The Five Questions to Ask Your Next Senior Hire

When interviewing senior leaders, the quality of your questions matters. A CV tells you where someone has worked. The right questions show you how they think, how they lead, and whether they can shape the future of your organisation.

Over time, I have developed a set of questions that I ask consistently. They combine technical, behavioural and strategic angles, and they quickly reveal the mindset of a candidate. Here are five of my favourites.

1. What did you walk into when you started in your current role, and what will you leave behind?

This is often my first question in an interview. It is deceptively simple but incredibly powerful. It gives you an overview of what someone inherited when they arrived, and what they have contributed since.

It also reveals where they place importance. If someone talks about walking into a demotivated team and leaving behind a resilient, high-performing one, that tells you they care deeply about people and leadership. If they talk about compliance going from poor to excellent, that tells its own story too.

In short, this question helps you understand contribution and impact, without needing to trawl line by line through a CV.

2. Tell me about a time you failed. What did it teach you, and what would you do differently next time?

This is a more honest and revealing version of the old “what’s your biggest weakness?” Leaders with long careers will have made mistakes. What matters is whether they are self-aware, and whether they learned from them.

When someone can speak openly about failure and show how it shaped their approach, that is a mark of maturity. When someone struggles to identify a failure, blames others, or cannot show what they learned, that tells you just as much.

3. How have you motivated your team through challenging times?

In housing and public services, challenges are constant. Progress is often incremental, and resources are stretched. The best leaders know how to motivate people even when times are tough.

There is no single right answer. Some focus on practical measures such as job design, hours or pay. Others emphasise morale, culture and pastoral care. What matters is understanding how a leader thinks about motivation, and whether it aligns with what your team needs most.

4. How do you identify, build and manage key stakeholder relationships?

Strong leadership today means working across boundaries. No one can succeed by operating only internally.

This question goes deeper than “how do you manage stakeholders?” It asks how someone identifies who really matters, how they build those relationships, and how they sustain them over time. I look for candidates who can distinguish between the obvious and the overlooked (the senior executive and the grassroots influencer) and explain why both matter.

5. Tell me about a time you challenged the status quo. What was the outcome?

Every organisation has processes that exist simply because “that’s the way we’ve always done it.” Great leaders are the ones who ask why.

I use this question to see how someone identifies when change is needed, how they approach challenging the norm, and how they manage the outcome. The answer often reveals creativity, courage and innovation – all qualities in demand when we are asked to do more with less.

Final thought

These questions are not an exhaustive list, but they are revealing. They uncover more than competence; they uncover mindset. They show whether a leader has self-awareness, resilience, empathy and strategic thinking – qualities that are just as important as technical ability.

When appointing your next senior leader, these are the conversations that help you move beyond the CV and discover who will truly take your organisation forward.