AI can do a lot for you before a meeting.
It can help you anticipate questions, surface insights, and tighten your message. But once you walk into that meeting, it’s not about the tool anymore. It’s about you.
AI can help sharpen your message, but it can't read the room. It can't tell you when to pause for impact, when to pivot, or when to let the message land.
Those moments belong to you. Your tone, timing and professionalism still carry the weight.
AI can prepare you with insights, but only you can make people feel confident in what you're saying.
Executives don't need the full backstory. They need relevance and AI is a great tool that can help you find it. It can tell you what a role values, which KPIs matter, and what challenges they might be facing. Connecting those insights into a strong point of view? That's where you come in.
Lead with impact:
“Here’s how this helps your team reach the goal faster.”
“Here’s what this means for your Q1 objectives.”
If you find yourself getting tactical or staying low in the value pyramid – features, functions, processes – zoom out. Executives think in outcomes. They want to know how what you're saying drives outcomes, not just how it works.
AI gives you information. It's your job to bring the point of view.
Executives may set a casual tone. They might joke or share something personal, and that's great! There's nothing wrong with building a connection with an executive that is deeper than "fine weather we're having today." In fact, these moments of authentic rapport can be some of the most valuable parts of your professional relationships.
But just because it feel casual, doesn't mean it is casual.
The best professionals make connection look effortless. A quick chat about golf, travel, or family can warm the room, but it never derails the agenda or loses sight of what needs to be accomplished. They understand that warmth and competence aren't opposites; they're actually complements.
Professionalism doesn’t mean stiff or scripted. It means measured.
Think of it this way: when an executive asks about your weekend, they're not off the clock. They're reading you, building relationship equity, and creating space for more honest conversation. This casual moment is often the prelude to the serious one. Stay present, stay genuine, and stay sharp.
Pro Tip: If small talk lingers too long, be the one to move it forward. Don't wait for the executive to shift gears. They'll notice that you can read the moment and keep the momentum.
When an executive asks a question, take a breath. That brief pause signals control. It says, “I’m thinking, not reacting,” showing that you're treating their question with the seriousness it deserves instead of filling space with the first words that come to mind.
If you’re not sure what they mean, ask for clarity. Doing so isn't a sign of weakness; it's a sign of precision. A simple "Just to make sure I'm addressing the right angle, are you asking about timeline or approach?" can save you from a five-minute answer that misses the point entirely.
It’s better to pause and align than to rush and miss the mark.
AI can help you anticipate questions, but it can’t read tone or intent. That’s where your instincts take over. And when you use AI in prep, don’t just repeat what it gives you. Treat it like a thought partner; a way to sharpen your ideas, not a script to memorize.
Good answers start with curiosity.
Use AI to sharpen your insight and save time, but remember: professionalism, empathy, and judgment are what close the gap between prepared and effective.
A conversation isn’t reciting what the machine gave you. It’s showing up with a point of view, engaging with curiosity, and building trust in real time.
Chad Wilson
Walking out of a meeting knowing you held your ground, stayed composed, and added value. That’s one of the best feelings in business.
AI might open the door.
But your awareness, tone, professionalism, and ability to add value are what get you invited back.
Solutions like Wyn can accelerate your preparation — helping you rehearse, refine, and receive real-time coaching. But Wyn doesn’t replace your instincts; it amplifies them. It’s how modern professionals turn AI preparation into human performance.