The Hidden Ceiling

Why being indispensable to your organization eventually limits your growth

Lawyers who were high-achievers early on in their career often stall out in the corporate world without fully understanding why. It usually happens while they’re still working insanely hard and making tons of sacrifices in their personal life. And it ends up being a recipe for burnout.

The underlying problem isn’t effort or ability. It’s that the very traits that drive early success in their legal careers eventually start producing the opposite effect in the business world. These high achievers rely on personal effort to excel at every level until they reach a point where they can no longer increase their impact through individual contribution alone.

That moment is an inflection point. Continuing to grow scope and influence requires a fundamentally different lens on the job: delegating work to others, aligning stakeholders, and tolerating ambiguity or temporary underperformance. You can’t simply work harder and expect a quick road to superior results.

This shift is uniquely difficult for lawyers who were all-stars early on in their careers. Much of it stems from professional training in law firms and the legal profession’s implicit values, rules, and standards of behavior—many of which are deeply ingrained and almost impossible to unlearn.

The insights I’ll share come from the entirety of my professional experience practicing law at two law firms, hundreds of conversations with in-house & law firm lawyers, and working at 3 different high growth startups.

This is not about changing jobs. It’s about changing what your effort is optimized for.

Law Firms: Where the Habit Is Learned

Law firms are not structured the way most business are; they usually don’t have resale value so they don’t have any enterprise value.

In most companies, there’s an incentive to design operations around systems and processes because it increases the company’s resale value. This resale value, ie. “enterprise value” is often shared among owners, employees, and stakeholders through equity.

Law firms, on the other hand, operate under a different incentive structure. The economics are driven by annual profits that are distributed each year rather than by long-term, capitalized value. There is little direct upside to making work more repeatable or less dependent on specific individuals.

As a result, there is also little downside to over-relying on those individuals. Reliability and responsiveness are rewarded immediately, while building systems that reduce dependence is deprioritized. When something breaks, stepping in personally is not just encouraged—it is rational. Even if the work is low value.¹

Why Heroics Make Sense

Working late, absorbing problems, and being the safety net all make sense when value is measured by individual throughput rather than the durability of the system. These “heroics” are not a cultural accident. They are the predictable result of the unique dynamics at law firms.

This is why many high-achieving lawyers default to personal effort as the only solution to all problems. If something is broken, the fastest and most reliable response is personal intervention.

To be sure, there are some exceptions. Some firms are intentionally designed around process, e.g. the apocryphal small firm that relies on a few managing lawyers to oversee process & paralegals to complete the work. Firms like these are more similar to typical companies than law firms.

But they are the exception rather than the rule.

Personality Versus Incentives

It’s tempting to explain this broader pattern as a matter of personality. Perhaps it’s not incentives; instead, it’s that law attracts people who are more risk-averse and therefore prefer certainty and control.

It’s possible that personality-driven behavior has some effect. But I’d argue that it’s a function of the law firm economic model. We all know plenty of lawyers who are willing to take risk when the structure rewards it.² In my experience lawyers have similar views to risk as other high performing professionals.

In my view, incentives encourage the development of habits and values that work extremely well inside firms. High-achieving lawyers learn from day one that personal excellence solves most problems, and that reliability is the highest form of value. When something is broken, the right response is to absorb it yourself.

Those habits produce success in environments that reward personal throughput vs. system throughput. The problem begins when lawyers move into environments that reward something else. Let’s talk about what happens when these lawyers move in-house.

In-House: Where Effort Stops Translating Into Influence

Corporate legal teams are not viewed the same way as revenue-generating functions are. They are cost centers by design. That framing is more than just a label, it impacts how work is described, how lack of bandwidth is addressed, and more.

Because the legal department is not directly tied to growth, the value an individual in-house lawyer brings is often unclear. In that vacuum, responsiveness and availability become proxies for usefulness. Being fast, helpful, and accommodating is the safest way to signal contribution.

Many in-house lawyers respond to this dynamic by taking on more work personally. They stay extremely close to the business, absorb extra context, and step in wherever ambiguity appears. The effort they put in is very real.

But the returns here are very limited.

When Responsiveness Replaces Leverage

While legal teams grapple with these challenges, the overall business continues to grow. Demand for legal increases but corresponding headcount doesn’t: Legal is expected to keep up with demand without proportional investment.

Once again, personal effort typically fills the gap. The legal team could establish internal SLAs, leverage AI/tech, or rely on outside providers like law firms or ALSPs. But it’s just much simpler to just work longer hours. The company keeps moving forward with no added costs and with no interruption in service.

But the system does not improve.

The deeper problem is that prevented problems don’t earn any credit. No one gets credit for the “dog that never barked.” What gets noticed is speed, or lack thereof, in the moment.

This is usually is where frustration sets in. Despite long hours and high responsiveness, legal is looped in late, bypassed entirely, or treated as an afterthought. In house lawyers are viewed as a bottleneck that needs to be overcome.

Who Actually Breaks Through

In practice, there is only one reliable path for in-house lawyers who want to increase influence: expanding their scope.

Those who break through this barrier shed the“lawyer” label. They take on adjacent responsibilities and become accountable for more than legal output. The modern CLO role can sometimes include ownership of HR, compliance, risk, or other functions that sit closer to the business’s core operations.

This is a relatively new trend that’s just starting to take off. From this column on Bloomberg Law last year:

This shift has led to the “GC Plus” model—in which GCs assume multiple C-suite roles, such as chief human resources officer or chief operating officer . . . As companies increasingly rely on GCs to balance risk, strategy, and operations, the boundaries of the role continue to shift. Rather than operating as isolated legal advisers, GCs are integrating legal expertise with broader business priorities.³

To effectively expand your scope, you need to absorb more work.

Learning To Delegate

You cannot take on additional functions while continuing to operate business as usual. At some point, the constraint is no longer legal judgment on an individual issue/contract but time, attention, and decision capacity.

Expanding scope forces a shift away from personally executing every task and toward setting priorities, designing interfaces, and building systems that allow others to operate effectively. This is why scope expansion and delegation are inseparable.⁴

One is not possible without the other—and resisting that shift is often what causes otherwise capable in-house lawyers to stall just as their responsibilities begin to grow. This is often exactly where in-house lawyers feel burnout.

The irony is that many burned out lawyers leave to take a business role at a startup, in order to escape these constraints—only to encounter a sharper version of them there.

Startups: When Indispensability Becomes a Ceiling

Early-stage startups reward team members who can do everything. Jack of all trades. Knowledge of the broader operating context matters more than specialized expertise. Speed matters more than structure. The people who thrive are those who step in, figure things out, and keep the company moving.

For lawyers-turned-operators coming from firms or in-house roles, this can feel familiar (and extremely validating!). Personal excellence works again. Being indispensable is a huge asset at this stage of a startup.

In the early days, that’s exactly what the organization needs. But not for long.

Where the Pattern Breaks

As the startup grows, the constraints change. Volume of work in a wide range of domains skyrockets The organization adds a ton of new people. Capital suddenly becomes available which provides immense resources.

The bottleneck is no longer effort; it is now coordination.

A familiar pattern begins to emerge. An highly valued early employee learns the business deeply, earns trust, and becomes highly influential as a result. Work moves faster when they are involved. Problems get solved. Seems like all good news so far, right?

The Ceiling Appears

At some point, leadership faces a different question: is it better for the organization to promote and elevate that early employee? Or keep them where they are and hire a senior, experienced leader from the outside?

Too often, the answer is external. Not because the early employee lacks ability, but because they are too embedded in execution of the lower-level work to step back. They have become critical to too many day-to-day decisions.

In the cases where early employees do get elevated, one condition is almost always present: they are not so indispensable in execution that they cannot be removed from it. In a scaling company, work has to succeed without any single person as the point of failure.⁵

The Subtle Trap

This is what makes the trap hard to see. The behaviors that create early momentum are the same ones that eventually cap growth.

Staying close to the work feels responsible. Delegating feels risky. Letting go of decisions feels premature. But without that shift, indispensability becomes a ceiling rather than a strength.

For high achievers, this is often the first time personal excellence stops being enough.

Moving Up a Layer: From Individual Heroics to Systems

When processes don’t scale, high achievers step in to do the work. They fix what’s broken, smooth over friction, and keep things moving. In the short term, this works. The organization appears to be high functioning. But it’s not.

That’s because when high achievers consistently solve problems through individual heroics, system and process failures stop surfacing. And without visible failure, organizations don’t learn where there’s fragility. The very competence that keeps things running also prevents those systems from improving.⁶

What makes all this uniquely hard: Most organizations instinctively *want to* celebrate individual heroics. Leadership spotlights the person who stays up until 3 AM fixing a crisis is easy to recognize and easy to reward. Personal sacrifice is legible to the entire company. It reassures everyone that someone capable is paying attention.

For high-achieving lawyers, this form of contribution feels natural. It aligns with how value has been signaled throughout their careers in various contexts. When something breaks, stepping in personally feels like responsibility, not overreach.

How Heroics Hold Systems Back

I saw this play out at Logikcull, the first legal tech startup I worked at. There, we’d created an internal system of “Logik Props” to publicly recognize teammates who stepped up during unexpected emergencies. The intent was good. But eventually, an engineer correctly pointed out the flaw:

As an organization, we were incentivizing people to act heroically to cover up process gaps instead of fixing them.

There’s a relevant analog here: When high performers intervene consistently, system failures stop surfacing. And without visible failure, there is no pressure to redesign the system.

Letting Problems Surface

Moving up a layer requires tolerating short-term messiness. Problems have to emerge. Work that was once handled by an A player is now done by someone less capable. Quality dips. Edge cases are mishandled. Issues become visible in ways they weren’t before.

Those problems are not regressions. They are diagnostics.

The temptation to step back in—to “just fix it”—is constant. But each rescue reinforces the same pattern: the organization leans on you, and the system never matures. Over time, you become indispensable in exactly the role you need to leave in order to grow.

What ultimately happens is that your day-to-day work doesn’t disappear; it changes. There are fewer visible wins and fewer hero moments. Feedback is delayed. Credit is diffuse.

You are designing for a system where the dog never barks.

But this messy period is exactly the point at which your personal effort starts to compound and grow. Moving up a layer is not about withdrawing effort. It is about redirecting it—from solving the same problems over and over to preventing them from occurring through a process/system based solution.⁷

The Inflection Point

The pivotal moment is when you realize that incremental personal effort no longer results in corresponding gains. Instead you realize that the system now rewards leverage more than personal throughput.⁸

Gaining leverage is critical in scaling organizations. And the measure of whether or not a leader is using leverage properly is by evaluating the total output of the group he/she oversees.

This is not a concept I invented, by the way. It comes from Andy Grove’s masterpiece High Output Management:

The question then becomes, what can managers do to increase the output of their teams? Put another way, what specifically should they be doing during the day when a virtually limitless number of possible tasks calls for their attention?

To give you a way to answer the question, I introduce the concept of managerial leverage, which measures the impact of what managers do to increase the output of their teams. High managerial productivity, I argue, depends largely on choosing to perform tasks that possess high leverage.

When that realization sets in, you face a choice. You can remain indispensable in your current role, or you can begin the slower, less visible work of making yourself less necessary—so that you may focus on the higher leverage activities of the job at the next level up.

One of the hardest parts of this shift is that the work you do becomes less visible. When you stop stepping in personally, it can look—especially from the outside—like you’ve taken your foot off the gas. That perception gap is real, and it doesn’t close on its own.

Communication & Organizational Values

As your work shifts toward system design, prioritization, and leverage, you have to take the time to explain what you’re doing and why it matters. Without that explanation, stakeholders default to the most obvious interpretation: that you’re doing less.

This is especially true in environments that have historically rewarded visible effort over durable outcomes. Communicating the shift isn’t about self-promotion. It’s about shedding light on what appears to be work that would otherwise be invisible.

How this transition goes also depends on your organization’s self-awareness. Your leadership team needs to recognize and rewards it.

If leadership values heroics over durability, the system will keep pulling you back into execution. No amount of personal discipline can override that for long. The incentives will always win.⁹

Reclaiming momentum is not about opting out of the work. It’s about opting into a different definition of value—one that prioritizes compounding impact over immediate relief.

Conclusion: Operate At A Higher Layer By Managing Tradeoffs

Unfortunately there is no flip to switch. No magic bullet that suddenly shifts you from heroics to systems. No checklist, no playbook, no clean handoff where everything just works.

What actually exists are tensions—between speed and durability, visibility and leverage, control and scale. Learning to operate at a higher layer means learning to live inside those tradeoffs rather than trying to eliminate them.

Tension #1: Striking the right balance between doing the work yourself vs. delegating to others

That’s why this transition feels so hard. You’re not replacing one set of problems with another. You’re changing which problems you’re responsible for. At the same time, you can’t delegate everything on day one. During the adjustment period, heroics don’t disappear—they coexist with system-building.

There will be moments when you still have to step in personally. When the cost of failure is too high. When the system isn’t ready yet. That doesn’t mean you’re doing it wrong. It means you’re in transition.

The mistake is not using heroics temporarily. The mistake is letting them become permanent again.

Tension #2: Creating an imperfect metric that approximates measurement of your main objective

One of the hardest parts of moving away from heroics is knowing whether things are actually working. When you’re personally involved in everything, feedback is immediate. You feel productive. You feel useful.

When you step back, those signals disappear. In their place, ambiguity creeps in—and with it, the temptation to judge performance based on whether others are working the way you would.

This is why some form of objective measurement becomes critical. Metrics and KPIs help separate system performance from personal style. They give you a way to tell whether outcomes are improving even when execution looks messier than it used to.

Importantly, this doesn’t require perfect metrics. Even clearly articulated goals—what success should look like over a given period—create an external reference point.

Without that, it’s easy to fall into the trap of assuming the team is underperforming simply because they aren’t engaging in the same heroics you once did.

Tension #3: Aligning stakeholders with different perspectives & incentives who may never agree

None of this works without stakeholder alignment and leadership trust.

As your work shifts, your personal output becomes less visible. If expectations aren’t reset, that shift can look like a decline in performance rather than a change in contribution. People may conclude you’re disengaged when you’re actually working at a different layer.

You also need to make sure senior leadership recognizes the reality of the situation on the ground. Information from the front lines about realistic projections, bandwidth and capacity, and changing conditions have to make their way up.

On the flip side, you also need to make sure the front lines understand how their work fits into organization-wide objectives. That allows them to make the right tradeoffs, and helps them act autonomously to the benefit of the collective.

Alignment is key to all this. You need clarity with leadership about what your success looks like now, and trust that the organization will reward leverage rather than just effort. Without that, the system will always pull you back into execution no matter how disciplined you are.

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Moving up a layer isn’t about finding better answers. It’s about developing judgment—knowing when to step in, when to step back, and when to tolerate short-term discomfort in service of long-term momentum.

There’s no magic bullet. Just a set of tensions you get better at managing over time. That’s the job now.

Good luck, my friends.

1. In Profitable Misery I explained the source of the proliferation at law firms of low-impact, low value tasks I called “shitwork”

The more sh*twork you generate, the more money the firm makes. That’s how you end up in a situation where a bunch of junior associates run around building charts, reviewing documents, or my personal favorite—checking documents for typos and formatting issues. None of these things have a real impact on the case.

Put another way, when value is determined by hours worked, then all work is treated equal. Senior lawyers spending 10 hours managing junior associates effectively, improving system processes, etc. adds the same theoretical value as them individually spending 10 hours checking a brief for typos.

This is obviously an exaggeration. A client is not going to pay $3,000 an hour for a senior partner to check over typos. However, the general point remains—an hour of work that impacts one client, one matter is treated equally as an hour of work generating system-wide value for the firm.

2. E.g. Lawyers paid on contingency. Personal injury lawyers who are paid as a share of the recovery/settlement are a classic example. However, I wouldn’t analogize to all plaintiffs’ lawyers. Some types of plaintiffs’ firms that handle large scale class actions behave more similarly to a classic defense firm. The economics are such that there is still a lot of value in generating billable hours because they are used as a way to ensure the firm isn’t paid excessively on contingency. (The concept is called the “lodestar method.” Early in my career I was an associate at one of these firms, and I had similar pressure to do all the work, bill lots of hours, etc.)

3. To be clear, there is another way to be influential: working on matters where legal judgment is inherently strategic.

One example I always use to illustrate this principle is Belinda Johnson, Airbnb’s first general counsel who ended up becoming its COO. Instead of “merely” being responsible for reviewing contracts or HR issues, Johnson was responsible for architecting Airbnb’s regulatory strategy, which was critical to enabling it to generate revenue. From my old article profiling Johnson:

Would an established hotel or housing lawyer know how to look at other industries by analogy? And sculpt a new regulatory framework? Probably not. Johnson, on the other hand, worked on exactly these types of high level issues at Yahoo. Remember those twelve years long f***ing years as deputy general counsel we talked about earlier? Dealing with PR crises and getting regulatory approval for an unprecedented partnership with Microsoft? This was the moment all that suddenly became really valuable:

Highly regulated environments often elevate legal’s role. But this is largely a matter of company or industry selection, not something you can manufacture once you are already in the seat. Someone like Johnson had to “choose” Airbnb; she likely couldn’t have made her own role more strategic at a, say, normal B2B SaaS startup.

That distinction matters. Scope expansion is something within your control and that you can pursue internally. Strategic centrality usually isn’t. Without one of these conditions, effort alone rarely translates into growth. You can be capable, responsive, and trusted—and still stall.

4. This is the promise of AI, ALSPs, and other providers. If you’re a GC who isn’t authorized to hire FTEs below you, you can still leverage other resources to absorb that work. A quick aside: Often many vendors claim that using their services/products will enable in-house lawyers to focus on more “strategic work” and yet many still are unclear on what that is. What I’m suggesting is that the strategic work is finding a way to build a system that can absorb more legal work without requiring you to work insane hours. To scale the legal function.

5. Here’s what it looks like from the early employee’s point of view, which is the topic of a Reddit post I stumbled upon years ago:

I have always been an early stage startup employee. I am pretty good at everything I do, but never been a master at things. This is extremely great for early stage because they kinda get a package deal. But everything changes once funding kicks in, Founders only want “experts” in respective fields who they give importance to/ better roles to, it’s understandable given that they want to increase the probability of success with industry best practices. Also, I think the investors kinda push them to hire like that.

Further reading: How To Keep Your Job As Your Company Grows by Steve Blank

6. This is exactly how high achievers become stuck in the system. To be very clear, this is not a personality flaw or a failure of execution. High achievers do not solve problems for selfish reasons. It’s not because they are trying to maintain centrality for job security or money.

They are doing it because they recognize themselves as the most reliable problem-solvers in the organization.

Meanwhile, the organization believes that these problems do not even exist! The high achievers are taken for granted, don’t get the support they need, and eventually become resentful. (Classic example: the overworked in house counsel)

It’s all a predictable outcome of scaling organizations that rely on individual heroics instead of systems and processes.

7. Problems reveal where expectations are unclear, where guardrails are missing, and where the system depends too heavily on individual judgment. When A players do the work, those weaknesses stay hidden. When others do it, the system shows you exactly where it breaks. For the individual, this shift feels deeply uncomfortable. You move from producing excellent work yourself to overseeing work that is merely average—or at times, below-average. Subjectively, it all feels like regression. It feels like everything is falling apart.

8. You can tell when you’ve arrived at this inflection point by comparison. Maybe you know someone whose scope or impact increases despite them appearing less involved in doing the actual work. What’s happening: they’re being rewarded for solving processes problems while you’re being rewarded for fixing one-off problems. The system rewards the two very differently.

9. Incidentally this is why driving system wide process change is so difficult at large law firms.