Previously I presented a heuristic for prioritizing what to work on as a leader at a startup based on how effectively it derisks the grand vision.

That heuristic is useful but can be difficult to apply when working as an IC, or at a larger company, or where there might be lots of valuable and important ways to derisk the vision.

Here, I expand on that original heuristic with one a little bit more complicated, but hopefully more general.

You should always seek to work on projects with the highest expected value where the expected value is a combination of:

• How important is the success of this project to the company?
• What is the probability this succeeds with / without your help?
• How much time will it take you to do?

The first point orients work around the companie’s grand vision and is applicable from the earliest startups to the largest public companies. There’s always a set of priorities at the highest level.

The second point is about how much of an impact you can have on the project. It’s very likely the smartest, most capable, and most visible people in the company are already working on the highest priority projects. As a Junior IC you may be able to stand out more by contributing significantly to the success of priority number 3 than number 1.

Simiarly, as a leader, it’s tempting to assume you should always lead the highest priority projects. It may be the case, however, that your team can accomplish the highest priority project easily without you but you have a unique skillset that can help with the second biggest priority project. This can help you figure out how and where to delegate.

And lastly, you should understand how much time and effort will take. As a leader and an IC you most likely will have to juggle multiple responsibilities. It may be that as a leader you are responsible for a slew of 3rd tier priorities that, for various reasons, only you can accomplish. If you can contribute 1 hour a week and significantly move the needle on a lower priority project that may be more valuable than contributing 50 hours a week to the highest priority project.