What questions to ask when Scrum Master meeting Product Owner first time?

Why not explore any questions the Product Owner might have for you, considering that the initiative has already been underway for some time? What do they hope might change? What might stay the same?

When I start on new teams, I sit down 1:1 with each member of the team in a basic format:

- tell me more about your role

- what do you think the team is doing well and what it could improve on (to ground them, I sometimes ask, "If you were sitting with friends and family and rated this team from 1-10, with 1 being to tell them to run away and never join the team, and 10 is everyone in the world should join the team, what would you rate it and why?")

- what is your experience with Scrum? any training? on-the-job experience? how do you feel that Scrum is working on the team?

- any questions for me?

For the PO, I'd particularly ask questions about they see their role on their team, where they're getting work from, how they're communicating priorities, how they understand the customer, and how they follow Scrum. This would help me determine how to interact with the PO in the context of Scrum and what coaching might be needed.

For example, are they prioritizing the backlog? Are they pushing work onto the team rather than allowing the team to select their own work? Is the PO being pressured to deliver by certain deadlines from someone in leadership?

It takes work to build a solid relationship with a PO but it's also one of the most rewarding relationships in Scrum. Good luck, Sri!

I really like your answer Season. I've met with the team collectively but not on a 1:1 format to start with and get their individual thoughts on the system. I've done that with the PO though.

I typically go in with the mentality of learning the current implementation while letting everyone know that I'm a curious person and ask several 'why' questions, with the intention of defining what makes the team the most successful today.