Knowing what to leave out is a skill.

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Honest reflections. Practical frameworks. Lessons learned the hard way, written by someone who's been in the trenches and is still learning.

Whether you're learning to deliver under pressure or protect your energy during busy seasons, this newsletter is here to help you play the long game.

This week…

Why people fall into the trap of overexplaining, and the simple habit I’ve built to avoid it.

Let's get to it!

Aaron

Over the summer I interviewed a candidate to teach for us at Wall Street Prep.

The interview format is simple. We give the candidate a prompt, 20 minutes, and a fake student. I play the student. I pretend to know nothing about real estate, I ask the questions a real student would ask, and I watch how they manage the situation.

This candidate knew the real estate content cold. Years in the industry, sharp, clear communicator, handled every question I threw at him. He decided to build a model from scratch, live, and take me through it line by line (remember, we’ve only got 20 minutes).

He ran over. Not by a lot (OK, it was a lot), and I let him. When we debriefed afterward, the feedback I had for him had nothing to do with what he knew.

The hardest part of teaching for 20 minutes is deciding what to leave out.

It’s also the hardest part of presenting at investment committee, pitching a new client, or leading an internal project launch…

I hear a version of this from people new to presenting in many different contexts: a weekly update, a client call, an interview answer. The instinct is to prove you did the work by showing all of it.

Almost nobody wants you to cover everything, though. They intentionally gave you 20 minutes, or one page, or a thirty-second answer. The constraint is the assignment. Covering everything is an easy way to fail it.

When I gave the candidate his feedback, I told him what I tell a lot of people: we tend to go more complicated than we need to, or than we have time for. He agreed. He said he'd gone back and forth on whether to keep it simple, then decided to throw his student, me, into the deep end.

I understood the choice. I've made it. Complexity feels like proof you did the work. If you show the whole model, nobody can say you don't understand it.

The problem is the audience. They'll walk out with one to three things, no matter how much you put in front of them. If you don't decide which three, they will, and you probably won't like what they pick.

Once something is on the slide, in the memo, or in your notes, it's very hard to skip in the moment. You put it there, so it feels like it matters. And when the clock is running, you speed up to get through it instead of dropping it.

I've presented detailed investment theses with plenty of rigorous math underpinning them just to watch my audience get lost by page 12 (why were there 12 pages to begin with?). The numbers were all there. The story wasn't. Numbers for the sake of numbers don't convince anyone, and neither does thoroughness for the sake of thoroughness.

So, plan what you’re going to leave out before you get to the presentation, not during. Every extra item you carry in with you is a small decision you'll have to make live, under pressure, in front of people. Make those decisions while you’re preparing, when it’s easy and you can still change your mind.

At Wall Street Prep, we tailor our materials to our clients, but they always rhyme because math is still math no matter the audience. Interns seeing a cash flow model for the first time see similar files as associates who've been building them for years. The biggest change is how we teach it. We read who's in front of us and adjust live: bringing people in, meeting them where they are, slowing down or skipping ahead based on what the group is grasping.

That's the second half of leaving things out. You decide what matters before you start, and then you keep deciding once you're in there.

I've had to learn to walk out of a meeting having said less than I prepared. It felt like a loss for a long time. It isn't. Everything I cut goes in a back pocket. If someone asks, I have it. If nobody asks, it was never needed.

Before you build anything, write down the one to three things your audience must leave with. Craft your message around hammering those points home.

And before you finalize your materials, cut the extra page. Anything you'd drop if time ran short comes out now. Keep it in a back pocket for questions. The appendix is your friend.

Once you're presenting, watch. If they're ahead of you, skip. If they're behind, slow down.

As long as your audience leaves with three things, and they're the right three, you did the job.

One of my favorite parts of writing this newsletter is hearing how these ideas show up in real life.

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