Communicating with Executives

Yes is the most expensive word in business. No is the most valuable.

Executives live by that. The one thing they optimize for above almost everything else is time, and they guard it. And product leaders live or die on the ability to communicate up: you're constantly asking them to fund things, to trust evidence over their gut, to kill work they were attached to. None of that happens if you can't make your case in their language, fast. So connect to what they care about, back it with data, and believe it yourself, because if you don't, no one else will either.

But how they want you to respect that time is not one size fits all. Some want it in ten seconds, some want two hours in the weeds. The people who lead up well read the person in front of them before they open their mouth.

Read the person first

Most advice hands you a rule and tells you to run it on everyone. That's exactly where people go wrong. Reading the specific executive is the skill, and it's empathy, the same muscle you use on customers. Empathy is not just a buzzword. It's how you get an executive to actually hear you.

I learned this the hard way. I'd spent years skeptical of NPS as a metric. Then I worked for a chief product officer who loved it. My first presentations left NPS out, because I didn't think it mattered, and they went badly. Once I built it in, the exec leaned in. Same work, same me. I'd just been communicating in my own preference, not theirs.

The miss wasn't the metric. It was failing to read the person. So learn them. What do they ask for? What makes them lean in, and what makes them reach for their phone? Find the people who already present to them and ask.

The exec-preference menu

Once you've read them, you'll usually land on one of a few types. Figure out which one and design for it.

• Short. Some want it punchy and get annoyed by anything more. If they've got ten minutes, polish it down to ten minutes.
• Into the weeds. Some want the deep, two-hour conversation and trust you less if you can't go there with them.
• The data. Some want the model, the numbers, the whole picture before they'll move.
• The email pre-read. Some want the detail in writing first, so the meeting can be a decision instead of a download.

If you email them, keep it tight. Open with the ask. One or two sentences at a time, not paragraphs. Anticipate their questions, answer them in bullets, put a deadline on it. My gut check: if the whole email takes more than thirty seconds to read, it's too long.

Lead with the outcome, your default

When you don't know a leader well yet, or you just want the move that works more often than not: lead with the outcome.

The most common mistake is thinking out loud. Walking an executive through your whole process, every consideration, every twist of how you got there. They very rarely care about the details. They want the headline: the good or bad thing that happened, the result, and just enough about how you got there. They don't care that Johnny the engineer went on vacation for three weeks and blew up your timeline. They want the outcome. If they want more, they'll ask.

Two standard structures make this easy. STAR and CAR are tried-and-true frameworks you may know from interview prep, not anything I invented.

• STAR. Situation, Task, Action, Result. Set the scene briefly, name what needed to happen, say what you did, land on the result.
• CAR. Context, Action, Result. The leaner version. A little context, the action, the result.

Both end on the result and keep the context short. They're a starting point, not a script. Lead with the outcome, then flex the depth to the person.

Delivering bad news

When the news is bad, all of this matters more, not less. Get to it quickly, lead with the result, don't bury it or dress it up. The truth rises to the top, and in a full room, someone usually already knows and will call you on it. My process for delivering it is four steps.

1. Outline the problem. Brief, enough for them to understand who's impacted. Something like: "We had a problem with the site last night. Traffic spiked around 10pm and took it down for thirty minutes, and anyone mid-order lost their cart." No finger-pointing.
2. Name the organizational impact. What it cost, in dollars, customers, trust.
3. Bring your solution. Why you chose it, what's already in motion, when it lands, what you need from them. Ask how often they want updates, then hit that cadence.
4. Execute. Steps one through three mean nothing if you don't fix it. This is the only one that builds trust.

Executives have seen every version of someone softening bad news. They trust the one who tells them straight, then goes and fixes it.