10 Essential Questions to Ask a CEO in an Interview
Shourya Mehta- Jan 23, 2025
- Rootstaff
The Fortune 500 companies spent an average of $2.6 million on each failed CEO hire in 2023. Make sure your next executive job doesn't end up like so many others. Even though this number is shocking, it's not even close to how much it really costs. When we look at repercussions over time, like bad decisions and missed market chances, low employee confidence, and strained relationships with stakeholders, the real cost often goes up by ten times the initial investment.
Think about what it's like to be a senior executive in the difficult business world of today. A study from McKinsey says that in the first 18 months, almost 40% of CEOs don't live up to standards. This number is even more important when considering that the average CEO term dropped from 8.2 years in 2016 to 6.9 years in 2023. It's clear that there is a lot less room for mistakes in choosing executives now.
Hiring leaders who are great at developing other leaders is a must. An executive search firm can help you find the right leader for your organization by providing specific insights. In this blog, we'll look at the most important questions that separate great CEO candidates from good ones. These questions are one of the best ways to find leaders who can keep the organization growing and deal with the problems that come with being a corporation today. These lists are the result of years of searching for CEOs and are constantly changing.
What Kind of Questions To Ask?
Gone are the days when asking "Where do you see yourself in five years?" would give you any meaningful insights when hiring leaders. Today's business world moves at lightning speed – a recent report suggests that about 80-90% of executives say their business models need to change every two years just to stay competitive. That's why we need questions that dig deeper.
The Questions That Actually Matter (And Why)
Enhance your strategy for CEO interviews with the expertise of an executive search firm. Here's your cheat sheet of questions that actually tell you something useful:
Tell me about a time when everything went wrong – and how you fixed it.
it works: 73% of CEOs around the world believe global economic growth will decline over the next 12 months. You need someone who can handle the heat.
How do you decide what to delegate and what to do yourself?
Reality check: CEOs who are good at delegation get higher revenue according to Deloitte.
Walk me through your biggest tech decision in the last year.
Fun fact: 77% of successful CEOs prioritize digital transformation according to IBM. If your candidate looks blank when you mention AI, that’s a red flag.
How do you keep your best people from leaving?
Real talk: Talent retention is the #1 concern for 82% of companies according to LinkedIn Learning’s 2023 Workplace. This isn’t just small talk.
What’s the hardest truth you’ve had to tell your board?
This one separates the politicians from the leaders. Transparency matters – 91% of employees say it’s crucial for company success (Glassdoor).
Tell me about a time you completely changed your mind about something important.
Why ask: 85% of the jobs that will exist in 2030 haven’t been invented yet (Dell Technologies). Adaptability is everything.
How do you get bad news to you early?
The kicker: Companies with strong feedback cultures are 8.9x more likely to outperform their competitors (MIT Research).
What is your risk-taking philosophy and how has it changed over time?
You know what the context for this question is, right? This question is very important for choosing leaders who know how to handle a complex environment of calculated risks.
How do you balance quick wins with long-term thinking?
Reality check: Around 70%-80% of companies focus too heavily on short-term results. Your CEO needs to buck this trend.
What’s the biggest misconception people have about being a CEO?
This one’s gold for seeing how self-aware they really are.
Why These Questions Work?
What makes these questions on hiring leaders so powerful is not just the questions themselves, but also the insights they generate. They are great icebreakers that reveal a lot about a person's leadership style, problem-solving abilities and thought process.
Such questions help an executive search firm make sure that choosing leaders isn't just about filling a role, but also about giving leaders chances to grow and improve their skills, which leads to long-term success.
According to recent research by Stanford's Graduate School of Business, the most successful CEOs share three key traits:
- They're adaptable
- They're excellent communicators
- They have high emotional intelligence