Transitioning From a Large Company to a Startup

Problem

I transitioned from a large, well-established company with 100k+ employees, initially to a national mobile and Internet provider with 8k+ employees, and then to a small startup of only 80 engineers. It was an exciting journey through which I transitioned from a rigid organizational structure, strict hierarchy, meticulously planned roadmaps, clear expectations, mature processes, and well-defined roles and responsibilities to a highly ambiguous environment characterized by unpredictability, flexibility, and ambivalence.
 

Actions taken

In an ambiguous environment with yet-to-mature processes, I had to rely on feedback I was regularly receiving from my boss and peers heavily. When you are in an unpredictable environment with many unknowns, it is hard to assess if you are doing things right. Also, oftentimes metrics are not in place, objectives are not yet well-calibrated, and in general, processes to measure success are still evolving. This is why I was trying to collect and compare feedback received by different people and use it to plan my activities.
 

Also, I found discussing my ideas with as many people as possible and involving them in the planning process to be critical. Our startup is a closely-knit environment where people are genuinely curious about different ideas. Many are experts in their domains but open to my ideas and willing to help me evangelize them. I was steadily able to build a network that I could translate into concrete support.
 

One of the key challenges I faced was how to find a balance between developing a structure for rapid scaling and allowing for some ambiguity that was a prerequisite for agility. While large companies could be slow due to their hefty structure and complicated hierarchies, small startups could use their fluid and ambiguous processes for their own benefit. Though I wanted to move fast, I didn’t want to break things. Not immediately. For the first six months, I did everything the same way the old manager was doing without imposing any drastic changes. It allowed me to see for myself if a specific approach would be effective and, if not, propose a change. Following my observing phase, I was more confident to propose new changes, particularly to revise roles and responsibilities and introduce some new approaches to management.
 

Lessons learned

• Let clarity guide you. Be clear about things you want to achieve/introduce/propose. Your messaging should be precise, concise, and tailored for a specific audience.
• Don't hesitate to navigate across different domains and share your experience with multiple teams. Unlike large companies, startups are heavily dependent on expertise-sharing and people willing to wear many hats.
• Adapt to the context and don’t stick to a theory, no matter how plausible it is. Theories could enrich your knowledge, but you will have to apply them to specific circumstances.
• Be open-minded to fluid processes and a fast-paced environment. If you are a less experienced manager, the transition may be harder than you would expect. As with any significant change, be prepared to embrace mistakes and make them an integral part of your learning experience.