20 Questions

Questions to Ask When Transitioning into a New Role

Strategic questions to help you navigate role transitions, understand expectations, and ensure a smooth transition into your new position.

1

What are the key expectations for this role in the first 30, 60, and 90 days?

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Why this works

Provides clear milestones and helps you understand what success looks like at different stages of your transition.

2

Who are the key stakeholders I need to build relationships with?

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Why this works

Reveals important relationships and helps you understand who you need to connect with to succeed in your new role.

3

What are the biggest challenges facing this role and how can I prepare for them?

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Why this works

Shows potential obstacles and helps you understand what challenges you might face and how to address them proactively.

4

What resources and support will be available to help me succeed?

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Why this works

Reveals available support and helps you understand what tools, training, and assistance you'll have access to.

5

What's the team culture and how do people typically work together?

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Why this works

Shows team dynamics and helps you understand the work environment and how to integrate effectively with your new team.

6

What are the communication preferences and expectations?

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Why this works

Reveals communication norms and helps you understand how to communicate effectively with your new team and stakeholders.

7

What are the performance metrics and how will my success be measured?

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Why this works

Shows evaluation criteria and helps you understand how your performance will be assessed and what metrics matter most.

8

What are the development opportunities and growth paths?

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Why this works

Reveals career development options and helps you understand potential growth opportunities and advancement paths.

9

What are the current priorities and what should I focus on first?

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Why this works

Shows immediate priorities and helps you understand what to tackle first and how to prioritize your initial work.

10

What are the tools, systems, and processes I need to learn?

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Why this works

Reveals technical requirements and helps you understand what systems and processes you need to master to be effective.

11

What are the decision-making processes and who has authority over what?

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Why this works

Shows organizational structure and helps you understand how decisions are made and who has authority over different areas.

12

What are the team's current challenges and how can I help address them?

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Why this works

Reveals team needs and helps you understand how you can contribute value and support your new team's success.

13

What are the best practices and lessons learned from previous people in this role?

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Why this works

Shows historical insights and helps you understand what worked well for others and what you can learn from their experiences.

14

What are the team's goals and how does this role contribute to them?

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Why this works

Reveals team objectives and helps you understand how your role fits into the bigger picture and team goals.

15

What are the feedback mechanisms and how often will I receive feedback?

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Why this works

Shows feedback processes and helps you understand how you'll receive guidance and feedback on your performance.

16

What are the team's strengths and areas for improvement?

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Why this works

Reveals team dynamics and helps you understand the team's capabilities and where you might be able to contribute most.

17

What are the team's communication channels and how do people stay connected?

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Why this works

Shows communication infrastructure and helps you understand how to stay connected and communicate with your new team.

18

What are the team's values and what's important to them?

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Why this works

Reveals team values and helps you understand what matters most to your new team and how to align with their values.

19

What are the team's current projects and how can I get involved?

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Why this works

Shows current work and helps you understand what projects are underway and how you can contribute to them.

20

What are the team's expectations for collaboration and teamwork?

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Why this works

Reveals collaboration norms and helps you understand how to work effectively with your new team and contribute to team success.

Best Practices for Role Transitions

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

Best Practices

Focus on Understanding First

Ask questions that help you understand the role, team, and expectations before jumping into work. Take time to learn before acting.

Build Relationships Early

Ask about key stakeholders and team dynamics to understand who you need to connect with and how to build effective relationships.

Clarify Expectations and Success Metrics

Ask about performance expectations and success metrics to ensure you understand what success looks like and how you'll be evaluated.

Question Sequences

The Expectations Sequence

1
What are the key expectations for this role in the first 30, 60, and 90 days?
2
What are the performance metrics and how will my success be measured?
3
What are the current priorities and what should I focus on first?
4
What are the team's goals and how does this role contribute to them?

The Team Integration Sequence

1
Who are the key stakeholders I need to build relationships with?
2
What's the team culture and how do people typically work together?
3
What are the team's values and what's important to them?
4
What are the team's expectations for collaboration and teamwork?

Common Pitfalls

Don't Assume You Know Everything

Even if you have experience in similar roles, each team and organization is different. Ask questions to understand the specific context.

Don't Rush Into Action

Take time to understand the role, team, and expectations before jumping into work. Rushing can lead to mistakes and misalignment.

Don't Ignore Team Dynamics

Pay attention to team culture, values, and communication styles. Understanding team dynamics is crucial for successful integration.

Conversation Templates

The Expectations Template

1
Step 1: Start with: "What are the key expectations for this role in the first 30, 60, and 90 days?"
2
Step 2: Follow with: "What are the performance metrics and how will my success be measured?"
3
Step 3: Deepen with: "What are the current priorities and what should I focus on first?"
4
Step 4: Connect with: "What are the team's goals and how does this role contribute to them?"

The Team Integration Template

1
Step 1: Begin with: "Who are the key stakeholders I need to build relationships with?"
2
Step 2: Explore with: "What's the team culture and how do people typically work together?"
3
Step 3: Understand with: "What are the team's values and what's important to them?"
4
Step 4: Learn with: "What are the team's expectations for collaboration and teamwork?"

Further Reading

"The First 90 Days" by Michael Watkins
"Onboarding New Employees" by various authors
"Team Integration Guide" by organizational development resources
"Role Transition Best Practices" by HR organizations

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