First PE Meetings: Do’s, Don’ts & War Stories

It’s not Dragon’s Den. It’s not a bank meeting. It’s a two-way conversation between people who could, if all goes well, be working together for years.

And while every meeting is different, the same themes, and the same mistakes, pop up again and again.

So, we asked the YFM team to share their “war stories” the memorable, awkward, and occasionally brilliant moments from first PE meetings that have stuck with them. Here’s what they said are the do’s and don’ts.

“DO make the session as interactive as possible. Ask ahead of time for a list of topics or questions to cover, it makes the whole thing flow better.”

The founders who come in curious, not rehearsed, always stand out. It’s not about dazzling investors; it’s about connecting with them.

We’ve all had a meeting go sideways. One investor recalled the time a founder’s presentation clicker died three slides in — cue panic, sweating, and frantic laptop swapping. Eventually, the founder laughed, shut the laptop, and said: “You know what? Let’s just talk.”
It turned into one of the best first meetings we’ve had. Sometimes, the unplanned moments show more authenticity than any amount of prep.

Confidence is good, but reading through a 40-slide presentation word-for-word is a sure-fire way to drain the room.

One investor compared it to a bad first date: “They spent 45 minutes talking about themselves without asking a single question. Great deck. Zero chemistry.”

First meetings are supposed to start with friendly chit-chat, something light, something safe. In this case, the investor picked a topic the founder was famously into and thought he’d nailed the perfect icebreaker. But the harmless opener somehow morphed into a low-key competition neither side meant to start. Within minutes, the vibe had gone from “nice to meet you” to “this is weirdly tense for a Tuesday.”

No shouting, no drama, just that unmistakable sinking feeling when a conversation slips out of your hands and into the abyss. The meeting wrapped up early, everyone stayed polite, and absolutely no one suggested a follow-up.

It was a reminder that even well-intentioned rapport-building can veer off-course if you misread the moment. Early meetings are as much about chemistry as numbers, and once the mood turns, it’s hard to steer things back.

The best meetings are team efforts. Everyone contributes; nobody dominates. “Trust your team to present, it’s always awkward when someone in the room doesn’t join in.”

It signals confidence and culture, two things’ investors care about as much as numbers.

A clever way to break the ice? Ask the PE firm to present first. It gives you a breather, sets the tone, and helps you see what matters to them before diving into your own story.

“It’s a small thing that changes the energy in the room. It stops feeling like you’re being grilled.”

After one meeting, a CEO offered a lift to the train station only for the investor to find themselves squeezing into a car between kids’ car seats surrounded by crisp crumbs and toys.

Both ended up laughing about it, and the conversation that followed on the short drive turned out to be the most valuable part of the day.

Lesson learned: moments like that show everyone’s human. You don’t need polish; you need connection.

“A lift to the station after a meeting always goes a long way, it’s a great chance for a one-on-one chat, away from the meeting room.”

• Trying too hard to be “corporate.” We just want to get to know you and hear about your business.
• Focusing on the deck, not the discussion.
• Letting nerves take over.
• Forgetting the small human touches that build trust.

If there’s one line that separates the prepared from the not, it’s:

“What would partnership success look like for you?”

It shifts the tone instantly, from selling to collaborating.

• Know your “why” what are you looking for from an investor?
• Decide who’ll cover which areas in the meeting.
• Read up on the firm’s portfolio where do you fit?
• Prepare a couple of thoughtful questions.
• Have one story ready that shows resilience or change.
• And yes, check your clicker works.

The best first meetings feel effortless because they are. They’re honest, conversational, and a bit human.

Bring curiosity, a story or two, and a sense of humour, that’s the stuff partnerships are built on.

At YFM Equity Partners, we’re committed to supporting ambitious entrepreneurs as they scale and grow. For more entrepreneur news, take a look at our other articles and videos, and subscribe to our newsletter. Watch The Entrepreneur Experience Video Series for more insights and advice from leading UK entrepreneurs and thought leaders in the business ecosystem.