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Employee retention survey questionnaire: great questions for retention cohorts at every stage

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Adam Sabla

·

Sep 11, 2025

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Creating an employee retention survey questionnaire requires different approaches for different employee cohorts – what works for new hires won't work for veterans.

Asking the right questions at the right time reveals why people stay or leave.

This guide covers great questions for retention cohorts, including the first 90 days, 6–12 months, and long-tenure employees. Each group faces unique challenges and sees company culture from a distinct lens, so customizing your approach is key for actionable feedback.

First 90 days: onboarding experience and early impressions

In their first three months, new employees are deciding if they made the right move. This is when expectations meet reality, and small roadblocks can have a big impact. Given that 33% of new employees quit within their first six months, often due to poor onboarding and unmet expectations [3], careful listening is more than a formality—it’s preventive action.

  • How well does your actual role match what was described during the interview process?

  • What's been the biggest surprise about working here so far?

  • Do you feel you have the tools and resources needed to succeed in your role?

  • How comfortable do you feel asking questions or requesting help?

  • Have you received enough support from your manager or team during onboarding?

  • What, if anything, would have made your onboarding experience smoother?

AI-powered follow-ups can dig deeper when someone flags mismatched expectations or gaps in support. With Specific’s automatic AI follow-up questions, the survey isn’t static—it asks for clarity naturally.

If a new hire answers, “The role is different from what I expected,” the AI might follow up:


“Can you share which aspects of the role feel most different from what you expected?”

Tone matters: for new hires, every question should sound welcoming and genuinely supportive. That’s critical for trust-building early on—especially when onboarding can make or break long-term retention [3].

6–12 months: settling in and growth expectations

Between months six and twelve, employees are weighing whether they see a future in your organization. By this point, 38% of employees resign within their first year [9], often because development and feedback needs aren’t met. It’s the perfect time to check in on growth, recognition, and career clarity.

  • How satisfied are you with your professional development opportunities here?

  • Do you see a clear career path for yourself within the company?

  • How would you rate the feedback and coaching from your manager?

  • Have you been recognized for your contributions recently?

  • What obstacles, if any, are getting in the way of your job satisfaction?

  • Is there anything that would make you more likely to stay in the long term?

These aren’t just boxes to check. By turning surveys into conversational surveys, we surface development needs that might otherwise hide beneath the surface. When employees talk about unclear career paths, an adaptive AI can probe candidly:

“Could you describe what would make a future career path here more appealing or attainable for you?”

With more settled employees, the tone can shift from supportive to direct, focusing on growth opportunities. Specific’s AI survey response analysis identifies trends in feedback, like career path confusion, so you can act before dissatisfaction turns into turnover.

Sample prompt for analysis:


“Show me patterns in how employees 6–12 months in describe their career growth experiences and obstacles.”

This approach pays off: 94% of employees say they’d stay longer if employers invested in their careers [4]. In other words, targeted, actionable feedback here can pay retention dividends for years.

Long-tenure employees: engagement and future commitment

Employees who’ve been around for two years or longer know your organization inside and out. Their loyalty is hard-earned but should never be taken for granted. They offer a trove of institutional knowledge—and if disengaged, their departure is costly: Replacing an employee can cost up to 200% of their salary [6].

  • What keeps you motivated to stay with our company?

  • How has your job satisfaction changed over the past year?

  • What would make you consider leaving?

  • Is there anything the company could do to improve your long-term engagement?

  • How do you share your experience or mentor newer team members?

  • What changes would make you recommend us as a great place to work?

For veterans, I adopt a peer-to-peer tone—respectful, candid, and focused on long-term impact. The right questions challenge assumptions and unlock nuanced insight that generic forms miss. See how the approach differs:

New hire questions

Veteran questions

“What could have improved your first week here?”

“How do you help new employees adjust? What onboarding advice do you share?”

“Are you finding the support you need?”

“What resources or changes would make your long-term work more fulfilling?”

Specific’s AI-powered survey editor lets teams easily adjust question tone and topics by tenure group—whether you want the AI to ask about legacy handoff, mentorship, or uncover “flight risks.” When a veteran flags knowledge gaps, AI follow-ups might probe for detail on succession planning or mentorship:

“You mentioned mentoring newer team members. What support would help make this process more effective?”

This approach transforms the classic check-in into a true conversation—one that values veteran expertise while surfacing retention risks in time to act. It’s worth noting that only 28% of organizations conduct stay interviews to get these insights at all [5].

Automated cohort targeting and adaptive conversations

With conversational AI, we don’t have to ask everyone the same questions. Modern survey tools like Specific deliver automated cohort targeting, triggering surveys as employees hit tenure milestones—first week, 90th day, annual mark, and so on.

The conversational tone adapts by cohort:

  • New hires: warm, supportive, simplifying the process

  • 6–12 months: collaborative, candid, focused on development

  • Veterans: peer-level, respectful, surfacing strategic advice

Here’s how the same question can shift based on tenure:

  • New hire: “How are you finding the team dynamics so far?”

  • Veteran: “How have team dynamics evolved during your time here?”

Follow-ups reflect this too: new hires get gentle encouragement (“Anything else that could have helped in your first month?”), while long-tenure employees get nuanced dives (“What has kept your team culture strong during tough changes?”).

Specific’s in-product conversational surveys automate targeting, so every employee gets a tailored, relevant experience—and so you get honest, useful insight without survey fatigue. The result? A true two-way conversation, not just another form.

Build retention surveys that adapt to every employee journey

Understanding employee retention means following the whole journey—from onboarding jitters through years of expertise and even moments of doubt.

With Specific, you get a modern, conversational survey experience designed around adaptive questions, smart AI follow-ups, and effortless feedback for every employee. Capture real, honest insights from each cohort—without the hassle of creating new surveys every time your team grows or changes.

Create your own employee retention survey questionnaire instantly—tailored for every stage in your employees’ journey.

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Sources

  1. Paycor. HR Statistics You Need To Know.

  2. Paycor. Employee Retention Statistics.

  3. TestGorilla. Employee Retention Statistics: The Ultimate List (2024).

  4. Zippia. 19+ Employee Loyalty Statistics [2024]: Facts On Loyalty At Work.

  5. People Element. 6 Employee Retention & Stay Interview Statistics.

  6. Flair HR. 200+ HR Statistics (2024).

Adam Sabla - Image Avatar

Adam Sabla

Adam Sabla is an entrepreneur with experience building startups that serve over 1M customers, including Disney, Netflix, and BBC, with a strong passion for automation.

Adam Sabla

Adam Sabla is an entrepreneur with experience building startups that serve over 1M customers, including Disney, Netflix, and BBC, with a strong passion for automation.

Adam Sabla

Adam Sabla is an entrepreneur with experience building startups that serve over 1M customers, including Disney, Netflix, and BBC, with a strong passion for automation.