How to interview leaders: Examples & Tips

When it comes to interviewing leaders, you need to build a strong foundation on which to work.

To begin with, determine which positions are most in need of leadership skills. Then decide the best way to vet the candidates and who will be involved in the hiring process.

Once you have that narrowed down, think about the questions you’d like to ask. Your goal is to find a well-rounded candidate that matches the skills required for the job and be on the lookout for any red flags that would indicate unsuitability.

Finally, when you’ve found the perfect candidate, make sure to offer them a generous package that will entice them to choose your company over the rest.


Image Credit: Christina Wocintechchat Unsplash

Which Positions Require Leadership Skills? Common Examples

Leaders can be found in unlikely roles, but there are certain positions for which leadership skills are a prerequisite. Choosing the right candidate is essential to success–not just for the role or even the department, but for the business as a whole.

A true leader can catapult the company to the highest levels of success. By the same token, a poorly chosen one can send it into bankruptcy. That’s why you should seek out the cream of the crop when hiring for the following C-level positions:

  • Chief Executive Officer (CEO)– The highest-ranking executive, and the person responsible for reporting to the board of directors
  • Chief Financial Officer (CFO)– Individual in charge of the company’s financial matters
  • President– May be the same as the CEO at small businesses, or the second-ranking officer beneath the CEO at large corporations
  • Chief Operations Officer (COO)– The person responsible for running the day-to-day internal business operations
  • General Counsel– This professional handles all the legal matters for the business

Hiring Leaders—How To Find The Best Candidates

Finding the right candidate isn’t an easy task, but it can go smoothly enough if you follow the proper protocol.

Your first step is to spread the word about the position. That’s the only way to attract the eye of a potential C-level hire. This is one of those occasions when a solid talent acquisitions team can work wonders. Advertising and plain word of mouth are other avenues to follow.

Once you’ve received an acceptable amount of applicants, it’s time to start separating the wheat from the chaff. Go through the list, and toss out the ones who clearly aren’t qualified or who simply need a bit more grooming. For more information on reviewing CVs, see the separate section below.

When you’ve narrowed the pile down to include the most attractive candidates, you can start the interview process. All you need now are the right questions to ask–and the tools to determine the right answers.

Seeking Out Suspicious Elements in CVs

While you’re sorting through the stack of CVs, keep a sharp eye out for candidates that look a little too qualified. Remember, anyone can write words down on paper. Their skills and job history need to match up with what’s on the page.

Here are some of the potential red flags you need to watch out for:

  • Long gaps in employment history- Beware of candidates who have regularly been out of work for months or even years. There are always extenuating circumstances, of course, with the COVID-19 pandemic representing one recent example. But for the most part, candidates for C-level positions should have no problem finding work.
  • Failure to list the most recent position at the top- This indicates a lack of experience, as it’s common practice to list positions in chronological order. It could also be a ploy to distract you from any of the gaps we’ve just discussed.
  • Too many “perfect” qualifications-If the candidate sounds too good to be true, they probably are. It’s rare for the list of qualifications to match up perfectly with the applicant’s skill set.
  • Short stints at previous jobs-Even if the candidate seems to be professional and hardworking, a short contract indicates that they didn’t stick around long enough to play a true leadership role. Worse, it could mean that they were difficult to get along with.

How To Interview A Leader-Candidate

Before you start the interview process, map out a structure to determine the best course of action.

For example, will you interview the candidate right away, or send them to the assessment center first? The former strategy allows you to get a good first impression without outside influence, but the latter could help to weed out unsuitable applicants.

You should also have a rough idea of how long each interview is scheduled to last. Most interviews take 30 to 60 minutes on average, but for leadership positions, you might want to plan on a longer meeting.

Are you planning an in-person interview, or will the question and answer session take place online? In-person is generally preferable, as you’ll get a better feel for the person’s confidence and demeanor. Organizing online interviews can also be awkward when there are multiple people involved in the hiring decision.

Speaking of which, you should decide in advance how many people will be present for the interview, and which ones are invited to join. That way, there won’t be any misunderstandings at the eleventh hour.

General Interview Questions

When you’re drafting interview questions, try to use at least a few of the following examples. These will give you a sense of what the applicant is like as a person, and not just as a potential employee.

Describe your first 90 days at your previous job. How did you spend them, and how did it go?

You want to find out if the person was truly willing to take initiative and drive results, or if they were content to sit back and passively learn the ropes. You’re looking for an energetic individual who wants to move the company forward right from the beginning. Hearing about the candidate’s early accomplishments—or lack thereof—in their previous job will help you decide if they meet that criteria.

What is the biggest challenge you've ever faced in your professional life, and how did you work to overcome it?

The second part of the answer is the key here. The challenge itself isn’t nearly as crucial as the problem-solving process. Whether the candidate’s strategic thinking skills were sufficient, or whether they needed to ask for help in order to find a resolution, they need to demonstrate proficiency when it comes to overcoming challenges.

Don’t be afraid to ask follow-up questions, especially if the candidate seems hesitant to blow their own horn. Here are a few examples:

  • How many teammates did you connect with in trying to devise a solution?
  • Did you keep the customer informed of the situation?
  • Did you let the company leaders know what was going on in advance?

In addition to cluing you in about the applicant’s problem-solving skills, their answers should demonstrate how forthcoming they’re willing to be when faced with difficult situations.

How do you think your former co-workers would describe you?

Ask for a list of specific adjectives, such as “focused,” “driven,” “easygoing,” or “reliable.” Then ask for examples of what they did to earn these designations.

One other approach might be to question which methods they prefer when it comes to leadership. Do they tend to take on most of the important work themselves, or are they skilled at delegating? Are they more inclined to focus on smaller details or the big picture? Do they follow rules to the letter, or are they willing to take shortcuts even if it means bending the rules a little?

What improvements would you like to make in your professional life, and how are you going about it?

Any candidate who believes themselves to be perfect is not the employee you’re looking for. Still, it’s interesting to note how they might be seeking to iron out their imperfections. Some might be taking public speaking or anger management classes, while others may go so far as to hire a coach or mentor. If they’re unsure how to respond, then there’s a good chance that they lack the fundamental drive that’s necessary for professional growth.

Describe why you're the best candidate for this position.

After hearing the candidate describe their shortcomings, give them the opportunity to focus on their best qualities. Good leaders are capable of articulating why they would be a good fit, what they can bring to the table, and why you’d be missing out if you chose anyone else for the job.

What’s more, the ability to handle questions like this is one of the very qualities you’re looking for. When it comes to leadership, confidence is key.

These are some of our favorite questions, but yours might differ somewhat. Which ones have you found to be the most useful? Did it make a difference whether you were the candidate being interviewed or the one behind the desk? Feel free to share your own preferred queries in the comment section below.

Questions For C-Level Candidates

The following questions were designed specifically for applicants who have their sights set on C-level positions. For professionals of this caliber, you’ll need to alter your interviewing style accordingly.

Have you thought about how you might help shape the future of the company? If so, describe what steps you would take to achieve that goal.

True leaders are take-charge individuals who aren’t afraid to talk about their plans. Any candidate who doesn’t have any ideas about how to take the company in the right direction is probably not the best fit.

Describe a meaningful relationship you developed with a co-worker, an employee, or a customer. How did you establish the relationship, and why do you believe it was successful?

Strong relationships form the backbone of every successful business. You’re looking for an individual who’s capable of building relationships with individuals on every level, whether they work for the company or not.

Tell me about a project or accomplishment that you're especially proud of.

In this answer, you’ll be able to discern the candidate’s leadership style. If they were able to motivate a number of team members to do their best work, then they should be a worthwhile asset to the business. If they describe a situation in which they did most of the work themselves, it’s not necessarily a red flag–it only means that they’re a perfectionist who wants to oversee every detail.

What improvements would you like to make in your professional life, and how are you going about it?

Any candidate who believes themselves to be perfect is not the employee you’re looking for. Still, it’s interesting to note how they might be seeking to iron out their imperfections. Some might be taking public speaking or anger management classes, while others may go so far as to hire a coach or mentor. If they’re unsure how to respond, then there’s a good chance that they lack the fundamental drive that’s necessary for professional growth.

How well do you work under pressure?

It’s a C-level executive’s job to meet important deadlines and deliver the kind of results that lead to company growth. Anyone who isn’t able to handle high-stress situations should be shown the door.

Tell me about a time you failed at work. How did you handle the situation?

The failure itself is less important than the resolution. The ideal candidate will have faced the situation with humility and been willing to take responsibility for the mistake.

Download our Interview Questions Template

Skill-Seeking Questions

The above interview questions should tell you what you need to know about the candidate’s integrity and leadership style. But what particular skills are they bringing to the company?

To find out, use some of these common questions.

-How effective are you at communicating with others? This refers to both verbal and non-verbal communication. For example, responding to e-mails promptly indicates strong non-verbal communication skills.

-Are you willing to take advice from other team members? This indicates a readiness to collaborate, as well as a sense of humility.

-What steps would you take to alleviate a stressful situation? Candidates who combat negativity with an “it could always be worse” attitude aren’t helpful. You want someone who’s capable of shifting the focus to the positive side of things.

Tell me about a time when you were faced with a heavy workload. How did you respond to the situation? Your goal here is to find out specifically what the applicant does in stressful situations.

-How long did it take you to adapt to your last job? Quick learners are always an attractive asset.

-Have you ever pushed outside your comfort zone to help a co-worker with a task? A “yes” answer will demonstrate a willingness to be flexible, along with a helpful nature.

-Have you ever had to deal with a problem employee? How did you handle it? The applicant may be hesitant to bad-mouth anyone, which would be a positive sign. However, it’s important to determine how they would respond to this particular issue.

-What are your greatest strengths, and how would they help you succeed here? You should be able to tell from their response how much research they’ve done on the company.

-Using your own words, attempt to sell me this calculator. Alternatively, you can use a pen, notebook, or whatever piece of office equipment is close at hand. The effectiveness of the pitch is more important than the item itself.

-What would you say is most important to you in life, and why? It’s fine if they describe something that’s non-work-related. Your goal is to get a sense of the person as an individual.

-What challenges are you most excited about? The answer to this question should tell you what you need to know about the interviewee’s problem-solving skills.

-What specific skills will you bring to the company? It’s always interesting to hear how people present themselves, and their responses will tell you whether their skill set is in line with the position.

-Why do you want to work here? This is another useful way to find out whether the candidate has done their research.

How To Tell If Candidate Is Being Truthful

For amateur interviewers, it can be difficult to tell whether the candidate is telling the truth about him- or herself. Your goal is to weed out the ones who aren’t talking about their own accomplishments, but merely saying what they think you want to hear.

One way to spot potential lies is to focus on the words they use to describe their achievements. If they use general language–for example, “I’m a reliable worker”–with no examples to back it up, it might be a fabrication.

Also, pay attention to their posture and body language. The candidate should sit upright and make frequent eye contact. If they slouch in their seat, refuse to meet your eyes, appear nervous, frequently cover their mouths with their hands, or are overly fidgety, there’s a good chance that they’re trying to hide something.

You should also take note of what the applicant chose to wear to the interview. Professionals know how to present themselves in these situations, and will dress accordingly. A slovenly appearance indicates a lack of interest in the job. Even their hairstyle (and makeup, especially for potential female leaders) can tell you a lot about their level of professionalism.

Red Flags

Listen carefully to the way the applicant words their answers. The ideal candidate will be mindful of how they come across, and should take care to phrase things in a positive light.

The following is a sample interview question, followed by responses that should be regarded as red flags. We’ve also included “right” answers that indicate what we wish the applicant had said instead.

-Describe a time when a project failed, and your client was unhappy as a result.

Wrong Answer: “They weren’t the easiest company to deal with.”

Right Answer: “We should have done a more thorough job when researching the company.”

Wrong Answer: “Their expectations were unrealistic.”

Right Answer: “We should have been clearer about our ability to meet the client’s expectations.”

Note that the “right” answers indicate a willingness to take responsibility for the errors, instead of passing the blame on to someone else. That’s the accountability that you should seek out when hiring a leader for your company.

Tips On Keeping Candidate Interested

Let’s say you’ve made it through the interview process, and you think you’ve found the man (or woman) for the job. That’s a great spot to be in, but your work isn’t done yet.

Top candidates tend to have more than just one offer on the table. Your competitors know that they wouldn’t leave their current positions if they couldn’t find a better package elsewhere. It’s up to you to ensure that your offer is the most appealing one they get.

To attract the cream of the crop, make sure to offer a comprehensive benefit package. This should include some or all of the following components:

  • A competitive salary
  • Health, dental, vision, and life insurance
  • A flexible schedule, possibly involving a hybrid-remote work option
  • Vacation time, sick days, and PTO
  • Maternity or paternity leave

In Conclusion

Now that you know what interview questions to ask, you’re ready to go out and find the best leader to fill your vacant position.

The staff here at Key Search understands the importance of this process, and we’re willing to contribute whatever help we can to ensure that you hire the right leaders. Visit us today to find out more about what we have to offer!

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