Building a healthy startup team...
Building a healthy startup team...

From May 2018 - February 2019, I worked on a SaaS startup in Chicago. We worked through iterations of design prototypes, built a landing page, created relationships with interested customers and almost had a functional web platform. I took on the technical aspects of our platform while my co-founder focused on the business side of things. After 10 months, lack of communication led us to have different views on how we should proceed and instead of compromising, we split ways. In this post, I’d like to share a few things I learned about building a founding team. If I could redo it, these are the questions I would bring up every 2 weeks and discuss answers that aren’t the same between co-founders. More than anything, it lets everyone know that it is OK to talk about difficult subjects.

  1. What are our respective personal goals for the startup?

    Do you want a sustainable business spinning off cash or high growth and a liquidity event? This requires thought and an honest answer even when it’s easy to agree with other co-founders.

  2. Do we want to raise money? If so, how much and when?

    Like the previous question, this can lead to a lot of frustration if a co-founder isn’t interested in bootstrapping. Bring this up often so that a compromise can be reached and everyone is satisfied.

  3. How will we pay for things/what are our current expenses?

    Do we have a shared bank account? Do we have a monthly budget? Are we agreeing on what is being spent? For example, during pre-revenue one co-founder decides to pay for a coworking space individually. What happens when the company starts bringing in revenue and other co-founders don’t agree with the cost of the coworking space? If this conversation is not brought up often, it is tough to change minds on what is being spent later.

  4. What responsibilities is each of us tackling?

    The point here is writing down a shared checklist of items for everyone to see. This avoids cases where each co-founder only works on things he/she thinks is a priority. Everyone has different priorities, but to build a highly cohesive team, everyone needs to know what efforts are at the top of the list.

  5. Are our time commitments about the same?

    Initially, we didn’t care that one of us was full-time and the other was part-time. This quickly grew tiresome when only one person had updates. If I could redo it, I would avoid working with a team that doesn’t have the same time commitments.

  6. Do we have a similar cultural vision?

    Is this still fun? Does it feel like a 9-5 day job? Are you micro-managing or more of a hands-off person? Even so, people tend to claim their managerial style based on what they want to be not what they actually are. Help your team members understand their natural tendencies so they can improve and grow into the person they want to be.

More questions I think can be worth bringing up.

In addition to the questions above, I think it is worth evaluating if you and the people you work with are good team players. The below questions came up often but instead of addressing these concerns, I ignored them. In retrospect, I should have taken the time to bring these up with the team.

Red flags I noticed but ignored :triangular_flag_on_post: :

  • Are all options considered when decisions need to be made?
  • Is there a sense of shared ownership?
  • Does he/she/I tend to quickly blame other people?
  • Does he/she/I believe the team is the strongest asset?
  • Is he/she persuadable? Am I persuadable?
  • Is he/she enjoyable to work with? Am I enjoyable to work with?

If the answer to most of these questions is no, I’d bring it up with the team and come up with actionable solutions. If the problem is you over and over again, it might be time to consider whether you’re compatible with this team and decide if you need to leave. But it’s a different story when a fellow co-founder is bringing a toxic environment especially if he/she is the majority owner. This is a dangerous combination that allows this person to make rash decisions without consulting anyone on the team. In our case, my co-founder decided everyone else should leave because we didn’t fit his idea of a team.

The answers to these questions don’t reveal themselves in days or weeks. It takes months and for things to go horribly wrong before you see a glimpse of your co-founders’ true personalities. Take time every few weeks to gauge yourself and your co-founder(s) to help you decide if you should continue. The truth is, learning these lessons would have been impossible without going through this process. Taking an active approach to building a healthy startup team can be the difference between a successful startup and a dysfunctional team. Hopefully, you learn from my mistakes and I wish you the best on your journey! :)