In a small company one is not just an engineer, product manager, head or sales, or CTO, but one typically wears many hats. That's especially true for founders since they had to do everything by themselves at the beginning and they only gradually hire people and delegate responsibilities. While cost of communication between different roles is greatly reduced if all these roles are played by a single person, wearing multiple hats has lots of deficiencies with the most grave being severe lack of transparency. If a founder fires head of sales for example, he'll have to explain himself at least to the board. But if the founder stops wearing hat of head of sales nobody will notice until sales pipeline dries out. Another example is the relationship between product manager and CTO who should frequently confront their opinions about direction of the product. But if the confrontation happens only within one head wearing two hats others cannot participate in discussion and final decision about product direction is made in secrecy of one's mind. Yet another example of confusion caused by people wearing many hats happen at meetings where you never know which hat is speaking at the moment since you only see a person and not the hat he is wearing. For small companies fact of people wearing many hats is given and cannot be changed, but it can be greatly alleviated. For starters, company should strive to have people wearing just a few hats (max. 3). Second, people wearing multiple hats should be aware of it and make it explicit to others by saying "As a founder I think....". Third, internal discussions between different hats should be externalized either by putting opinions of different hats on paper or discussing ideas with at least one other person. Finally, one should realize that passing hat to another person will consume much more resources than originally thought due to overhead of additional communication and the lack of common knowledge that hats on the same head enjoy. A good rule of thumb is that each hat passed to another person requires a whole head just for itself.