5 essential questions you should ask your new employee (and why they matter)

So, you’ve got a new team member.

They’re probably equal parts stoked and scared.

And you’re probably keen to see them fly, not flop.

This early phase is super important when it comes to helping your new teammate to succeed. But just as critical as telling them what to do are the questions you ask them. Arguably, these are even more important.

Whether you’re new to management or a seasoned CEO, these five questions will ensure that they are on the right path and set you both up for a trusting, productive relationship.

1. "How do you like to receive feedback?"

Feedback is just what the doctor ordered when it comes to growth, but it needs to be delivered in a way that resonates with the person who’s receiving it. Ask your new hire how they prefer to receive feedback. Do they like immediate, in-the-moment pointers delivered straight up and to the point, with no sugar coating? Or would they prefer you to go a bit more gentle or schedule reviews where they can reflect first? Check in with them on what you should avoid and what you could bear in mind when it comes to giving them feedback. This shows you respect their working style. Equally important, let them know you’ll be asking for their feedback too. This shows you want to know what they think, it models the importance and value of feedback, and it’s more likely to build that culture of mutual trust and continuous improvement that you’re aiming for.

2. "What does success look like for you in one month, three months, and six months?"

Setting expectations early is the way to go if you want performance. This question helps you both to align on their goals and provides insight into both how they measure progress and what motivates them. Do they focus on mastering specific skills, delivering results, or building relationships? It also gives you a chance to check you’re on the same page when it comes to progress and allows you to shift the goalposts slightly if necessary. By talking through these milestones, you’ll both have a clear roadmap of what success looks like, which reduces ambiguity and helps with accountability.

3. "Where do you feel more confident and less confident in your role?"

Everyone comes into a new role with strengths and areas where they feel a bit out of their depth. Asking this question allows your new team member to be vulnerable and honest about where they may need extra support. Equally, it lets you know where they’re raring to go and can shine. Follow this question up with: “What would support look like from me in those areas?” and let them know what you can commit to or offer (then follow through!) so they know you’re actively invested in their success also.

4. "What frustrates you at work, and conversely, what lights you up?"

Knowing what drains and energises your new hire is another gem of a question. Is it too many meetings? Not enough clarity? On the flip side, knowing what excites them can help you tailor their tasks in ways that harness their enthusiasm. By understanding their motivations, you can better tap into their potential and create the environment where they’ll thrive.

5. Co-create the one-on-one agenda.

This isn’t officially a question but it’s a conversation starter for those early days. One-on-ones are where the real relationship-building happens. Rather than dictating the format, treat these meetings as a collaborative process. Together, decide what should be on the agenda—whether it’s ongoing projects, personal development, or roadblocks. This is an opportunity to ensure the conversation is relevant, helpful, and meets their needs as much as yours. Extra tip: one of the biggest mistakes leaders make when it comes to one-on-ones is to make them all about progress on tasks only. Too often, these meetings are purely WIPs that run along the lines of “where we’re at with things?”  Make sure you include “how are we going?” questions too, such as those I outline in this blog.

By asking these thoughtful questions and co-creating a structure for ongoing communication, you’re setting the stage for trust, open dialogue, and a productive partnership.

Leadership is about unlocking the potential in others. These conversations will help you make that happen.