Start with these questions:
- How long have you been in this role?
- What are your essential duties and responsibilities?
- What does a typical day look like?
- Who are the people and teams you work most closely with? How well is that relationship working?
- Regarding the project we’re working on, how would you define success? From your perspective, what will have changed for the better once it’s complete?
- Do you have any concerns about this project?
- What do you think the greatest challenges to success are? Internal and external?
- How do you expect your interactions with other people inside or outside this organization will change based on the outcome of this project?
Then, there are the more specific questions that depend on the project. Stakeholders may themselves be users, often of back-end systems or administrative functions:
- What are your most common tasks with the system?
- What problems have you noticed?
- What kinds of work-arounds do you use?
- Have you any concerns about this project?
- Is there anyone else I should talk to?
For each stakeholder, note the following:
- What’s their general attitude toward this project?
- What’s the goal as they describe it?
- To what extent are this person’s incentives aligned with the project’s success?
- How much and what type of influence do they have?
- Who else do they communicate with on a regular basis?
- To what extent does this stakeholder need to participate throughout the project, and in which role?
- Is what you heard in harmony or in conflict with what you’ve heard from others throughout the organization?
You’ve interviewed enough people when you feel confident that you know:
- Who all the stakeholders are.
- Their roles, attitudes, and perspectives.
- Their levels of influence, interest, and availability over the course of the project.
- How they stand to benefit or suffer with the success or failure of your work.
- The likelihood that any of them have the power or potential to prevent project success.
- All the ways that the workflow will have to change to make your project a success.
- The resources you have available for your project process.
- The resources required to support your project once it’s complete.
- All the business requirements and constraints.
- Whether your team and core stakeholders agree on the goals and definition of success.
- Whether the stated goals are the real shared goals, or whether anyone has a hidden agenda.
- How people outside the project team view this project.