); it just wasn’t what was actively holding the team (and me) back. My failure to actively look for gaps caused me to jump onto the first one that presented itself.
<h3>How do we identify the gaps that matter?</h3>
Before you lock yourself in a cabin in the woods and beautiful-mind all your faults on a wall, here are a few questions that you should consider instead:
What makes you angry, frustrated, nervous or anxious?
The things that make you uncomfortable are often an indication of an area where there’s a lot of friction, outcomes are subpar, or you aren’t confident about your ability to deliver. Following that thread will often lead to a set of gaps in your belief, behaviors, or competencies.
How can you 2x your output in a year?
If you had to double your personal output in a year, what would you do? What behavior or competencies are holding you back from producing more, having more responsibility, and delivering more impact? If you are in a leadership position (management or IC), how can you help the team 2x its output in a year? Are there ways to tighten up existing execution? Or is a significant shift in people, process, or culture necessary.
Who is the best person you know who is amazing at this role?
Is there someone who is absolutely amazing at this role? What are they doing? What makes them great?
Don’t just settle for someone good; instead, find someone who sets the bar! What are the behaviors and competencies that causally make them great? It’s worth emphasizing that what you’re looking for are the causal factors that make them successful and not just any skill they might be good at. An excellent way to find out is often to talk to them about it or find multiple people that are successful at the role and see what they have in common.
It’s tempting to go through this gap analysis alone, after-all, it’s uncomfortable to let others into our shortcomings. However, you can learn a lot about your gaps from an outside perspective; and the best outside perspective on the subject is your current manager.
Involving your manager gives you two benefits:
<ul>
<li>Perspective: Their familiarity with your work puts them in a great position to see your blind spots.</li>
<li>Support: The very act of involving your manager primes them to give you better and more frequent feedback and access to opportunities.</li>
</ul>
This is one of the many reasons to actively build a strong relationship with your manager, one that is characterized by trust and safety. It makes vulnerable conversations about weaknesses not only possible but welcoming.
<h2>Practiced: From zero to hero</h2>
<blockquote>
Some people get twenty years of experience, while others get one year of experience… twenty times in a row.
-Angela Duckworth
</blockquote>
Once you’ve identified the gaps that are holding you back, it’s time to move to conscious competence. This stage is marked by effort but also the reward of seeing the beginnings of success from deliberate practicing of skills.
<h3>First 10%: declarative knowledge</h3>
The first step of learning anything is to gain a formal understanding of the subject. The good news is that for any subject you’re trying to learn, there’s likely someone who spent years studying it, and most of them have written their thoughts down somewhere. Find these credible sources and consume their books, documentations, and presentations. Reach out to people inside and outside the company. It’s surprising how many times they are willing to chat.
Wade’s litmus test for checking your declarative knowledge is: Can you confidently give a great TEDx talk on the subject.
Many people stop at the first 10%, assuming they’re done (which explains TEDx talks). However, this is equivalent to a fifteen-year-old who just passed their written driving test thinking they’re an expert driver. They might know the theory behind driving but little of the actual practice of it. What they lack is the hands-on experience that leads to true proficiency.
<h3>Next 70%: deliberate practice</h3>
In her book Grit, Angela Duckworth records an exchange she had with cognitive psychologist Anders Ericsson on why experience doesn’t always lead to excellence. Duckworth shares that she’s been jogging for several hours every week for over a decade.
Duckworth: I’m not a second faster than I ever was. I’ve run for thousands of hours, and it doesn’t look like I’m anywhere close to making the Olympics.
Ericsson: Do you have a specific goal for your training? Do you have a target in terms of the pace you’d like to keep? Or a distance goal?
Duckworth: Um, no. I guess not
Ericsson: I think I understand. You aren’t improving because you’re not doing deliberate practice.
Many of us approach our professional growth like Duckworth approached jogging, focusing on quantity of practice over quality of practice. We carry this from the beginning of our careers where showing up was enough because everything was a stretch goal back then. However, as we progress through our careers, passive learning opportunities diminish, and growth flatlines. In fact, Wade emphasizes that:
<blockquote>
The higher you go, the more specific and deliberate learning needs to be.
</blockquote>
Even though deliberate practice is the longest step in the entire framework, it’s the least useful to write about. Much of practice is specific to the skillset you are looking to build, and the things that are generally applicable have been written extensively by much more insightful experts than me.
<h3>Last 20%: mentorship</h3>
By the time Wade joined Twitter, he had been a VP of Eng for 15 years. However, he found that he didn’t know how to influence a large organization. Wade looked around and found a few individuals who were consistently listened to and acted upon. He sat down with them and asked them for advice on how he could improve in this area. Wade took every opportunity to practice influencing and run his talking points or writing through these mentors who helped him hone this skillset.
Finding experts at what you’re trying to learn and having them give you specific and actionable feedback can accelerate and raise the ceiling on your learning.
<h3>Should I stay or should I go?</h3>
The last thing worth discussing here is the age-old question: Is growth easier if I stay in one company or go to a new one?
Wade’s advice is: be honest with yourself and look in the mirror. Are you looking for someone to fix you? Are you hoping that a reset will magically work?
There are switching costs to go from one company to another. You have to build a new relationship with the manager, learn a new tech stack, etc. Often, these things feel like growth because you’re learning something. But when you zoom out, you’ll often realize that these learnings don’t enable you to get to the next level because they weren’t the gaps that were holding you back. On the other hand, if you know where your gaps are, and neither practice nor feedback is available at your current company, it might be appropriate to go somewhere that excels in those areas.
<img src="/images/posts/competence.jpeg" alt="Competence">
<h2>Mastery: Consciously choose to close the gap!</h2>
<blockquote>
For everyone of us, there is a gap between who we are and who we want to become. There is a gap between where we are and where we want to be. What helps us close those gaps are the small things that we consistently choose to commit to over and over and over
-Joshua Medcalf
</blockquote>
By identifying your gaps and deliberately practicing your competencies, you can finally reach a state of unconscious competency. You’ve practiced the behaviors and competencies for the role to such an extent that they’re now virtually automatic. And as your reward, you’ll gain the time and mental energy to start the cycle all over again.

An approach to debugging your career shared by Wade Chambers at ELC

Debugging Your Engineering Career (ELC: Wade Chambers)

A guide to one on ones from principle to practice

A guide to one-on-ones

<blockquote>
Word: manager
Definition: a person responsible for controlling or administering all or part of an organization.
Origin: from Italian maneggiare “to handle, touch,” from Latin noun manus “hand”.
Example usage: I hate my manager.
</blockquote>
<h2>The Good</h2>
You are feeling excited. Maybe you’ve been working towards this gig for a while, or, if you’re like me, you were thrust into it by your boss. Either way, you’ve been promoted to an engineering manager! You’re unsure of all the implications but you already notice some differences. Your sphere of ownership has grown significantly and has ventured into new directions. The company just put you in charge of a team, and more importantly, its people. You are a boss — literally. You realize you have some newfound powers like the authority to hire and fire people and to approve expenses or vacation days (some powers are more glamorous than others). You’re also now in charge of setting the team’s direction for the quarter or introduce that one process you think the team so desperately needs. Glancing at your calendar, you are surprised to find invitations to closed-door meetings like leadership offsite and engineering staff meetings. Other teams want to set up time with you and have you make decisions on behalf of your team. And finally, you look up the career ladder and find that there are clear steps from you all the way to the very top. This is the chance you’ve been waiting for; to show the world what you’re made of and you’re gonna take full advantage of it!
<img src="/images/posts/top-of-the-world.png" alt="Top of the world">
But, I’m here to give you some bad news. It’s not all rainbows and butterflies.
<h2>The Bad</h2>
Your day is no longer your own, and your calendar is filled with other people’s meetings and they always need something from you. You start noticing that those hours of focused heads-down time that made you feel like a 10x engineer aren’t happening as often, if at all. Stress levels are noticeably higher and it doesn’t turn off after the workday is done. You realize that now, the buck stops with you. You’re responsible for the volume, content, and quality of the team’s output. You’re also responsible for your team’s motivation, retention, and morale. It’s no longer enough for you to identify and flag problems on the team. It’s now your job to fix them. From the company’s perspective, they’ve equipped you with everything necessary for success, and therefore, they retain the right to blame you for any failure.
A good friend of mine once said this about the transition from engineering into management:
<blockquote>
The highs are not as high, the lows are much lower, and it swings wildly back and forth in the span of the day.
— Tim Rodriguez
</blockquote>
<h2>The Ugly</h2>
And what’s at stake?
From the company’s perspective, they’ve taken a huge gamble on you. Depending on your team size and seniority, you’re managing anywhere from $500k to $2M of yearly personnel expense. They’re also very aware that if you fail, it won’t happen elegantly. Because managers (unintentionally) tend to drag morale and employee retention down with them as they crash.
If the company is betting big on you, then your direct reports are all in! Ironically, they likely didn’t get much of a say in having you as their manager but now you’re one of the most impactful people in their day-to-day lives. Studies show that work ranks higher than family responsibilities and health concerns as a form of stress in the American psyche. Additionally, 75% of people say the most stressful part of their job is their immediate manager. That’s why the saying goes: People don’t leave bad jobs, they leave bad bosses.
The failure modes are many. Managers can:
<ul>
<li>Be overly-prescriptive and micromanage.</li>
<li>Be underly-prescriptive and detached.</li>
<li>Be neglectful of the individuals on their teams and their growth.</li>
<li>Steer into the wrong product direction and fail to launch.</li>
<li>Steer into the wrong architectural direction and create tech debt.</li>
<li>Be self-serving and put their career growth over the team’s success.</li>
<li>Fail to gain the respect of their peers and the executives.</li>
<li>Be rude in the name of directness.</li>
<li>Be too uncritical and fail to keep people accountable.</li>
<li>Contribute to the gossip of the company.</li>
<li>Be too strategic and fail to execute.</li>
<li>Be too tactical and fail to form a vision.</li>
<li>Be a bad information conduit.</li>
<li>Not be technical enough to gain the respect of the team.</li>
<li>Fail to follow through and see initiatives to their completion.</li>
</ul>
The list goes on and on.
<img src="/images/posts/bottom-of-the-world.png" alt="Bottom of the world">
Now that I have you sufficiently sober, let’s start.
<h2>The Start</h2>
Management is not the next iteration of your old job, it’s a brand new one. This reality can be challenging to internalize. Firstly, because not a lot seems to have changed. You are still at the same company, office, team, code-base, and project. You still have the same boss and you’re surrounded by the same people. But don’t let that lull you into a false sense of stasis. Secondly, in all of your previous promotions, you were likely performing at the higher level for months before receiving the title. However this time, the transition is immediate. From 0 to 1 in the span of a week.
Here are three starting principles to help you through the transition.
Embrace discomfort: Like trying to learn to write with your left hand (or right hand — I’m not biased against left-handed people), management mechanics can initially feel unnatural. Your preference will be to fall back to old instincts that made you successful in the first place. Don’t. Embrace the discomfort and work at the new. It’s different for everyone but here’s some of the familiar cast:
<ul>
<li>Become more organized and take notes.</li>
<li>Practice and enforce good development lifecycle hygiene.</li>
<li>Spend time planning and prioritizing your day.</li>
<li>Delegate (completely) the important technical parts to someone else.</li>
<li>Spend more time writing docs.</li>
<li>Take in opposite opinions and respectfully consider them.</li>
<li>Do 1:1s with everyone (including all your former peers).</li>
<li>Give hard feedback to someone as their boss.</li>
<li>Get hard feedback from someone as their boss.</li>
<li>Be more responsive and over communicate.</li>
</ul>
Focus on the things that make you uncomfortable because they’re likely your biggest levers for experiential growth.
Hit the books: When learning a new technology, it’s often easiest to download it and play around with it. Management, unfortunately, doesn’t have an equivalent to the “side project”. However, what it does have is decades of written wisdom in the form of management books. These books can range from very instructive to more inspirational. Both are good. They can also range from career-defining to a complete waste of time. The following books I’m suggesting are optimized for industry relevance (tech), practicality (prescriptive), and ease of reading (engaging).
<a href="https://chrisgchiu.vercel.app/reading-list">Here's my reading recommendations</a>
Outside of hands-on experience, reading is the fastest ways to grow as a manager. And unlike experience, you can accelerate the rate of learning by reading more.
Warren Buffet once said this while addressing 165 students at Columbia Business School:
<blockquote>
Read 500 pages like this every day. That’s how knowledge works. It builds up, like compound interest. All of you can do it, but I guarantee not many of you will do it.
</blockquote>
Bias towards conservatism: It’s tempting to want to enact changes right away. After all, as a former member of the team, you have many opinions about how things should be done. However, it’s best to adopt a conservative mindset for the first few months and avoid the type of changes that are “high risk, high reward”. Learn and listen before acting. The reasons are:
<ol>
<li>The team is already trying to adjust to new leadership.</li>
<li>You may be wrong, and time will give you more context.</li>
<li>With time, you’ll be better skilled at driving changes successfully.</li>
<li>You don’t have a proven track-record to buffer a large failure yet.</li>
</ol>
<h2>The End</h2>
You’re now equipped with an appropriate appreciation of the task at hand and a few rudimentary tools at your disposal. Success is just a matter of thought, intention, training, and a lot of humility. Because to be a good manager, you don’t have to always hit the bullseye, just don’t miss the board.
<img src="/images/posts/dart.png" alt="dart">

How to navigate becoming a manager without failing spetacularly

Transitioning from IC to management

Throughout the interview process, I made a lot of mistakes. I was lucky to have a strong network who helped guide me through. Here’s the blog I wish I read before starting.
Searching for a new job is one of those things that have a disproportionate amount of impact on your life, and you’re probably doing it too casually. For a season, this choice cements: what you will be spending most of your time doing, who you will be doing it with, and in all likelihood, what your biggest source of stress is. Can you afford to work for the wrong cause, wrong team, or wrong boss?
Now that I have you sufficiently anxious let me reassure you that a small time investment is all you need. The hours you put into conscious thought and preparation will pay career and financial dividends for years to come.
<h2>Figure out what you want</h2>
If you’re a senior developer looking for a job, remember: it’s a seller’s market. Pretty much every tech company is hiring for senior developers. Don’t settle for only companies whose recruiter reached out to you. A recruiter’s dream is to successfully engage a cold candidate and hire them before they have the chance to check out other opportunities and find out what their skills are worth. Don’t be a sucker. The world is your oyster, what are the chances that the best pearl was in the first oyster to send you a LinkedIn message?
Find an opportunity that is the next iteration towards whatever your goal is. Balance the long-term plan with items that are important for you today.
Here are some questions to get you started:
<ul>
<li>What company size: small (0–250), medium (250–1000), or large (1000+)?</li>
<li>Backend, front end, full stack, mobile?</li>
<li>Remote work? Remote coworkers?</li>
<li>Flexible vacation policy?</li>
<li>What language, frameworks, and other technologies do you want exposure to?</li>
<li>What vertical do you want to be in?</li>
<li>How important is compensation?</li>
<li>B2B or B2C?</li>
<li>ML or AI opportunity?</li>
<li>How important is rapid company growth?</li>
<li>Do you want to specialize or remain a generalist?</li>
<li>How important is a brand name?</li>
<li>Organizational chaos or stability?</li>
<li>9–5 or 80 hour work week?</li>
<li>How much do you want to be mentored vs mentor others?</li>
<li>More technical or more leadership?</li>
<li>What kind of boss do you want?</li>
</ul>
Once you have a mind map of what you want, boil it down to ten things you will be using to judge each opportunity.
<h2>Practice! Practice! Practice!</h2>
If you don’t take time to practice interviewing, then expect your first couple of interviews to be your practice. Hopefully you weren’t interested in those jobs anyway.
“But Chris, I’m a strong developer, I’ll just breeze through an interview.”
Wrong!
Here’s the thing about interviews:
<blockquote>
Interviews measure a proxy of your skills, not the skills themselves.
</blockquote>
It’s done by necessity because companies can’t interview you for the three months it would take to figure out if you’re any good. Instead, they resort to making you write code on a whiteboard, architect twitter in 20 minutes, and talk about how you resolved a conflict in your team. It’s done in hopes that those activities are good indicators of your actual ability to perform your job. Practice the proxy skill! Not because you want to give an inflated view of your abilities, but because you want to give an accurate one.
Here are a few ways you can practice:
<ul>
<li>Go through Cracking the Coding Interview. Work the solutions on a notebook and pen.</li>
<li>Brush up on your system design. Here and here.</li>
<li>Pick an interesting technical project and practice drawing boxes and arrows and talking about individual pieces.</li>
<li>Brush up on your vocabulary. Find the right technical words to describe the attributes of an architecture. “This service is stateless” sounds a lot better than “this service doesn’t have a database.”</li>
<li>Write out answers to culture fit-ty questions like: a time you had disagreed with a technical decision, or a time you had to mentor someone.</li>
<li>If you’re interviewing for a leadership position, get very crisp at talking about what you did, how you did it, and why you did it that way.</li>
</ul>
<h2>Setup a searching funnel</h2>
You’ve probably heard about the hiring funnel before? If not, then a conversion funnel. And if still no, then you’ve probably seen a funnel? Anyway, you need a searching funnel. A great funnel is one that gives you the most amount of information for the least amount of time invested. Let’s talk about the attributes of this metaphorical funnel. The top is wide with all the companies you should initially engage. The bottom is a single point that represents the job that you will take. At every step, you will either disqualify a company, have that company disqualify you, or mutually deem it worth further exploration. Finding the right filtering function at every step is critical, too loose and you will waste your time, too narrow and you will miss out on opportunities. The deeper down the funnel you go the exponentially more the time investment. An Asana board work surprisingly well to project manage the searching funnel.
Here are the top three mistakes people make with their funnels.
The first mistake is to have a too narrow top of the funnel. Any company that checks three or more boxes is probably worth reaching out. Set your status on LinkedIn and AngelList to “open to opportunity.” You want a wide top of the funnel because most of the drop off happens on the first two steps. If you don’t do this well, several weeks into interviewing you will find yourself with too few choices. You will be forced to supplement the top of the funnel again. And guess what, those companies are now way behind the cohort. Do you want a scheduling nightmare? No? Then cast a wide net early!
Here are a few tips to fill the top of your funnel:
<ul>
<li>Companies that reached out to you</li>
<li>Companies you’ve heard good things about</li>
<li>Companies you network suggested you apply to</li>
<li>Companies you found on job boards (Glassdoor, LinkedIn, the muse, angel list, etc..)</li>
<li>Companies you found in respected VC’s portfolios</li>
</ul>
The second mistake people make is to not polarize companies along the process. Don’t let the narrowing of the funnel be purely a function of which companies let you through the next step. Remember, it’s a seller’s market! At every step, look to find out more information and rate the company against your criteria. This applies to recruiter calls, phone screens, and on-sites. If fast growth is important for you, then figure out what the company’s hiring plan is for the next 6 months. If working on customer features is essential, make sure that the role is for a product team. If you fail to do this, two things will happen: First, you will waste a lot more time interviewing at places that are not a fit, and second, you will blindly perform to get an offer only to find out you don’t know enough about the company to be confident about a decision.
The third mistake is not to get three good offers to choose from. It’s common knowledge that humans make bad decisions when presented with only two options. “Well, I don’t like how rude Travis is, I guess I’ll go out with heroin-Noah instead.” It’s a false dichotomy. Three options encourages you to choose what you want, instead of the lesser of two evils. Three offers also give you much stronger negotiating power. “You’re telling me I’m worth this much, but you’re in the minority, these two other companies have my market price at that much.” Don’t overdo it. Having four or more offers will not give you anything more and it wastes everyone’s time.
<h2>Negotiation</h2>
If I have to convince you to negotiate hard, it means you’ve never done it before. Because anyone who decided to bite the bullet came out of it understanding just how much money those fifteen awkward minutes can generate. It’s one of the most significant financial decisions you can make. If you live in the bay area, you shed a tear every month when you write that rent check.
<blockquote>
How great would it be if your company covered your year’s rent? That’s the amount of money negotiating can get you.
</blockquote>
<a href="https://www.kalzumeus.com/2012/01/23/salary-negotiation/">Here’s a much better entry on negotiation by Patrick McKenzie</a>
“But Chris, money doesn’t motivate me. It’s not my thing. In fact, I take pride in living a simple, minimal life. Do I still have to negotiate?”
YES!
Because negotiation is not just about money, it’s about expectation. In education, a teacher’s expectation of their students often turns into a self-fulfilling prophecy of that student’s performance. It’s a fact of life that high performance comes from high expectations. If you settle for a low offer you are telling your boss to expect you to generate low value. If taking in the extra cash goes against your philosophy, set a max-salary for yourself and donate everything else to <a href="https://www.ijm.org/give">IJM</a>. That frees you to negotiate without feeling selfish and greedy. Think of the children!
Here are a few tips for negotiation:
-Don’t ever be the one to share your number first. They will always ask, and you should never say. Tell them “I’m interviewing with companies of all sizes and my comp expectation is different for each one.” Small and medium companies will drop it at that because they don’t ever want you comparing their comp packages with Netflix’s.
<ul>
<li>Don’t push negotiation on the offers you’re not interested in. Doing so will make recruiters and managers there have to jump through hoops to try to get you in only to have you reject them. It burns bridges.</li>
<li>Do share information whenever it’s beneficial for you. Tell your top choice that they are your number one choice so that they’re more likely to advocate internally for you. If your top choice came in with a weak offer, share the numbers of the other two, so they know what your market rate is.</li>
<li>If you feel awkward negotiating money, make it not about money. What do you want to do with the money? Travel? Maybe buy a house? Help your parents? Sharing some of those reasons helps humanize the conversation.</li>
</ul>

A guide on how to approach job search in a structural way

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