20 Questions

Questions to Ask Stakeholders

Strategic questions to engage stakeholders, understand their needs, and build strong relationships that support project success and organizational goals.

1

What are your primary goals and objectives for this project?

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Why this works

This question reveals their expectations and priorities, helping you understand what success looks like from their perspective and align your efforts accordingly.

2

How do you prefer to receive updates and communication?

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Why this works

Understanding their communication preferences is crucial for maintaining effective relationships. This question reveals their preferred channels, frequency, and format for updates.

3

What are your biggest concerns or risks about this project?

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Why this works

This question invites them to share their worries and potential issues, helping you address concerns proactively and build trust through transparency.

4

What would success look like for you personally?

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Why this works

This question reveals their personal stake in the project and what outcomes would make them feel successful, helping you understand their individual motivations.

5

How do you typically make decisions about projects like this?

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Why this works

Understanding their decision-making process helps you know how to present information and what factors influence their choices.

6

What's your timeline and what are the key milestones for you?

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Why this works

This question reveals their schedule expectations and priorities, helping you align your project timeline with their needs and constraints.

7

What resources or support do you need from us to be successful?

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Why this works

This question reveals their needs and expectations for support, helping you understand what they require to contribute effectively to the project.

8

What's your experience with similar projects in the past?

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Why this works

This question reveals their background and expertise, helping you understand their perspective and what lessons they've learned from previous experiences.

9

How do you handle changes or unexpected challenges?

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Why this works

This question reveals their flexibility and approach to problem-solving, helping you understand how they adapt to changing circumstances.

10

What's your preferred level of involvement in the project?

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Why this works

This question reveals their desired engagement level, helping you understand how much they want to be involved in day-to-day activities and decision-making.

11

What are your expectations for reporting and accountability?

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Why this works

This question reveals their requirements for transparency and oversight, helping you understand their expectations for project governance and reporting.

12

How do you measure success and what metrics matter most to you?

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Why this works

This question reveals their success criteria and key performance indicators, helping you align your project metrics with their expectations.

13

What's your approach to risk management and mitigation?

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Why this works

This question reveals their risk tolerance and management strategies, helping you understand how they handle potential problems and uncertainties.

14

How do you prefer to handle conflicts or disagreements?

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Why this works

This question reveals their approach to conflict resolution, helping you understand how to navigate disagreements and maintain positive relationships.

15

What's your vision for the long-term impact of this project?

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Why this works

This question reveals their strategic thinking and long-term goals, helping you understand their broader objectives and how this project fits into their larger plans.

16

How do you typically evaluate and provide feedback on projects?

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Why this works

This question reveals their feedback style and evaluation criteria, helping you understand how they assess progress and what they look for in project performance.

17

What's your approach to stakeholder engagement and communication?

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Why this works

This question reveals their communication philosophy and engagement strategies, helping you understand how they prefer to interact with other stakeholders.

18

How do you handle competing priorities and resource constraints?

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Why this works

This question reveals their approach to prioritization and resource management, helping you understand how they balance different demands and constraints.

19

What's your preferred approach to project governance and oversight?

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Why this works

This question reveals their governance preferences and oversight requirements, helping you understand their expectations for project management and control.

20

What questions do you have for us about our approach and capabilities?

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Why this works

This question invites them to share their concerns and questions, helping you understand their perspective and address any uncertainties they may have.

Best Practices for Stakeholder Engagement

Expert tips and techniques for getting the most out of these questions.

Best Practices

Listen Actively and Take Notes

Stakeholders often share valuable insights and requirements. Take detailed notes and ask follow-up questions to fully understand their needs and expectations.

Ask About Both Success and Challenges

Understanding both their goals and concerns provides a complete picture of their perspective and helps you address potential issues proactively.

Focus on Building Relationships

Stakeholder engagement is about building trust and relationships. Ask questions that show genuine interest in their success and well-being.

Question Sequences

The Goals Explorer

1
What are your primary goals and objectives for this project?
2
What would success look like for you personally?
3
What's your vision for the long-term impact of this project?
4
How do you measure success and what metrics matter most to you?

The Process Investigator

1
How do you prefer to receive updates and communication?
2
How do you typically make decisions about projects like this?
3
What's your preferred level of involvement in the project?
4
How do you prefer to handle conflicts or disagreements?

Common Pitfalls

Don't Focus Only on Project Details

While project specifics are important, also ask about their personal goals, concerns, and how they prefer to work. This builds stronger relationships.

Avoid Making Assumptions

Don't assume you know their needs or preferences. Ask specific questions to understand their unique perspective and requirements.

Don't Ignore Their Concerns

Always ask about their worries and challenges. Addressing concerns proactively builds trust and helps prevent problems later.

Question Templates

The Goals Explorer

1
Step 1: Start with: "What are your primary goals and objectives for this project?"
2
Step 2: Follow with: "What would success look like for you personally?"
3
Step 3: Explore with: "What's your vision for the long-term impact of this project?"
4
Step 4: Connect with: "How do you measure success and what metrics matter most to you?"

The Process Investigator

1
Step 1: Start with: "How do you prefer to receive updates and communication?"
2
Step 2: Follow with: "How do you typically make decisions about projects like this?"
3
Step 3: Explore with: "What's your preferred level of involvement in the project?"
4
Step 4: Connect with: "What questions do you have for us?"

Further Reading

The Art of Conversation by Catherine Blyth
How to Win Friends and Influence People by Dale Carnegie
The Charisma Myth by Olivia Fox Cabane

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