What questions should Scrum Master ask in 1-on-1 meetings with developers, PO and stakeholders?

A more fundamental question would be if a Scrum Master should be having (regular) 1-on-1 meetings with anyone.

There may be times when the Scrum Master is teaching, mentoring, or coaching someone on an individual basis, but I wouldn't consider this a 1-on-1 meeting. During regular work, the Scrum Master may have to work together with an individual to help remove impediments, but this also isn't something I'd consider a 1-on-1 meeting.

When starting to work with a new team, it could be helpful to have some time to get to know everyone on the team, individually. In the time of working in the office, this could be getting coffee or having lunch with someone. In the world of remote work, this would more likely be a short video call. The purpose would be to get to know everyone's background, their views on the current state, what they see as problems and impediments as well as opportunities for improvement and find the best ways to communicate and work with everyone. But I wouldn't have these regularly - one or two sessions per person when joining a new team or when someone new joins the team.

What questions should Scrum Master ask in 1-on-1 meetings with developers, PO and stakeholders?

Open questions might be helpful, in order to encourage a train of thought. A Scrum Master seeks to build a consensus view of reality by bringing these people together.

I'm going to flip your question around.  What kind of questions would team members ask a Scrum Master in a 1-on-1 meeting?  If you have a hard time answering that question, then you are starting to understand that 1-on-1 meetings are really helpful as a Scrum Master.  I agree with @Thomas that some discussions early on can help people start to understand each other.  But it should go both ways.  The team member needs to understand the Scrum Master as well.  After that, just the daily interactions will help to strengthen the bonds.

As for the kind of questions to ask, @Ian hit the nail on the head.  Ask questions that will invoke thought.  You aren't telling people how to do things, you are helping them understand what needs to be done and encouraging them to come up with the solutions.

What do you think about the question ¨How are you doing today?¨ and ¨What can I do for you?¨.

Agree with everything shared above.

Will add that 1:1 discussions can become an issue if Team members are bringing to you, what they ought to have courage and openness to bring to the Team. Consider how transparency and inspection may be impacted by having private 1:1 discussions, instead of open discussions as a Team.

As a Scrum Master, it's essential to understand how team members are feeling about the team and collaboration. Holding one-on-one meetings with each team member is a great way to gather their individual perspectives and address any concerns. Here are some questions you can ask during these meetings:

1. How do you feel about the team dynamics and collaboration within the team?

2. Are there any aspects of the team's collaboration that you find particularly positive or beneficial?

3. Are there any challenges or obstacles you are facing when it comes to working with other team members?

4. How comfortable do you feel providing feedback or sharing ideas within the team?

5. Are there any improvements you think we can make to enhance collaboration and teamwork?

6. Do you feel that everyone's contributions and ideas are being equally valued and considered in team discussions?

7. Are there any specific communication issues you have observed or experienced within the team?

8. How do you feel about the level of trust among team members?

9. Are there any team rituals or ceremonies that you find particularly helpful or ones that you think we could improve?

10. Is there anything you'd like to see the team do differently to enhance collaboration or create a more positive work environment?

11. Do you feel that you have the necessary support and resources to perform at your best within the team?

12. How do you feel about the overall alignment of the team towards achieving common goals?

13. Are there any conflicts or disagreements within the team that you believe need to be addressed?

14. Do you have any suggestions on how the team can better celebrate achievements and foster a sense of camaraderie?

15. Is there anything you'd like to discuss or any other concerns you have about the team or collaboration in general?

Remember, the goal of these one-on-one meetings is to create a safe and open environment for team members to share their thoughts and feelings honestly. As a Scrum Master, actively listen to their responses, validate their concerns, and take appropriate actions to improve the team's dynamics and collaboration. I hope this will help you.

Hello,

I think the best way to start a 1:1 meeting is to use Lyssa Adkins words: "There’s a trite, but true, saying in coaching: A friend loves you just the way you are. A coach loves you too much to let you stay that way."

what the relations between stakeholders and Customers ?

what the difference between Coaching and mentoring?

@Joseph Morcos, a customer is one type of stakeholder.  There are many others like people inside of your organization for example like sales, leaders, managers, etc. , partners, influencers and more. Have a look at https://www.scrum.org/learning-series/stakeholders-and-customers for more details.

As for Coaching vs Mentoring, have a look at the links in the Professional Scrum Competencies here: https://www.scrum.org/resources/professional-scrum-competency-developing-people-and-teams 

thanks Eric Nailbur,I wish you Happy New year !!

Schedule regular meetings with the Product Owner, development team, and other stakeholders to discuss challenges, updates, and concerns about Agile. 

https://www.scrum.org/forum/scrum-forum/80176/typically-10-or-fewer-people-slope

As a Scrum Master is accountable for team effectiveness, why not focus on the team. 
One-on-one meetings might be insightful for yourself as Scrum Master, but does this bring transparency to the team...?
There is no such thing as an individual's problem. As this typically always affects the team in one or another way, it becomes a team's problem.

I've learned through experience that it is better to openly discuss within the team, and reduce one-on-one meetings to the max. Only reason I still do this exceptionally is to cool down some emotions in conflict situations - while even then a self-managing team should be able to deal with this in time.

Hope this helps.
Feel free to shoot more questions!
 
PS You might be interested in my blog posts about the fundamentals of the Scrum framework. If so, please check out this page: https://boostyourscrum.com/professional-scrum-foundations-series/

Thanks everyone, I've just started a new job in a start up, there is a lot of work to do here, to build proper team collaboration and transparency, to educate the management about "real" Agile culture, and all your answers in this post are extremely helpful!

Love the Scrum community 

xx