The 5 most important questions for meeting with the CEO at your new company

So there you are, you’ve got your offer letter for that dream job! You worked so hard to find the right position at the right company, tailor your resume and cover letter, and lock up the interview process. Now, you are preparing to start in your new role and your first day will be here before you know it.

What is the absolute best thing you can do in your first week? Meet as many people as possible, and prepare for those first meetings. Think about how to make an amazing first impression, and set yourself up for a stellar working relationship.

To really do this well, you just have to remember one guiding principle: listen. You are trying to gain an understanding of what’s been happening in the organization before you got there - why is it structured the way it is, why are the processes set up a certain way, and what’s working and what’s not.

Your meetings with different people within your new company will give you varying levels of insight from the long term vision to the biggest challenges for the next quarter. Arguably the most important meeting you will have in your first few weeks of your new startup is a meeting with your CEO. In larger companies, this might be the head of your division or business unit.

The CEO sets the long-term strategy for the company, and it’s her vision that will propel all your colleagues forward. In addition, the CEO plays a critical role in setting the culture of the company. This is especially true if the CEO is also the founder.

Objective: Get a broad view of the company. What's the vision for the future? What are the milestones she has set out for investors? Where do you as an employee fit in the quest to achieve that vision?


1. Where do you see the company five years from now?

This is a nice positive open ended question to spark the conversation. CEO’s love talking about their vision and the potential they see in their product and the team they have recruited. It’s also her chance to welcome you and inspire you to get excited about this professional journey you are about to embark on. Pay attention to her level of confidence, her tone, and the specificity of the picture she is painting for you.

2. What's the biggest obstacle to achieving that vision?

This question will orient you towards understanding what the CEO sees as the biggest challenge to tackle, and therefore, the biggest priority. It’s an opportunity to understand where resources will be allocated, and the brightest minds in the company will most likely be working on this problem. While she is answering the question, think about ways in which you can contribute to the solution. If the moment is right, you might come up with some useful suggestions on the part of the problem that are within your domain of expertise.

3. What's the company's most important short (3 months) term goal (increasing market share, revenue, etc.)?

In a startup, three month goals can change quite rapidly depending on factors like shifts in the market, user demand, and competitive landscape. It’s important to understand both the long term goals and the immediate needs of the company. Just like the previous question, try to come up with useful suggestions on the part of the problem that is within your domain of expertise. This positions you as a problem solver, and will maybe even allow you to participate in a higher profile project.

4. With respect to the competitive landscape, what do you see as the greatest threat?

The answer to this question will give you insight into how the CEO sees the company’s place in the market. The answer should also dovetail with the unique differentiators that are part of the CEO’s vision for the company in the first question. As you listen to this answer, think about ways in which you can contribute to your company’s response to this threat.
5. What could I accomplish in my first 90 days that would be the most helpful to the company's goals?

Listen very carefully to the answer to this question. You will incorporate it into your 90 day plan, and it should be at the very top on your list of priorities. Even if the CEO does not have a clear answer to this question, it presents an opportunity for you to follow as you progress. If you have any deliverables that track to points that the CEO mentioned in the answer to this question, you might consider sending an update email referring to this conversation.

The best way to use the information you receive from your meeting with the CEO is to thoughtfully incorporate it into your plan for your first 90 days. As you prioritize and accomplish tasks, you might consider (if it's appropriate given your organization's structure) directly updating the CEO on your accomplishments. 

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