Working in a startup as the first employee

photo by JC Dela Cuesta

Reflections, thoughts, and what I would have liked to know before diving into the startup world.

This blog post has been lingering in my draft folders for a while now. After I had left the startup scene in 2017, a friend asked me “What would you have liked to know before?”

I thought, what a great question and reflected on my experience through the lens of this question. So even though I learn best by actually living experiences myself, there are obviously things where I look back and think, it would have been a bit easier to know all that before, so I don’t have to experience it all. But since life often doesn’t work like that, here my reflections.


  • I would have liked to know, that I have to give myself permission to do things myself. And I have to give myself that permission again and again and again. Because there will be just no one else who will give it to you.
  • That just because people are young and ambitious and tech-savvy doesn’t mean that our mindsets are automatically wired for flatter self-organized work structures. Authority thinking is deeply ingrained in all of us through external structures. We are wired for an authority centered and linear way of thinking. Just because we use the hyper-connected and fluid internet, doesn’t mean that our minds automatically work like this in all other fields.
  • That I will think over and over again, “Why don’t I just have a normal job where someone just tells me exactly what I have to do and what the outcome will be?!” and in the next second something amazing and completely unexpected happens and you get reminded why you work in the rather unpredictable space of innovation.
  • I would have liked to know, that I need to set boundaries on the time I invest in work, no matter how freaking exciting it is. Because sprinting a marathon isn’t effective and healthy in the long run.

Team, relationships, and communication

  • I would have liked to know, that if you work with first-time founders, there is very little teaching about making hard decisions like hiring but also letting go of people.
  • I would have liked to know that letting people go is a very tricky and emotionally challenging act. Though, being honest and open with people is the highest form of respect I can show and often gets you through those challenging moments.
  • I would have liked to know that there are people who are just not made for working in a fast-paced startup environment and that you have to pay close attention while hiring to startup fit, especially when you are in the early startup phase.
  • I would have liked to know, that not everyone is keen on making decisions and that some people really just like to be given a direction or clear instructions instead of having to figure it out.
  • One of the things I find most fascinating is the fact that this early bunch of insane people who either found a company or join as the first employees share some close bonds with each other. Either because they know each other from another job before or because they have been friends and developed a deep level of trust and respect for each other and genuinely enjoy spending time with each other.

Work environment

  • Life in an early-stage startup feels very often like walking on floating ice. The moment you think you have reached some stability, things fall apart or start to shake. Another metaphor I like to use is that an early startup feels like a boat that drives in high-speed across the vast ocean of the unknown sea while still being build and the crew being picked up along the way.
  • That leaving the shore and finding new land is a quote that fits well for an innovation process. It sounds highly poetic and romantic but doesn’t feel like it when you are out there in the big rough ocean, trying to understand in which direction you should stir the boat especially when the light of your north star hides sometimes behind some dense fog.
  • I would have liked to know that working in tech means, hanging out with a lot of men and often wonder where the heck are all the women in this world? And even though this is a common cliché and one of the biggest challenges of the tech scene, I didn’t expect it to be like that when I started. Having never worked in tech before, I was quite surprised about it and stayed surprised.

On the motivation to work in an insane environment

  • That positive user feedback is a powerful motivation to get up in the morning and sometimes the only thing which gets you up in the morning.
  • That believing in a vision that is big and bold is essential to push your own limits and your team limits.
  • That working on something truly innovative means you keep meeting people who don’t understand what you are talking about or will tell you why that thing will not work out or that you will probably run into some difficult problems. You’ll learn, that innovation isn’t just fun and glory but often the complete opposite.
  • I would have liked to know, that I’ll be the guinea pig for experiencing the adventures of being the first employee in a startup and growing company, and this can be exciting and exhausting at the same time.

Roles, positions

  • A thing which happened along the way was, that I realized I have the chance for experimenting and trying out the role of a culture designer and I saw that happening with a lot of other people. You do have a real chance to explore and try out roles when the company is young and structures, processes, and roles are not super fixed.

Language and communication

  • Innovative products and services often come with a gap or mismatch with the words you have available to describe what you are doing. Besides inventing a new product, you literally often have to invent a new language for describing it and that is easier said than done.
  • I would have liked to know, that if you bring a diverse team of scientists, engineers, business and creative people around a table, finding a common language is one of the most important and most challenging elements in working together.

Structures and organization

  • At some point, I realized that being the first employee means that I’m technically employed at a company that kind of doesn’t quite exist yet, besides the legal construct, a first prototype product, a bold vision for the future, and the small team of three people. The organization has to be built by the first few people in the team, alongside building the product. It meant, that every single structure and process and responsibility, etc. needed to be made clear and build by the first ones. I often looked at everything I did or needed or didn’t get even though I would have needed it through the glasses and perspectives of every future team member.
  • Structures, processes, and clarity on decisions and responsibilities is something that might be annoying to figure out, yet is one of the biggest times and energy savers you should work on.
  • Being clear about the way how you want to work and explore the best way for your team is something that is rather easy to start when you are a small team. When you are a team of around 15 people, you are writing the company culture DNA. What you do, what you don’t do, and what’s important to the team and works as a behavior of the company will only scale up the bigger you get. It will most likely only get more and more challenging changing behavior and mindset. I must really say we did a damn good job in starting to design the way how we work with each other when we were around ten people and considered the work of the company and culture-building an integral part of our daily work. And my lesson learned is, that I can only recommend everyone taking the time to focus on the way how you want to work with each other the moment you have a small team working on an ambitious idea. Don’t push it to the times “when you have the money or reached that one milestone or have a proof of concept.” Do it now. Reaching goals depends on the operating system as a team and needs focus and attention as much as all other areas in your business.

Looking back I must say, I’m glad that I was clear on my goal what I wanted to get out of this startup experience. If you are not clear and just looking for a job, I would say an early startup is probably not the right place to work for you. Even though the ending was much rougher than I expected, I actually achieved what I wanted to achieve: to get to experience how to build an organization from scratch. The role of a first employee isn’t something you get offered all the time. I’m still grateful for this opportunity because it was one of the richest and most intensive learning experiences I’ve had so far and if you are up for a crazy ride and are ready to pick up some scratches and scars, I can only recommend it:)

Post was first published on medium in June 2019