When slicing work in to valuable pieces, I notice that many people get stuck on the notion of business value. "How will I know if it's valuable?"
My quick hack is to reverse the situation. "If you didn't do this thing, who would be upset and why?"
If the answer is that nobody would be upset then there's no value here. Do something else instead.
If someone would be upset then that person is your customer and the reason they're upset is the value.
@mike_bowler How do you think about this for proactive/preventive work, or situations where your perceived value and others' perceived value may not be aligned?
Example 1: You work to make the system more reliable and improve observability. If you didn't do this, and there is an outage, it would take longer to detect and resolve.
Example 2: You refactor the system to make it less error-prone. If you didn't do this, deliveries would be slower and have more defects.
@mike_bowler In both cases, understanding the risk and impact requires experience with failure, right?
Suppose that you've operated production systems at scale and your CTO has not - how would you communicate those risks so that they can make a good prioritization decision, given that the risks & risk reduction are not easily quantifiable? For example, it's hard to say whether an outcome is a 1-in-100 or 1-in-1000 event, or that your work can reduce the odds of occurrence from X to Y.
@jawnsy I would certainly hope that if you have more experience than your CTO then they had hired you for that and will listen to what you have to say ;-)
I wouldn't say that you have to experienced the failure yourself to be able to work with it. You certainly do need to be able to understand risk and probability.
Mike Bowler
Jonathan Yu