Here's an activity you can do right now to help your team grapple with talking about risk and uncertainty. There is nothing new/groundbreaking about this idea, but I am amazed by how few teams slow down to do this as a team.
What happens instead? A small group of people get together and fill out a persuasive PRD. They internalize the risks and try to boil things down at a super high level. The risk section has a couple bullets, but they never get revisited. Or the team slips into the vortex of traditional project management: exhaustively listing risks related to schedule and nothing else.
The basic idea is that you write a checklist of questions related to initiative risk. As a team. To catalyze good conversations. To do that you:
Engage a cross-functional team in the activity.
Get exhaustive. 100+ questions is common during group brainstorming. After grouping you might end up with ~25.
Get specific. Less experienced team member should be able to answer the questions. Examples help for this. Otherwise everyone will say "technical risk" and "business risk" (which aren't specific enough).
Pressure test the questions by running historical efforts through the list. Did anything happen with those efforts that wasn't covered?
Continuously revise and tweak your list.
Avoid gatekeepers like the plague.
It is very important to not turn this into theater. An example might be some kind of review board that grills teams using this questions. Why? If you stage a play, all you get will be theater. The whole idea is that with a better sense of the risks involved, a team will be able to plan a contextually appropriate approach. And have a good conversation.
Stepping back, this helps address one of the big problems I see when chatting with teams. Mono-process. A one-size fits all approach.
With the help of folks on twitter, I gathered some examples. This is not meant to be an exhaustive list. Do not copy this list. Make your own list with your team.
Is this an incremental improvement to an existing workflow?
Have we worked in this area of the codebase?
Will this introduce new nouns/verbs to the product?
Have we done prior research with these users?
How accessible are these customers? Do we know how to reach them?
Does the new initiative have a third party integration risk?
Can adoption happen organically, or will we need to intervene?
Is some sort of organizational change required on the part of the customer to get value out of this?
Are we attempting to actually change user behavior?
Is this a brand new system component? Or is it extending an existing one?
What if some other organization does it instead?
Can we expect customers to roll with a transition period? Or does it need to just work out of the box?
Has a competitor ever tackled this? How did it work out?
Has any team member tackled something like this at a past company?
Does anything like this already exist? Anywhere?
What if we don't do it? What will actually happen?
Does this introduce any new interaction patterns?
Are there opportunities to pivot/proceed based on new information?
Is this building on a solid architectural foundation?
Is this addressing a problem which has been difficult for us in the past?
Is it a multi-sided problem of some sort (e.g. content creator and content consumer)?
How difficult will it be to measure impact?
How many teams must collaborate to make this successful?
How many diverse opinions exist on how we should proceed?
Is the CEO watching this like a hawk? Is this a political minefield?
Is there any reasonable scenario under which this new initiative could cause the company to cease to exist?
Schedule this for the next two weeks if you don't have a list like this in place. Good luck!