5 Tough Interview Questions Executives Need to Master
5 Tough Interview Questions Executives Need to Master
There are some tough interview questions “floating out there” for today’s executives and managers. As if your job isn’t tough enough, you now have to worry about these additional obstacles that can sometimes challenge even the most seasoned interviewer; e.g. “How long are you willing to fail, before you X”?

Answering tough interview questions like these are something you will need to prep for before that next job interview for your next great executive or management role.

Put your hiring cap on for a moment: Whether you are part of hiring a new employee or not, you know that asking the right questions MAKES ALL THE DIFFERENCE when extracting information from a candidate. This way, you can identify if this person is the right fit for your organization’s culture.

Sometimes these seemingly unconventional interview questions don’t necessarily have a right or wrong answer. In some cases, the hiring manager is merely trying to determine your thought process. As you might suspect, there can be multiple approaches and solutions to the same operational challenge.

What first comes to your mind when dealing with a particularly challenging staffing or financial issue?

How would you approach a solution when a particular problem is affecting staff morale and sales?

Maybe the company is seeking your counsel on an issue they are already facing, but want an unbiased, outside opinion on how to handle?

There are many valid (and sometimes not so ethical) reasons why companies seek answers to some of the toughest interview questions.

What do you think will be the key information you can tell an interviewer about yourself and your experience?

List of Tough Interview Questions That Executives & Managers Needs to Master & Answer

These might not be the most important question an interview will ask, but these are a few of the toughest interview questions you can prep for:

1. What skills are you lacking?

The interviewer is trying to find out if you have gaps in your level of knowledge and expertise, and if so, how you articulate this and what you have planned to remedy these skills gaps.

You might be wondering how best to go about handling this interview question.

First, make a list of the skills from the company’s job description that you don’t currently possess.

For the sake of this example, let’s say the company is seeking someone who can cohesively work with the product development department to help improve the company’s current product line to better serve clients. If you’ve never worked with product development teams, this can certainly be a skills gap.

Second, scope out from of the free online resources that can help you rapidly educate yourself and narrow your skills gap. For example, have you ever heard of Lynda (now called LinkedIn Learning), an online learning portal that was acquired by LinkedIn in 2016?

Few have heard of this.

LinkedIn Learning is available free of charge to premium LinkedIn members. So, if you’re paying to maintain a LinkedIn premium account, be sure to their new “go to learning” link at the top right of your LinkedIn profile.

Another resource to help boost your education is good-ole YouTube. Once you sift through all the cat videos and young teenagers doing stupid things, you quickly realize the YouTube practically offers MBA training for nearly any specialization.

Of course, there are paid alternatives too; e.g. tech schools, online certification programs, and so on.

TIP: You don’t want to answer this question in such a way that it brings attention to your inability to do the job. Try to position your solution in the best positive light, touching on the skill gap, followed by an example of how you are working on developing and resolving it.

Use the above example to help you.

2. How long are you willing to fail at this job before you succeed?

This question is often used to see how managers and executives react; e.g. indecisive when answering or visually uncomfortable. The interviewer may not have a specific answer in mind.

Stumped on how to handle such an unusual interview question?


There’s the simple, straightforward approach:

I’m willing to do what it takes for as long as it takes to see results.

This shows you have endurance and are committed.

There’s the not-so-straightforward answer:

I plan to fail as quickly as possible so I can learn from my mistakes and move forward.

This shows that you are aggressive and not afraid to fail – something some companies like.

There’s a more political answer:

I don’t believe in failure. When I fall, I fall forward and therefore I don’t believe in quitting.

This might not be the best answer, as some companies don’t have a tolerance for continuing to throw good money at a project, program, or a bad manager that’s continuing to fail.

When you are failing as a manager, you need to plan for that as well.

Are your abilities up to the task of what the company needs? If not, you need to take a step back and determine your next move. Either gain the skills your employer needs or take a deep-dive look at the skills of the staff you have reporting to you. Maybe your lack of performance has more to do with the failure of your staff? Maybe. Maybe not. But examining this further can go a long way to answering that dreaded, “how long are you willing to fail at this job before you succeed” interview question.

3. What would your boss, who you didn’t get along with, tell me about you?

This question tests your self-awareness and how you talk about weaknesses from someone else’s perspective.

TIP: 3-point approach—be positive about your work relationships, be honest about your limitations, and be direct about what you have learned.

Don’t do the obvious: point a finger at your annoying boss. This is an all-too-traveled path we see with inexperienced managers and executives.

Lily Zhang, a writer over at TheMuse.com offers 3 great strategies for answering how your boss or co-workers tell about you. Lily outlines these possible solutions:

First, reference something positive from a recent performance review. Don’t just highlight how creative or dedicated you are as an employee, provide the interviewer with specifics and examples of your most recent performance that’s reflected your successes in these areas. Remember to “sell, don’t just tell.”

Second, share a specific company story that outlined a challenge and the solutions you and your team introduced. A great story could be specific to something you know would be of interest to the hiring company. For example, maybe you had a particularly challenging issue with a former employee who was draining employee morale. You could briefly talk about the challenge and how you resolved the situation; e.g. reduction to staff turnover and improvements to team performance.

4. Tell me what you felt was unfair in your last position.

There’s no sugar coating this question. The question is designed to get the “dirt” about your last position and/or employer. You could choose not to answer, but this may show you as unforthcoming to potential employers.

Recruiters and hiring managers know that, at some point, there are situations that are unjust or biased. When they ask this question, they are looking for how you dealt with the situation.

TIP: Describe the unfair situation so they know the context and then shift to the proactive steps you took to solve the issue.

There are a few key areas you could use to answer this question that won’t reflect badly on you.

For example:
  • How to acquired a less than stellar staff.
  • How you were straddled with a tight budget.
  • How you were charged with more job responsibilities when your salary remained the same.
5. What are you most proud of in your career?

Don’t hesitate when answering.

You should know yourself and what you have achieved over the life of your career better than anyone.

Don’t hesitate when answering.

You should know yourself and what you have achieved over the life of your career better than anyone.

TIP: Be prepared with several responses to a interview question like this so you can highlight the achievement that best matches the strengths the company is looking for in the executive they want to hire.

Describe the impact the company experienced from the results of your achievement, the hurdles you had to overcome, etc. And you are proud because….. you reached a personal goal, or whatever it was for you.

Preparing and practicing your responses to questions like these will help you ace the interview!