Photo by Efe Kurnaz on Unsplash

Jason Cohen founder of WP Engine asked a good question on Twitter and LinkedIn last week:

This was my response:

Not easy. Here’s how my mind approaches these types of problems:

1) Working backwards – based on where we want the business to be by xyz timeframe, which ‘item’ gets us closer to (or de-risks) that future state?

2) % Allocation – instead of picking one, can we decide on an allocation of resources that makes sense ie 20% bet on cancellation prevention, 60% bet on increase sales, and 20% on tech scale.

3) Time-constrained bets – which ‘item’ is best now (this sprint, this month, this quarter)? Often this helps clarify the right option, since current context does matter.

4) Most likely outcome — how much could we reasonably reduce cancellations with xyz amount of bandwidth? What’s that worth? What’s most likely outcome of investing that same amount of bandwidth in the increase sales project?

Not silver bullets, but helpful.

How do you prioritize ‘incomparable projects’?


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