6 Conversations Starters With Your VP

How to start off strong when meeting your skip-skip-skip...skip-skip-level in an adjacent function (jk) for a "get to know you" meeting.

Oct 24, 2024

👋 Hi! I'm Yue. Chief Product Officer turned Leadership Coach. My personal mission is to help women and minorities break through to the C-suite. Subscribe to get future posts in your inbox.

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(On a farm, Teddy the Corgi, Spain)

There’s one question I get asked at almost every community office hour or class Q&A: I’m meeting or want to meet with my "super senior, not involved in my day-to-day, has a ton of authority or power, or a tad bit fearsome leader. What do I say? How do I put my best foot forward?

Curiosity, Not Fear

Many of us have this talk track in our heads as we imagine the conversation: What if he/she doesn’t like me? What if there’s nothing to say? What if I don’t make the most of the precious 30 minutes? What if it destroys my entire reputation and career!!??

The first step is to remove the fear of the meeting with three simple steps:

Make a plan (more on this below)
Practice your self-introduction
Shake off nerves right before — do a little dance, relax your breathing, and scroll through some favorite photos. Take 4 deep breaths.

Remember, they are also just people. People with families, friends, wants, needs, and goals. They want to get to know you (or they wouldn’t have taken the meeting). They also do not want an awkward or waste-of-time meeting.

Nail your self-introduction

Have you done a 5-minute introduction to receive a blank look back? You lost the leader somewhere in the monologue. Many of us focus too much on tactical descriptors when we do an introduction, trying to tell the other person everything about our work history and often throwing in a ton of acronyms or project-specific context. This is super difficult for an executive to follow. Instead, find 1-2 commonalities in your work, and focus on that in your introduction.

Where are the current points of collaboration? Who on their team do you work with? What projects have you collaborated with his/her team on?
Do you have commonalities in your background? Education, places lived, hobbies, interests, previous workplaces, shared commute pain points?
What do you admire about the person? What makes you feel connected to him/her?

Instead of this:

Hi, my name is Yue. I am a product manager on identity and security in the enterprise mid-market team. I work on many of our SSO and multi-user access features. We recently rolled out SSO to all enterprises with more than 1000 people and built out admin functionality for the product. I’ve been with the company for 3 years and work with a team of 10 engineers. Nice to meet you!

Try this:

Hi, my name is Yue, PM for identity and security. Our teams recently collaborated on the launch of Single Sign-on for enterprises globally. This feature was a multi-quarter effort and led to your team signing 3 new contracts worth $X Million in annual revenue. Like you, I went to college in upstate New York and am just getting into cycling. I recently heard you speak at an all hands about sales strategy for 2025 and would love to learn more about your vision.

Conversation Starters

Once you’ve nailed the introduction, you need some tactics in your pocket to continue the conversation and build rapport. What can you talk about to put your best foot forward? Here are some thought-starters for conversation:

What do you admire about them and their work? I don’t know anyone who doesn’t like praise and appreciation. What does your leader do well? What was a specific thing that they said at a company-wide event or group meeting that resonated with you?
1. I saw you do x at y event. It was super well done!
2. I find that you are one of the best x at the company.
What is top of mind for you today? Ask them about their work. Often, because their work is at an entirely different level, this question will bring up useful but previously unknown information to you, and you can bring curiosity to the conversation. Talking about a problem out loud can also be helpful for the leader to help them process their thoughts. Try being specific on the questions. Avoid questions like “What are your biggest concerns?” or “What are the biggest problems the company is facing?” because 1) they likely won't share that with you in a first meeting 2) it sets the bar for the answer too high. Instead, stay smaller:
1. What is one change you’d like to see at the company?
2. What’s one issue that has been bothering you recently?
What are some things you’re looking for help with? Leaders almost always have an ongoing list of tasks they’re looking for volunteers for. Ask them about it. Chances are there is one thing you can help with in some way. And even if you don’t have a match immediately, you might come across a helpful resource in the upcoming days or weeks, allowing you to reach back out.
Give them your on-the-ground perspective: Executives and leaders are operating at a different level. This means that oftentimes difficult for them to know what is happening day-to-day, and get honest, unfiltered feedback. It turns out that your subjective take on the problems you face in your day-to-day work, what you know and don’t know about the direction of the company, can be really valuable insight for leaders to know what’s working and what is not. Take some time in advance to jot down some points of feedback or interesting observations to bring into the conversation.

Keep It Short

If the conversation comes to a natural pause 5-10 minutes before the scheduled time, consider giving the time back. Executives are super busy, and most would appreciate a small break to grab a snack or water. If you’ve had a great, effective conversation and gotten your points across, then don’t be afraid to end on a positive note with the gift of time.

See you next week at 3:14 pm!

Yue

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Thank you so much! ❤️ I am grateful for your support in engaging with this post to help spread the word to other women and minorities looking to grow their careers.