Communicating With Executives

Professional communication has been one of the steepest learning curves early in my career. During high school I made sandwiches at a Firehouse Subs, and throughout college I bartended at a Chili's - two roles where conversational communication mattered more than direct, executive-facing dialogue.

Since stepping into a corporate setting, I’ve learned several principles that make executive communication more effective.

What Do Executives Actually Care About?

When communicating up the chain of command, you must filter your message to what leaders actually need to know. Remember: they have dozens of people just like you sending them updates every day, and their time and attention are spread thin.

So how do you decide what’s worth including? My simple rule of thumb is to consider the action an superior could take based on the information you’re sharing. If the detail doesn’t change a decision, a timeline, a risk, or a business outcome, it probably doesn’t belong in the message. This mindset keeps your communication sharp, relevant, and respectful of their time.

What Not To Say

We’re rewriting part of the backend because the current implementation is messy and hard to maintain.

• Nothing about business impact, timing, or risk
• Giving an update just for the sake of giving an update

What To Say Instead

We’re refactoring the backend auth service to reduce outage risk and improve deploy reliability. It will take two sprints and lowers our incident probability by ~20%.

• Ties the work to risk reduction
• Sets a timeline so they can plan accordingly
• Frames the outcome in business terms
• Filters out unnecessary technical detail

Deliver Clear, Structured Messaging

Executives don’t have time to dig for the point, you need to lead with it. Start with the conclusion, then offer only the context required to understand it. Keep your message brief, direct, and free of jargon or technical rambling.

A reliable structure is conclusion → key points → recommended next step. This ensures your message is immediately clear while still giving enough substance to act on. You can always dive deeper if asked, but don’t make leaders wade through unnecessary detail up front.

What Not To Say

So yesterday we had this long issue with the deployment pipeline, and after going through multiple logs and retries, I noticed the caching layer was acting weird. Then I realized the artifact step was misconfigured, and I think that’s why it failed… anyway, we’re working on it.

• Buries the conclusion
• Rambles through background
• Feels like problem-dumping

What To Say Instead

The deployment is temporarily blocked due to a configuration error. I’ve identified the fix and will confirm resolution by 3 PM. No customer impact, and I’ll escalate if the timeline changes.

• Leads with the point
• Uses minimal context
• Defines the next step
• No jargon, no noise
• Signals readiness to go deeper if asked, not upfront

Build Trust Through Consistency and Ownership

Communication isn’t just about what you say, it’s about how reliably you follow through. Your leadership needs people who surface issues early, take ownership of outcomes, and deliver updates without being chased. Surprises erode trust, transparency builds it.

Whether something is on track or slipping, be the person who communicates clearly, owns the result, and offers solutions rather than excuses. Over time, that consistency signals professionalism and makes your leaders confident they can rely on you.

What Not To Say

The migration slipped because the platform team didn’t get us the API updates in time. I’m not sure what the new timeline is yet.

• Deflects blame
• Signals lack of control
• Provides no path forward
• Leaves the executive with uncertainty

What To Say Instead

The migration is tracking one week behind due to a delayed API update. I’ve synced with the platform team, and we’re aligned on a new delivery date of Friday. No action needed from you, I’ll update again if anything shifts.

• Takes ownership of communication
• Flags the blocker early
• Provides a new timeline
• Reduces surprises
• Shows follow-through

TLDR

Communicating effectively with executives is less about sharing every detail and more about delivering the right information, in the right way, at the right time. Mastering upward communication isn’t just about professionalism - it’s one of the fastest ways to stand out, build trust, and accelerate your career.