I would assume that at first, when you have 5 employees, everyone is working, hands-on, together. When you have 50 employees, many may be doing things that are regulated by other dynamics in the company and where the executive mostly just makes sure he/she's available to advise, mentor, and more rarely take action.

But you are likely to still have those new and exciting initiatives, where a small group of people needs to work together to make it happen. So you might have an executive and four employees working together, hands-on in this.

But you are right to worry about employees being afraid to speak up. This is why it is important to have a culture of openness, collaboration, and collegiality, and where leadership and followership are distributed.

One other caveat: because of the market we are in we are likely to be hiring older developers with at least some self-employment experience. At some point if we start hiring younger folks I would expect the transition will be a slower one with a lot more mentoring. I would worry a lot less about all this with older developers who have been their own bosses and are clearly told we want them to continue to be their own bosses to the extent possible than I would folks without that experience.