The Interview Skills Gap: Why Senior Professionals Overestimate Their Readiness

Why Past Interview Success Doesn’t Predict Future Performance

It's natural to look back at a successful career and assume your interview skills must be strong. You've climbed the ladder, earned promotions, and built an impressive professional reputation. Each job offer feels like validation of your ability to present yourself effectively. But this narrative overlooks several critical factors that may have had little to do with your interview performance.

You Haven’t Interviewed Competitively in Years

For many senior leaders, it has been five, ten, or even 15+ years since their last real interview. During that time, hiring practices have evolved dramatically with very different expectations and the questions being asked currently bear little resemblance to those from just a decade ago. Today’s executive interviews often include:

• Behavioral and competency-based questioning
• Strategic case studies or business presentations
• Cultural leadership and alignment assessments
• Multiple rounds of panel and video interviews

If your last interview occurred before these became standard, your “interview muscle” has weakened, whether you realize it or not. The confidence you remember may have been built on techniques and approaches that are now outdated.

Executive Interviews Require New and Higher-Level Skills

Interviewing for a mid-level management role years ago is not the same as competing for a VP, SVP, or C-level opportunity today. Executive interviews now require you to:

• Demonstrate strategic thinking and long-range vision
• Show depth in crisis leadership and change management
• Communicate cultural leadership in a measurable way
• Articulate value in a business-outcomes-focused format

These are learned skills; not career byproducts. The stakes are higher, the scrutiny is more intense, and the competition is fiercer. Your previous success interviewing for a director position doesn't predict your ability to interview for a vice president or chief officer role. They're essentially different skill sets, yet many candidates assume their earlier wins transfer seamlessly up the ladder.

The Time Factor: When Was Your Last Real, Competitive Interview?

Perhaps the most significant blind spot in self-assessment comes from failing to recognize how many career moves weren't truly competitive. Think back honestly: how many of your positions came through genuine open competition versus internal connections? For most professionals, the answer is revealing.

That VP role where your former colleague was on the hiring committee? The executive position where the CEO was your client for years? The opportunity that came from a board member you played golf with? These weren't tests of your interview skills. They were relationship-driven opportunities where the interview was more formality than evaluation. Your contact had already sold you internally. You simply needed to avoid disqualifying yourself.

In these cases, the interview was a formality—not a proving ground.

But today, when facing 15–20 equally qualified candidates in round one, the landscape changes. You may be competing against:

• Individuals with deeper credentials
• Candidates who have recent interviewing experience
• Professionals with strong internal advocates
• Leaders actively training with professional interview coaches

There's nothing wrong with leveraging relationships to advance your career, but it's crucial to recognize that these experiences didn't actually test or develop your competitive interview skills. When you finally face a true competitive process, where no one in the room knows you and three other equally qualified candidates are vying for the same role, you may discover your interview abilities aren't what you assumed. This will put you at a disadvantage.

What It Really Takes to Compete in an Executive Interview

“When was the last time I interviewed competitively for a role at the level I’m targeting?”

If the answer is never or not in more than a decade, you’re likely overestimating your readiness. This isn’t a judgment on your abilities. It’s a reminder that interviewing is a skill set that must be practiced and updated. You should approach interview preparation with humility and intention rather than assuming your experience will carry you through.

How to Close the Interview Skills Gap and Improve Your Performance

Recognizing this skills gap is the first step toward addressing it. Senior professionals who want to compete effectively need to treat interview preparation as seriously as they would any other high-stakes business challenge. This means:

• Practicing behavioral interview responses with concrete examples
• Preparing for case studies and presentation requests
• Updating your understanding of current interview best practices
• Conducting mock interviews with professionals who will give honest feedback
• Developing clearer, more compelling executive storytelling techniques
• Researching the specific company and industry thoroughly

Your impressive LinkedIn profile might attract a recruiter to reach out. Your network might create opportunities. But in a competitive executive interview, it's your ability to articulate your value, demonstrate strategic thinking, and connect authentically with interviewers that will determine whether you land the role.

Always remember that a competitive interview means there are competitors. In round one there are usually 15-20 very well qualified candidates. Some of them will have more experience. Others will have stronger credentials. Perhaps more than a few have a good friend from college or a first cousin on the inside pulling for them. How will you level the playing field or catch up? How will you compete effectively if even one of them is putting in the hard work with a professional coach?

Your resume may attract interest, and your network may open a door. But your interview performance determines whether you step through it.

Why Interview Coaching Levels the Playing Field

In competitive executive hiring, there are always candidates with insider support, deeper experience, or recent practice. A professional interview coach helps you:

• Sharpen your messaging and executive presence
• Communicate impact through metrics and outcomes
• Answer difficult questions with clarity and confidence
• Stand out against equally accomplished peers

Even one competitor working with a coach could shift the odds against you.

The Path Forward in Your Executive Job Search

The senior executive leaders who succeed today pair their experience with a beginner’s mindset. They understand that interviewing is a performance. It's one that requires practice, structure, and strategy.

Your achievements are real. Your leadership is proven. But translating that value into a compelling, competitive interview conversation is a separate skill. Recognizing the gap, and choosing to address it, is what puts you in the strongest position to win your next executive role.



Explore further how we help executives, SVPs, VPs, and directors land a new job or make a career pivot on our Executive Job Search page, and then reach out on our Contact page when you're ready to partner with Endeavor's expert career coaching services.