Prioritization Via Questions Not Formulas

If you work in tech, particularly on the product side, you can't scroll more than 500px without encountering a prioritization framework, whether it's on Twitter (I haven't come around to calling it X yet!), LinkedIn, or in an email newsletter (The irony is not lost on me :p ).

All of them seem to share a common pattern, wherein they view prioritization through the lens of return on investment. This perspective seems to nudge us toward risk aversion, short-term horizons, and non-compounding tasks — basically towards actions that offer a higher guarantee of return, regardless of how they stack up over time. This approach comes at the cost of inventiveness, imagination, and exploration. Each task is evaluated based on what it can give us, now. Add to that all the assumptions that go into standard prioritization frameworks; they are usually way off base and prone to confirmation bias.

I propose we look at prioritization through the lens of how we want to spend our time. By steering away from solely pursuing the end goal (return on investment), we open ourselves up to enjoying the journey, granting us the freedom to take scenic detours and adopt a long-term perspective.

My prioritization approach is based on the following three questions, asked in sequence. There are no weights or formulas or box diagrams.

Question 1: In a year, what would I wish I had started working on a year ago? At times, answering this question can be challenging. Therefore, an alternative could be asking what you wish you had begun a year ago, based on your current position. The purpose behind this question is to bubble to the top significant undertakings that we might have bypassed due to their complexity, extensive time requirements, or high degree of ambiguity.

It is human nature to procrastinate and defer the hard things, instead of doing them first. Eating healthy, exercising are perhaps the most common examples.

Question 2: How does it align with the mission (long term goal)? Tasks guided by quick wins and short-term thinking often revolve around KPIs and goals. Unfortunately, this focus loses sight of the ultimate mission, favoring altitude gain over reaching the mountain summit—even if it ultimately leads us off a cliff.

Tasks that align with the mission have a compounding effect over time.

Question 3: What is the hardest thing? It's important not to confuse hard work with tackling hard things. Prioritize hard tasks first; they're likely to push us beyond our comfort zone and lead to genuine innovations.

The outcome of any prioritization process is a list. How do we know the list is good?

1. The list is short. If it contains more than five items, it's too long! Start over. Once those five tasks are completed, you can always add more. The aim is to have a prioritized list that guides our time allocation, not a laundry list!
2. No two items hold equal importance, the list requires a hierarchical order — no exceptions. The list should aid conflict resolution, not trigger the need to restart debates which will happen if two items share the same level of importance.