Startup Growing Pains — Lessons & Questions — Part 1 — Culture

Learn from our mistakes so you don’t repeat them.

This is not a ‘how to’ guide. If you are looking for quick answers, there are plenty out there written succinctly by experts more qualified than me. This post was edited from the notes I wrote for myself, to record the lessons learned from my own and my friends’ experience in startups, and to remind myself to ask the right questions when I’m at the scaling phase next time. It is intended to be used as a reference by those of you that may be anticipating or experiencing the pains, and want to think deeper and come up with your own solutions.

No two startups are the same.

What I mean by ‘startup growing pains’

While I use the term ‘startup growing pains’, what I’m referring to is the pains suffered by startups that are changing in scale, those known as ‘scale-ups’ in Europe. When scaling rapidly, various aspects of the business change, consciously or unconsciously, leading to greater opportunities but also potential breakdowns in critical components of the business.

As entrepreneurs, we make mistakes all the time and continuously learn from our mistakes. Over the last few years of my ‘scale-up’ journey, there were a number of times I felt we made fatal mistakes and broke the business. But as a matter of fact, we survived and managed to reach a successful exit. If you are experiencing similar issues or feeling screwed, don’t let fear of failure cloud your mind. Look at where you started, keep your original aspiration in mind, take an objective view of the issues at hand, and act decisively.

I will now dive into the changes, my lessons learned, and the questions I would ask myself when I’m at the startup scaling phase next time.

Part 1 — Culture

As a startup that managed to successfully get to the scaling stage, it’s almost certain that you have a great culture which has been key to your achievement so far. But what is your culture? Can you immediately recognise it in life, beyond the few words or statements written on your website and communicated to your staff? If the culture changes when the company scales, what are you doing to protect it and minimise the negative impact?

The Story

Shortly after we exited from a startup, I asked a number of former colleagues:

What’s the first thing coming to your mind as a mark of when our startup culture changed?

To my surprise, many of them gave the same answer:

When the bar was gone.

We had a bar at the centre of the office since early days, where we used to gather for breakfast/lunch/snacks/drinks, carve Halloween pumpkins, introduce new starters, fire direct questions at the leadership team, run ‘lunch-n-learn’ sessions, have quick meetings/catch-ups, etc.

The bar took the space of 8 desks and was admittedly the messiest part of the office. When we scaled and needed more space for desks, we thought of getting rid of the bar. We ran an all staff poll. They voted ‘NO’, made very strong comments against the proposal, some even threatened to leave. We announced the result, kept the bar, and squeezed out budget for more office space. A year later, an experienced corporate executive joined as [CXO]. A few months later, he got rid of the bar, without a poll. I expected the same reactions from the teams as last time, but there weren’t any. It was surprisingly easy and quiet.

So what was gone with the bar? To name a few among others…

  • Frequent social gatherings, where chats took place between people from different functions, between new starters and those they haven’t met, between junior employees and senior management.
  • 5-minute catch-ups, which used to happen a lot around the bar. The alternatives were booking a meeting room (very limited availability), going out for a coffee (take too long), or doing it at desk (lacking privacy) or in the kitchen (too much distraction).
  • ‘Ask the leadership’ time, when anyone could ask any question to the leadership team in front of all staff, and the questions had to be answered immediately, unprepared. This was replaced by a box for questions to be submitted, reviewed and answered in the next all staff meeting.
  • Weekly ‘lunch-n-learn’ sessions, which used to take place over free lunch and anyone could join, leave, walk by as they wish. This continued as online sessions and soon disappeared due to significantly reduced attendance.

Lessons Learned

In hindsight, the bar was an unspoken icon and played a vital role in shaping our culture. When the bar was gone, it was a statement of change. While most early employees blamed [CXO] for the culture change, as he was openly against the statement “we’re a startup” and suggested we need to “mature as we scale to the next level”, if I’m honest, he wasn’t the only reason.

The entire management team were informed of [CXO]’s decision to get rid of the bar, why did no one push for a second poll? We knew our teams would have voted ‘NO’ again, but none of us wanted to spend our energy fighting for the bar or confront the [CXO]. Me included (full confession here), I was the one running the poll the first time. We left the bar and those behind it unprotected.

Why did the staff not push back when the bar was removed, and not make comments like they did before? They no longer felt in a position to openly express their opinions. They no longer wanted to risk their personal image/career to defend our culture.

We didn’t immediately see the culture change when they took place. We didn’t realise the changes in ourselves. We didn’t really know what the bar stood for, and the consequence of removing it. We talked a lot about culture, spent a huge amount of time defining our ‘goals, values, practices’ and making sure everyone remembers them, but we didn’t recognise our culture when it was standing right in front of us.


  • What stands for your startup culture? It’s something real that people can relate to, not the few words people have to memorise or get quizzed regularly to make sure they remember. Do you recognise it?
  • Are you and your management team true advocates of your culture and leading by example? Take 2 minutes at the end of each day to think about this — Have you seen behaviours reflecting your culture today, and if so, what proportion were from senior managers? It’s often easy to spot negative behaviours, but we tend to take the positive ones for granted and not realise when they start to disappear.
  • When you have limited budget and have to choose between investing in growth and “keeping the bar”, which one is your priority? I’m not trying to convince you to choose the latter. I’m only asking you to not under-estimate seemingly trivial decisions like this, as it may have a lasting and irreversible impact that is not immediately obvious.
  • When a change in unavoidable, what are you doing to mitigate the negative impact? Have you properly analysed the impact, offered suitable alternative solutions, or are you expecting the teams to work it out themselves?

Coming next:

  • Part 2 - Organisational Structure (link will be added once published)

About me

I founded 3 businesses🚀 , helped creating 17 companies from university labs🔬, and spent 6 years building and managing operations in a scale-up📈. I write this blog to share my first-hand experience, lessons and thoughts with fellow entrepreneurs. I hope you don’t mind that, in order to share fully and freely, I have to write anonymously🥷 to avoid having some of the stories and quotes traced back to the companies/individuals involved.

About this post

This is one in a series of blog posts covering the topic of Startup Growing Pains I’ve seen from my own and my friends’ experience. If you find it interesting or helpful, please give me a few 👏🏼 , follow me, and share with anyone that may be interested. Thank you!



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