“What Should I Be Asking?” – 5 Strategic Questions for HR to Ask Leadership in 2026

You don’t need to have all the answers to be strategic in HR — but you do need to ask the right questions.

If you're looking to gain more influence, align with the business, or elevate your HR role in 2026, try starting with these five powerful questions.  Ask your CEO, or your manager if you don’t have access to the top.  Each one opens the door to deeper collaboration, better communication, and smarter HR planning.

Here’s how to use them — and what to do with the answers.

Q: What are the top 3 priorities for the business this year?

This question sets the foundation for everything else. When you understand where leadership is focused — whether it’s growth, retention, innovation, or something else — you can make sure HR is helping drive that vision. It also positions you as a business partner, not just an internal support team.

➡️ Tip: After the conversation, pick one of your current HR goals and align it directly with one of the business priorities they shared.

Q: Where do you see the biggest people-related risks right now?

You may be worried about compliance or turnover, while your CEO is more concerned about a manager who’s derailing their team. Asking this question helps you get ahead of issues before they blow up — and lets you be proactive, not reactive.

➡️ Tip: Use the answers to start an internal mini risk review — even if it’s just a spreadsheet with three things to keep an eye on.

Q: What would make you feel more confident in HR this year?

It’s a bold question, but it shows maturity. You’re opening the door to feedback and showing you care about delivering value. Whether the answer is more frequent updates, a better system, or stronger communication, you’ll know how to respond.

➡️ Tip: Don’t defend — listen. Then follow up with one action step you’ll take based on what they told you.

Q: Where are we underinvesting in people?

This isn’t just about budgets — it’s about asking where your people feel overlooked. It might be training, onboarding, middle management, or wellness. Leadership doesn’t always have the answers, but starting this conversation often leads to fresh insight.

➡️ Tip: Suggest one pilot program (low-cost or even free) that could address the gap — and track its impact.

Q: How can I help you be a better leader this year?

Yes, it’s a bold move — but it signals that HR is here to support leadership, not just manage people issues. When you offer to help your leaders succeed, you open a powerful door to long-term influence.

➡️ Tip: Offer quarterly check-ins with your leadership team focused on team dynamics, communication, and growth strategies.

These aren’t one-time questions — they’re relationship builders.

Use them in your next leadership meeting, strategy session, or casual coffee chat. The more you ask, the more you learn — and the more strategic your HR voice becomes.