The key to understanding the staged nature of the job is first to find the time to analyse yourself. I used to do this through a personal ‘offsite’ twice a year when I blocked everything and added a day to an existing business trip that was somewhere away from the rest of the team. I would advise any CEO to do the same. You would then spend that day looking through high-level reporting of how the company has performed over the last six months (P&Ls, engineering/product reports, customer updates) and looking at plans for the next six (roadmaps, strategic views on the competition’s moves, budget and forecast). Then, for every major piece of activity that has to be achieved (hit target X in sales, deliver product Y by a particular date, etc), dig into how it is going to happen and how you are going to help.
If you discover yourself unable to answer the question, you have scaled too quickly – it’s time to go a bit deeper again. If the answer shows that you are a bottleneck, you have not scaled enough – it’s time to hire someone new to take on part of what you have been doing.
I think many early-stage CEOs make the mistake of scaling too early and many late-stage CEOs make the mistake of scaling too late.
As a company makes the journey from the founding stage to Series A and B, a great CEO will still have the pulse of company. They will be keenly aware of how product and tech, sales and marketing, organisation and human resources, finance, legal and so on are thinking and what they are doing.
Of course, you will have experts in each area who handle the details but, if necessary, you could drop in with minimal friction and understand the detail. If you hand over these areas of responsibility too early, then your company could grow in unexpected ways at an early stage and that could set unhealthy trajectories. For example, if you hand over all legal control to a general counsel at Series A then you might create an overly conservative organisation. If you hand over all product to a hired CPO at before Series A then you might miss a crucial development in the external environment that means you plateau as a business.
Conversely, after you have spent the first few years being a bit of a control freak, from Series B/C and onwards it’s crucial to hire experts who bring playbooks that can get scale quickly. This is particularly true in areas that many CEOs hold dear – two classic cases are engineering and product, and sales and marketing – and it’s important to be able to let go. Instead, put all of that energy into hiring the best possible people to replace yourself in these roles.
My biannual ‘personal offsite’ allowed me to catch these moments of over- or under-scaling fairly quickly and revert as necessary – ensure you have some sort of mechanism like that to be able to proactively think about where you are at.