The biggest mistake people make is assuming their success travels with them anywhere they go. The truth is that it does not, necessarily.
Just as a person moves through stages of life, each with its own demands, companies move through the same stages, and each one calls for a different set of skills. The mistake many people make is believing that because they succeeded in one place, they will succeed everywhere.
Every company's situation differs by its environment and by the stage of life it is in. The larger a company grows, the more its requirements change, and with them the environment inside it changes too.
I have worked in different environments and organizations of different ages. I do not claim to understand this better than anyone, but I have seen enough to grasp the difference, and to know what suits me and what does not.
The founding stage
It resembles birth and infancy. Resources are scarce and the challenges are large. Yes, you may be the CTO, but you are also expected to be the CISO, the programmer, the DevOps engineer, to run the servers, and to talk to customers. You have the title, but in practice you do everything you possibly can.
After founding
It resembles childhood. You know what you want to do, but you need someone to hold your hand. You may be the CTO with a small team, but you will still write code yourself, prepare reports, and follow up daily. You are a manager some of the time, and a hands-on employee most of the time.
Adolescence
Things become clearer and the team settles. As CTO, your focus shifts to managing your function, but you still step in sometimes to teach the team, to reassure people, and to absorb their frustration. You are a teacher, a parent, and an expert, and you all learn together.
The prime years
The harvest stage. The manager's job is genuinely to manage. What is expected of you is direction, accountability, and full awareness of what is happening.
Maturity
The decision that used to take two days now takes two months. Your role is to protect the system: to establish governance, and to build teams that work without you. The skill this stage demands is political patience and the ability to move quietly inside a large, slow organization, the very skill that would suffocate the founder of a startup.
What stays constant: if you succeed at a company in its maturity stage and an offer comes from a company that is still being founded, do not assume your success will be the same. What you grew used to and learned may not fit the age of the new company (it is like teaching quantum physics to a third-grader).
Success is not a trait you carry with you. It is a match between your skills, the company's stage, and the environment you are in. Know your stage first, then judge yourself.
And your company, what stage of life is it in right now?
I have spent 19 years across companies of every age, and I have seen how the same skill thrives at one stage and stumbles at another. If this sounds like you or your company, you can submit a request and tell me what you are dealing with. No commitment, just an honest conversation.