When a PM presents a roadmap, I expect them to be able to answer the following questions about each initiative:

1. What exactly will happen if we don’t solve this problem? What will happen if we simply don’t do anything about it?
2. How much money are we losing each week by not solving this problem? How does that compare to the money we are losing each week by not solving other problems?
3. How exactly will this benefit our customers? What becomes possible? What will they be able to do more quickly, enjoyably, profitably, efficiently, accurately, etc.?
4. Why now instead of one month, six months, or one year from now?
5. Why this instead of something else? Compare it against 3+ other potential initiatives
6. Who will this benefit? I’m going to run a query on our user/customer list, pick up the phone, and do some research. What query do I use?
7. What assumptions must hold true for this initiative to remain the most important thing we can work on?
8. What could our competitors do that would render this work obsolete?
9. How will this added complexity impact future iterations of the product?
10. Have users adopted the last three things we have delivered? If not, why is this more important than making sure those things work?
11. What about our current product is leaking value? Why this new thing instead of fixing that?
12. Is this the lowest hanging fruit? If I asked your team to spend the next week fixing “small things with a big impact” would this top the list? Would it have a greater cumulative value?
13. Can this be broken down into a set of smaller problems? What is the soonest we can get something into the hands of our customers to validate our assumptions?
14. How do you intend to validate the direction you are taking? Can you commit to a “pivot/proceed” decision point? When will we stop iterating on this? Please draw a line in the sand
15. Describe what failure would look like for this effort. How do you plan to make sure this either 1) happens quickly or 2) doesn’t happen?
16. What would you try to fix if perceived blockers were not blockers? What are those blockers? If removed those blockers would you opt for that thing (the thing you believe is blocked) over this proposed initiative?