Strategic Leadership Interview Questions to Ask Senior-Level Candidates

When I interview for senior-level roles, some of the most impressive candidates aren’t the ones with exceptional technical knowledge. Rather, the candidates that stand out the most to me are those who are obvious leaders: skillful delegators, creative motivators, and expert communicators who will have no trouble managing a team.

So, how do I determine a candidate’s leadership abilities? By asking the right interview questions. 

Here, I’m sharing some of my best tips and favorite questions for identifying the soft skills that indicate a strong leader when interviewing for upper-level positions. 

What Makes a Great Leader?

What makes a great leader depends on who you ask, but I’ve interviewed hundreds of candidates and met some truly great managers in my career, so I think I’m qualified to speak on the topic. These are the top traits I look for.

• Character. Do they have principles? Will they do the right thing, even when no one is looking? What are their values, and do they align with those of the company?
• Vision. A strong leader has a keen understanding of what’s ahead–or the possibility of what might be, with the proper direction.
• Self-awareness. Self-awareness means understanding oneself, both one’s strengths and weaknesses. Good leaders are great at hiring to compensate for what they personally lack.   
• Creativity. Being open to new ideas and willing to try new things are key ingredients for progress.  
• Respect. A leader must be trusted in order to be effective. Trust has to be earned, which starts with treating everyone with respect and fairness regardless of their role on the team or position in the hierarchy. 
• Inspirational. Top leaders bring out the best in those who report to them and have a knack for getting others to buy into their mission. 

The Purpose of Strategic Leadership Interview Questions

Being an effective leader takes more than knowing what to do. The right individual needs to see the company’s vision and help others embrace it. They also need a high level of integrity and must be capable of managing diverse individuals. Leadership interview questions help you discern whether a candidate has these qualities. 

The interview questions you ask will also help you identify when you’ve found the right person for the job. This happened to me in a recent interview. I was speaking with an internal candidate who, to be frank, didn’t have the skills on paper that the more experienced external candidates were coming in with. 

I asked him, “What do you want to do in this role that you can’t already do in your current job?”

“Simple,” he said. “I want to develop the best recruiters around. I can see my team’s potential, and I think I can help them reach it; I can’t do that if I’m stuck writing job descriptions.”

His answer blew me away. For a company that heavily emphasized employee development and continuing education, I knew I had found someone who “gets it.” It took asking the right question to get the right answer. 

For new leaders, interview questions can help you identify their strengths while pinpointing areas where they may need further leadership training. 

When you’re hiring for a major leadership role, like a director position, the questions you ask are crucial in getting the information you need to accurately compare candidates against one another and determine the strongest fit. 

Types of Strategic Leadership Interview Questions to Ask

Management

Look for an understanding of how they motivate team members and inspire them to work toward company-wide goals. Ask about how they identify strengths and weaknesses among their reports and how they approach employee training and development. 

Example questions:

• How do you motivate your team?
• How would you describe your leadership style?
• What are your greatest strengths?
• How accepting are you of new ideas?
• How do you decide who to hire?
• What’s your process for giving employees feedback?
• How do you promote employee development?

Delegation

To be effective in a leadership role, a candidate must be able to separate the team’s daily tasks from their broader responsibilities as a manager. Ask questions to learn about their system for delegating work and how they strike a balance between empowering their employees and maintaining accountability. 

Example questions:

• How do you delegate tasks?
• How do you set priorities?
• What tools do you use to monitor your team’s performance?
• How do you measure your own performance?
• How will you empower your employees?

Communication

Communication is one of the most important leadership skills. A winning candidate should be a strong communicator in the interview and be able to describe their strategy for conveying information to staff, company leadership, clients, and stakeholders.

Example questions:

• How would you describe your communication style?
• What’s your preferred method of communication?
• How do you encourage your team to share feedback and concerns?
• How do you handle confidential information? 
• How do you go about delivering bad news?

Conflict resolution

One of the less appealing aspects of management is being the point person for resolving conflicts. How do they keep workplace disputes from interfering with productivity? What past experiences have prepared them to effectively control conflict on a team of this size or type?

Example questions:

• How do you handle disagreements between team members?
• Describe a time when you made a mistake at work. How did you handle it?
• How do you respond to criticism?
• How would you handle a disgruntled employee?
• How do you keep office politics and other distractions from interfering with work?
• Have you ever had to fire an employee?

Decision making

Ideally, when interviewing for a management role, you want to get a glimpse of how a candidate’s brain works regarding their job. This will tell you a lot about whether their leadership style aligns with your company culture. Prompt them to describe how they make decisions and ask for specific examples of times when they’ve succeeded and failed.

Example questions:

• What does your process for making decisions look like?
• Describe a time when you had to make an important decision at work.
• If you’re selected for the job, what’s the first thing you’ll do in the role?
• What changes would you seek to make on this team?
• Who else do you involve when making decisions that impact your team?

Values

Who the candidate is as a person matters a lot, especially for upper management roles. Values can make the difference between two well-qualified applicants who are similar on paper. Use the interview as an opportunity to drill down to what’s important to the candidate and why they felt compelled to apply for this job. 

Example questions:

• Who’s a leader you admire?
• Why do you want this job?
• What do you like about the company?
• How do you balance professional and personal responsibilities?
• What are the most important qualities of a good leader?

More Tips For Interviewing Leadership Candidates

Research the candidate

You should always review a candidate’s resume before an interview, but if you do a bit more due diligence, you’ll learn a lot and be better prepared to ask the right questions. 

Run a Google search for the candidate’s name and see if they’ve made headlines for any of their professional achievements. Peruse their social media profiles to see whether the persona in their application matches the one they display online. Look at their endorsements and connections on LinkedIn to gain some context about their professional network. 

While we’re not trying to dig up dirt (that’s what background checks are for!), doing a little extra research can give you a more complete understanding of a candidate’s character and what they’ve accomplished in their career thus far, which you can use to inform your interview questions. 

Use behavioral and situational questions

Most candidates for leadership roles will be prequalified with a certain level of experience, so your questions should focus less on their technical skills and more on how they’ll behave in a manager’s chair. Use behavioral and situational interview questions, which ask a candidate to ‘describe a time when…’ or to imagine how they’d react in a certain situation. 

Related: The Best Behavioral Questions to Ask Candidates

Example questions:

• Describe a time when you had to manage a difficult employee.
• Company leaders order you to reduce your department’s spending by 20% by the end of the week. How do you make the cuts?
• What would you do if you disagreed with the instruction from our managing director?

Be creative

Creative interview questions serve a few purposes. First, they can help you assess a candidate’s ability to think on their feet and see how they react in unexpected situations. Second, they allow you to see more of their personality beyond what you get with the typical questions that a candidate can rehearse answers for. 

Example questions:

• Recommend me a book.
• If you could have any superpower, which would you choose and why?
• When was the last time you did something totally out of character?
• What fictional character would make a great CEO?

Read their body language

The intel you gather in a job interview isn’t limited to words. A candidate’s body language can tell you a lot about them. Look for a confident posture, sustained eye contact, a firm handshake, a warm smile, and facial expressions that project interest and engagement.

Since nonverbal communication is an important element of strong leadership, I consider it equally as important as what comes out of a candidate’s mouth.

Use alternative interview methods

Alternative interview methods are great for breaking up the lengthy hiring process and gaining additional perspective on a candidate, Panel interviews, for example, allow you to gather feedback from multiple company stakeholders, while a job audition can help you see a candidate’s leadership capabilities in action. 

Related: Interview Formats to Use When Hiring

Watch for red flags 

No matter what type of leadership role you’re hiring for, a few candidate behaviors are almost always a bad sign. Here are a few of the biggest red flags to look out for:

• Negativity in describing past jobs, employers, or experiences
• Inaccurate information in the resume, application, or interview answers
• Arrogance, know-it-all attitude, or condescending tone
• Rudeness to the interviewer, receptionist, or other staff

Finally, have a strong exit strategy to end the interview on a high note. Give the candidate a chance to ask their own questions, which can be another tool for identifying their priorities and learning more about how they think as a leader.

Related: Resume Red Flags

Excel at Leadership Hiring with Expert Assistance

If you need to hire a proficient communicator who can motivate and develop their reports, turn to a team with decades of successful leadership hiring experience. At 4 Corner Resources, we regularly find and vet senior-level candidates for our clients’ most impactful roles, identifying individuals who have the blend of hard and soft skills necessary to drive progress and maintain strong staff engagement. 

From sourcing passive candidates to developing questions and conducting interviews, our end-to-end recruiting solutions will help you attract qualified applicants and hire the brightest leaders. Let’s talk about what you’re looking for in your next leadership hire–connect with us now to get started.