How to Join A Startup Team with a Strong Culture

Less than a month ago, I joined Startup Institute as Director of the Chicago program. I was thrilled to be part of this company and ready to hit the ground running… but the team in Chicago was already well established. Since they are all alumni, of Boston and New York respectively, they had a strong history and affiliation with the program.

I was a newbie twofold – as an employee of Startup Institute and to this team of four. All summer, these four helped to build Startup Institute Chicago from the ground up; and they had been doing it without me. How could I join this team and make an impact on the startup without stepping on toes and changing the dynamic of the team that already seemed to work so well?

If you decide to join a startup as a non-founder, you will face this issue at some point in your career. As the fifth or fiftieth employee of a startup company, you will always have a steep learning curve in your role, but also within the team culture.

So, what did I do?

I let my team lead the way. I did everything to show them that I could fit in and contribute, but mostly I practiced these three behaviors:

1. Listen and observe. I cannot emphasize enough how important it is to actively listen and observe when you are starting anywhere new:  a job, school, or dodgeball team. Try to understand how the people around you interact with each other. Observe how they respond to requests, suggestions, general questions, criticism. If you can gather informal information about the people with whom you will be working most closely, it will be invaluable to you for the rest of your time on that team.

2. Ask stupid questions! During the first few days, I would smile, nod and kind of stare at my team with NO idea what was going on between them. They had a lot of inside jokes and nicknames, all of which made the four of them laugh uncontrollably without explanation. At a certain point, I asked, “What does it mean to ‘draw the f$%king owl’?” They happily explained  but it took some courage to just ASK. (For the curious, drawing the owl is a Twilio saying that basically means, ‘Figure stuff out; do not wait around for someone to show you how, just get it done.’)

3. Use your outsider status to your advantage . It can be good to be an outsider. I am not married to the way things were done before I arrived at the company. After listening and observing the team, I established with the leadership a culture of continuous improvement. The novelty of your presence is an asset, for a while, because you can lend a fresh perspective on how things might be done better.

I am still figuring it out. At any startup, you will go through these same feelings of trying to understand what is happening around you while also trying to make a meaningful impact. I am  thankful to my team for welcoming me into their world with open hearts and open minds.

Best of all,  I am thankful that when I need to get work done, they tell me to, “draw the f$%king owl”.


Jenn Yee is the Director of Startup Institute Chicago. Jenn has worked on several bootstrapped and funded startup launch teams and has served as a career coach for those looking to transition from traditional careers to startups or high-tech companies. Say hello to her on Twitter, @mbasocial or via email at  jenn [at]