How to Become the Person Your C-Suite Actually Wants to Meet With

How to prepare, facilitate, and pivot during 1:1s with the C-suite to cement yourself as a trusted advisor at your company.

Welcome to Reframed by Ashley Rudolph. One idea, every week, that changes how you see your career.

Last week, I spoke to Heather D’Angelo about her epic career journey that includes: founding an indie band that was featured on Twin Peaks, founding a luxury perfume brand, and now leading brand and communications for an AI company. We talked about AI, how she sees her career, and what makes leaders stand out these days. It’s worth a read.

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Déluge Magazine

C-Suite leaders get energized by people who make them think, who ask the right questions and level with them. Walk in ready to be that person.

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BACKGROUND STORY

How I nailed my first 1:1 with my CEO

As a manager, I took on a high visibility project and ended up on the CEO’s radar. The CEO (let’s call him Bob) wanted to make sure that my vision was aligned with his, so he put a surprise invite on my calendar. This meeting was the first time I’d have any one-to-one exposure with a member of the C-suite. Bob had a reputation for being short on patience and sometimes too direct.

I texted my friends for help.

I decided there was only one logical thing to do: immediately start working on a slide deck and talking points.

When the day came, I walked into the meeting nervous but confident I’d done all the “right” things to prepare.

I sat down and whipped out my laptop. I couldn’t wait for him to see how smart I was.

I put Keynote into presentation mode, beaming with pride at the first few slides, they mimicked the progression of his monthly all hands presentations. I kicked off our meeting with the company vision. Except, I mistakenly used a slide deck template with the old vision statement.

He noticed.

He looked at me….slightly incredulous and said “that vision statement is from 2 years ago”.

I wanted to close my laptop, get up, and quietly slink out of that windowless conference room. But I didn’t.

I pushed through, clicking through slide after slide. Although my confidence was rattled, I still landed my talking points. It just…didn’t feel like a dialogue, I felt like I was delivering a presentation to an audience of one.

Then, he paused me. He wanted my thoughts about something new happening in the industry. I was candid: “it’s an interesting concept but it’s not going to move the needle.”

THAT caught his attention.

I could offer that insight because I'd done more than curate information for our meeting, I'd formed a POV. We exchanged a few more ideas. And now, instead of leaning back in his chair looking bored like before (lol), he leaned in.

I couldn’t have predicted what he did next.

He grabbed my laptop and clicked through my deck, stopping on the slides that mattered to him so that we could discuss them further.

He walked out of the room and told the rest of the c-suite that he was excited about where I would take that line of business. I walked out of that room still slightly spiraling over my vision statement snafu.

Then someone put me out of my misery and told me that he was thrilled with how the meeting went.

The meeting went well because of my ability to think on my feet, not the slide deck I agonized over.

I grew that line of business 5x in one year after that conversation.

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Research in HBR found that companies now prioritize strong social skills above technical expertise and financial stewardship when hiring executives. The ability to navigate conversations with the C-suite isn't a nice-to-have. It’s a key factor in your ability to advance to senior levels of leadership. If you want to level up your exec comms, book a consult with me.

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How to have an effective 1:1 with someone in the C-suite

I knew immediately that I wanted my friend Sammy to weigh in on this topic. He’s a Senior Director of Finance with 20+ years of experience across luxury fashion (Diane Von Furstenberg, Frette), law, and corporate finance at General Assembly. Sammy has navigated C-suite relationships across every type of organization you can imagine. He has a knack for cementing himself as irreplaceable. Not just because of his expertise (he’s incredible at what he does, okay!), but because of his ability to say the right things at the right time to the right people.

Here's what Sammy and I recommend when it comes to having effective conversations with the C-suite:

1. They don't need the details. They need you to translate them into something meaningful.

Sammy puts it simply: “Executives care most about how your work drives the company forward, manages risk, or saves money.” So be prepared to quickly and confidently share a top-level read out about what’s happening on your team. What are the wins? What are the issues and how are you planning to solve them? How does all of it connect to company goals? This is the prep that matters.

If you’re struggling with zooming out, try this framework for structuring your thoughts:

1. Here’s what I’m seeing → “Two of our Q3 deliverables are at risk because they’re getting stuck in the approval stage.”

2. Here’s what I’m doing about it → “I flagged it for the finance team, their main approver is swamped with another initiative, so they shifted the responsibility to another team member with capacity.”

3. Here’s how it impacts the organization → “This keeps us on track for the Q3 launch and protects the revenue tied to it.”

That’s the whole playbook.

2. Come prepared, but be ready to throw your plan out the window.

This is critical. Sammy adds: don’t use this time for routine updates that could have been an email. Use it to solve tough problems. When you show that you understand their pressures and speak their language of “results,” you move from being just a staff member to a reliable partner.

Execs are constantly context switching. The most pressing thing on their radar last Monday may have shifted down their priority list by this week. That doesn’t mean they’re not thinking strategically. It just means their context changed. Bring an agenda but know they may want your thought partnership on something more pressing.

3. Don't walk out without answers to your urgent items.

Flexibility is a good thing, but don’t abandon urgent items on your own issues list in service of theirs. If things are moving fast, interject with something like: “I have something I need your input on. Do you want to start with your items or can we tackle mine quickly first?”

That’s how peers talk to peers, it’s not overstepping.

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FACILITATING EFFECTIVE C-SUITE 1:1s BY SAMUEL COLON →

And, like most of the overachievers I know, Sammy made a screenshottable chart to highlight how best to communicate, problem solve, and give feedback like an executive. I found the common mistakes column particularly useful.

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CLOSING THOUGHTS

The right mindset is the key to effective communication; having good meetings with C-suite executives is no different. Walk into those meetings as if you are a peer (even if you don’t share a title), because you have information and insights they genuinely need.

The moment you enter a conversation afraid to take up space, they no longer see you as a strategic partner. They see someone who needs to be mentored, guided, and developed. Someone who still needs to grow. And if you’re reading Reframed, I know that’s not how you want to be seen.

C-suite leaders get energized by people who make them think, who ask the right questions, and level with them. Walk in ready to be that person.

Thank you to Sammy for graciously sharing his thoughts. What surprised you most?

Good luck. See you next week!

Ashley

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