What I've Learned About Communicating with Executives

I've made my share of mistakes in executive communication. Emails that were too long. Updates that buried what actually mattered. Meetings where I walked in with a problem and nothing else.

Most of it I figured out the hard way. Here's what I'd tell someone earlier in their career.

Test your email on your phone before you send it

This is the most practical thing I know. Before any important email goes to a CEO or senior leader, I send it to myself and read it on my phone. If I'm scrolling before I get to the point, it needs to be rewritten.

Most executives are reading on their phones between meetings. The window is short. If the first thing they see is context and setup rather than the actual message, there's a real chance they never get to what matters. The phone-screen test forces you to put the most important thing first, which is where it should have been anyway.

Don't bury the lede

Journalism has a term for this — burying the lede — and it's one of the most common mistakes I see in business writing. The news goes at the bottom, after the background, after the context, after the explanation of how we got here.

Whatever you need the reader to understand or act on, that goes first. The supporting detail can follow. You can't count on someone reading to the end, and you shouldn't make them work for it.

Come with options, not just the problem

Early in my career I had a habit of escalating issues without a clear point of view on what to do about them. I thought that was appropriate — bring the problem, let leadership decide.

What I've learned is that the people closest to a problem are usually the ones best positioned to think through the options. Coming in with two or three paths, the tradeoffs involved, a recommendation, and the guardrails you'd put around it — that's what being a trusted partner actually looks like. It doesn't mean you have to have all the answers. But you should have done the thinking.

A few other things that have mattered

Subject lines are underrated. 'Quick update' is not a subject line. 'Q3 pipeline risk — decision needed by Friday' is. Busy people triage by subject. Write them like they matter, because they do.

Send context before important meetings. Executives who walk in cold tend to redirect the conversation toward the things they're uncertain about, which often means you spend the meeting re-explaining rather than deciding. A short pre-read — even three bullet points — changes the dynamic.

And when someone is asking a lot of clarifying questions in a meeting, that's usually a signal the framing isn't landing, not that they need more information. I've learned to pause, reframe, and try again rather than adding more detail on top of something that isn't working.

None of this is complicated. Most of it is just about respecting how busy people process information and making it as easy as possible for them to engage with what you're bringing.