It’s All About People

It’s All About People (not money…)

10 Learnings of My First Startup Experience

I would like to share a work experience I had a couple of years ago. After some time traveling and working independently I was thinking about my next steps. Would I choose to work in an organization again, or would I try to make a living as an entrepreneur? My gut feeling told me I had to experience the first one again.

Good intentions

Before I knew it I heard of a new, inspirational, startup. I got in contact with the founders and after several interviews, I got the job. The startup’s purpose sounded wonderful and I couldn’t wait to start. Also, the working environment sounded great. It would be built on the basis of trust, openness and with space for professional growth. The startup already had an investor so we could start building right away.


I started working for the startup and was looking forward to implementing what I had learned myself in the last couple of years. Initially, I had a good feeling about the founder’s approach, but after some weeks this started to change and the longer I worked there the more I started questioning it. He was a very intelligent man, but having a lot of content expertise is something else than the expertise of people management.

Time and money

I was asked by the founder to share my knowledge on different, forward ways of thinking, theories and perspectives on working together, on paper. Due to lack of time of the founder, this never led to really talking about it though.

There were times the investor talked to me and shared other information and wishes with me than the founder, which was confusing. My experience at this startup made me realize that having money, from the foundation of a startup on, is not a guarantee for a positive end result and might sometimes even have a negative effect.

New way of working

Initially, we would work partly from home and have no weekly scheduled meetings. We soon changed this into having one weekly ‘start of the week’ meeting, in which we would share about our weekend and workweek. It ended up being a very personal and sometimes emotional two hours. Work-related topics were hardly discussed and I was questioning more and more if this was leading to more connection between the team members.

The connections between the team members, in general, didn’t seem to go smoothly. On the working from home days, contact was little. Some team members had never worked online, from home, and seemed to have a hard time with this (or just had a long weekend). But also when we were together at the office, not much was being shared. From my own analysis, this was partially due to the fact of the different personality types of our team. We seemed to have more introverted people in the team. Another important aspect can have been the role of the founder, who showed more and more authority, which of course affected the team.

During my last months, even though I am more extroverted, I experienced that because of the atmosphere that arose, I became more and more silent. I kept trying to connect, for example by having individual walks with team members and organizing a team event. This actually made me realize the importance of one-on-one contact moments.

Cultural differences

We were working in a team with people from different countries. This sometimes led to tensions and misunderstandings in our team. I tend to see people in different positions just as them having different roles, which doesn’t mean that they have more power over anyone else. I had been working in ‘new ways of working’ teams (flexible, online/offline and result not time-oriented) for years. Some team members came from countries where the founder is still ‘the boss’. To give one example. One time I had a different opinion than the founder and expressed this, while all my colleagues were in the room. Later on, I heard that he felt like I had been questioning his authority, while I just saw it as expressing my ideas.

Old ways of working

After some months the founder thought that the amount of ‘freedom’ was one of the main causes for our limited effective communication and our little progress. Instead of talking about this, he decided to radically change things. As the way to move forward, traditional structures were chosen. We had to be at the office 5 days a week during a certain time frame and daily meetings were introduced.

In that time period, my ‘new’ way of thinking was often put aside with negative remarks. I was confronted with my struggles with authoritarian behavior. To me, the choices seemed not at all beneficial for the teamwork. I still tried to put theories into practice. The most important thing I did, while I was riding my bicycle to work in the morning. At times I had to emotionally prepare myself because I wanted to talk about sensitive, unspoken topics. I then focused on opening my mind and heart in order to be able to leave judgments and pointing fingers towards others outside the conversation.

I sometimes struggled with my role, which was different than in my previous jobs. I was part of the team, not an outside advisor and was often asking myself when I could share my observations on what was happening.

Captain on a ship

Given the freedom and possibilities for growth we were promised, I thought we would have a lot of space to experiment. The reality was different. The answer we mostly got, when we came up with an idea or new project, was: ‘not yet, not now’. There was very little room for giving expression to our expertise and individual qualities. One time I described our situation like this: the founder was like a captain on a ship, with a lot of sailors around him. The problem was that he would never look at the sailors, listen to them or ask them for advice, although they had a lot of knowledge and energy to give. At least for a long time, until they did not believe in their captain anymore.

My 10 learnings

Reflecting on my time at this startup, there were several learnings I got out of it:

1. If you want your team members to contribute in the best possible way, then give them the opportunities to experiment. They might fail sometimes, but that will make them learn and grow their strengths even more.

2. The combination of working together online and offline asks for good communication. If there are people in your team who have never experienced working online before, then you will probably have to guide them in the beginning. The intention should be to come to a collaboration in which the individual and team working needs are functioning at their best.

3. More personal oriented meetings can be good for your team, but be sure to facilitate it well. For very sensitive personal issues it might be better to have one-on-one conversations.

4. People management is a specialty. People might be content experts, but this does not mean they will be good at guiding a team forward.

5. Not only team meetings are important, for giving each other updates and feeling connected, but also one-on-one contact moments. People simply share important different things in a different setting.

6. Have clarity about the communication between team members, the founder and the investor. At times it might be good to involve (certain) team members in meetings with the investor.

7. Money is not the key factor for making a startup a success. Having money from the start, might even sometimes have a negative effect.

8. Being part of a team, instead of being an outside advisor, confronts you with different challenges, because you are not paid to advise.

9. It is challenging to put theories into practice, especially when you are faced with people who are rejecting them, but it’s not impossible.

10. Even with a team of people with the best intentions in the world, a project can work out totally differently than initially dreamed of.

All in all, it has been a great learning journey for me. I look forward to hearing your thoughts!

Would you like to connect with the PEOPLE of Unleash Leadership?

Are you a High Performance Manager? A Founder? An Expert? A Team Leader? From Small Medium Enterprise, Corporation, Government, Startup or other Organisation? Then have a look at the programmes of Unleash Leadership. We offer state-of-the-art, human-centered learning experiences.

© 2017 UnleashLeadership — All rights reserved