This as-told-to essay is based on a conversation with 38-year-old Kristina Simmons, founder and managing partner at Overwater Ventures. The following has been edited for length and clarity.
The interview stage of the hiring process is really important for understanding a person’s underlying motivations — what makes their brain work and their heart tick.
Throughout my career, I’ve conducted job interviews with prospective candidates across a wide range of roles. From 2008 to 2012, I worked in e-commerce and digital teams at Lululemon. Then I spent roughly two years as a partner at Andreessen Horowitz. From 2017 to 2021, I worked at Khosla Ventures as an investor and chief of staff. I now run my own venture capital firm, Overwater Ventures, where I interview CTOs, CMOs, AI engineers, and more for the companies we fund.
These are the mistakes I see people make in job interviews, and what candidates can do to stand out from others.
1. Being dishonest
Hands down, the most common mistake people make in interviews is not being authentic. It’s very clear when people say what they think the interviewer wants to hear versus what they authentically believe.
Once, during an interview, I asked the candidate, “Are there any skeletons in your closet?” because a good interviewer will find out the person’s strengths and weaknesses. The person said no, but then I did find skeletons in their closet. I called them and asked if they could explain what I found, but they weren’t honest up front, which felt like a dealbreaker.
2. Not explaining the ‘why’ behind their career moves
People can also make the mistake of walking their interviewer through their career journey, and saying, “Hey, I worked here, and then I went here,” without explaining why they made those choices. The intentionality around the why really makes a difference. It helps you see whether they had a thought process around how they wanted to contribute to their role, company, or field, and what they wanted to learn.
I love it when I ask a candidate why they made a non-linear or unconventional career decision, and they have a good answer. Maybe they wanted to learn how to be a great manager, so they took a job you might not expect them to have taken to gain these skills.
3. Not asking questions
One of my red flags is when the candidate doesn’t ask their own questions in the interview, and it’s not a dialogue. The best candidates aren’t just being interviewed, but they’re interviewing me to see if the company’s a good fit for them. They’re asking questions like, “What should I know that I don’t know about this company?” and “What are the challenges at this company?”
Creative and thoughtful candidates stand out
One thing that separates a good candidate from a great one is how creative and proactive they are. Once, at Lululemon, someone sent us a rap video about how they could innovate the company to try to get our attention before the interview. It really stood out to me. They hustled and showed initiative.
The follow-up from candidates after the interview is really telling. I’m looking for people who follow up right away, demonstrating that they’re really interested and have the hunger and the grit for the job. I’m also looking for thoughtful responses. Not just “thank you for the interview,” but something that will make me learn something as the interviewer, like, “If I were to start tomorrow, these are some ideas I already have.”
Do you have a story to share about job hunting in 2026? Contact this reporter at [email protected]
Read the original article on Business Insider
The post I was chief of staff at Khosla Ventures. Here’s the most common mistake people made in job interviews. appeared first on Business Insider.
