Seven Strategic Interview Questions to Ask Candidates as a CEO

Before diving into that CEO interview, I explore the candidate’s professional background via LinkedIn and look for any mutual work connections we might have, and then talk to them. When I don’t find anyone I resort to what I call my “secret references”; I go deeper to identify their previous teams and leaders, trying to get anyone on the phone who already worked with this person.

Another infallible method I use is my vast leaders and CEO network across Latin America. We all use each other to exchange insights on mutual work connections, which can come in handy if you want to know what it is really like to work with a specific person. This is a common and effective practice among the best leaders I know.

Lastly, I review the candidate’s resume and my team’s assessment notes in detail before jumping into that call. Furthermore, depending on their field, I directly engage with their work—analyzing marketing campaigns, testing products, or evaluating software—to fully understand their contributions and skills.

From the simplest to the trickiest, here are my 7 golden strategic interview questions to ask candidates, to determine a perfect match:

1. Why do you want to change jobs?

This question helps me determine whether they’re seeking a positive move toward something better or simply running away from an undesirable situation. I need to know their motivations to ensure they are making the big decision to change jobs for the right reasons.

2. What is special about this job that makes you want to leave your current role?

By asking this, I aim to discover what unique aspects of the position we are offering attract the candidate. This tells me if they are genuinely interested in the role itself or not.

3. What are your goals for the next 5, 10, or 15 years, and how do you see yourself achieving them?

Understanding a candidate’s long-term career aspirations helps me evaluate if we can provide the path they want to take. It’s about aligning their future with our opportunities, ensuring a mutually beneficial relationship. This is super important for taking a proactive stance in regard to retention.

4. How did you impact your previous roles with measurable results?

This question helps me discern how candidates track their success and impact in their roles. I ask about their key achievements and the improvements they’ve made, which shows their ability to set goals, monitor progress, and adjust plans to get results. They should know their numbers by heart, and if not, it’s a red flag.

5. What did you like and not like about your last job, and what are you looking to do or avoid in the future?

This helps me analyze if the job is a good fit for both of us right from the start. It’s important to make these things clear early on, just like when starting any new relationship.

6. Tell me about a project that didn’t go well, why it happened, and how it could have been prevented.

I need to see if they can explain what went wrong and what they could have done differently. I’m looking for them to take responsibility and not just blame others. This tells me a lot about whether they are good at teamwork and self-reflection. People who can look inward and learn from their mistakes are usually the best hires.

7. Can you show me the last project you worked on and explain your involvement and the outcome?

If you want to have a look at their hands-on experience and communication skills, this is your question. By listening to how they describe complex ideas, you can get a better sense of their knowledge and how they think.

Beyond technicalities, two main features help me determine whether a candidate is suited for my company:

Growth Mindset

I’m on the lookout for people who are always learning, adapting and are devoted to their craft. If they’re not open to new ideas or methods, they likely won’t fit into my team.

For instance, when hiring a marketer, I ask about their sources of inspiration and which companies they believe are leading in the field. For product managers, I inquire about their favorite products and their development over time. Regarding developers, I’m interested in what they’ve recently learned and their goals for future learning. 

Honesty and Integrity

The human component comes first. What matters to them as a person? If their main goal is just to travel and relax, they’re not a fit for my team. I look for someone who prioritizes personal growth and values their roles not just as a professional, but as a human being, whether as a friend, sibling, parent, or partner relationship—these qualities reflect strong principles.

Additionally, as my team takes notes along the way, I check for consistency between what candidates tell me and what they’ve told my team. I’m trying to detect any possible lies and embellishments—to me, one of the major red flags when interviewing a candidate. I have to be able to trust the person.

For every candidate interview, my main approach centers on a basic formula: “data + reasoning = proof”. My inspiration for this strategy comes from ‘data reasoning’, the multidisciplinary process of deriving meaningful insights or conclusions from data through logical analysis, pattern recognition, and inference.

How does this apply to strategic interview questions to ask candidates? This method helps me clarify if candidates can explain all their metrics and sustain their decisions based on these numbers.

Essential questions are: 

• What were your key milestones or projects?
• What was their impact on your numbers?
• Why did you make certain decisions? 

The proof lies in the candidate’s ability to come up with solid conclusions supported by a perfect balance between numbers and logical thinking.

As a CEO you don’t want to make this an uncomfortable situation—neither for the candidate nor yourself—. This should be an enjoyable experience that can be a powerful insight for both of you to determine your compatibility. Here are a few things that may help you:

Have a structured and transparent process from beginning to end

Also, don’t forget to give visibility about what your company does and the tasks they’ll be involved in when assuming the role.

Break the ice

Most people don’t make it to the last interview. Let them know the great job they’ve done so far to alleviate tensions. Remember: this instance is as much about them as it is about you as the final evaluator.

Be an expert on your candidate

When you jump into that call, you should demonstrate you did a deep research on them. Both of your times are very valuable, so avoid going through their CVs all over again—they already did this with your team.

Be ready

Show up on time, have your camera and mic on, and be ready to take some notes.

Listen actively

When I’m on the call, I’m taking notes the entire time so I don’t miss anything important. Turn your notifications off and have your notebook or doc at hand to focus on the conversation with your candidate and come back to any point or question you want to address later.

Putting It All Together

If you own a company, especially a startup, hiring should not be taken lightly. Building a strong initial team will determine a lot of your organization’s growth and success. You should dedicate time and effort to each candidate—even if you are the busiest person in your organization. Keep this in mind: the smaller your company is, the greater the impact each new hire will have on your company.

Lupa empowers you to make smart hiring decisions, ensuring you find the perfect candidate match for your company’s needs. Learn more about how we support your interview and filtering process here.