As the number of meeting attendees grows, the usefulness of the information communicated drops in an inverse power relationship. Put more simply: big meetings are mostly useless for attendees.

To be clear, I’m not advocating that you skip all large meetings. After all, most of us must attend some big useless meetings if only to look like team players and remain employed. C’est la vie. 

But at the margin, it’s a superpower to overcome your FOMO and choose not to attend meetings where you stand to learn very little. And one of the best predictors of whether a meeting will be useful to attend is the number of people on the invite.

 Where Interesting Information Comes From

Let’s say that you have a 1:1 meeting with a peer somewhere that you can reasonably assume you won’t be overheard. In the course of that conversation, you will probably feel free to express yourself openly. 

It’s still work, so you might not talk about politics or other sensitive topics, but if you have a reasonably trusting relationship, you’ll probably feel comfortable discussing office gossip, speculative observations, or personal topics.

These one-on-one conversations are the venues in which the most interesting information is exchanged. The confirmation that someone got promoted, news of a coworker’s departure, an important reorg, and the unpublished results of a recent product launch are almost always broached here first. 

It’s why it’s so ominous for a boss to put an unexpected 1:1 on your calendar without explanation. It’s also why 1:1s can be so much fun: they are a space not just to conduct business and complete projects, but build trust and learn about your coworkers in a more personal setting. 

1:1s are the ultimate source of useful information because the attendee count is exactly 1.

Where Interesting Information Goes to Die

Now imagine a meeting with 100 attendees. The people leading that meeting must be very careful about how they communicate. A single ad-libbed response or tasteless joke can be misinterpreted, offend, or both. 

The people who lead big meetings tend to be senior leaders. Their job is to herd the organizational cats in a particular direction. Misinterpretations and offense fundamentally undermine their ability to accomplish that task.

So senior leaders do the rational thing. They memorize talking points, scrub their language of any ambiguous phrases, and relentlessly emphasize the positive. Truly exceptional senior leaders can do these things and still communicate important information, but for the majority, useful information is collateral damage in this preparation process.

This results in an information density for attendees towards the right side of the graph.

Experiment With Strategic Non-Attendance

Everyone is busy. There are always too many things to accomplish and too few hours in the day. The only way you’ll be able to tell for sure if you absolutely must attend a meeting is to try not attending.

If you’re right and that meeting was just noise in your schedule, you just created time out of thin air! You can use it to get ahead on deliverables, catch up on email, or prep for an important presentation. 

If you’re wrong and you really did need to attend the meeting, you’ll probably get negative feedback very quickly and can attend the next one. 

So what are you waiting for? Take a look at your schedule for the upcoming week, identify a meeting with too many invitees and try using it as a focus block instead.

Your calendar and sanity will thank you.

There is an incomplete truth at the heart of most performance review processes: that you get rewarded with a promotion when you make your customers more successful. 

In the tech industry, this connection between the actions you take and the benefits that accrue to customers is called “impact.” As in, “I had huge impact this quarter when I shipped that new feature.”

But in medium and large organizations, this relationship breaks down. If you work on a team that builds release infrastructure for a big company, it’s essentially impossible to draw a causal relationship between the work that you do and the success of your customers. Customers might notice when a release goes wrong, but it’s very hard to quantify the effect of a release occurring 5% faster on a customer’s purchasing decisions.

Since managers still want to reward high achievers and those high achievers want promotions for their work, something other than customer success must be used.

Small Orgs Can Promote on Results

When a team is small, it’s sometimes possible to measure individual performance. In this phase, the connection between a person’s actions and customer success can at least occasionally be said to be causal. 

Maybe a key customer mentioned the feature you just shipped as a reason for them signing up for the product. Or maybe the conversion events from an ad campaign that you ran led to a measurable uptick in profit this quarter.

When the team is small and everyone knows approximately what everyone else is doing, cause and effect are more closely linked. In this environment, you can get promoted on the basis of results. If you’re really good at your job, you can reap outsize rewards and build a reputation for excellence.

Of course, there’s no guarantee that just because the organization can measure and reward success that it will actually do it. Maybe your boss is a jerk or the owner of the company has already decided to promote their nephew to run your team. In either of these cases, you are unlikely to get promoted just by  delivering superior results. But at least it was hypothetically possible! 

Large Orgs Frequently Rely on Patronage

In large organizations, measuring performance is borderline impossible. So, large organizations rely on different sources of signal about promotion readiness. The most common pattern I’ve observed is simple patronage. This both makes a lot of sense and is deeply discouraging.

Even if you’re unfamiliar with the term, you’ve probably experienced patronage at work. It’s when a person or organization bestows an endorsement or encouragement upon another person. 

To be clear, patronage is not illegal. It’s not even particularly unsavory in some contexts. When the president of the United States is elected, he or she gets to choose their cabinet of advisors. Most people accept this patronage system as an efficient way to create a government.

On the flipside, if you’ve ever worked on a team where your boss has an obvious favorite, you’ve probably experienced the darker side of patronage. This practice is inextricably linked with all the isms of the modern world because the people in power tend to form relationships and show preference for the people most like them.

Learning From Example

So with this context, how do you figure out where promotions come from?

Look around your org and find people who have been recently promoted as well as managers who have recently promoted members of their team. Ask them about those decisions and start constructing a data set not about what the HR handbook says about promotion, but what is actually happening.

Did two managers describe promoting on the basis of personality traits? That’s a strong signal that people are being promoted on the basis of patronage. 

Does your org share promotion packages or specific business result benchmarks? That’s a strong signal that you’re working in a results-driven organization. 

There’s no one-size-fits-all approach to getting a promotion, especially as you become more senior in your career. But you can increase your odds by being clear-eyed about what is actually driving promotion decisions with current managers and then optimize for the things they care about.

What’s Next?

I think it’s really important to understand the way the world actually works, not just the way people tell me it works. In this way, I think understanding results vs patronage promotion is a valuable framework, but ultimately it boils down to gathering the data about how your peers are getting their promotions and how best to position yourself to ride that way.

During World War 2, a statistician named Abraham Wald was asked by the US Navy to recommend ways to minimize bomber losses to enemy fire. As a starting point, he was provided with data about where bombers that returned to base had been hit. His data looked a bit like this: 

Looking at this data, Abraham recommended to the Navy to reinforce the armor in the parts of the planes that hadn’t been hit. 

Wait, what? 

This is counter-intuitive, but remember where his data came from: planes that made it back to base. He assumed (correctly) that the parts of the planes that didn’t have bullet holes were the parts that, if hit, would destroy the plane and kill the crew.

This is a real-world example of survivorship bias. Survivorship bias leads us to conclude all sorts of wrong-headed things about the world. Here are two examples you’ve probably run into:

• “They don’t make ‘em like they used to.” Things made in the past are supposedly better than the obviously cheap, low-quality things of the present. In reality, most things in the past were low quality too, and broke or were discarded such that only the best stuff remains today. 

• “The best entrepreneurs are college dropouts.” Bill Gates and Mark Zuckerberg are enormously successful and both of them dropped out of college. Dropping out must, therefore, be a good way to achieve business success! This ignores the fact that the overwhelming majority of businesses fail and college dropouts earn less on average than graduates.

In both of these cases, the selection pressure (things breaking over time and people failing at business ventures) are ignored. This makes backward causal relationships look plausible. Survivorship bias in action!

The Sampling Problem and Career Advice

If you’re trying to get ahead in your career, whose advice would you pay more attention to? 

1. A coworker who has 15 more years of experience in your discipline, but is the same level as you in your current organization.

2. A Vice President in your discipline at the industry-leading company with 10 fewer years of experience.

The overwhelming majority of people would choose to listen to the younger VP. The justification for that preference is touted as simple common sense. How can you learn the best path to get promoted to senior leadership by someone who hasn’t themselves accomplished that feat? Plus, the second person must be extra talented because she achieved a senior title while still young!

But that’s backwards. It’s akin to looking at the airplane damage diagram above and concluding that the way to save planes is to add armor to the wingtips. 

Most conventional career advice demonstrates both extreme sampling and survivorship bias.

So What Can You Do?

So how should you acquire actionable, unbiased career advice?

Simple: solicit advice from many people who are a little ahead of you that are also demographically similar. Let’s break that down a bit:

Getting Lots of Advice

Everyone’s path is different. What works for one person won’t work for another. Maybe you need to stay in a particular town to take care of an aging relative. Maybe your top priority in life is to travel the world, and staying in one place is a non-starter. 

Everyone works within different sets of constraints. If you rely on only a few career mentors, you’ll get advice that isn’t helpful to your circumstances.

A Little Bit Ahead of You

When you are learning a skill, it’s tempting to seek out a teacher that is the best of the best. But that’s actually counter-productive. 

Someone who has 30 years of experience playing the violin suffers from a profound curse of knowledge: they’ve forgotten what it’s like to be a beginner. 

You would be better off finding a teacher who is only a couple of years further along than you. They are more likely to remember what it’s like to learn basic posture and finger positions. They can immediately recall the experience of not knowing what they’re doing and help another person with that transition. 

Demographically Similar

The world is deeply unequal and unfair. The sooner you understand this, the more effective you’ll be at furthering your career. 

If you are a middle-aged mother of 3, the way that you succeed is quite different from a 23-year-old recent grad and first generation US immigrant. Society has all sorts of ‘isms that constrain both people, but they are radically different. People that don’t experience the world in a similar way are likely to give you bad advice.  

Putting It Together

Hopefully in this post, I’ve convinced you that most career advice is essentially unusable due to survivorship and sampling bias. 

Luckily, it’s not the end of the world. By averaging together the suggestions of lots of people who are a little ahead and similar to you, you can accelerate your career better than any Master Class could ever do.

I studied film at college. One of the films that I’ll always remember is Glengarry Glen Ross, which is about an unscrupulous real estate speculation company. Towards the beginning of the movie, Alec Baldwin’s character delivers a speech to motivate the sales team in which he repeats a now-infamous slogan: “ABC - Always Be Closing.”

During his speech, one of the sales reps tries to refill his coffee and is told that “coffee is for closers.”

Our culture worships the concept of people who finish things. We’re exhorted to never quit and to always follow through. There are motivational posters, classes, and seminars focused on pushing through and finishing what you start at whatever the cost. Nike’s slogan is Just Do It and my favorite meme of the last decade is Shia Labouf’s Just Do It about finishing what you start.

But I think this culture of Always Be Closing overlooks the benefits of being really good at starting, not necessarily finishing, a particular task or project. Knowing which skill you excel at is extremely important for your career.

Organizations Need Starters

To be successful, every organizer must have a mix of people who excel at starting and people who excel at finishing tasks. If you don’t believe me, consider what it would be like to work with a group of people who never take a risk on a new project or initiative. The team might excel at finishing nearly-impossible projects, but they won’t have the risk tolerance or imagination to dream up new innovations.

Even more damning, a team that is too heavily focused on finishing things for the sake of finishing will systematically over-invest in projects that are failing. When the act of finishing becomes all-important, important signals will get overlooked and the organization will dump resources into something that shows every sign of being a failure for individuals and the broader group.

5 Signs You Might Be a Starter

Here are 5 signs that you might be a starter, not a finisher:

1. You find new opportunities exhilarating, even when pursuing them would require you to discontinue or wind-down in-flight commitments.

2. The risk of failure doesn’t fundamentally scare or intimidate you.

3. You can’t help but think of new products, services, or processes.

4. You thrive on constant change: predictability doesn’t engage you.

5. Peers and bosses have told you that you are charismatic and capable of leading others.

If these traits sound familiar, Alec Baldwin might not let you get coffee. You might be a starter, not a finisher. 

That’s okay. 

In fact, your skills may be exactly what your team or company needs. But you’ll only be able to leverage your skills if you recognize and lean into your strengths. 

Finding Your Niche

If you are a finisher, you will probably excel in a mature organization in which goals and measures are well understood and outcomes are easy to measure. Larger companies are a great place for this skill set because they have de-risked much of the ambiguity that makes starters so successful. What’s needed in most larger organizations is the grit and consistency to implement tough ideas. When there are a lot of people in the mix, there can only be so many projects and leaders before chaos ensues.

By contrast, if you are a starter, you should seek out opportunities either in new business groups at large companies or in smaller orgs that haven’t reached product / market fit. These are environments with high risk / reward profiles that experience constant change. To be successful, someone must take the reigns and lead the way. Starters aren’t just welcome, but they are necessary.

What’s Next

If you haven’t guessed already, I’m very much a starter. I spent the first 10 years of my career wondering what was wrong with me. Why couldn’t I just settle down, take it easy, and focus on shipping the 901st iteration of the product? It’s not trivial to do that work - just ask the Windows team at Microsoft.

Finishing is valuable, but don’t let mainstream narratives tell you that your starter skills aren’t equally important. Every business needs a visionary that thinks up new billion dollar ideas. Every friend group needs someone that’s comfortable organizing new activities. Every relationship needs someone willing to propose new date ideas.

Know your strengths and play to them.

I love learning about history because a good history book can tell you how the world really works. This is especially important if you want to accelerate your career growth. In no other genre of learning are there such strong incentives to obscure what’s really going on and why, but well-researched history can peel back those layers of misdirection.

Among historical topics, the founding of the US has some great stories. I’ve read quite a few books on the subject, and so I was thrilled when Lin Manuel Miranda combined both my love of rap and history in his musical Hamilton, released in 2015.

For those that haven’t seen the musical, it follows the story of Alexander Hamilton who fought in the revolutionary war and eventually became the first secretery of the treasury. His peers included a who’s-who of American politicians: James Madison, Thomas Jefferson, and Benjamin Franklin to name just a few.

By all accounts, Hamilton was unusually brilliant, hard-working, and ambitious. But so were hundreds of thousands of young men of his generation. Plus, he had enormous disadvantages. He was born poor. His father abandoned his family. His mother died while he was young. The family member who took over his care committed suicide. He arrived in the country penniless, with no family and almost no connections to recommend him. 

So how did he come from the humblest of beginnings to creating the most influential banking system in human history and having his face printed on our currency? 

One man: George Washington. 

A Historical Pattern

Over the course of several decades, George Washington’s sponsorship opened critical doors for Hamilton. Washington gave him entre to meet his wealthy future spouse, become a commander in the revolutionary army, and occupy several critical cabinet and political appointments. 

So why did Washington go so far out of his way to support and nurture the ambitions of the unpolished, bastard immigrant? We’ll never know the whole story, but what we do know suggests that Washington just liked him. 

Think about that for a moment. George Washington, the founding father of the US democratic experiment and one of the wealthiest humans alive at the time gave another person the opportunity to shape the entire world financial system because, at the end of the day, he liked hanging out with him.

Of course, this wasn’t a surface-level connection. The two men worked side by side in deplorable conditions for years during the revolutionary war. They were starved, frozen, and shot at together. They agreed on many key topics, gained one another’s trust, and struggled for the same ends.

Their working partnership was exceptionally deep, but I think those sorts of partnerships are the rule rather than the exception in organizations. We all want to be a part of a cohesive team, doing great things, with people we respect and admire. 

Those with power, influence, and capital seek those connections too, but their need is even more difficult to meet. They have to filter for sycophants who are always trying to gain their favor by faking that most critical ingredient: real human connection. 

Finding someone that they want to spend time with that is also capable of repeatedly getting things done well is so rare that when it happens, it’s a small price to pay to sponsor and give them opportunities.

How To Find Your George Washington

Searching, confirming, and developing a sponsorship relationship is anything but straight-forward, but here are a few steps I’ve found that can help:

1. Put relationships first. Projects, market conditions, and release dates come and go. A project can’t sponsor your career, but a person can. Make sure that you invest in getting to know your bosses, peers, and reports as people first and foremost. Be open and clear with them that your working relationship comes first. 

2. Be vulnerable. You can’t form meaningful relationships if you aren’t willing to be authentic. Some people find it off putting to cut the chit chat and go straight to real topics, but in my experience, those people probably weren’t going to sponsor you anyways. Don’t be weird, but talk less about the weather and your commute and more about topics you actually care about.

3. Be interesting. You don’t have to be a world traveler or famous author to be interesting to others. Demonstrate curiosity. Read a book. Learn a hobby. Memorize some work-appropriate jokes. Take a course. Fix something broken in your apartment. Start a blog. The more experience and overlap you have with others, the higher the probability you’ll connect with others beyond the superficial water cooler discussions.

None of these tactics guarantee you’ll find someone who earnestly believes in you and has the power to give you important opportunities. But they each increase your odds. 

And at the end of the day, you only need to find one George Washington to have a huge impact on the world.

Most companies have formal performance review processes that involve writing peer reviews. These are reviews that employees write about one another assessing skills, strengths, and areas for improvement. 

At large tech companies, these peer reviews are taken quite seriously. And as a PM, the number of peer reviews you are asked to write can get to be an overwhelming amount of work. On some previous teams, I was asked to provide 30+ peer reviews during the performance cycle. At a couple hundred words each, that’s a lot of time and effort. 

After a couple cycles of this, I perfected a way to write peer reviews for everyone that requested one while also not having it consume all of my time.

Here’s how I do it.

Always Accept Peer Review Requests

Meta and Google both provide a way for managers to request peer reviews for the folks on their team. Typically, managers target a particular number of peer reviews per report. The idea is to get a sense of their performance by averaging out the feedback of several people in different adjacent roles. 

I know firsthand from my experience as a manager at Salesforce and then Meta that it’s a pain to track down peer reviews for every member of your team. And when you come up short, you need to go herd cats to hit your target.

This creates an opportunity for you to quickly and easily demonstrate value to the team. Even though peer review requests are technically optional, unless there are extreme extenuating circumstances, I never turn down a peer review request. 

That may seem like an insane waste of time, but if you follow my guidance here, you’ll be able to write them quickly and cheaply. This makes peer reviews an activity that offers a very high return on investment.

Timebox Your Writing

One of the pitfalls I’ve seen many people fall into is thinking that they need to write novellas about every peer. That’s certainly well-intentioned, but it actually doesn’t help Vivek all that much unless he’s going up for promotion this cycle. 

If a peer isn’t going up for promotion, then a peer review is fairly binary. Either the person is doing well in their role or they aren’t. If it’s just binary, you can relax a bit. 

What I do is set a timer for 10-15 minutes for each peer review and just crank them out in one block of time. By setting a timer, you force yourself to only give feedback about the most important topics and ignore any temptation to write long and detailed reviews. Just hit the main topics and move on.

By Default, Don’t Share Feedback Directly With Peers

I realize this might be controversial, but I rarely share reviews directly with my peers. I instead opt to share with their manager only. This might seem overly bureaucratic, but I think there is a strong reason not to share feedback with people directly.

By sharing feedback only with a peer’s manager, it frees you to be blunt and to-the-point in your writing. Remember, you’ve only got 10-15 minutes per review, so you don’t have time to carefully wordsmith every phrase to avoid offending someone. 

If you do want to share negative or mixed feedback, you can do so quickly and move on. But I think you should reserve negative feedback in particular for outlier cases.

Give Negative Feedback Sparingly and Directly

Unless someone has really bungled something important, I try to be charitable in my feedback. We all have bad days and we all appreciate others giving us the benefit of the doubt. So if a peer hasn’t been an absolutely stellar partner or has made a few mistakes, I will generally overlook that and focus instead on their positive contributions.

But every now and again, you’ll work with a peer that is objectively toxic or incapable of doing their job effectively. In those cases, I think it’s always a good idea to speak with their manager directly and off the record prior to giving written feedback. Be direct about what you will write and the problems you’ve encountered. The manager may choose not to solicit your feedback that cycle for all sorts of perfectly justifiable reasons.

In even rarer circumstances, you’ll work with a peer that you think is actually great, but has made an important mistake. In that case, if you think that you can give that person constructive feedback in a non-judgemental way, pull them aside and ask permission to give them feedback. If they seem receptive, set up a dedicated 1:1. During that time, explain what’s going on and how you think they can fix it. Only after you’ve had that conversation should you give them written feedback.

Some of the most helpful conversations I’ve had in my career have resulted from these constructive feedback sessions, so if you feel up to it, definitely consider doing this. 

Peer Reviews Are High Return on Investment

If you follow all of the above steps, you’ll be able to help the managers on your team run an efficient performance review, reduce the time it takes you to write peer reviews, and give feedback in only the most receptive forums. 

For just a couple hours of your time, you can demonstrate that you are likable, and that’s worth a lot.

Two years ago, I was concluding a multi-month job search that ultimately landed me at Google. As I was deciding between offers, I used a decision making framework that has served me well. 

Instead of focusing on the typical stuff like the team, technology, or product, I created a prioritized list of my values, cross-referenced those values with the things that could not be easily taken from me after I joined. I then ranked my offers according to those attributes.

It might seem overly dark to consciously consider what can be taken from you, but I’ve found it to be a liberating exercise. When things inevitably get unpleasant at your new role, you can think “well, at least I got what I wanted.” And as a famous poet once said, that can make all the difference. 

Here’s how it works.

What Is Difficult To Take From You?

Employment in the US is at-will. That means most of us can be laid off without cause at any time. In a very real sense, everything about your job can be taken from you. 

But at least in the tech industry, even during the present downturn, there are some things that are difficult or inconvenient to take from you. In descending order of difficulty to revoke, they are:

1. Employer’s reputation

2. Base salary

3. Title

4. Location

Everything else about a role can and should be treated as transitory: your boss, team, project, tools, go to market strategy, bonuses, promotions, products, even the company’s customers. Keep this list in mind and don’t get too attached to these aspects of your work!

What Do You Want?

If you don’t know what you want in your next role, I won’t be able to help you, unfortunately. Only you know what it’s like to live in your skin 24 hours a day. As 50 Cent so eloquently put it: 

“Look in the mirror, ask yourself who are you?

If you don’t know who you are, how could your dreams come true?”

-50 Cent

But you don’t need to be an internationally famous rapper to discover what you want and need. Just start listing out what you feel drawn to. Don’t try to filter the list and keep the wording simple. 

Here was my list for the job hunt that landed me at Google:

1. Work with a manager or team I’ve worked with previously.

2. Work in person with a team in Austin, Texas.

3. Work for another company with a good industry reputation.

4. Transition back to being a product management individual contributor.

5. Work on a team that is building a 0 to 1 effort.

That’s a pretty long list, but you gotta reach for the stars!

Are You Getting What You Want? 

Google has been great, but no company or role is perfect. Here’s a comparison of what I wanted and what I got:

1. Work with a manager or team I’ve worked with previously.

2. Work in person with a team in Austin, Texas.

3. Work for another company with a good industry reputation. 

4. Transition back to being a product management individual contributor.

5. Work on a team that is building a 0 to 1 effort. 

Notice anything about this list? 

I’ve been at Google for a little over two years. I’ve managed to keep 100% of the things that I wanted and are difficult to take. I work in-person with folks here in Austin, for a company with a great reputation, and my title has remained the same: Senior Product Manager. 

Meanwhile, I wasn’t able to get my #5 preference and the manager I joined the company to work for left 6 months after I joined.

I feel great about the outcome. I joined with a clear understanding of what I was likely to get … and that’s exactly what was delivered.

Why Is This Important? 

There are always days when work is challenging. On those days, it can be tempting to look back and wonder if you made the right choice when accepting a new role. Regret can easily lead to fear and frustration. And as Master Yoda put it: “Fear leads to anger, anger leads to hate, hate… leads to suffering.”

So there you have it. From 50 Cent to Star Wars, you can’t afford not to subscribe to this newsletter.

When I first joined Meta (then Facebook) back in 2018, I went through orientation along with ~200 other people. At the time, the company was hiring people so quickly that when you joined, you were assigned an onboarding cohort. Each cohort was sort of like a graduating class at a university. We attended the same training sessions, completed the same course work (yes there was coursework), and “graduated” together 6 weeks later. 

I was in the 8/20 n00b group and I made friends with the dozen or so other PMs that joined Meta that same week. Remarkably, many of us still remain in touch 6 years later.

My fellow 8/20 n00bs and I spent a bunch of time together, so we had a lot of time to swap stories about work, career, and life. One peer in particular – we’ll call her Rachel – had a particularly interesting theory of career development that I’ve often shared when mentoring other folks. I think it’s a practical framework for avoiding burnout and maximizing career advancement.

Wanting to Get Off the Treadmill

Working at enormous, competitive, industry-leading companies can be tiring. Working at Meta, for instance, felt like sprinting on a treadmill. If you slowed down or stopped, you would be physically thrown off. At the same time, running a bit faster didn’t do much for your career. There were just so many high performers that even if you pushed yourself hard, it was difficult to stand out.

While Salesforce and Google foster better work / life balance, both push their workforce hard too. At Salesforce, it was the constant marketing, demoing, conferences, and press panels. At Google, it’s the relentless technical self education and social networking required to be effective.

After you work at one of these companies for a while, it is mighty tempting to get off the treadmill and take a breather. And if done strategically, it can also be a really good thing for your career, too.

Save Points

Old video games wouldn’t let you save your progress at arbitrary points in a level or campaign. You had to reach a predetermined place in the story or level where you could save your progress before venturing further. Rachel, my peer in the Meta 8/20 n00b cohort, used this metaphor to describe her career strategy. 

The idea is to modulate how much energy and focus you expend on your career over long stretches of time to ensure you don’t get trapped on an unproductive treadmill. More concretely, it means intentionally moving between large, well-established companies and smaller startups every couple of years.

The “save point” is the big company. Your biggest growth opportunities are your stints working at smaller companies. Most of your forays into smaller companies won’t pan out, but that’s okay. Over the course of decades, you only need to get lucky 1 or 2 times.

How it Works

So how exactly does this strategy work? It’s actually pretty simple: you seek out roles at large, established tech companies and work there for a couple of years. Then, you take a risk and dive into a smaller company. When you make the transition, you negotiate a more senior title and responsibilities. Then, you work at the smaller company for a couple of years.

Most of the time, the smaller company dies, you get reorged, you get laid off, or the role you were originally hired for disappears and there isn’t much opportunity for growth. In those cases, you reload your save file, and interview with a big company again for the role you had when you left. True, you lost out on a year or two of big company compensation, but you can’t win ‘em all.

And, if you try this approach many times, you might get lucky. 

If you happen to join a high-growth company, you can rapidly move up the ranks in a way that the fierce competition at a place like Meta would never allow. If you do get lucky in this way, you can then return to a big company, but use your experience to get a better title and compensation package. And once you’ve been a director at a large, well-known company, you can leverage the company’s reputation to decline less senior offers. You will have “saved” your career at a more advantageous place.

Limitations and Advantages

In 2024, this nomadic approach to career growth might seem a bit useless. Due to layoffs and tightening budgets, it’s a lot harder to move between positions than it was a couple years ago.

But I think the approach is still workable. Instead of moving between a big company and a small company, you could instead move between a mature team and an experimental team inside the same company. Or you could pick up more risky projects within the same role. 

If you’ve gotten this far in the post, you might also wonder why I’m not practicing what I preach. If the save points theory is so great, why haven’t I followed it in my own career? The answer is pretty mundane: kids! Since 2016, we’ve been raising a family, which has forced me to be a bit more risk-averse in my career than I otherwise would be. 

If you’re ambitious, aggressive, and interested in maximizing the chances of getting to be a director or VP, however, I think the save points theory is a great approach.

Company prestige matters a lot.

But a company’s prestige is always changing. Between 1998 - 2002, Yahoo was one of the most popular websites in the world. It was very cool to work there in the late 90s. Today, working there isn’t nearly so cool.

So, which tech companies have the most prestige in 2024?

Top Large Tech Companies

“FAANG” was first coined by Jim Cramer in 2013 and stood for Facebook, Apple, Amazon, Netflix, and Google. There have been quite a few iterations and variations on the acronym, but the idea behind was always to shorten the list of tech companies that drive returns on the S&P 500. 

Eleven years later, and that list looks a bit different. For one, Facebook is now called Meta, Google is now a subsidiary of the Alphabet Corporation, and Netflix failed to grow as quickly as its 2013 peers. Meanwhile, a humble GPU manufacturer, Nvidia, has managed to ride the crypto and AI wave to becoming a top-5 contender. 

Here are the top 5 technology companies in the market today:

Of course, the biggest companies aren’t always the most prestigious, but they are important movers and shakers in the industry. And if you just want to impress your family at Christmas this year, you could do worse than work for a company that everyone knows about. 

Perhaps not coincidentally, this list looks a lot like the one generated when computer science college students were asked to name their top 5 employers last year [source]:

I’m going to put my thumb on the scale a bit and say that Nvidia is more prestigious than Netflix nowadays. If you agree with me and you’re dying for an acronym to replace “FAANG,” my favorite is MAAAN.

So, if you care about working for a household name or think college students know what companies are best, seek out the MAAAN.

Top Startups

Prestige doesn’t just come from working at the biggest and most profitable tech companies. You can learn faster and exercise more autonomy at a startup. 

Any list of the top startups to work for is going to be subjective. Many startups aren’t public and don’t publish financial reports. That means you have to take their claims about team size, profitability, and growth with a pinch of salt. With that said, I think my alma mater, YCombinator, has a pretty good list. 

Here are the top startups that I think are the most prestigious to work for in 2024:

There’s a lot of breadth here: from finance to CRM to delivery to search. And while these companies don’t have the instant name recognition of the biggest companies above, they’re definitionally a great place to learn skills and grow a career.

Where You Work Matters

Company reputations have a real impact on your career, whether you like it or not. Luckily, you can choose where you work and it’s not impossible to land a job at Google or wherever else you want to contribute.

I’ll be writing more about the actual steps you can take to get your dream offer here on Silicon Ladders.

It’s nearly impossible to objectively measure performance in the workplace. Yet managers must make promotion decisions regularly, and despite the slowdown in the tech industry, people are still getting promoted. So what’s going on? Are managers just randomly pulling names out of a hat and promoting those people?

There are a lot of important ingredients to a good promotion packet. In fact, I’ll be covering more of them here, so subscribe if you’d like to get my take on the process!

But among all the myriad factors to getting that sweet, sweet promo is project visibility. What am I talking about? And why does it matter?

Don’t Be Invisible

Visibility is mostly what it sounds like: do leaders in your management chain know what you are working on? If your boss’ boss’ boss knows what you are working on then, then you’re probably working on a highly visible project. 

If only your immediate manager knows what you are working on, the project is probably low visibility. 

If even your own manager seems a bit clueless about the project you’re working on, congratulations, your work is invisible.

The visibility of your work matters because human attention is a limited resource. Human attention and getting a promotion might seem unconnected, but they are about as interconnected as can be.

Most organizations restrict who can actually promote someone. In big tech, depending on the team and the promotion level, it’s probably a director or VP. Those leaders are given promotion allocations. Even very senior leaders can only promote a certain number of people each cycle. Reports in their organization are stack-ranked against one another according to perceived impact. Since it’s damn near impossible to measure impact objectively, middle managers are tasked with making reports seeking promotion look as good as possible. 

But those middle managers have a limited amount of time to make their case during performance reviews. Worse, all middle managers quickly learn how to make their reports look as good as possible, which makes it really hard for senior leaders to do the stack ranking.

This is where visibility comes in. 

The Known Entity Advantage

Let’s say that your manager has 5 minutes to pitch all of your accomplishments for the last 6 months to a room of senior managers. If that sounds crazy, I can assure you from first hand experience that it isn’t.

If your manager has to start at square 0 and repeat your name to the group, explain why you’re doing your current work, and only then discuss your amazing accomplishments, you’ll be at a considerable disadvantage.

It would be much better if all the other managers already knew you, what you are working on, and the value of that project. If that was your situation, your manager could just jump right into the performance pitch and explain exactly why and how you kicked so much ass. 

If this situation describes you, then your manager listing all the ways you kicked ass in that performance conversation will mostly just be for appearances, anyway. The people making the promotion decision already work with you regularly. Maybe you lead a big project update meeting. Or maybe you are briefing senior leadership about a customer escalation. That contact – that visibility – will enable senior leaders to gauge your readiness for a promotion well before the next performance review.

This is the connection between human attention and promotion: there are only 24 hours in a day and senior leaders can only pay attention to a small handful of projects in that time. The scarcity of human attention is ultimately what limits the number of high visibility projects that exist at any given time.

How Do You Get a Slice of Leadership Attention?

In a word: relationships. 

Everyone that has accomplished great things in their career has a career sponsor. A sponsor is someone who is willing to risk their reputation to recommend you for roles that you aren’t yet qualified for. But critically, they believe that you’ll be able to do those jobs well given some time and coaching. 

In most cases, career sponsors do this because they like and respect you as a person. (Another plug for the necessity of being likable!)

Finding sponsors is exceedingly difficult and I haven’t found any shortcuts in my 16 years in the industry. You just have to work with a lot of people, prove your worth, develop relationships, and give back more than you take. If you do that repeatedly and you get a bit lucky, you’ll find someone in a senior position who just thinks you’re a great human. They will go out of their way to endorse and support you. You will be given the opportunity to work on high visibility projects that lead to promotion.

And if all of these good things happen, you will repay that kindness by always kicking as much ass as you can, staying humble, and remaining aware of your good fortune.

If you have never worked at a big company, you’ll probably find it to be a strange and foreign land. People will do and say things that don’t make sense. They will get upset about things that seem trivial, and be unconcerned with things that seem important. If you are coming from a smaller company, you may be deeply surprised to learn just how important workplace politics are.

But even if you join a big company with years of experience working at similar-sized behemoths, your first role at the new company is still probably going to suck. Why is that and what can you do about it? 

The Dynamics of Suckitude

First, let’s explain the simple game theory that goes into the process of hiring externally at a huge corporation.

At any large company, there are hundreds or potentially thousands of qualified internal job candidates at any given time. These people have a huge leg up on someone applying externally. They will have learned most of the organization’s values and processes. They will have much better knowledge of the team’s reputation. They can casually chat with the hiring manager. 

On the flip side, hiring managers at big companies have strong incentives to hire internally for all the same reasons. They can informally check on the work quality of an applicant. They can often view former team assignments and performance ratings. They can meet internal candidates in a more informal setting to determine their interest. 

If you are a hiring manager, you probably want to hire internally. If you are an applicant, you want to be hired internally. That means that for most roles, if you’re being hired externally, you are very likely taking a role that no internal candidate wants.

Think about that for a moment: hundreds or potentially thousands of qualified internal candidates with better information than you looked at the job you’re about to take and said “nah, I’ll pass.” 

That’s a very strong signal that it’s a role that has critical problems. If you’re really lucky, the only big problem is that the hiring manager (your future boss) is really bad at hiring. More likely, there are a slew of problems: it’s probably in an org that doesn’t have a great reputation, working for a new manager, on a problem that’s poorly-understood or low priority. 

Avoiding the Suck with a Personal Recommendation

So, is there any way to ensure that your first role at a big company doesn’t suck? 

Yes, but it requires that you never apply for a job in the first place. 

If you have a personal introduction to either the team or the hiring manager, you can often break out of these lose-lose game theory dynamics.

Let’s assume that rather than posting a job and going through the normal hiring process, a hiring manager thinks “hmmm, I really wish I could convince my awesome former coworker to help us solve this problem.” 

Then, rather than posting a job description, they reach out to you and pitch you informally. If you seem interested, they finally create a job description. This job description isn’t posted to collect applicant information and go through the normal recruiting process. It exists solely to provide a way to formalize their intent to offer the role to you. 

In this case, all of the adverse signaling goes away. Internal candidates didn’t turn down your role because it was never offered to them. The problem is also probably real and urgent, otherwise the hiring manager wouldn’t be willing to stake their reputation on hiring a particular person.

Sidestepping with An Internal Transfer

Even if you aren’t able to get recruited by a hiring manager for a real and pressing problem, you can always do the next best thing: transfer internally. Here, the play is to take whatever is given to you as your first role, knowing you’ll probably need to find another one soon after joining. This isn’t as terrible as it sounds: remember that you’ll have all the advantages of an internal applicant for that next search. 

In my own career, I’ve used both of these strategies to find roles that are compelling. When I was younger and had less experience, I had to simply take what I could get and transfer later. Now that I’m more established, I’m fortunate enough to rely on personal introductions. 

Whatever your strategy for finding a big company role that doesn’t suck, just remember not to blame yourself for your first team’s dysfunction. There are powerful forces at play that make it tough to succeed in your first role in a big organization.

It’s darn near impossible to measure an employee’s performance, even for easily-observable work on a small team. It’s not impossible, of course, but it’s probably a safe assumption that your boss knows a lot less about the quality of your work than you think she does. And by the time you get to your skip-level boss or a senior executive, they would be lucky to know your name, let alone whether you do good work. 

But there is one quality of your work performance that is extremely easy for your peers, boss, and senior executives to measure: whether or not you are likable.

At some level, this whole post is just an expansion of the idiom that people will forget what you said, but not the way you made them feel. There are outliers to any maxim, of course. There are assholes who do absolutely stellar work and there are extremely likable coworkers who are incompetent. But at the margin, learning to be likable is probably the best skill you can acquire. 

But what is it that makes someone likable? There are dozens of skills and behaviors that go into being likable, but here are the 3 that I think are most important.

Be an Active Listener

Here are some active listening traits that are worth practicing:

1. Never interrupt someone intentionally. Over video calls, this happens somewhat regularly by accident. When that happens, always cede the conversational right of way to your partner.

2. Take notes. Nothing makes someone feel important like writing down what they are saying. This isn’t always appropriate or possible of course, but during important conversations it’s a pro move. During an interview or mentorship session, for instance, taking notes enables you to absorb more content and sends a powerful signal that you care about what the other person is saying.

3. Use the same words as the people you are talking with. I mean this very literally. If you are in a conversation with someone and they say “team B has 3 big challenges,” when you are responding, try to say something like “it does seem like there are a couple of big challenges facing team B.” Notice that you didn’t repeat exactly what they said, but you almost did. This demonstrates that you were listening and that you understood not just the words being spoken, but their contextual meaning. This is a tough skill to learn. If you’re struggling, you can leverage note-taking to help. During important conversations, I write down unique words or phrases that I hear and then remix those into my responses.

There’s lots more to being an active listener, but these should get you started. Everyone loves talking to an active listener.

Agree More Than You Disagree

The lower threshold is 3 agreements to every 1 disagreement. If you want to really shine, try to keep your ratio at 5:1. It might seem like I’m encouraging you to be a sycophant, but it’s more subtle than that.

If you find the concept of agreeing with most of what your peers or boss say abhorrent, you might be in the wrong team, company, or profession. But even if you do feel well-matched on those fronts, it can feel unnatural to be so agreeable. Shouldn’t you speak truth to power and never compromise your ideals? Isn’t that what real leaders want? Hardly.

Among peers at work, it’s fine to be sarcastic or make jokes about dysfunction and mishaps. But if a peer asks you to do something and you decline more than you accept, you’ll garner a reputation for being tough to work with. This is even more attenuated in your relationship with your boss and management. If your boss asks you to do something and you want to be promoted or remain in the organization’s good graces, your default answer must be “yes.” You can, in very limited situations say “no,” but it’s very expensive to do that. Use your disagreements wisely.

If agreeing more than you disagree requires you to do or say morally odious things, consider leaving. If you can’t afford to leave, you’ll have to make the tough choice between moral rectitude and financial hardship.

Remember Personal Details

I’ll readily admit that I’m terrible at this, but then, there’s always room for growth. There’s nothing more charming than a coworker who always remembers details about your personal life and takes steps to accommodate you. 

Maybe you share with a coworker that your mother is very sick at the moment. Later that week, there’s a mother’s day office celebration and your boss pressures you to attend. Your thoughtful coworker swoops in and asks if it would be okay for you to meet with them instead because such-and-such project is behind. After people go to the party, your coworker reveals that they just wanted to ensure you are doing okay and not to feel obligated to attend.

In this scenario, your coworker did a couple of extremely likable things:

1. They listened when you told them about your mother.

2. They took the next step to simulate what it might be like in your head and some of the emotions you might be feeling.

3. They proactively identified that the celebration might make you uncomfortable and sad.

4. Without revealing any of your personal information to others, they created an opportunity to check in and ensure you are feeling mentally safe and protected.

Maybe you were fine to attend the mother’s day celebration after all. No harm done, you can just tell your boss you were able to quickly resolve the topics with your coworker. But if you were feeling vulnerable, scared, or otherwise exposed, your coworker did you a solid.

This sort of skill is very, very difficult to pull off successfully, but when done, is the highest order of likeability. 

Personally, I’ve always struggled with this. It’s hard to get my brain to commit this category of information to memory. Lyrics to Linkin Park’s Hybrid Theory album? That’ll be in memory until the day I die. But the names of my new coworker’s two children? No way.

If this describes you, one trick is to use a spaced repetition flashcard program to commit the information to memory. It works really well, but requires a substantial up-front investment. I’ve also occasionally used a lightweight CRM - typically when I’m onboarding onto a new team.

What’s Next?

Remember: in a couple of months, most of your coworkers will probably have forgotten the work that you’ve done. In a year, all but your most important 1 or 2 contributions will be completely forgotten by your boss. In 5 years, nobody will remember what you did at all, but they will remember how you acted around them and whether they liked you. 

So, put in the effort to learn or improve the skills that make you likable. It’s gratifying to be liked by people, but it’s also a killer way to advance your career. Because when it comes down to it, measuring performance is nearly impossible and everyone would rather work with a likable person.

Years ago, I was working as a product manager on a team that had serious trust issues. Engineering didn’t trust the product team, the product team didn’t trust engineering, UX felt sidelined and ignored, and the project was behind schedule.

My boss sent out an email to me and the other members of the team asking for a status update on our projects. I responded with an update on what I perceived as failures on the part of my engineering partners. I wasn’t extremely harsh, but I also wasn’t very charitable.

Then my boss accidentally forwarded my response to the wider team. Not only did my engineering team see what I’d written, but so did everyone else. Ooops.

In less than 10 minutes later, my skip-level boss corralled me, my boss, and our engineering leaders into a room. The truth of what I’d written wasn’t material. It highlighted the bad faith in the team’s working relationships and made me look mean spirited and incompetent.

I apologized without reservation and in-person to everyone affected. I took my engineering team out to get drinks and paid the tab. Through the good grace of my coworkers and a willingness to forgive, we were able to move forward and ship the product.

But the whole incident should have never happened. I learned a painful and powerful lesson that day: you should never write down what you wouldn’t say in person to a coworker. Better still, whenever you are at work and you write something, before you send it, imagine if you would be comfortable standing up in front of your entire business group and reading your words. If you feel a tinge of embarrassment, don’t send it.

You Can’t Communicate Directly At Work?

At this point, you might be tempted to react with concern about blunt and honest communication. If you can’t write down anything negative about any coworkers ever, how can productive work be done? Surely, a bit of conflict is good for every team, right?

Absolutely. In fact, I think that having negative conversations with coworkers is one of the most important skills that you can develop in your career. But you should still never write down those words because written communication doesn’t communicate intent clearly.

Humans have a bunch of ways to communicate information. There’s tone, body language, inflection, verbal emphasis, appearance, facial expression, and then the actual words you use. Without these other forms of communication, words can be easily misinterpreted. Even if you have something negative to say, there are ways to communicate that information without necessarily causing offense. Here’s an example.

The Worst Meeting

I spent the first 7 years of my career running two of my own startups with my best friends. We were all college friends and the companies remained small, which is to say that I avoided learning a bunch of necessary corporate skills.

I got my first “real” job after leaving my second company in 2015. I was hired as the PM for mobile products at a now-defunct SF-based real estate startup. A couple weeks into the job, I organized a meeting with my boss and our user research lead. I thought the meeting went okay, but afterwards, our research lead pulled me aside.

“Could I give you some constructive feedback, George?”

“Yeah, what’s up?”

“I think that was the worst meeting I’ve ever attended. Could I give you some pointers about how to run meetings in a more effective way?”

My first reaction was to be offended. I was an experienced startup founder. I’d built two profitable businesses in my career already, who was she to tell me I wasn’t good at organizing a meeting!? But - and here’s the critical part - she delivered those words with such empathy and concern that I not only said yes, but I listened patiently while she listed all the ways my meeting sucked.

In hindsight, my meeting organization skills did suck and she was right to call me out. To this day, I use the tools that she taught me to run more effective meetings. I’m thankful that she addressed her feedback directly to me rather than writing a nasty email to my boss.

Recap

Never write down what you wouldn’t read aloud to your coworkers. Not only does it protect you from painfully embarrassing missteps, but it pushes you to behave like my coworker and improve the performance of those around you.

As I’ve written previously, getting to L6 is skill, but getting to L9 is luck. If you want to get to L9 and beyond, it might seem like there’s nothing you can do. Luck is, by definition, something that happens to you, not something you can do for yourself. But you can learn behaviors that increase your odds of getting lucky in your career. It just boils down to optimizing for exposure to random good events. Here are 3 behaviors you can use to increase your professional luck.

1. Cultivate a Broad Professional Network

After the first 5-10 years of your career, most opportunities will come through your network, not recruiters or job postings. You are much more likely to get a really good opportunity from your network if your network is large. 

If you’ve only ever worked with 5 people, even if they all thought the world of you, they probably won’t have a lot of opportunities to hire you later in your career. And even if they do offer you excellent opportunities, there are a hundred small details that might not work out. Maybe your friend wants you to co-found a startup, but you just bought a house and can’t afford the financial instability. Maybe you get an offer to lead a large and innovative business group in China, but you don’t want to live abroad right now. On and on. Finding truly excellent career opportunities is a numbers game: the more chances you have to play, the more likely you’ll be successful.

2. Learn Interdisciplinary Skills

If you have spent 10 years becoming an experienced marketer, you’ll be able to see and resolve some kinds of marketing problems. Let’s just use the variable X to stand in for all the marketing problems you can identify and resolve. 

If you spend the next 10 years continuing to double down and deepen your marketing skills, maybe you can increase your skill a bit, but you’ll be hitting diminishing returns. Maybe you can get to 1.3X. 

But let’s say that you decide to pivot and spend the next 10 years learning something else entirely - say corporate accounting. At the end of that time, you will be able to identify and resolve a whole new set of problems. We can denote all of these problems as “Y.”

It’s natural to assume that in the latter case, your skill at identifying and resolving problems can be expressed as X + Y. But multidisciplinary perspectives are at least multiplicative. You’ll be able to identify and fix X * Y problems, perhaps even X^Y or Y^X. That means you’ll be massively better-equipped to deliver real-world results to the business you work for.

3. Regularly Seek Out New Problems to Solve

If you want to get lucky, you need to optimize for breadth. Not just in your network and skills, but in the problems you choose to tackle. That means regularly seeking out new challenges to work on.

This doesn’t have to mean switching companies. It could mean switching roles within a company. It could just mean switching your projects within a team. And don’t let formal career definitions constrain your search for interesting problems. You could learn to build something with wood in your free time, or volunteer with a nonprofit, or become a career mentor to someone else.

If you are constantly seeking out new problems to solve, you’ll get better at learning itself. That should enable you to more quickly identify and fix critical issues that come up in your career.

What’s Next?

If you want to reach the extreme heights of success in your career, it’s not enough to be very skilled and very hard working. You also have to be very lucky. There are always counter-examples of extreme specialists hitting it big. With that said, I think the dominant way to become very lucky is to maximize your exposure to random opportunities.

Remember that there isn’t a causal relationship between behavior and extreme success. There are only strong correlations. You can best correlate your behaviors with extreme success by thinking about the size and quality of your network, the breadth of your skills, and your exposure to new challenges. Then, maximize your long term gains by investing in each like an index fund.

Although I would love for this to not be the case, most human organizations become less democratic as they become larger. You can easily see this dynamic in governments, large companies, and political parties. It’s comparatively easy to debate complex topics and make good decisions when there are only a couple of well-informed decision makers. But it becomes nearly impossible when you get to even a small team size. To prove the point, try to find a lunch restaurant to satisfy 10 of your coworkers. Seriously, try to do it this afternoon and record how long it takes and how satisfied people are with the outcome. 

By the time an organization comprises 1,000 people, the only way that we humans have found to retain group cohesion and decision making is to give some people more authority. But for this to be an effective strategy, there have to be a small number of people in authority.

The simple fact that large human organizations require a small number of leaders has a profound impact on the connection between skill and reward in your career. 

Luck and Senior Leadership

Imagine that you run a large, highly competitive tech company. You only hire workers that can demonstrate that they are in the top 10% for their skill set. Because your company doesn’t need a lot of employees to be very profitable and the labor market is pretty big, you have an essentially unlimited talent pool to recruit from. Because it’s very difficult to measure performance on the job, let alone in an interview, workers at your company appear to have a pretty much undifferentiated level of total skill. Some will be better at coding, marketing, internal office politics, presentations, or management, but for a senior leader without intimate knowledge of what each person is doing, they all appear to be bright, hard-working people.

Your large organization can only remain effective and cohesive with a small number of senior leaders. But to you, all of your workers will appear to be pretty much equally skilled. So how can you differentiate the top 1% from the merely top 10% and promote them accordingly?

Rewarding Business Results Reinforces Luck-Based Promotion

Most organizations solve this (at least on paper) by promoting senior leaders on the basis of real world business results. After all, a corporate entity places no intrinsic value on being fair. The point of a business is to generate profit, and it makes sense to promote leaders who have done that in the past. 

This isn’t a problem for the business, but it is a problem for anyone aspiring to be a senior leader. Although skill, work ethic, and a dozen other positive traits are positively correlated with getting good business results, there isn’t a strict causal relationship. The world is random.

MIT graduates do better than the average college graduate in their careers, but some won’t do well at all. At the same time, some graduates of local community colleges go on to lead fortune 50 companies.

Driving Business Results

From the perspective of an employee at a technology company where everyone is already an MIT graduate, driving significant business results and being promoted to senior leadership largely boils down to luck. If you are a software engineer, you would have had a pretty good shot at driving huge business impact as employee #5 at Facebook in 2005.

But in 2005, Facebook looked like most other high-risk startups - there was absolutely no guarantee that it wouldn’t just fizzle out in 18 months. Those that took the risk and stuck with it got rewarded, but those that worked at a dozen other promising social network startups at the time got nothing.

The same winner-takes-all dynamic is at work in a large organization’s promotion choices. Those that work on projects that succeed get promoted on the basis of having delivered real world results. But often, those results are a product of having been at the right place at the right time, not skill.

So how do you hack the system and get to L9? Increase your exposure to lucky events.

That may sound like tongue-and-cheek sarcasm, but it’s not. There are behaviors that you can cultivate that will make you more lucky. Check out my post next week to learn what they are!

Years ago, I worked for a boss who was substantially more senior than me. I was in my early 30s and he was in his late 50s. He’d been around, worked at lots of companies, and had become wise in the ways of corporations and technology.

We were working on a doomed project at the time. Everyone on our team knew it. The tech didn’t work, sales couldn’t sell what did work, and office politics were tearing the team apart. The constant topic of conversation in hushed 1:1 meetings was how long the business would keep funding what seemed to obviously be a losing bet.

This situation was pretty challenging for me. I’ve always struggled with internalizing failure. From a very young age, if something went wrong, I assumed it was because of something I had done. When things went right, I assumed it was due to someone else or something else. Neurotic? Yes. Difficult to rewire my brain? Also yes. 

This tendency to internalize failure had inevitably spilled over into my career. Here I was, almost a decade into my career, and it felt like none of my products had been super successful. I had begun to wonder if perhaps I was the weak link.

The Revelation

But over lunch one day, I decided to ask my boss about success in his own career. “How many times have you worked on a team that functioned well, with technology that worked, in a market that actually wanted what you were building?”

He paused, introspected, and then in a nonchalant way said “twice.” He then took another bite of his lunch as if this answer was to be expected and didn’t warrant further discussion.

I was shocked. This guy’s LinkedIn page looked like a who’s who list of the best-known tech companies of all time. And he hadn’t just been a random employee at these places: he had worked on some really important products and technologies. And here he was admitting that in 35+ years across dozens of companies, product launches, teams, managers, and tech stacks, the stars had only ever really aligned for him twice.

That lunch was a sobering reality check. Up to that point, I had assumed my undignified tenure in the tech industry was abnormal. I was sure that everyone else was working with cutting-edge tech, supportive and highly-skilled coworkers, in a fast-growing vertical. 

A Reality Check

But if you step back, that definitionally can’t be the case. Companies don’t pay people to work on solved problems where things are already going well. They pay people to solve new problems, and solving new problems is highly prone to failure. If there was no risk, you wouldn’t be paid. 

So, if your project is failing and your team is dysfunctional and the market doesn’t want what you’re building, just remember: what you’re experiencing is the norm. And it’s almost certainly not your fault. Hopefully, this realization will even make you more effective. Whereas previously every little dysfunction and failure might have been painful to behold, you can now simply expect them. And, when something goes right, a launch is marginally successful, or a coworker acts like an adult, you can think “wow, that exceeds my expectations!”

Imagine that you start a small restaurant in your town. At first, it’s a one-person show: you are the cook, the cashier, the marketer, and the janitor. But after a while, business picks up and you decide to hire someone to help clean the dishes. You’re still busy with all the other work you had before, but at least you don’t have to worry about scrubbing plates.

At first, things are great - you have more hours in the day to get things done and the new employee is punctual and busy. But then you get a bad review from a customer about their utensils being dirty. You decide to observe your new employee more closely, but it seems as though they are doing their job well. So you relax a bit and weeks go by. 

Then, you get another bad review from a customer complaining that their plate had not been cleaned at all. This review includes a picture, so you decide to politely confront your employee and show them the evidence. But they claim the customer simply took a photo of their plate after they had eaten their meal and that the plate had been clean when it was served. 

You decide to put off some of your other duties and work exclusively in the kitchen alongside your employee the next couple of days to put the matter to rest. You spend time inspecting plates, utensils, and cups a couple times per day, but all of the items you inspect are clean. Despite this, you get another review from what appears to be a new and different customer about a dirty plate.

Even When the Work is Obvious, Measuring Performance Isn’t

Here we have an example of a work task that is very easy to evaluate. Most people are likely to agree whether or not a plate is dirty or clean. Despite this, it’s unclear what to do in this situation. Your employee is punctual and appears to be doing their job. But you can’t watch them every second of the day and so you can’t be 100% sure that they aren’t shirking their work when you aren’t looking. It could also be the case that your dishwasher is partially broken, or that some dishes have lost their enamel coating and so hold onto food scraps despite being washed. Finally, you could just have some very picky customers who see a tiny fleck of pepper on their plate and fly off the handle about it being disgustingly dirty.

The world is complicated, employers have limited time to assess performance, and even when the work should be easy to measure, human behavior complicates the picture.

Now imagine that instead of a single dishwasher working in a restaurant you own and operate, you employ 10 people at a digital ad agency. Two are artists, two are salespeople, two run ad campaigns, two are project managers, and two are software engineers. Half of the team works remotely, the other half comes into the office 3 days a week. Let’s assume that you have professional experience in sales, but not in the other disciplines.

How would you decide who was doing well and who wasn’t?

Let’s make it even more difficult and assume that you are running an organization of 500 people with many layers of management between you and the employees doing the day-to-day work. How would you know if the line employees are performing well? Would you trust your senior leaders? Would you take the time to speak with direct team managers on a regular basis? 

How to Measure Performance When You Can’t

The point is that it is really, really, really hard to evaluate whether someone is doing a good job or not. As a result, most employers and managers use a lot of signals to decide who to hire, who to promote, and who to fire. Many of those signals aren’t really related to job performance. For instance, if you are punctual, visually healthy, outwardly polite, responsive, and consistent, you’re probably a top 50% employee already. Note that none of those traits is “producing good work” or “being good at the thing you’re hired to do.” Just nailing the basics goes a long way towards convincing other people and your boss that you are effective.

The other big category that bosses use to determine the performance of employees is what other people say about them. If you have the baseline professional skills worked out (see above), there’s a fair chance that the difference between being promoted and being ignored comes down to how well you can get other people to sing your praise. You might think that this is unfair work politics - after all, shouldn’t the quality of your work speak for you? Hardly. 

It takes effort to get others to speak well of you. And if you are successful at doing that, you’ve demonstrated a very important and valuable skill: influencing other humans. Especially among knowledge workers, people who can do that are more valuable to the organizations that employ them.

What can you do with this knowledge? Nail the basics. Don’t be fooled by increasingly informal workplace culture: punctuality, responsiveness, and literally just showing up are hard behaviors to display consistently. Invest in those behaviors. After you’ve mastered them, invest in influencing other people to recommend you to your boss. 

Mastering basic professionalism is a huge competitive advantage and can lead to significant career advancement, even if you aren’t the best dishwasher in the world and occasionally miss a plate or two.

There is a common myth in the tech industry that big companies like to hire people with startup experience. The story goes that companies like Google and Meta want to hire the best talent. One way to identify good talent is to recruit startup founders and employees that have proven their mettle shipping real products to real users. 

This logic is actually pretty good. I spent the first 7 years of my career running two of my own startups. Being a startup founder required the most skill of any job I’ve had. If you aren’t really good at what you do, you will fail fast running your own startup.

So, this logic is sound, but the problem is that working at a startup will actually hurt your chances of getting an offer from a FAANG company. The reason is that working at big companies is radically different from working at a startup. 

Here’s an example.

Back in 2014, my cofounder Scott discovered that we had a bug in our implementation of Stripe. This bug had caused us to receive no customer payments for the last week. We hadn’t noticed because at that stage, we were making so little money. But because we had so little money, the problem was existential. At the time, site traffic was so low that we decided it made sense for us to optimize for speed and test in production. That day, we pushed to prod 11 times. By late evening we had resolved the issue. It had been a trivial misunderstanding of Stripe’s integration docs.

We were quite proud of having fixed it so quickly. From discovery to fix took only 8 hours. Considering what a mess the codebase was, how many systems were involved, and how sleep-deprived we all were, it was a serious technical achievement.

But now reflect on what sort of skills that experience reinforced: hacking through a codebase quickly, adding loglines where there probably shouldn’t be any, ignoring the dev environment, and testing in real time with a payment system.

At a big company, being good at any of those skills wouldn’t just be a waste of talent, it would be actively dangerous. If an engineer in the Google Ads team decided to test a fix to a payment system in production, that could easily become a billion dollar problem. And don’t get me started on the reputational risk of doing something like that. 

Startups hire from other startups because the skills necessary to be successful in that environment are directly transferable. The same is true for midsize and FAANG companies.

And the data prove it. In the last 9 years working at large tech companies, I’ve worked directly with hundreds of people. Only about a dozen of those folks came from the startup ecosystem. The people who work on startups tend to come from other startups. The people who work for FAANG companies tend to come from other FAANG companies.

So, if you want to work for a FAANG company, the best thing you can do to gain the right skills and reputation is to work at a FAANG company. That may seem like a catch-22, but there are ways to substantially increase your odds of success. Subscribe to get my future posts and I’ll share actionable steps you can take to get a FAANG offer.

But even if you don’t subscribe, don’t make the mistake of working for a startup because you think it’s a path to getting an offer from Meta or Google. It almost certainly isn’t.