The Interview Mistakes That Kill Your Chances

After 7+ years navigating interviews across startups and Fortune 500 companies, I’ve seen candidates make the same critical mistakes over and over again. Whether you’re interviewing at a scrappy 20-person startup or a multinational corporation, certain phrases will instantly damage your credibility—while others can set you apart from the pack.

Here’s what I’ve learned about what NOT to say in interviews, and more importantly, what to say instead.

The Curiosity Killer: “I Don’t Have Questions”

Why this destroys your chances: Nothing screams “I’m not genuinely interested” like having zero questions. In my startup days, we’d immediately write off candidates who didn’t ask anything. It suggests you either didn’t prepare or don’t care enough to dig deeper.

What to say instead: “What would success look like in the first 6 months of this role?” This shows you’re already thinking about impact and results—exactly what hiring managers want to hear.

The Desperation Red Flag: “I’m Looking for Any Job Right Now”

Why this backfires: I’ve been on both sides of this conversation. When candidates say they’re looking for “any job,” it tells me they’re not being strategic about their career. We want someone who chose us specifically, not someone who’s casting a wide net.

Better approach: “I’m looking to use my XYZ strengths, and I’m excited about how this role aligns with my goals.” This shows intentionality and genuine interest in the specific opportunity.

The Boss-Bashing Blunder: “I Hated My Last Boss”

The problem: Even if your previous boss was genuinely difficult, speaking negatively about them raises red flags. Will you talk about us this way if things don’t work out?

Professional alternative: “I learned a lot in my previous job, especially about X, but I’m excited for a new challenge now.” Focus on growth and forward momentum, not past grievances.

The Preparation Gap: “I Don’t Know Much About Your Company”

This one particularly stings in the startup world, where company culture and mission are everything. At larger corporations, it’s equally damaging—it suggests you’re not detail-oriented or genuinely interested.

Show you’ve done your homework: “I’ve researched the company and I’m particularly impressed with X—I’d love to hear your perspective on it.” This demonstrates preparation and opens up valuable dialogue.

The Salary Trap: “How Much Does This Job Pay?”

Why timing matters: While compensation is important, leading with this question sends the wrong message. You can usually find salary ranges online anyway.

Strategic approach: “I’m excited about this opportunity, and I’d love to understand the comp range to ensure it fits my expectations.” Frame it around mutual fit, not just your financial needs.

The Weakness Minefield: “I Don’t Have Weaknesses” vs. “I’m Not Great at Time Management”

Both extremes are problematic. The first makes you seem arrogant and self-unaware. The second is often a cop-out that doesn’t show real introspection.

The growth-focused response: “Time management has been a focus for me—I now use X tools to stay organized and hit deadlines consistently.” Show the weakness, the action you took, and the positive result.

The Termination Conversation: “I Was Fired from My Previous Role”

Handle with transparency and growth: “My previous role ended unexpectedly, but it gave me the chance to reflect and strengthen my skills in X.” Don’t lie, but frame it around learning and improvement.

The Career Goals Stumble: “I Don’t Really Have Career Goals”

Especially at startups where everyone wears multiple hats and growth is rapid, having no direction is concerning.

Show ambition and alignment: “My short-term goal is to excel in this role, and long-term, I aim to grow in X areas.” Connect your goals to the company’s trajectory.

The Promotion Timeline Trap: “When Can I Get Promoted?”

Why this misses the mark: It suggests you’re already thinking about leaving the role before you’ve started. Focus on contribution first.

Value-focused alternative: “What does career growth look like, and how are employees supported in reaching their potential?” This shows ambition while emphasizing mutual benefit.

The Underqualification Complex: “I Know I’m Not Qualified, But…”

The mindset shift: Don’t undercut yourself. If you got the interview, you’re qualified enough to be considered.

Confident reframe: “I’m excited to use my experience to learn into the challenges of this role and learn and grow quickly.” Show enthusiasm for the challenge, not doubt about your abilities.

Additional Red Flags I’ve Observed

The Remote Work Assumption

Don’t assume work-from-home policies without asking. Instead: “What does the work environment and flexibility look like for this role?”

The Immediate Vacation Question

Asking about PTO in the first interview suggests wrong priorities. Save this for later conversations or HR discussions.

The Technology Complaints

Avoid criticizing tools or systems you’ve used previously. Instead, focus on what you’ve learned to work with different technologies and adapt quickly.

The Micromanagement Concerns

Rather than asking “Is this a micromanaging environment?”, try: “What does the management style and team collaboration look like here?”

The Startup vs. Corporate Context

Having worked in both environments, the core principles remain the same, but emphasis differs:

In startups: Show scrappiness, adaptability, and willingness to wear multiple hats. Demonstrate you can thrive in ambiguous, fast-moving environments.

In corporations: Emphasize process orientation, stakeholder management, and ability to work within established systems while driving results.

My Final Interview Framework

After years of both giving and receiving interviews, here’s my simple framework:

1. Prepare thoroughly - Research the company, role, and interviewer if possible
2. Show genuine interest - Ask thoughtful questions that demonstrate engagement
3. Focus on value - Always connect your experience to how you can contribute
4. Be authentically positive - Enthusiasm is contagious and memorable
5. Think partnership - Frame conversations around mutual fit and success

The Bottom Line

Interviews are conversations about mutual fit, not interrogations. The best candidates I’ve hired—and the best interviews I’ve had—felt more like collaborative discussions about solving problems together.

Your goal isn’t to be perfect; it’s to be genuine, prepared, and focused on the value you can bring. Avoid the common pitfalls above, and you’ll already be ahead of 80% of other candidates.

Remember: if you got the interview, you’re already qualified. Now it’s about showing them who you are and how you think. Make it count.

Cheers,

Sim