Executive One-On-Ones: How to Prepare for a Strategic Update with Your CEO

Common Mistakes, Strategic Shifts, and How to Elevate the Conversation

You know that one-on-one with your CEO or President? It’s not just another update—it’s one of the most high-leverage conversations you’ll have all month. Handled well, it moves big decisions forward, resolves friction points, and keeps momentum on what matters most. But when it misses the mark, it’s because the message doesn’t rise to the level of strategic clarity the moment calls for.

Let’s break down some of the most common misssteps we see people make in executive one-on-ones and what to do instead.

Common Mistakes We See in Executive One-on-Ones

Mistake 1: Starting with “Here’s everything I’ve been working on…”

The instinct to “show your work” is strong—especially when trying to prove value. But CEOs aren’t looking for activity—they’re looking for impact. This isn’t a performance review; it’s a strategic checkpoint.

Try this instead:

“Let me give you the top headline, then a 60-second overview of why it matters.”

Mistake 2: Using internal jargon or team-level acronyms

What’s clear to your team may be cryptic to the CEO. If they have to stop you to decode the language, you’ve already lost altitude.

Try this instead:

“In plain terms, what we’re seeing is ___, and that means ___ for the business.”

Mistake 3: Bringing problems without context or a path forward

You may not have all the answers—but you need to bring perspective. The CEO isn’t there to fix your issue. They want to know that you understand the stakes and are thinking ahead.

Try this instead:

“Here’s what we’re seeing, the risks I’m watching, and the options I’m exploring. I’d value your view on which direction makes the most sense.”

Mistake 4: Thinking out loud in real time

Your executive one-on-one is not meant to be a sounding board experience. They expect you to have filtered your thinking. Half-baked ideas cause confusion and ripple effects. Of course, if what you really need is a white board brainstorming session, ask for that and see if they’re game. Many CEOs will dig that from time to time, as long as they know that’s the plan.

Try this instead:

“We’ve vetted this across key stakeholders. Here’s where we’ve landed—and the key decision point I’d like your input on.”

What Strong Executive Communication Looks Like

Powerful Phrases That Elevate the Dialogue

Here are a few executive-level phrases that help ground the conversation in clarity, trust, and shared accountability:

• “Here’s the core issue I think you need visibility on, and my recommendation.”

• “From a strategic perspective, here’s how this ties to our top priorities.”

• “Let me anticipate the top three questions you’re likely to ask and address them briefly.”

• “To move forward, I suggest we align on this next decision point and timing.”

• “Is this directionally where you’d like us to go?”

These phrases convey preparedness, strategic thinking, and respect for your CEO’s time.

Communicating with executives isn’t about talking more—it’s about thinking higher. Elevating your message starts with preparation, intention, and the discipline to say less—but mean more.

Every executive one-on-one is a chance to earn credibility, sharpen alignment, and move the business forward.