Good Careers at Bad Companies

Someone once asked me whether you can join a dysfunctional company and still have a good career. They assumed dysfunction is rare—something you'd see in advance and choose to join or avoid. But my experience is that most companies are dysfunctional in some significant and non-immediately obvious way, so a better question is: how do you build a meaningful career when those kinds of companies are the norm, not the exception?There are, broadly speaking, two types of companies:Companies that are going somewhere (or have gotten somewhere) andCompanies that are going nowhere (or are slipping back to nowhere)Trajectory is important because it correlates with that company's impact on your career.Companies that have gotten somewhere (such as the BigCos, FAANGs, and industry equivalents) and companies going somewhere (rocket ships with fast growth and fawning coverage) offer a pedigree, a reputation halo for your resume, and an opportunity to work alongside some of the top talent or top operational structures in an industry. They also have great pay packages that compensate for whatever issues you'll experience working there. These companies can end up massive (tens to hundreds of thousands of employees) but they make up a small subset of all employment. Not everyone is the number one in their industry, or on track to be. Good for you if you work for them!The remaining majority of companies are those that are going nowhere or those that are sliding back in that direction. Because trajectory, management, and quality of operations are strongly correlated, zero or negative growth typically signals that something is wrong or broken at a company, and it isn't being fixed.1 The company has some disconnect in the feedback loop between performance and accountability. These companies are not at the top of their game and the toughest challenges you'll encounter at them are navigating the dysfunction without becoming jaded or burning out.That's what makes them, in common parlance, "bad companies". Most people work for these kinds of companies, or will work for a company like this at some point in their career. And most companies I have worked with, in that regard, have been "bad" companies.2 That's why I'm writing this. To flip Tolstoy's wisdom, great companies are all contextually unique and idiosyncratic outliers, while bad companies are bad in mostly similar ways.

Because of those similarities, there are takeaways from working at bad companies that are useful and applicable to any company you work at. The arc of working at a bad company looks like this:You arrive optimistically – things seem nice from the outside!You notice the dysfunction.You try to fix things.You learn how intractable the problems are and the limitations of what you can do.You realize that this probably isn't the place where your work lands a magazine cover unless it's pay-to-play marketing. A meaningful, successful tenure here will mean... something different.So you practice skills, extract experiences, and build relationships.And then you move on. There's little reason to stay once you've learned 80% of what is available to be learned or practiced. If you stay, you will stagnate.So can you build a good career across such environments? Yes, but not in the same way that you'd do it at a company with a great trajectory. Two things you're certain to take away from a bad company are (1) your reputation and (2) the experience, knowledge, and confidence in dealing with dysfunction and messiness. And so career growth at a bad company comes from learning to survive, navigate, and then solve mostly human-caused problems without burning out. In many ways, that's also your career arc: with survival comes learning; with learning comes experimentation, experience, and growth; and eventually you'll find yourself both in the position of being able to make an impact and having the skills and wherewithal to do so.But mostly, you first have to survive.How to SurviveAvoid Stepping on RakesBeing right is often extremely context-specific while being wrong is often pretty universal.3 So learning what the universal mistakes look like and subsequently avoiding them has been more effective for me than trying to be overly clever, innovative, and correct.Being clever, innovative, and correct is especially tough early on in your career because you likely lack the experience to distinguish between superficial similarities and significant differences (and vice versa) between situations. And what passes for early-career innovation is often a rediscovery of existing techniques, principles, and observations, that when presented as novel insights is read by the rest of the room as inexperience and chutzpah. (That's been me, in many rooms). That's not to dissuade you from trying.

There is no learning without risk of failure, and you don't know what you don't know; that's the essence of inexperience. So as a corollary to avoiding stepping on known and obvious rakes along your path, here's my kit of heuristics for what does work:Respect the Overton window for change management. Big changes at companies come when there is some sort of shock to the system: an important person is either joining or leaving, or the company is navigating some crisis. This is when someone can come in and without much pushback say that "we're doing things differently moving forward", or when a company can change its strategy 180 degrees to address a challenge. (As Rahm Emanuel put it: "Never let a serious crisis go to waste.") At all other times, companies, teams, and people will be resistant to any change that isn't at most a half-step forward. Don't lead with ego. People typically don't want to work with someone who takes up all the air in a room, or someone who makes them feel stupid, intentionally or not. You don't want to be so smart that you discount the observations or thoughts of your colleagues because you've already figured things out. Have some humility, and listen more than you speak. People want to feel respected, heard, and appreciated. Lean into that. I've put my foot in my mouth too many times to count by jumping in to finish other people's thoughts, only to later learn that not only was I wrong, but it also made them want to work with me less. Many situations can be worsened by opening your mouth inopportunely, and many situations can be improved by keeping it closed. You don't need to let everyone know how smart you are. Be curious about other people's perspectives. Help other people look good, let them take credit from time to time. Win allies. Success comes easier when you make friends, not enemies.Over-communicate, and keep your word. Learning to communicate well – succinctly, clearly, and at the level of detail matched to your audience – is one of the most important skills you can work on. And for anything important, you need to over-communicate. Tell people what you're going to tell them, then tell them the thing, then tell them what you told them. Then follow up about the thing you told them about.

Never assume that someone understood, or is on the same page as you, or knows what the next steps are. You'll end up wrong far more often than right. And if you ever say you're going to do something – you better do it, and do it well. Keeping your promises is the foundation of your reputation and credibility. There are many times when I have gotten ahead simply because I was the only one who left a meeting, did what we had talked about, and brought it back to the team. Periodically check the balance in your reputational bank.Reputation takes a long time to build and a short time to lose. All the usual wisdom applies: don't make promises you can't keep, don't over-promise and under-deliver, don't pursue high-risk, high-failure projects unless you have some reason to be confident in the outcomes you want. If you've been at a company for a while and 'can do no wrong', you've probably saved up enough reputation that you can cash in for a big initiative or gamble. And if you're not effective or sidelined at meetings, practice some introspection as to why you're not able to make things happen. Reputation is an external measure – it is a reflection of other people's views of you, and you may need to put in some effort to improve those views. And lastly, Don't try to apply philosophical approaches to management without catering them to your specific context. This is very specific advice and what I mean is, don't try to apply blanket changes such as "We did X at my last place, so we'll also do it here" without figuring out how "here" and "my last place" are different. Every company has a flavor of processes that has been optimized for the specific context in which those processes exist. What works for one company may not work for another. Don't try to steal management advice wholesale from other teams and other companies, and don't try to solve what you imagine other company's problems to be when you have your own very real problems to deal with. This is what is meant by "Google's problems are not your problems."All of these are simple in principle but rare and difficult in practice.

Navigating DysfunctionDysfunction Scares Away Quality Candidates; That Creates Opportunities for ProgressionIf you’re willing to “eat dirt” (take on additional responsibility without additional compensation), especially early in your career, you’ll be given opportunities to take on increasingly bigger challenges which lead to operating above your title.4As an example, early in my career I was able to take on responsibilities in data work and user research because I was volunteering for them without asking for anything in return (early enough, being hands-on and learning was reward enough).Similarly, I was afforded a lateral career move from marketing into product management because a company's product team had imploded and no one wanted to lead that department for fear of getting failure on their hands. I volunteered to lead that team in addition to my then-current responsibility. (My risk analysis was, "well I can't do it any worse than the last two guys.") I was able to turn the team around, and it became the doorway I needed to move full-time into doing product and engineering work... a door that would have been hard to open otherwise. In fact, much of my career advancement has come from volunteering to do the work no one else wants or has time to do, and not expecting to be paid better up front for it. (The compensation is the practical skills developed and the challenges you get to work on.) Being especially attuned to how opportunity windows open and close, I'm often the first one in to ask if I can help, or take on some adjacent responsibility when a window opens. But you need to be strategic about it: aim to take on opportunities you can learn from, tell a good story about, practice something new, or test a theory. Avoid work for the sake of extra work, and avoid taking on work that isn't valuable in some way. There's a fine line between being exploited and seizing a moment to make the most of your circumstances. To go back to company trajectories: in a good company, it's easy to work on valuable things. In a bad company, you have to drag value out for yourself.As a corollary, turning such 'dirt' into actual title progression is often easier when you're switching companies, not intra-company. When you're inside a company, a promotion is tied up in budget changes, title and staffing politics, seniority calculations, and ceilings on acceptable changes.