One of the liberating things about making hiring decisions is the freedom to make sweeping generalizations about a person to evaluate whether they are good enough to fit into your group.

Let’s be honest. Chances are, you weren't sitting at the cool table in high school, but now the tables have turned. You’re a part of the in-crowd, and it’s them trying to sit at your table.

Sometimes post-interview analysis of a candidate feels kind of ‘Mean Girl’-esque; the conversations necessitates jumping to conclusions based on observations of statements made, minute gestures, and questions asked.

“I don’t know…something about him rubs me the wrong way. I can’t put my finger on it. Maybe it’s his tonality and his stance. The things he was saying made sense, but something about his general presence just doesn't sit well with me.”

As precise as I normally try to be with expressing my reasons why or why not I believe something, I hear myself make these nebulous statements about candidates and wonder if they are really grounded in reality, or if I was just being ultra-sensitive because I was hungry.


We, as human beings, are incredibly irrational. Daniel Kahneman, in Thinking, Fast and Slow, discusses how confidently we form new world views based on the tiniest bit of information; we jump to conclusions based on such small data points.

Interviews provide this forcing function that makes it a requirement to judge a person in an incredibly short amount of time. Arguably, a decision to make a hire, particularly an early-stage hire, is one of the most important factors in the success of your company and company culture. Yet, many speed through the process.

Over the past couple of months, I've sorted through hundreds of resumes, spoke to 40 candidates on the phone, brought in 15 candidates for in-person interviews and have found only a small handful that I thought were worth hiring.

I enjoy hiring and finding people to join our team, but it’s extremely difficult. You are given so little time with a person that it’s so easy to jump to wild conclusions based on the information displayed in half a day. Not only that, but the information you are given is probably only a tiny curated sliver of their true self. Interviews are typically not the time to be vulnerable - it’s your time to put your best face forward and sweep your weaknesses under the rug. The candidate talks about how great they are, how excited they are to join the team, while the company talks about their great company culture, the challenging environment, and the great opportunities at hand. It’s all free snacks and lunches, beer Wednesdays, unlimited vacation days, rainbows, and sunshine .

At Chewse, oftentimes we try to do something quite different.

Many times in the interview process, I feel like my job is to throw them off balance - to see what they are like when they are on tilt. It’s easy to be pleasant and sharp when everything is going well, but what about when everything is going to shit? How might I catch a glimpse of realness behind this veil of perfection that they try to put up? Everyone has weaknesses and strengths, and this feeble attempt at trying to be a perfect person just feels fake.

So, when describing Chewse, I make sure to mention that this working environment is NOT all good times. There will most certainly be dark times ahead. There will be times where we will have worked a 16 hour day and still don’t see the light at the end of the tunnel. There will be times where we feel like no matter what we try, nothing is working. There will be times when we want to quit. For me, it’s important for these candidates to understand the reality of startups, and how different that may be from the romanticism of this lifestyle. If they can accept the dark side of startups, and are even motivated by it, that’s when I feel like we’ve found the right fit.


Over the past couple of months living in San Francisco, I have made a pretty horrible effort at meeting new people. As much as I can say that my work takes up all of my time, I know that we all make time for the things we want to do. I can’t use work as an excuse.

Digging deeper, and being more honest with myself, part of it is a fear to meet new people, for fear of what they will think of me. It’s been a very long time since I’ve felt the need and pressure to impress someone. Here, living in a new city,for the first time I find myself a little self-conscious of what people think of me. I am a confident person. Something in me knows that I will be just fine in the long term, but that only slightly dulls the sharpened awkwardness of my present day-to-day social interactions.

I was comfortable in Los Angeles. I had such a strong foundation and safety net(work). Here, sometimes I feel like I’m falling and grasping for a rip cord to prevent me from nose-diving into a pit of introversion.

I guess now I need to point out that I’m not lonely. In fact, for those that know me, I probably seem fairly well-rounded and social. I have a great group of people that I surround myself with on a regular basis - but I’m not creating new relationships. Spending all my time with people who already knew me feels safe. It feels as though I’m not taking risks. It feels too comfortable (will I ever want to be comfortable?).


With this new focus on relationships, I find myself thinking constantly about what makes me connect with some and not with others. What is it that makes someone instantly like me upon first meeting me? Conversley, what is it that makes someone not like me?

Just like in the interview process, we all make snap judgments outside of the work place as well. When meeting new people in the city, I wonder what impression I’ve made. Some people I have met have become new friends, but some have not. Generally, I have definitely made an effort to become as inclusive as possible, but for whatever reasons, reasons I may not ever understand, we did not connect.

The reason I’m fascinated by understanding the mechanics of relationships is because I believe that relationships are the most important thing in life. The power to create a bonded feeling with any other individual would be an incredibly valuable superhero power. Some people are born naturally with a charismatic draw. To most others, not embarrassing yourself in a social setting is a significant enough win.


Luckily, being an employer and hiring has given me the opportunity to evaluate first impressions on a regular basis and establish a framework to evaluate why people like each other and why people don’t. Through the process, I have become pretty adept at understanding some major components that facilitate connection.

  1. Vulnerability and Authenticity

Social norms dictates that there is a natural progression of human interaction. First come the pleasantries and the discussion of safe topics, like your job and the weather. After some amount of time, you can move into slightly more personal things. Perhaps you talk about your family, or recent things you’ve done in your spare time. Then, after building that trust with the person, walls start to come down and you begin to dig into the personal. But social norms dictate that is only safe to be honest and open once you trust the person. I actually think the opposite. I think that honesty creates trust. If you’re honest from the start, you come off as more authentic, and that creates more of an opportunity for connection. By putting yourself out there and being yourself, including your faults, you are allowing people to connect with the most honest version of yourself.

2. Passion

I see passion as an internal fire in a person. That light, that flame, draws me like a moth. When people talk about something they care about, you see a light behind their eyes, and it makes them compelling. I think passion draws people in and makes that connection easier. Passion makes you interesting, gives you something to talk about, and shows that you care about something. Passion takes many forms - some people channel it in this blazing inferno, and some people maintain it through a slow and constant maintenance of burning embers.

3. Empathy

Connecting is so much easier if you have a genuine compassion and interest for the other person. If you have the ability to understand another person’s feeling, that creates a bond. The ability to put yourself in another’s shoes and see the world from their perspective strengthens that relationship. I think empathy is probably best defined in Regulating the Costs of Empathy: The Price of Being Human: Empathy is blurring the line between self and other.


It feels a little bit silly, trying to break down human connection into a set of rules. But, for me, creating a framework around how to connect with others gives me something to try. And, in an effort to be authentic, this is kind of how my mind works. Instead of blindly navigating unknown territory, I have a simple set of rules that help me accelerate feeling connected with others. Open yourself up, talk passionately, and actively seek out to understand others, and we’ll find human connection so much easier. It’s not about presenting the safe and best version of yourself. There are too many people in this life, and you can’t make friends with everyone. Instead, be your true self and put yourself out there and you’ll likely connect with the people that accept you for who you truly are.

Here’s to pulling the rip cord.