How do you ensure that the engineering team understands all the scopes of the project?

This is a continual process! It is important to have regular syncs with the engineering team to discuss progress, open product questions, and review next steps. I don't think this can be done in stand ups, but rather having a weekly 30 min sync has worked for me. 

I don't think it's possible to spec out every single detail of a product up front. It's important that you have ~70-80% of the details defined before engineering starts work, but as you start to define the rest of the 20%, sync with the engineering team regulary so that you can clarify the scope. 

Ask them to repeat it back to you in their own words. "Explain it to me like I'm 10 years old!"

Ask them where they have the most confidence and the least confidence about what they are delivering.

Can they identify all the points of failure in their approach?

Ensuring that the engineering team understands the project scope is a joint effort between product management and engineering. To do this effectively, there are a many strategies that can help. The key is to lean into collaboration and communication structures that allow for understanding and refinement. Effective communication, documentation, and collaboration are key components of achieving this understanding. Here are some strategies that I have used successfully:

• Project Documentation Infra: Have a standard set of project documentation that includes project scope, objectives, and requirements. This typically includes discovery docs, PRDs, Tech Specs and enables everyone on the dev team to operate from the same base understanding.

• User Stories and Use Cases: This is table stakes these days but make sure you break down the project into user stories or use cases that describe specific functionalities from an end-user perspective.

• Collaborative Sprint Planning: Engage the engineering team in collaborative sprint planning sessions. Discuss the upcoming sprint's goals, prioritize tasks, and clarify any uncertainties.

• Technical Discovery Sessions: Organize technical discovery sessions to explore the current state of the technology stack and any potential technical challenges.

• Regular Check-ins and Feedback Sessions: Schedule regular check-ins and feedback sessions to assess the team's understanding of the project scope.

• Review and Refinement Meetings: Plan review and refinement meetings at the end of each development cycle to discuss what was accomplished and to review the next set of tasks. This helps maintain alignment between the engineering team's work and the overall project scope.

• Clear Definition of Done (DoD): Maybe most importantly, clearly establish a Definition of Done for each task or user story. This includes criteria that must be met for a task to be considered complete. Having a shared understanding of the DoD ensures that everyone is on the same page regarding the expected outcomes.

Engineering should be part of your planning journey and not be brought in only when scoping. Couple of ways to driving the understanding to your engineering team:

1. Throughout the year, create a forum to discuss new opportunities with your engineering as you discover them. This will make sure nothing is a surprise when planning comes by. This also helps engineering start the thinking around engineering requirements sooner than later. 

2. When planning activities begin, I would strongly suggest at the least, a 1-pager on the what & why that you can have engineering use to help with scoping. Written communications always drive alignment faster.  If you have talked about this with the team earlier, the 1-pager should throw no surprises but will unlock further discussion needed for scoping. 

3. When drafting a PRD, have your engineering sign off as an approver on completion of PRD, which also drives accountability and clear handoff on the scope of work.