Compression Obsession: How Less Is Sometimes…Less

"True eloquence consists in saying all that should be said, and that only." — Marcus Tullius Cicero

My first role in BigLaw is a period I often describe as being forged in fire.

I had landed a partner-facing position at a top global firm, and within my first week was emailing partners, clients, and cross-functional teams. My management held our work to the highest standard. Inaccuracies, mistakes as small as typos, cut corners: none of it tolerated. Imposter syndrome crawled up my neck and down my arms to my fingers every time I drafted anything.

My previous role had centered on helping families and children slow down, to center and breathe, to feel and then to think. My new role moved at triple speed, and my emails landed in inboxes of people with serious intolerance for unnecessary verbosity. "What's the bottom line?" governed my correspondence.

Yet the devil does live in the details. I eventually learned the balance: where to let brevity govern, where to expand and offer deeper analysis. What I also watched, over and over, was the cost when someone else got that balance wrong. Small miscommunications that amplified into billing mistakes. Duplicated effort. Client messaging that missed its mark because someone along the communication chain made a brevity choice and left an important detail on the cutting room floor.

There is a premise embedded in almost every conversation about AI and professional productivity: shorter is better. Compression is progress. If a twenty-page memo can become five bullets, the bullets are the deliverable. This instinct is not wrong. There is genuinely too much text. Partners are unlikely to read your careful three-page email, and pretending otherwise is its own form of magical thinking.

What I want to push on is the assumption that compression is a direction rather than a tool, that the correct move is always to make things shorter. In legal and finance contexts especially, the cost of getting it wrong tends to be paid in orders of magnitude.

The exception that does not survive summarization: a matter budget update contains, buried in the middle, a note that the deal has shifted from routine diligence into a more complex regulatory issue. The partner knows this. The team knows this. The client may know this.

But the summary that moves upward says the matter is tracking over budget.

The burn rate is elevated, but not alarming enough to stand out. The margin pressure is real, but not dramatic enough to make the first three bullets. The reason the numbers changed is there, technically, but it does not survive compression.

The person who wrote the update knew that sentence mattered. They knew it was the difference between a matter that was simply running hot and a matter whose economics had changed for a legitimate reason. The AI summary, or the human summary written under a "be brief" mandate, may or may not surface that distinction, depending on how many other items competed for prominence.

The summary reads cleanly. The exception did not make the cut.

Now senior leadership is looking at the matter as a profitability problem, or a project management problem, when it is actually a scope-management problem. The numbers look worse than the work. Nobody intended for that to happen. The budget was not wrong. The summary was not wrong. It was just too clean to carry the thing that mattered most.

The dangerous summaries are not always the ones that get something wrong. They are the ones that leave something out and look complete. This is especially true when you compress billing and pricing communications into the minimum viable format, and lose the judgment layer.

I have seen frustrations mount time and again between lawyers and support staff, because while everyone is speaking the same language, they are not speaking the same meaning. This fuels a relationship where the parties view each other as difficult, inept or obtuse and the cost is in a breakdown of communication. No one is eager to reach out when they don't feel the feedback will be helpful.

When I join a new team, I sometimes inherit these types of relationships. The remediation almost always runs through the same fix: not shorter, but clearer. A longer report that is better formatted, with small concise overlays explaining the different data points, becomes a document of actual value. Compare that to an email with an embedded chart that nobody can contextualize without calling to ask. If decision-makers do not know what they are looking at, turnaround time and email length are secondary to a larger problem.

The professionals who navigate this well are not the ones who compress everything, or the ones who resist compression entirely. They are the ones who know which things to protect and are not afraid to send a longer email. That is, stubbornly and essentially, a human judgment.