Essay · March 2026

The memo that wasn't

The cost of an ambiguous email lives downstream.

I once sent a quick email to a direct report, asking them to locate an important communication that another team had shared with the Board. This should be easy, I thought as I dashed it off.

That was on me. I had not been clear: I had used the word "memo" generically, without stopping to check what the artifact actually was, who had produced it, or where it lived. Three lines, thirty seconds: I had sent ambiguity.

There was no memo; slides had been shared instead. My quick email set off a cascade: multiple people started chasing documents, preparing talk tracks, tracking down non-existent artifacts, and one person even started planning to write the memo for me. All of it resolved only after several back-and-forths, once someone surfaced the gap.

The cost of my imprecision landed on several people. They chased ghosts for days because everyone wanted to solve the problem I had given them, not stop and ask what the problem actually was. I had sent ambiguity; they had executed on it.

This is what I call the memo problem. The cost of an ambiguous email lives downstream. It is in the cascade of execution the email triggers: the people who start filling gaps, making assumptions, and producing work that may or may not be what the sender meant. A three-line email can generate days of wasted work, distributed across multiple people, none of whom were doing anything wrong.

The research confirms the pattern. Work by Justin Kruger, Nicholas Epley, and colleagues at NYU and the University of Chicago found that senders estimate their emails land as intended close to ninety percent of the time, while recipients correctly interpret the tone and intent of closer to sixty percent. The sender's confidence is so far out of line with the receiver's experience that the two are effectively in different conversations. A 2022 Grammarly-Harris Poll survey estimated the annual cost of poor communication at roughly $1.2 trillion, or about $12,500 per employee per year. Most of that cost comes from memo problems: small daily moments when someone fills a gap and executes on the wrong version.

Here is the mechanism: email is a broadcast medium. The sender composes alone, re-reads their own words, confirms for themselves that the intent is clear, and hits send. Every one of those steps operates inside the sender's own frame. The receiver opens the email inside their own frame, with the sender's voice, body, context, and mutual history all stripped out. Whatever ambiguity survives the translation lands in the receiver's lap. The receiver resolves it with whatever assumptions their frame provides, and then starts executing on that resolution rather than stopping to ask.

This compounds across an organization: every forwarded email is a translation of a translation. Every group email is a single message being decoded by ten people, each running the interpretation through their own frame. The output that emerges, when the work is done, looks like misalignment from a distance. Look closer and it is something else: faithful execution on ten different interpretations of one unclear message.

The correction has two parts. First, use email only for what email is good at: distributing information that does not require interpretation, like confirmations, documents, and read-this-before-Tuesday notifications. Anything where the receiver's frame might reasonably differ from the sender's belongs somewhere else: a five-minute phone call, a three-person video check-in, a walk down the hall.

Second, build the pause. When you receive an email you are about to execute on, ask yourself whether the sender might have meant something different from what you just assumed. If there is any chance, do not execute. Ask. This is the harder discipline, because the instinct is always to solve. The operators who build this habit save their organizations weeks of rework, and they build it on the receiving side as much as the sending side. The memo problem is rarely a sender failure alone; it is the sender's ambiguity meeting the receiver's eagerness to act.

The memo I asked for did not exist; the email went to one person. The cost landed on several people and days of work, and was only caught because someone finally pushed back. Most memo problems never get caught. They get executed, shipped, and become the organization's quiet tax.

The memo problem shows up anywhere communication is ambiguous: meetings, hallways, Teams messages. Email is where the pattern leaves a trail. The discipline is the same everywhere.

Pick up the phone. Ask the question. Stop before you solve.