Many candidates go into interviews focused on the obvious areas:

1️⃣ Deal flow
2️⃣ Team structure
3️⃣ Compensation

All important topics — and rightly so.

But far fewer candidates ask about something equally, if not more, revealing:
how deals have gone wrong.

It might feel like an uncomfortable question, but it’s often the most insightful one you can ask.

Understanding:
1️⃣ What went wrong in previous investments
2️⃣ How the team responded in difficult situations
3️⃣ What they learned and how it shaped their approach

…can give you a far deeper view of a fund than a discussion around its successes.

Anyone can talk confidently about wins.

But the best teams are defined by how they handle setbacks — how they analyse mistakes, adapt, and improve their decision-making over time.

For candidates, this isn’t just about curiosity — it’s about understanding the culture, transparency, and intellectual honesty of the team you’re joining.

At Circle Square, we work closely with candidates to help them ask the right questions and truly understand the opportunities in front of them.

If you’re exploring your next move or want a clearer perspective on the market, we’d be delighted to have an informal conversation.