Ask These 9 Interview Questions to Hire Leaders Who Deliver Real Results

Hiring executives or deeply experienced employees can be difficult, especially when you have no domain expertise in the type of work they will be responsible for. Most upper-level candidates are good at climbing the corporate ladder, but they won’t all be helpful at your company.

The job interview gives you a valuable chance to learn more not only about each candidate’s experience, but also about their personality and work ethic. These factors can help you to determine the potential impact a candidate could make, and asking the right interview questions can help you get the information you need to make a well-informed hiring decision.

I’ve asked all of these questions when interviewing potential leaders and find that they reliably help me to determine if a candidate will bring value to my business. I find that the most helpful interview questions fall into three categories.

Category 1: Can (and do they want) to get their hands dirty?

Some of the most effective leaders are those people who aren’t afraid to do the hard work that goes into building a business. These are the people who are absolutely dedicated to a business’ success and who will work right along with the staff they’re supervising when it’s needed. The following questions can give you a sense of whether a candidate is ready to jump right into the trenches.

1. When was the last time you built/executed something versus having someone on your team do it?

Asking about a candidate’s previous involvement in a project can give you a sense of how hands-on they are, as well as what skills they would bring to projects in your business. This question also gives candidates an opportunity to show off a little and discuss successful projects as well as their approach to project management.

2. When was the last time you used a new software system to accomplish your job?

Since technology rapidly evolves, it’s important that a candidate demonstrates that they’re willing and able to learn new technology, including new software systems. This question can open up a discussion about the types of software and programs your business uses and the candidate’s experience and comfort level with them.

3. Describe a scenario where you will have to roll up your sleeves — will you be comfortable doing it?

Since this question is so open-ended, it’s up to the candidate to define “rolling up their sleeves.” Their answer can be a great way to gauge how involved they see themselves being in your business, as well as their overall attitude toward helping out.

Category 2: What experience are they adding to your company that you need?

Before you ask about a candidate’s experience, think carefully about the skills that are most valuable — and essential — to your business. Keep these skills in mind as you ask the following questions:

4. Where do you think you can deliver the most value to the business?

Giving a candidate the chance to identify their value helps you to understand their experience and skills. This question also plays the important role of highlighting the candidate’s understanding of your business, what the role will involve and what challenges you currently face.

5. What information do you need to know about the business to decide if you can add value?

Opening up a dialogue about the business’ strengths, weaknesses, challenges, and growth plans can really give you a sense of a candidate’s potential value and their approach to the role. Look for a candidate who asks thoughtful, detailed questions, such as questions about your short-term and long-term goals, what is and isn’t working, upcoming projects and major obstacles that you’re facing.

A good leader might also ask about team structure and particular challenges within the team, which frankly in my experience isn’t always easy to reveal to someone who isn’t actually working with you yet. However, this gives you the opportunity to practice transparency, and it offers them an excellent opportunity to discuss their leadership style and past obstacles that they’ve helped teams overcome.

6. What skills on the job description are your weakest, and what are you doing to improve those skills?

Look for a candidate to be honest about their shortcomings, but to also have a plan about how to improve on those weaknesses. Consider how the candidate understands the implications of those weaknesses for your business.

Category 3: How quickly can they make an impact?

When you’re hiring leaders, you’ll be paying them a high salary, so you’ll need them to pay for themselves rather quickly. As a result, it’s important to ask not only about the value they can bring, but to get a sense of how soon they’re likely to make an impact on your bottom line.

7. What would you do in their first 90 days with the business?

Asking about a candidate’s theoretical plans for the first 90 days helps ensure you’re both on the same page, and it also establishes the fact that you’re looking for a leader to take action and start immediately making a difference. The candidate should be able to identify potential concrete goals, and even specific actions and the approximate amount of time that it would take to achieve those goals.

8. What’s the first high-impact thing you did at your last job, and when?

A candidate’s past performance can give you a sense of how quickly they get working and the types of results you’re likely to see from them early on. More importantly, follow up by asking how long the candidate had been with their employer before performing that high-impact thing.

9. What types of support do you need from the business to get started?

This question can reveal what a candidate expects from the onboarding process, as well whether they work independently or prefer a more collaborative approach as they’re getting started with a new business. The question can open up a valuable discussion about the onboarding process and its overall timeline. Be sure to ask about previous onboarding processes that the candidate found worked well, as well as those that didn’t work as smoothly.

Given the time investment and cost of recruiting, hiring and onboarding an employee, it’s essential to hire the candidates who are best for the job from the start. You can incorporate these questions into initial interviews to identify leaders who are likely to actually help your business, and they’re also valuable in follow-up interviews when you’re working to establish a deeper dialogue to get a more detailed sense of how well the candidate will fit within your business.

Thanks for reading! Do you want to create thought leadership articles like the one above? If you struggle to translate your ideas into content that will help build credibility and influence others, sign up to get John’s latest online course “Writing From Your Voice” here.