Spotting executive communication mistakes before they cost money

You can usually tell which mistake you made from the reply you get. Each item below has a tell: the response that means you did it. Watching for tells is more reliable than self-assessment, because your own note always looks clear to you.

What to take away

Tells in the shape of the note

1. The ask is in paragraph four.

2. You led with the process. The tell: "What do you need from me?" How the work was organized is interesting to you and to almost nobody above you. The principles of plain language put the reader's purpose ahead of the writer's, which is the same instruction in a different setting. They want the state and the decision. Process belongs at the bottom, if at all.

3. You hedged past the point of meaning. The tell: they ask someone else. When every sentence has a qualifier, the reader cannot extract a position, so they go to a source that has one, usually someone with less information and more confidence. Hedge the parts that are genuinely uncertain and commit on the rest.

4. You offered options with no recommendation. The tell: the decision comes back changed in a way that shows they picked on a criterion you never mentioned. You know things they do not. Withholding your view is not neutrality, it is a transfer of work upward, and it invites a choice made on the wrong basis.

Tells in what you reported

5. You reported activity instead of state.

6. You used their vocabulary and answered a different question. The tell: agreement, then no action. Borrowing commercial language while answering an operational question produces a note that sounds aligned and does not address what they asked. Answer the question they have, in whatever words; matching the register is worth nothing if the frame is wrong.

7. You wrote for the room instead of the forward. The tell: a question that would not have been asked if the reader had been in the original conversation. Senior communication travels without you. Shorthand, unlabeled numbers, and "the issue from Tuesday" all break the moment the note is pasted into another thread.

8. You surfaced a risk without its size. The tell: "Noted." A risk with no magnitude, no likelihood you are willing to characterize, and no trigger date cannot be acted on, so it gets acknowledged and dropped. Then, if it lands, you are the person who mentioned it, which protects you and helped nobody. Say what it costs, roughly, and when you would need to act.

Tells in habit

9. Your confidence did not match your evidence.

10. You updated on a schedule instead of on change. The tell: nobody responds, for weeks, and then someone is surprised by something that was in the update. A rhythm of low-information notes trains people to skim, and the important one arrives looking like the others. Send when something changed; when nothing has, say that in one line.

11. You buried a decision you had already taken. The tell: "When was this decided?" Presenting a made decision inside a status paragraph is read as concealment, even when it was ordinary and within your authority. If you decided something they would want to know about, say you decided it and say why.

The two-line test

Before sending, read the first two lines only.

Can someone tell what you want from them, and by when? Would those two lines still make sense pasted into an unrelated thread with no context?

If either answer is no, the fix is nearly always rearrangement rather than rewriting. The right sentence is usually already in the note, sitting three paragraphs too low.

More on structure in executive communication techniques, and worked versions of the same update in executive communication examples. The reasoning behind all eleven, which is how a senior reader triages, is in executive communication. Several of the tells are really about credibility rather than wording, and how that is built and spent is covered in leadership influence.

Common questions

The tells assume I get a reply. Mine mostly get silence.

Silence is itself a tell, and usually of the tenth mistake: a rhythm of low-information updates has trained the reader to skim. Stop sending on a schedule for a month and send only when something has changed. If the silence continues, ask directly what they want to see and how often.

Is putting the ask first not abrupt?

It reads as abrupt to the writer and as considerate to the reader. If it feels too blunt, the fix is one clause of context in the same sentence, not a paragraph before it: "To hold the quarter I need a decision on X by Thursday."

How do I give a risk a size when I honestly do not know one?

Give a range and say it is a range, and give the date by which you would have to act. "Somewhere between a week and a month of delay, and I would need to decide by the fifteenth" is actionable. "There is a risk to the timeline" is not, and it is no more honest.

I did make a decision quietly. Do I go back and flag it now?

Yes, briefly and without ceremony: what you decided, when, and why it was within your call. Raising it late costs a fraction of what being asked about it later costs, and the question "when was this decided" is the one you are trying to avoid ever hearing.