Game selection

The thing holding you back isn't lack of work ethic or inadequate intelligence, it's that you've chosen the wrong game to play

When you start out in the professional world, the entire game is about learning new skills and getting better at them. But somewhere along the way—after you become a high achiever—you will inevitably hit a wall, where you just can’t seem to break into the next level. In this article, I’ll explain why high achieving individuals need to focus their energy on something entirely different: something I call “Game Selection.”

Game Selection describes the act of making a deliberate decision about where you work and what you do. The goal is to find an environment where you have unfair advantages. If you’re a high achiever in the wrong environment, at some point you will reach a place where you have no competitive advantages—because every day you’re going up against other high achievers who look/act just like you. It’s incredibly hard to stand out playing that kind of game.

The principles I share today are applicable beyond individual career development too. CEOs of companies and Managing Partners of major firms all need to make sure they’ve chosen the right game for their organizations. Unfortunately, many leaders don’t realize this and instead of approaching Game Selection thoughtfully, they instead choose games by copying their competitors or prioritizing short term considerations.

My goal with this article isn’t necessarily to provide a full explanation of how to approach Game Selection properly. That’s a deep skill that takes decades to master. My aim today is to share a few examples and insights about Game Selection from my own experience that will hopefully illuminate some of the considerations you might want to take into account—both for your own career and the organization you lead.

High Achievers Playing The Wrong Game

Before I get into explaining the the whole concept, I’ll illustrate two made up examples of high achievers who struggle to “make it to the next level” due to poor game selection:

• An in-house lawyer with exceptional legal acumen struggles to be taken seriously by the executives at his high growth consumer startup. All they want is for him to rubber-stamp vendor contracts, but he sees risks everywhere. The in-house lawyer has a knack for identifying unexpected second or third order effects of otherwise innocuous legal positions and has helped the startup dodge several major risks. Instead of appreciating his value, the startup’s execs dismissively refer to him as “the department of no.” This in-house lawyer would do far better at a company with large sales contracts in a highly regulated industry, where his talent for seeing “ahead of the curve” would directly contribute to his organization’s top objectives.

• A superstar law firm associate struggles to make equity partner. She spends the first 7-8 years developing/mastering the core skills of her practice area—and yet the firm refuses to promote her to the partnership. The associate is informed that her lack of confidence around clients is what’s holding her back. The firm’s clients are mostly in a conservative industry where all interactions with outside counsel are extremely formal. The associate—who has a casual, direct style—is constantly nervous that she’s going to say something wrong in that environment. She would do far better at a firm serving the technology startup or venture capital industry, where her professional style matches the clients’ corporate culture.

In each of these examples, both lawyers are highly competent and would do just fine in their existing environments. But they would likely be interested in moving up, and in doing so—would be tempted to change something fundamental about themselves. High achievers are big on self improvement, so the natural tendency is to do things differently. Maybe they decide to make even more personal sacrifices and work harder.

What if there’s another way?

The Upside Of Switching To A Different Game

When you find the right environment it will feel like a breath of fresh air. That’s because when you’re in the wrong environment, you are absorbing all sorts of subtle rules/values that conflict with your personality and strengths. As a result you develop coping mechanisms that weigh on you. For example, I spent a couple of years working at a large, conservative law firm. I thought I did okay—after all, my performance reviews were pretty decent.

At the same time I could tell that something was weighing on me every day I walked into work. I didn’t realize it then, but I had developed all kinds of coping mechanisms to fit myself into the organization. I am not a naturally detail oriented person; I tend to move/act quickly, which can lead to mistakes. So as an associate, I would re-read my emails 10x and even print them out to review them for typos. Doing all this was incredibly taxing and I would be drained after just a few hours of work.

Meanwhile, the real talents I felt I had—socializing with new people, making jokes on the Internet, and public speaking—were all repressed. I mean, yeah I could occasionally post on my personal Facebook or speak at law schools. But none of those things directly contributed to my professional advancement. I had to fundamentally change who I was to fit in and potentially move ahead.

I didn’t fully appreciate how much I repressed until I joined a startup. Suddenly all of my talents were fully aligned with my organization’s top goals. I was able to lean on my natural tendency to move/act quickly. I had shifted to a sales role, which meant engaging with people and public speaking all the time. And somehow I found a way to use social media to make sales prospects laugh (and accept cold requests for meetings) leading to an unfair advantage in my career.

Having this strong alignment between my personality and my organization felt great! But more than that, it helped me avoid some aspects of professional life that I absolutely hated. For example, I did not have to gain credibility by constantly promoting my credentials. Nor did I have to play office politics to get ahead. Being a natural fit for my company meant I was good enough to almost avoid playing those games. Had I struggled in the core aspects of my work, I would’ve certainly had to play up my own credentials & play politics.¹

Don’t Copy My Strategy

I know I just wrote a bunch of stuff that makes working at startups sound perfect. Maybe some of you are thinking of copying my own move and leaving the practice of law to become a salesperson at a startup too.

Don’t do it!

Blindly copying my approach would be a mistake. In fact, working at a startup can actually be a terrible experience. Your company has zero brand, so you will constantly find yourself struggling to explain what you do to friends & family. Leadership will constantly change directions, and it will feel impossible to see any initiative all the way through. Salary and benefits will likely be worse than if you worked at a mature company.

Sales is also a very difficult job. You spend virtually all of your time begging people for meetings, and the vast majority of your conversations will lead to zero revenue. Meanwhile, your value is tied to how much you sell, and that number resets every week, every month, or every year. Most potential buyers will have zero idea of what your company offers, or what your product/service even does.

I say all of that to dissuade you from copying my exact move. Remember, the whole point of this article is Game Selection, which means you have to choose based on your own skills, talents, and personality. My own career pivot was made during a very specific period of time (in 2016, when cloud technology for e-discovery was in ascendance) and was designed for a very specific personality (me) and mix of assets on my career balance sheet (firsthand experience as a junior-to-mid-level litigator).

Unless all of these factors line up for you, it’s very likely that you will need to make your own choice about what game you should play. Maybe it is with legal startups; but maybe it’s going to a non-profit or government agency. Maybe it’s something creative or completely outside the business world. Whatever it is, it has to be your own choice that’s highly tailored to your unique circumstances.

That’s what Game Selection is all about.

Path Dependency

Like it or not, the game you choose will be heavily influenced by your past decisions. For example, my pivot to legal tech startup sales at the age of 33 was based in part on the fact that I had an extensive network of lawyers and several years of industry experience in the legal field. In other words, my own Game Selection decision in 2016 was overwhelmingly influenced by my decision to apply to law school back in 2006.

If I could “do it all over again” I’m not sure I would end up where I am now. Knowing what I know now about my personality and the world, I might have chosen something completely different coming out of college. Maybe I would’ve gone to a fintech startup, explored the crypto world, etc. I doubt I would’ve ended up in e-discovery software, CLM, or flex talent. Now that doesn’t mean I ended up in a suboptimal place; maybe my relative quick ascent in the alternative legal career path is directly connected to my exposure to Biglaw and having attention to detail hammered into my brain.

Path dependency plays a huge role in Game Selection. The more subtle point here is that you should not choose a game based purely on the optimal choice in a theoretical sense. In 2024, being a data scientist may be the optimal career path for a new college grad. But that doesn’t mean you should pivot to data science if you’ve spent the last 10 years doing M&A. Instead, maybe it makes sense for you to do corp dev in the AI space. Starting from zero—as if you had no work experience whatsoever—would be a big mistake.

This is why it’s so important for you to have a full understanding of what you bring to the table. Otherwise you will be swayed into making decisions based on trends and what the latest hot thing is—and end up worse off than where you started.

Business Applications of Game Selection

What’s true for individuals is also true for organizations. Take a typical successful startup as an example. Maybe they spend several years growing revenue hyper-fast while serving a niche market very well. Then one day they realize they’re starting to plateau. To continue to grow they will have to do one or more of the following: (1) focus on larger buyers in the niche, ie. move upmarket; (2) create new products/services and sell to the same buyers, ie. increase ASP; and/or (3) sell their core offering to an adjacent market, ie. expand TAM.

How do CEOs and their boards make the right choice? It’s incredibly hard. For example, I often see startups making poorly thought out decisions. Maybe they try to mimic the path of some other market leader in their niche. Or maybe they make decisions based on short term financial considerations, like boosting the valuation for an upcoming round of funding. Incidentally this seems to be why all legal tech startups are embedding generative AI into their offerings regardless of whether it makes sense; my sources tell me it helps increase valuation.²

To be clear, I have no idea what path these startups/companies should take instead. If I did, I’d become a CEO myself and make millions! But from what I’ve observed, startup leaders sometimes lack self awareness about what makes their companies unique. I’m not just talking about the product and the people; I’m also talking about the org chart and existing customer base. It’s the corporate version of what I said earlier—you have to take stock of where you are today. You cannot ignore path dependence.

Case Study

I’m reminded of a very specific example I witnessed several years ago as an early employee of Evisort. The founders had created proprietary AI designed to read existing contracts and tag specific clauses automatically. It was all super impressive. However, they made a strategic decision after they raised a Series A to move in a surprising direction. Instead of doubling down on their AI’s “post-signature” capability, Evisort decided to divert its energy towards the creation of a completely new “pre-signature” offering that helped manage contract approval workflows.³

On paper this was a shrewd decision. If you could manage both pre and post signature aspects of contracting, you could double your average sales price (ASP) and potentially own the entire workflow. Plus, Evisort’s biggest competitor at the time, Ironclad, had an outstanding pre-signature workflow product that customers loved.⁴ And perhaps even more importantly, Ironclad had just gotten a huge revenue multiple on its most recent round of funding. If Evisort could successfully copy Ironclad’s approach, that could potentially lead to dramatic revenue growth & valuation/multiple spike.

Or so we thought. In reality, building a pre-signature workflow was incredibly difficult. It was buggy and lacked key features. Plus, it wasn’t a natural fit for our ideal customer profile, which were largely big companies with lots of old contracts that needed analyzing. (Notably, Ironclad’s customers at the time were mostly startups, for whom contract approvals for sales agreements were of the utmost importance.)⁵

Maybe this is all a bit of Monday morning quarterbacking. But I distinctly remember having these thoughts while watching all this play out in real time. Evisort first made a splash in the market specifically because its founders were lawyers and data scientists who spent years building a robust AI engine. That founder profile/initial product led to specific choices and tradeoffs made in feature development and org chart design in the early days. It made little sense to copy what worked for someone else, without taking into account the events that led Evisort to where it was.

In my mind, the better decision would be to double down on the post-signature AI capabilities and find use cases beyond the legal vertical, like procurement or finance. They could also laser-focus on larger companies and their specific needs, like being able to index/tag industry specific clauses. Not much would need to change from a product development or sales/marketing perspective—so operational risk would be minimized. I don’t know if going that way would’ve ultimately been successful, but it probably had better odds of success.

Instead they chose the wrong game and likely burned lots of time/resources trying to compete in a place where they had few natural advantages.

Note: Several years later, Evisort was eventually acquired by Workday (Which I wrote about here.) If you take a look at the press release and media coverage, all of it focused on the “contract intelligence” or AI functionality. There is minimal mention of contract workflows. That should tell you all you need to know about whether that initiative succeeded.

Takeaways

Okay so I just spent nearly 3,000 words trying to explain Game Selection. I bet you’re wondering, what does this all mean for me? Here are a few key lessons/thoughts I hope you’ll take away with you:

• Is it time to change the game you’re playing? If you’ve been successful at something for a while, but suddenly feel like you’re hitting a plateau—it may make sense to change environments. Now, it’s possible that you can push past the plateau through skill development or executing better. This is definitely true if you’re early career, or still adjusting to a new environment.⁶ But that’s why I’ve added the qualifier “if you’ve been successful at something for a while.” That presumes that you have continued to improve and do well, and that now you’re hitting a wall. This is especially true in scenarios where there’s a lot of competitors. In those instances, working even harder is unlikely to get you the results you want.

• Do you know what makes you special? Make sure you take everything into account—including personality quirks, network & contacts, and work experiences. Don’t forget to take path dependence into account. Have friends complimented you for something throughout your entire life? Are there certain tasks that you find easy that other people inexplicably struggle with? Are there certain types of obstacles that bother others, but not you? Understanding what sets you apart is the first step in finding the right game to play.

• Are there “frontiers” where market dynamics are rapidly changing? All things being equal you want to be at a place where you don’t have to “wait in line” to prove yourself. In mature, established industries and sectors, there’s a lot of paying your dues. But in uncharted territory, everyone’s constantly trying to figure things out. Even in a relatively mature industry like legal, there are niches and pockets of activity where no one really knows what’s going on. If you can apply your superpowers there, you can really accelerate things.

• For managers and executives: Is your organization playing the right game? Are your people assigned to the right kinds of work? This is a super complex topic because there are so many moving parts and constantly shifting dynamics. But as an organizational leader, it is incumbent upon you to make sure employees are assigned to tasks they’re suited to doing, and that the ship, so to speak, is headed in the right direction.

Hope all this has been good food for thought. Best of luck my friends.

1. If you, on the other hand, are truly talented at organizational politics, it may make sense for you to work at & remain at a large company. I have met people like this, and marvel at their ability to work through the bureaucracy. I wish I could do it—but that’s just not my superpower.

2. These startups are not run by dummies. I believe that sub-optimal decisions are made not because execs/boards are unaware; but instead there are significant conflicts of interest involved. For example, a CEO who can successfully enlarge their startup’s valuation and successfully raise a large growth round may be able to sell off his/her own shares in that round, and achieve liquidity to buy a home, retire early, etc. The board/early investors win because the higher, marked-up valuation leads to huge paper returns for their investment fund, which allows these investors to raise a massive subsequent fund (that they then monetize through a 2% management fee). The losers of sub-optimal Game Selection decision appear to be the later investors and employees, all of whom are left holding the bag.

3. Pre-signature means all contracting activities before the agreement is signed by a counterparty, e.g. approval workflows, template generation, integrations with CRM databases, etc. Post-signature means contracting activities *after* the agreement is signed by a counterparty, e.g. clause identification, deadline/obligation management, reminders and alerts, etc.

4. Pre-signature was also viewed as superior because it could be used by customers regularly on an on-going basis. Post-signature software, ie. Evisort’s AI, theoretically only needed to be used once. After the clause data was extracted and exported, there would no longer be a need for the AI.

5. To tie it back to path dependency—Ironclad came out of Y Combinator, so they were deeply tied to the startup ecosystem. It was easy for them to gain quick traction serving the other startups in YC. Evisort had a completely different origin story: They were born out of Harvard Law/MIT, and their early customers were Harvard Law alums at older/larger companies. Those differences were calcified in the two’s respective product development choices, org structure, and team makeup.

6. A related thought: You absolutely cannot skip steps. Making the perfect game selection choice will mean nothing if you lack a baseline foundation of skills and experiences. Game Selection isn’t a shortcut; it’s a way to help you push past a wall or plateau.