The skills law didn't teach you
Why lawyers struggle with the gap between effort and outcomes
You did everything you were supposed to do. You worked hard, were thorough, met the standard and in many cases exceeded it. You put in the hours, took on the work, and delivered. By every measure that used to matter, you performed.
And yet something isn’t translating in the current state of your career. The workload feels unending, and there’s no light at the end of the tunnel. You’re burning out from doing all of the things you were told to do, and that’s what makes it disorienting.
If this sounds familiar, the gap is worth examining. Because the problem usually isn’t effort or ability. It’s something subtler, and almost invisible to those who have spent their entire careers practicing law.
1. Discovering the problem
There’s a version of this I hear often from lawyers who’ve moved into revenue or performance based roles. Sometimes it’s someone who moved into sales, but other times it comes from a newly promoted partner who suddenly needs to do more biz dev.
It’s a common fact pattern: This lawyer wlil describe getting on the phone with a potential client and feeling completely at ease. They know the subject matter, can handle tough questions, stay organized, and inspire confidence. When the phone rings, they’re outstanding. It’s not surprising then that they almost always tell me:
“Just get me on the phone with a client and I will close the deal!”
What they are completely blind to is that getting the phone to ring in the first place is the actual job! The calls where they perform brilliantly represent a tiny part of the valuable work. The main part is figuring out who to call, why they might care, how to reach them, when to push and when to let go, and which opportunities are worth pursuing versus which ones appear to look like opportunities.
Or, to borrow a term I used in a previous article, the ability to get on lots of client calls is the load bearing constraint.
That layer of the job requires a fundamentally different skill: using business judgment to assess what actually matters, and actively declining to focus on what doesn’t. Legal training develops many things, but this particular skill, prioritization judgment in a commercial context, is largely absent from it.
2. How legal work is assigned
When you’re coming up as a lawyer, someone more senior than you, a managing partner, a general counsel, a senior associate, looks at the full landscape of problems and decides which ones require attention, which are urgent, what the priorities are. Then they hand you a piece of it.
Your job, from that point forward, is to execute as thoroughly as possible on what you’ve been given: research it completely, draft it carefully, review it meticulously. The work that reaches you has already been filtered. You are working on a pre-selected set of problems, and thoroughness on that set feels like doing the whole job. It isn’t. The prioritization happened upstream, and someone else was responsible for it.
This division makes sense in legal contexts. The judgment required to triage a docket or decide which contractual risks matter for a specific client in a specific transaction takes years to develop, and handing it to junior lawyers before they’ve earned it would be a mistake.
But the consequence is that lawyers can spend years, sometimes entire careers, developing extraordinary execution skills without ever being asked to develop the judgment that sits upstream of execution. When they move into business roles, the pre-filtering disappears. No one hands them a clear task list with the hard prioritization decisions already made. They get the whole pile, and thoroughness alone stops being sufficient.1
What makes this particularly hard to see is that it’s not a junior lawyer problem
Hot take: Many of the most outwardly accomplished lawyers, GCs, CLOs, partners with decades of experience, never fully developed this skill either. Their careers advanced on the strength of execution, relationships, and subject matter depth, all of which are real and valuable, but none of which are the same as business judgment.
Title is not evidence of prioritization ability. You can advance very far in a legal career, and in many cases in a business career, without ever developing the ability to accurately distinguish high-value from low-value work in a commercial context.
A concrete example: I’ve seen senior in-house lawyers spend considerable time getting a company’s press release exactly right, sharpening the precision of a nuanced position on a controversial topic, ensuring no word could be misconstrued. Technically, the work was excellent. What got missed was the actual purpose of the release, which was to pledge loyalty and endear the company to its core buyer demographic.
The audience for that document was not a judge or a regulator. It was a customer who needed to feel seen—which means you need to take a stand and alienate some other group of people. Judgment means actively choosing to make that tradeoff instead of sending out a communication that feels “safe” but wins over no one.
The lawyer experienced this as doing their job well. The business experienced it as legal getting in the way and simply “not getting it.”
That pattern repeats across functions and seniority levels. It’s the underlying reason the business finds legal so difficult to work with. The problem has less to do with risk aversion (in my opinion) than with consistently answering the question asked instead of the question that matters.
3. My personal experience
I struggled as a young associate. I felt that I was genuinely good at one of the main core aspects of a litigator’s job which was evaluating reasoning across conflicting opinions, to produce a synthesized rule that helped the client. There were moments I did that better than partners who had been practicing for decades.
But I was terrible at keeping my head down. I couldn’t stop evaluating which work mattered and which didn’t. While colleagues moved efficiently through their assigned task lists with a temperamental ease I couldn’t replicate, I was distracted by the question of whether the task list itself was right.
That made me slower and less reliable on execution, and genuinely less valuable in an environment where the billable hour treated all work equally.
My colleagues, on the other hand, were well-suited to that system. Their instinct toward thoroughness and precision was exactly what law firms needed from junior associates, and they were rewarded accordingly. My instinct, to lift my head up, question priorities, figure out what actually mattered, was a liability in an environment where someone else was supposed to be doing that.
Ten years later after leaving the practice of law, I see the other side of that equation. The traits that cost me in law turns out to be the core of what business actually requires. Making tradeoffs and prioritizing objectives. And I can now see that many of the lawyers I who struggle in commercial roles are struggling precisely because they were excellent associates.
The habits that produced their success in law are the same ones creating friction now.
I wrote about a related version of this pattern in The Hidden Ceiling, which looked at why high-achieving lawyers stall out in corporate environments. That piece was about the trap of heroics: doing too much yourself, staying indispensable, never building systems.
This article is about something that sits upstream of that. Before you can figure out how to do work at the right level, you need to figure out which work is worth doing at all.
4. Self diagnosis
So what does this gap actually look like in practice, and how do you know if you have it?
The clearest signal is a mismatch between effort and recognition. You’re working hard, producing thorough output, and the business still seems frustrated or underwhelmed.
A second signal is that your contributions tend to resolve the question in front of you without changing how decisions get made.
A third is that you find yourself surprised, regularly, by what leadership actually cares about, as if the priorities you’re working from and the priorities that matter to the organization are operating on different frequencies.
The underlying pattern in all three is the same: you’re executing well on a task list you didn’t fully analyze. The prioritization judgment that should sit upstream of the execution hasn’t been developed, not because you’re incapable of it, but because nothing in your training required it.
Developing it is possible, but it requires stepping deliberately outside the frame of your daily work often enough that a different kind of attention starts to become natural.
The legal career path selects against this skill, systematically and without malice.
The system that produces excellent lawyers, rigorous training, careful supervision, thorough execution, also produces professionals who’ve had the prioritization layer done for them at every stage.
Some lawyers develop it anyway, usually because something in their career forced the question: a role without close supervision, an environment that punished over-lawyering visibly enough that the feedback was impossible to ignore, a mentor who named the gap explicitly.
But many don’t, and those who don’t tend to find that at some point, whether they’re a fifth-year associate, a ten-year in-house counsel, or a General Counsel with a seat at the table, the effort stops translating in ways they can’t fully explain.
That gap between effort and outcome is diagnostic. It suggests that the job may have started requiring something your legal training didn’t prepare you for.
The good news is that the skill is learnable. But you can’t develop what you haven’t named, and the first step is being honest about whether the signals above sound familiar. For those who want to go further, below I’ll share three specific things you can start doing differently.