On paper, the jump from Investment Banking into Private Equity or a Family Office looks straightforward.

In reality, the first six months often feel very different from what people expect.

We speak to candidates every week who have already made the move — and a common theme comes up:
the biggest surprises are rarely about technical skill.

They tend to fall into three broad areas.

1. How your time is really spent

Many bankers expect to spend most of their time on new deals. In practice, the mix is often very different — with far more time going into asset management, portfolio reviews, refinancing, reporting, or working with operating partners than expected.

For some people, that’s a welcome shift. For others, it feels very different from the “deal-driven” image they had in mind.

2. Culture and decision-making

Moving from a large institution into a fund — or especially into a Family Office — can be a shock to the system.
Fewer layers, more direct accountability, and far less consensus-building means decisions move faster… but they also feel more personal.

What feels like freedom to one person can feel like ambiguity to another.

3. Execution vs. ownership

In PE and Family Offices, you don’t just run processes — you live with the outcomes.
Whether it’s a lease-up, a refinancing, a bolt-on acquisition or an exit, you feel the result far more directly than you ever did in banking.

That shift in ownership is energising for many — but it’s also a big adjustment.

We’re curious to hear from people who have actually made the move.

If you’ve gone from Investment Banking into PE or a Family Office, what surprised you most in your first six months?

???? Head to our LinkedIn page to vote in the poll and (if you’re comfortable) share your experience in the comments. www.linkedin.com/company/circle-square-talent 

The patterns that emerge from these conversations are often far more helpful to candidates than any job description.

Not every good investment career has to follow the same track.

We’re seeing a growing number of bankers and PE professionals taking a serious look at Family Offices — not because they’re disillusioned, but because their priorities are evolving.

What’s driving that interest?

???? Closer proximity to capital
Working directly with principals rather than committees means ideas move faster and relationships matter more.

???? A longer investment horizon
Many Family Offices invest with generational capital, allowing for more patient underwriting and less pressure to exit on someone else’s timetable.

???? A broader mandate
Alongside direct deals, many roles include co-investments, public markets, and sometimes operating or strategic projects that wouldn’t sit inside a typical fund.

That said, Family Offices aren’t a shortcut — they’re simply a different path.

The things that matter most in FO careers are often underestimated:

• Alignment with the principal — values, risk appetite, and how decisions get made
• Comfort with fewer layers — less structure, but more personal accountability
• A quieter profile — but often with greater influence on capital and strategy

At Circle Square, we spend a lot of time helping candidates compare PE, Family Office, and other alternatives — not from theory, but from live hiring mandates and real conversations with principals.

If you’re starting to think about what the next 5–10 years of your career should look like, we’re always happy to share what we’re seeing — off the record and without any pressure.

If you’re moving from banking to the buyside, your CV doesn’t need to be clever – it needs to be clear.

Five tweaks that make a real difference:

1️⃣ Lead with deal experience, not responsibilities.
List 3–5 key transactions with your role, size, sector and outcome.

2️⃣ Be explicit about what you owned.
Did you run a workstream, build the model, lead parts of DD? Say so in plain English.

3️⃣ Quantify where you can.
If you helped drive a process to signing in 8 weeks, or supported multiple live deals at once, make that tangible.

4️⃣ Cut the jargon.
Your reader knows the technical language – they just don’t want to work to decode it.

5️⃣ Keep it to two pages or less.
More pages rarely equal more impact.

We review hundreds of CVs a month across M&A, Private Equity, Family Office and Restructuring.

If you’d like an honest view on whether yours is doing you justice, we’re happy to help.

We often hear that compensation, title, and brand name are the top priorities when candidates start thinking about a career move.

But once we’re deep into a hiring process — having real, honest conversations — a different story often emerges.

So we’re asking:
If you had to pick just one factor that matters most to you, what would it be?

• ???? Compensation

• ???? Culture & People

• ???? Carry / Long-Term Upside

• ???? Career Progression & Learning

???? Vote now on our LinkedIn poll and let us know where you stand:
???? Click here to vote

We’d also love to hear the why behind your choice — especially if your priorities have changed over time. Drop your thoughts in the comments.