#1 mistake that cost me multiple VC jobs

Hi! I’m glad you’re here. You’ve made it to issue #88 of VC Demystified🪄.

My name’s Nicole - I’m a Principal at an early stage venture fund, and I know firsthand that VC can often be a black box. Breaking into the industry may feel daunting and resources can seem scarce and inaccessible. I wanted to put together a newsletter to give others the playbook I wish I had when I first started.

Today’s deep dive: A reflection on the interview mistake I didn’t understand until I sat on the other side of the table

^{My personal mission is to open as many doors as possible for other people and this newsletter is just one avenue to do that. As always, I will continue to post VC insights daily for free across my socials. This newsletter may contain paid partnerships or affiliate links.}

Read time: 6 minutes

A reflection on the interview mistake I didn’t understand until I sat on the other side of the table

I did VC recruiting all wrong!

When I was recruiting for venture capital roles, I thought I was doing everything right.

I had the right experiences.
I could list my accomplishments clearly.
I knew the firms. I knew the markets. I prepared.

And still, I got a lot of no’s.

Ironically, some of those no’s came from firms I now work closely with. Sitting on the other side of the table today, that’s been one of the most humbling realizations of my career.

Looking back, I can see exactly where I went wrong.

I Optimized for Accomplishments, Not Storytelling

In my interviews, I focused heavily on what I had done.

I talked about:

• The roles I held

• The projects I worked on

• The outcomes I drove

• The responsibilities I owned

On paper, it all made sense.

But what I didn’t realize at the time was this: interviews aren’t about listing accomplishments. They’re about helping someone understand how you think, why you move the way you do, and what motivates you.

I gave interviewers the bullet points.
I didn’t give them the story.

Why Storytelling Matters So Much in VC Interviews

Venture capital is not a checklist job.

It’s a career built on:

• Judgment

• Curiosity

• Pattern recognition

• Long-term motivation

• How you navigate ambiguity

When an interviewer asks about your background, they’re not just trying to verify your resume. They’re trying to answer deeper questions:

• What pulls this person forward?

• How do they make decisions?

• What kind of problems do they gravitate toward?

• What will keep them engaged when things get hard or boring or slow?

You can’t answer those questions by listing achievements alone.

You answer them by taking someone through your journey.

The Missing Piece: The “Why” Behind Every Move

The biggest mistake I made early on was skipping the why.

I talked about transitions without explaining what triggered them.
I talked about roles without explaining what I was searching for.
I talked about skills without explaining how I discovered they mattered to me.

The why is what gives your story coherence.

Without it, your background feels like a series of disconnected stops.
With it, your background starts to feel intentional, even if it wasn’t perfectly planned.

How to Craft a Compelling Interview Story

If I were doing VC recruiting again, I’d spend far less time polishing bullet points and far more time crafting a narrative.

Here are the questions I now encourage candidates to ask themselves when preparing their story:

1. What caused each transition?

Was the driver internal (curiosity, dissatisfaction, ambition) or external (layoffs, opportunity, timing)?

Interviewers want to understand what moves you.

2. What felt missing in your previous role?

Every transition is a response to a gap.
Name it.

Were you craving more ownership? More exposure to founders? More strategic thinking? Faster pace?

3. What did you like that you wanted more of?

This shows self-awareness and pattern recognition.

It also helps interviewers understand what environments you thrive in.

4. What did you dislike and want less of?

This isn’t about complaining. It’s about clarity.

Knowing what drains you is just as important as knowing what energizes you.

5. What skills did you want to lean into more?

Strong candidates understand their strengths and actively seek environments where those strengths compound.

This matters a lot in VC, where roles are often loosely defined.

What Interviewers Are Actually Listening For

When someone tells their story well, interviewers walk away with answers to questions like:

• Does this person have conviction about their path?

• Do they reflect on their experiences or just move on from them?

• Are they intentional or reactive?

• Can they connect past decisions to future goals?

• Do they understand themselves well enough to make good long-term bets?

Those signals matter far more than a perfectly polished resume.

The Reframe That Changed Everything for Me

Once I internalized this, my entire approach to interviews changed.

I stopped trying to impress people with lists.
I started trying to bring them along.

That subtle shift made my background feel cohesive instead of scattered.

Final Thoughts

Everyone has a story. Most people just haven’t practiced telling it.

If you’re recruiting for VC roles (or honestly, any role built on judgment and ambiguity), spend time being introspective. Map the motivations behind your moves. Understand the throughlines.

Your story doesn’t need to be perfect.

It just needs to be true.

And once you learn how to share it, interviews stop feeling like interrogations and start feeling like conversations.

That’s all for now! See you next week 🪄

See you next week 🪄
Nicole