Prioritization is particularly important for decisions where you’ll invest days, weeks, or even months, so I’ve gathered a bunch of questions that my clients sometimes find useful for deciding between projects. 

There are too many questions here to be practical. I admit it. But you don’t need to answer all of them. I’ve just put them all here so you can find the ones that are valuable for you. You can just answer the most relevant ones. 

There’s a tricky catch - “most relevant” is a judgement call. If you haven’t thought these ways before, you might not intuitively identify the right questions to answer. For that reason, it might help to answer all of the questions for one project so you get a feel for them. 

Outline

Describe the task or project in 250 words or less. The description should include a vague outline of what the project entails, why it needs to be done, and how it is valuable. 

Motivation and enjoyment 

On a scale of 1-10, how exciting is this project? 

Would you have to force yourself to work on this or would it be draining to work on this?

Benefit

Why is this goal valuable? What does it help achieve, and why do you think it will help achieve that? How does it fit into your theory of change?

What skills or knowledge would be gained? 

Will this stretch your current capabilities and have good feedback loops? How much of this feels like deliberate practice? How often and how importantly do these skills impact your work? 

Estimate the total value of the project, make a list of all the pros and cons and put a dollar value on each of them wherever you can. This should be a fermi estimate, don’t spend more than 5-10 mins on this.

Consider the opportunity cost. What other projects could be completed by a similar person in a similar amount of time? How much would you be willing to pay to have an external contractor complete this project? 

What is the best case outcome of this goal? 

What is the worst case outcome?

Once you have a clear picture of the value that the project provides, apply the reversal test. If your sole aim was to create the value you suspect that this project brings, is this the method you would choose? Are there any alternative projects which might capture that value with fewer resources. Are there any other projects which simply win on this dimension? For example, if your project is valuable because it generates new EAs, is this the best strategy you can come up with to generate new EAs? How could you generate 10x the number or 10x the quality of EAs by doing a different project instead?

If you’re highly uncertain about the value of a project, check what information would reduce your uncertainty. What value would you get from perfect information? What is the most likely outcome?

Time required

How many days/ weeks will it take to complete this goal? This is the calendar time given the other things on your plate/how much time you have to devote to this.  

How many hours of work will it take to complete this goal? 

What is the lower bound for the ‘MVP’ or minimum action required to make some meaningful progress on the project?

What is the a maximum amount of time it would be worth spending on this project given your present information? If you find it difficult to make progress on the value estimate, how long should you spend gaining information before you decide whether or not to go ahead with the project?

If you did the quick version of the goal and took half the time, how much less valuable would the outcome be? Is there a way you can 80/20 the project? 

If you did the long version of the goal and took double the time, how much more valuable would the goal be? Is it worth spending the extra time? 

When is the final deadline for the entire goal? Is this a soft or hard deadline? 

Define stopping criteria using your proposed estimates - when you reassess the project? Pre-commit to abandoning the project if you hit the upper limit on any of the steps identified above and you have not made a significant update to your value estimate. 

Suggested approach

Spend 5-10 minutes thinking through how you would approach this project and write a brief summary here. The aim is to come up with a first-pass plan for how you will make progress on this project and eventually end up with a solid timeline and list of necessary activities. What are some initial next actions?

Define the expected point of diminishing returns (eg spending an extra hour trying to find a flight cheaper than £100 is unlikely to be worthwhile in expectation).

What activities are related to the goal but don’t push you forward on achieving your deliverable? (These are activities to avoid)

What activities or actions are vital to progress towards your deliverable?

How can you make it fail most quickly, if it’s going to fail? 

Deliverables

Think of deliverables as observable facts about the world that you expect to be true upon successful completion of the project. What physically observable final outputs will you produce? Imagine that you are writing a contract to engage a third party firm to complete this project, what criteria will you use to assess their performance?

What would you expect to see if the project failed? 

For hard-to-measure outcomes, consider setting a deliverable based on number of hours spent. 

Failure modes

Imagine you produce your deliverable, but it has failed to capture the value intended - why has this happened?

Imagine it is the final deadline and you failed to produce the deliverable for the goal - why has this happened? 

What do you feel worried or concerned about? 

Resources

Attach any pre-existing documents relevant to the project.

People are resources too - list all the people who have a key interest in this project, their areas of expertise and what level of support they might be able to offer.

Do you know anyone who has completed a similar project before? If so, ask them how long the project took, how many person-hours went into it and whether it was worthwhile in the end. Ask them what they would have done differently if they were to do it again.

Acknowledgements:

Kudos to Tara Mac Aulay and Harri Besceli for inspiring many of these questions. Thanks to Nora Ammann for her suggestions.