Evan McPhee's Profile

Thoughtful post. One item that particularly resonated with me was the thought about structure. One thing in my experience is that some employees that gravitate towards early-stage startups are particularly averse to ANY kind of structure (not just the oppressive, overly-intrusive kind). Part of the appeal of early-stage companies for this type of employee is precisely the lack of structure that’s common in these companies. One key determinant about the type of structure that’s appropriate has to be employee expectations, tempered by the needs of the business. Introducing new elements of structure will almost certainly cost you employees, which may be ok, but it’s definitely something to consider when tweaking the system.

This is extremely important- the metrics that you measure absolutely matter. It’s a foundational principle of hierarchy that middle managers will optimize around the metrics that are being measured, and can drive extreme differences in employees (or contractors in this case). I love the images you selected- they’re extremely telling.
I think the differences in these metrics also makes sense given the relative scale of these businesses- while Uber’s posture may seem more cold, it’s also probably the most directly scaleable metric to optimize around. Lyft, being much smaller, has to be looking to create reasons for users to prefer Lyft, even when they make have to wait an extra minute or two to get a ride. An emotional connection, or an especially chipper driver may be one way to get there.
I’m not sure I agree with Jose- there are a variety of ways in which you can influence the behavior of contractors. You’re not directly in charge of them, so you need to use more indirect methods, but tools like Uber’s stringent rating system for both riders and drivers, or the surge system can tweak the dials on behavior pretty significantly.

While I agree that the general question you pose is a tough one, promoting the old CEO to Chairman and recruiting a new CEO for a company seems doomed to failure (Company A above). Recruiting in a new CEO technically reporting to the old leader (the new Chairman) seems like an invitation for the old leader to snipe and question the decision-making of the new leader. Further, I think that experienced, capable new leaders are aware of this, and consciously avoid these types of situations, meaning that I’d question the judgement of any leader stepping in to a CEO role with the old CEO as Chairman.