Is your client a leader or manager?

It's important to understand if your client is a leader or a manager. Here are a few gems from Venkatesh Rao.

The Art of Gig, Volume 2: Superstructures

Leaders

• A leader is someone who can directly judge and use any thinking or work they sign off on. They are not intermediaries accepting counsel or advice on behalf of other individuals or groups, then sending it up or down a chain of command or into the blackhole that often exists deep inside large organizations. They are not applying inflexible standards controlled by others that they lack the discretion to override.

Managers

• When you work through non-leader intermediaries, there is high risk that you will end up doing the wrong thing or doing the thing wrong. For example, perhaps you do work for a low-agency middle manager who is sourcing a report that will be presented to the CEO. The CEO will actually sign off on the report, declaring it good or bad, but you never get to meet them while doing the work.
• Managers tend to control the risks they own and play more deterministic games, so it is appropriate to judge them based on their win rates.

If you are working for a middle manager type, you need be more conservative in your approach to work, more organized, and ensure you deliver on time and with a high quality. You basically need to be a good employee.

If you work with a leader, you can bring your ideas, do speculative work, and (tactfully) criticize their ideas. You need to be more of a consultant.

Most commonly, you will probably work with a manager type.

That's okay. Just make sure you know what their incentives are and act appropriately.

Manage your own expectations about the types of idea the manager will accept. But don't be afraid to throw some new ones out there. That's what makes being a 1099 fun.

Want the full playbook? Check out Going 1099.