(Note: For over two decades, I’ve been leading rooms filled with CEOs, founders, and top executives. Time and again, people ask me the same question: “How do you win them over so quickly?” It’s not magic—it’s a mix of subtle strategies, genuine curiosity, and a touch of fun. Here’s the breakdown of how I make it work.)

Ever found yourself standing in front of a room full of executives—people with big titles, bigger egos, and even bigger expectations? Leading that kind of room can feel intimidating, but here’s the good news: you don’t have to outshine them to make an impact.

The trick? Don’t try too hard. Instead, focus on these practical and surprisingly simple strategies to win their hearts and minds.

Start as a Non-Threat

Executives operate in high-stakes environments where competition is fierce. Walking in like you’re the smartest person in the room only raises defences. Instead, position yourself as a facilitator, not a competitor.

How:

• Introduce yourself disarmingly: “Relax, I’m just a designer. You are the experts. I’m here to ask the right questions and help us explore ideas.”
• Let them know you’re there to support their expertise, not challenge it.

Ask Simple, Powerful Questions

The fastest way to gain respect isn’t by talking—it’s by asking the right ‘wh’ questions (what, who, where, when, why). Quality questions demonstrate your expertise and show you’ve thought deeply without making you seem arrogant.

Example: When an executive once mentioned a target revenue for 2025, I asked, “What does this number say about us? Are we playing to win or just to participate?” That one question shifted the entire conversation and locked everyone’s attention.

Stay Curious and Connect the Dots

Executives often approach problems from the narrow perspective of their role. Your job is to zoom out and help them see the forest instead of the trees.

How:

• Be curious about everything.
• Pull insights from diverse disciplines.
• Connect seemingly unrelated ideas to create new solutions.

Refusing to stay in one niche positions yourself as a bridge across departments and perspectives. (Niches are for ants.)

Avoid Jargon

There’s no faster way to lose an audience than with industry buzzwords. Executives don’t want complexity; they want clarity.

Pro Tip:
Replace “Our framework aligns cross-functional strategies to achieve synergy” with “How do we get everyone working together?”

Understand the Room Dynamics

Before you walk into the room, do your homework. Know who’s in the room, what they care about, and how they interact. Once you’re there, observe the power dynamics. (Also, look beyond titles. Instead, focus on the human.)

How to Engage:

• Draw quieter participants into the conversation.
• Bring the focus back to someone who made an insightful remark.
• Make everyone feel heard and valued.

Go in Without an Agenda

Executives can sniff out ulterior motives from a mile away. Instead of focusing on pitching a solution, focus on uncovering the real challenge.

Mindset Shift: It’s not about how you can solve the problem—it’s about who in the room is best equipped to solve it.

Dress to Disarm and Delight

What you wear sets the tone before you even say a word. A playful outfit can be a game changer in an environment dominated by dark suits and safeties.

Why It Works: Execs live in a competitive world. Dressing in a way that’s fun and eccentric—think bold colors or quirky details—makes you approachable and memorable without being threatening.

Example: I often walk in wearing bright-coloured pyjamas or funky sneakers. It’s a conversation starter and signals that we’re here to collaborate, not to compete.

Closing Thoughts

Running a room full of bosses isn’t about dominating the conversation but facilitating it. Be curious, ask great ‘wh’ questions, and dress the part (with a twist). When you focus on making them shine, you’ll find that they’ll make room for your voice, too. Remember, it’s not about you. It’s about uncovering the real challenge.

The next time you step into a boardroom, remember: you don’t have to prove yourself. Just help them prove something to themselves.