Stay Interviews For Senior Finance: The Questions

Last week we talked about the reasons for high turnover in senior finance roles, and why it needs to be addressed by organizations of all types. If you missed last week's article, find it here: https://www.verriez.com/post/retaining-senior-finance-executives-guide-for-2026-part-1

One of the best ways to keep your best senior finance folks is with retention interviews. Let's look at some of the questions you should be asking, and why.

1. What aspects of your role inspire and engage you most?	Shows where their energy is focused. In high-stress environments, finance leaders typically highlight strategic work (FP&A, transformation) over routine compliance tasks. Helps you direct challenging assignments to areas where they'll thrive.
2. How has your role evolved in the past 12 months, and do you feel equipped to handle that evolution?	Reveals whether expanded demands: board expectations, investor relations, strategic finance, are supported or overwhelming. Identifies where they need help.
3. Can you describe a recent achievement or project that was particularly meaningful to you?	Different finance leaders value different wins. Understanding what feels important to this person clarifies what motivates them.
4. Where do you see your career heading over the next 2–3 years, and how does that align with growth opportunities here?	Vague answers signal weak succession planning. Finance leaders want concrete paths: controller roles, CFO advancement, FP&A expansion, or movement into COO or CEO positions.
5. What skills or expertise would you like to develop further, and how can we support that?	Finance professionals expect employer-funded training in automation, analytics, and data science. Without it, they'll leave for competitors who offer it.
6. How effective is communication and collaboration within your team and across the organization? What's working, and what could improve?	Team dynamics and organizational silos drive both engagement and burnout.
7. What additional resources, tools, or headcount would allow your team to operate more effectively and reduce unnecessary workload?	Identifies real operational bottlenecks. Finance leaders buried in manual processes or automation requests denied are actively job-searching.
8. How well does our organization support your overall well-being: work-life balance, flexibility, mental health support?	Many C-suite executives seriously consider leaving for better well-being support. This gives leaders permission to name burnout directly.
9. Are there any situations or pressures in your role that have made you consider leaving, even briefly?	Softer than asking directly "are you thinking of leaving?" but still reveals specific stressors: board dynamics, CEO misalignment, unrealistic timelines. Patterns signal systemic issues.
10. How clear is your understanding of where our organization is headed strategically, and how does the finance function fit into that narrative?	Finance leaders disengage when they're excluded from strategy. If they can't explain how finance connects to company direction, they lack engagement and will seek roles where they do. Also reveals whether the CEO includes them in strategic decisions.
11. What would meaningful recognition of your contributions look like to you?	Recognition needs vary widely: public acknowledgment, board visibility, equity, titles, or scope expansion. Understanding their preference is critical for retention.
12. How are you managing the pace of technology, and what support would help you feel confident leading your team through these changes?	Finance is disrupted faster than most functions. Leaders who feel unprepared for automation will leave. This invites them to voice anxiety without shame.
13. What would it take for you to commit to staying with us for the next 3 years, and what might push you to explore other opportunities?	Moves from diagnosis to action. Asks for both incentives and deal-breakers so you can address them concretely: promotion timeline, compensation, role redesign, or specific projects.

Remember, simply asking these questions won't retain talent. How you conduct the interview matters as much as what you ask. Next week we'll look at best practices for retention interviews. In the meantime, if you need help with your talent strategy or just want to talk about the market, feel free to reach out! Email Paul, Brent, Troy, or Tara, or give us a call at 519-673-3463.