20 Questions

Questions to Ask New Hires After 30 Days

Strategic questions that help you understand their onboarding experience, identify areas for improvement, and ensure they're set up for success in their new role.

1

How has your first month compared to what you expected when you accepted the role?

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Why this works

Reveals if there's a gap between expectations and reality, helping you understand if the job description was accurate and if they're getting what they signed up for.

2

What's been the most challenging part of your onboarding so far?

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Why this works

Identifies specific pain points in your onboarding process that you can address to improve the experience for future hires.

3

Who has been most helpful in getting you up to speed, and what made them effective?

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Why this works

Identifies your best mentors and onboarding champions, helping you understand what makes someone effective at helping new hires.

4

What questions do you still have about your role or the company?

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Why this works

Reveals gaps in information sharing and helps you identify what additional resources or documentation might be needed.

5

How would you describe the company culture to someone who's never worked here?

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Why this works

Gives you insight into how your culture is being perceived and whether it's matching your intended culture.

6

What's been the most surprising thing about working here?

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Why this works

Reveals unexpected aspects of the job or company that could be positive surprises or areas needing attention.

7

How confident do you feel about your ability to succeed in this role?

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Why this works

Assesses their confidence level and identifies if they need additional support, training, or resources to be successful.

8

What would you change about the onboarding process if you could?

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Why this works

Provides specific feedback on how to improve the onboarding experience for future hires.

9

How well do you feel you understand the company's goals and how your role contributes to them?

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Why this works

Ensures they have a clear understanding of the bigger picture and their place in it, which is crucial for engagement and motivation.

10

What tools or resources do you wish you had access to that you don't currently have?

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Why this works

Identifies gaps in resources or tools that could be preventing them from being as effective as possible.

11

How would you rate your relationship with your manager so far?

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Why this works

Assesses the manager-employee relationship early on, allowing you to address any issues before they become problems.

12

What's been the most valuable part of your onboarding experience?

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Why this works

Identifies what's working well in your onboarding process so you can replicate it for future hires.

13

How well do you feel you've integrated with your team?

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Why this works

Assesses team integration and identifies if they're feeling connected to their colleagues and part of the team.

14

What would you tell a friend who was considering working here?

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Why this works

Gives you insight into their overall experience and how they're likely to talk about the company to others.

15

How clear are you on your performance expectations and how you'll be evaluated?

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Why this works

Ensures they understand what success looks like and how they'll be measured, which is crucial for their performance.

16

What's been the biggest learning curve so far?

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Why this works

Identifies areas where they might need additional training or support to be successful.

17

How would you describe the communication style here compared to your previous workplace?

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Why this works

Helps you understand if there are communication style mismatches that could affect their success.

18

What's one thing you wish you had known before starting here?

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Why this works

Reveals important information that should be shared earlier in the hiring or onboarding process.

19

How supported do you feel in your role right now?

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Why this works

Assesses their overall support level and identifies if they need additional help or resources.

20

What are you most excited about in your role going forward?

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Why this works

Identifies what's motivating them and what they're looking forward to, helping you understand their engagement level.

Best Practices for New Hire Check-ins

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

Best Practices

Create a Safe Space

Make sure new hires feel comfortable being honest about their experience. Assure them that feedback is welcome and won't be held against them.

Listen Actively

Pay attention to both what they say and what they don't say. Look for patterns and themes that could indicate broader issues.

Follow Up on Concerns

If they raise concerns, make sure to address them promptly. This shows you value their feedback and are committed to their success.

Document Feedback

Keep track of common themes and feedback to continuously improve your onboarding process for future hires.

Question Sequences

The Onboarding Assessment

1
How has your first month compared to what you expected?
2
What's been the most challenging part of your onboarding?
3
What would you change about the onboarding process?
4
What's been the most valuable part of your onboarding experience?

The Support Check

1
How confident do you feel about your ability to succeed in this role?
2
What tools or resources do you wish you had access to?
3
How supported do you feel in your role right now?
4
What would you tell a friend who was considering working here?

Common Pitfalls

Don't Make It an Interrogation

Keep the conversation casual and conversational. Don't fire off questions one after another - let the conversation flow naturally.

Avoid Defensive Responses

If they raise concerns, don't get defensive or make excuses. Listen with an open mind and focus on understanding their perspective.

Don't Ignore Feedback

If they provide feedback, make sure to act on it. Nothing kills trust faster than asking for feedback and then ignoring it.

Conversation Templates

The Supportive Check-in

1
Step 1: Start with: "How has your first month been overall?"
2
Step 2: Follow with: "What's been the most challenging part?"
3
Step 3: Deepen with: "How can we better support you?"
4
Step 4: Connect with: "We want you to succeed here, so let's work together on this."

The Improvement Focus

1
Step 1: Start with: "What's been working well for you?"
2
Step 2: Follow with: "What would you change if you could?"
3
Step 3: Deepen with: "How can we improve the experience for future hires?"
4
Step 4: Connect with: "Your feedback is really valuable for helping us improve."

Further Reading

"The First 90 Days" by Michael Watkins
"Onboarding: How to Get Your New Employees Up to Speed" by George Bradt
"The Manager's Guide to Onboarding" by Sharlyn Lauby

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