You get 20 minutes with the CEO. Here’s how to nail it.

66% of the workforce is checked out. Show you’re engaged in the business with a few smart questions that demonstrate your ability to think high-low.

👋 Hi, it’s Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.

As CEO, I have three main responsibilities: finding growth, capital, and great talent. 

But the reality is, I rarely get 1:1 time with anyone who doesn’t report to me. So when I do (whether it’s in the back of an Uber on the way to a client meeting or at an offsite dinner), I’m paying more attention than you think. 

Most of the time, employees approach these as casual chats, and if so, they can be enjoyable, but unmemorable. But once in a while, I leave a conversation saying “we should invest more in that person” or “we should give this person more responsibility.”

This should be your goal if you get 1:1 time with the CEO. These moments don’t happen often, but when they do, they matter. So here’s our playbook to leave the CEO wanting to invest more in you.

– Greg

P.S. We’re testing a new format this month – ask us anything. Submit your questions about what you want to know that your CEO (or boss or mentor) isn’t telling you, and we’ll answer them in an upcoming newsletter.

Low frequency, high value moments

One-on-one time with an executive is rare, but it can happen when you least expect it. Maybe you end up together on a flight back from a conference, sitting next to them at the annual company offsite, or get a coffee chat scheduled as part of onboarding. Even though it doesn’t happen often, it’s easy to be ready for this type of conversation.

People who stand out in these conversations do two things:

1. They signal that they’re genuinely curious about the business

2. They demonstrate that they have a handle on their part of the business

Some of this can come through in your answers to questions from the CEO – especially if they ask for your opinion on a part of the business. If they do, be transparent, specific, and nuanced in your responses. Don’t speak in broad platitudes (“it’s going great” or “it’s not working”) – get specific about where you see upside, opportunities, and risk.

However, the best way to stand out in these conversations is to drive them yourself, and ask a few smart, specific questions that demonstrate your intellectual horsepower, curiosity, and acumen about the business.

The playbook

Great questions are often more memorable than great answers. In addition, asking questions can give you insight into the CEO’s point of view, which can help you later.

Approach the conversation through the lens of high-low. Start with the high (the CEO’s long-term ambitions) and make your way to the low (your specific team). To do this, ask questions that allow the CEO to express their perspective on one of three things:

1. Their long term hopes for the company

2. Their point of view on the current business (current or next quarter)

3. Their point of view on your team

CEOs are focused on creating business value in the next 1-2 years (or longer) while most of the organization is focused on the next 6 months. So asking a question about the CEO’s long-term ambitions helps you stand out as someone who can engage with the “high” part of high-low.

As we’ve written before, good questions for execs are specific, not vague. Here are some specific ways to ask about the long-term.

• Who do you want us to be competing with in the next 3-5 years?

• How do we expand our value to our current customer?

• What do you think is the most important moat for our business in the next 1-2 years?

Once you’ve talked about the long-term, zoom back into the current business. Here are some questions to get the CEO’s perspective on this or next quarter, without asking “how do you think we’re doing?”

• What part of the current business plan do you see the most upside in – and how can we better capitalize on that?

• If you had to double down on just one area of our business, which would it be and why?

• We just launched [X] product. How do you think it’s going?

• What’s the one metric/indicator you think is critical for us to improve this year to demonstrate product-market fit?

Finally, ask about your team or department. This is the most actionable part of the conversation for you, and where you can provide the most value. In this part of the conversation, aim to give your CEO 1-2 valuable insights into your part of the business.

Here are some questions to start the conversation on your team.

• What frustrates you most about how we operate internally?

• What’s a challenge or problem we’re not talking enough about?

• What do you wish my team was doing more of?

A few final tips: 

1. Have an answer to your own questions. CEOs will often turn the question around back to you. 

2. Make it a conversation. You’re not interviewing the CEO. Don’t pepper them with questions – ask one and then engage in a conversation and respond to their follow ups. It’s okay if you only get to two or three.

3. Be okay saying “I don’t know.” Don’t vamp or make up answers. If you haven’t thought about a topic you can say something like “That’s interesting. I haven’t thought as much about that yet, I’ve been thinking more about xyz.”

Our advice

Only a third of employees are engaged in their work and workplace. So engaging with the CEO about the business (not just your dog, the weather, sports) is a differentiator. We’re not saying don’t share these things – CEOs are human, and especially if this conversation is in person, it’s a chance to connect and demonstrate who you are. 

But in addition, asking a few smart, memorable questions about the business will not only help you better navigate your job – it will also help you stand out as someone who cares and is committed to the business, which is what CEOs are looking for.

Even after 10-20 minutes, the CEO can leave with an updated impression of your potential. And if the CEO passes this new (good) impression on to your boss, it can change their opinion as well. 

Minimum case, you want them to think “this person is smart and committed, and can handle their part of the business.” Best case, you want them to think “this person is smart and committed, and has more upside – I want them to contribute more.”

Have a great week,

Greg & Taylor