The CRE Fit Check Dilemma

You’ve got the meeting confirmed. The potential client is a growing startup that leases an entire floor in the nicest office tower downtown. Word on the street is, they’re expanding. You made the cold call, landed the meeting, and tomorrow’s the big day.

Your broker tells you, “Wear your best suit. Don’t forget to shine your shoes.”
And in your head, you’re like... do I really need to go full Don Draper for this?

You know that’s just the status quo. Your broker is a bit of a blast from the past. And now you’re wondering if showing up like the feds might spook the startup crew. You’d be the only person on the floor in a suit. Everyone else is in hoodies and Allbirds.

It sounds minor, but it’s not. The idea of what’s “normal” in CRE has changed.
And the dress code? It’s officially up for debate.

There Used to Be No Question

Not long ago, there wasn’t even a discussion. If you worked in brokerage, especially in major markets or with institutional clients, the rules were simple:

• Dress shirt, slacks, dress shoes, every day

• Suit and tie or blazer for meetings

• Polo shirts and jeans on Fridays (if you were feeling wild)

The people you were pitching were old school. They expected a broker to look like a broker, and a suit was what you wore when you were doing business.

Then the world went remote.

The Shift Was Already Happening

Yes, 2020 was a catalyst. But let’s not pretend this all started with the work from home revolution.

Years before that, the leadership teams brokers were meeting with had already begun to change. Instead of baby boomers who spent their careers in suits, we started meeting with execs in their 30s. Some were younger than us. Many of them had never worked in a traditional office. They came up in tech. They built their companies in coffee shops and their parent’s garage.

Wearing a full suit to pitch them didn’t make you look professional. It made you look out of touch.

This shift happened on the ownership side too. Smaller investors, mom-and-pop landlords, and sub-institutional players started being more active. They didn’t care what brand was on your business card. They cared if you were sharp, responsive, and got the job done.

And that’s when the old rules started to break.

But It’s Not One Size Fits All

There are still plenty of situations where dressing up matters. If you’re pitching an Institutional investor or a Fortune 500 corporate account, showing up in a hoodie probably won’t cut it. These companies have boards. They answer to investors. The optics still matter.

That might not always be the case, but for now, it’s still real.

So…what are you supposed to do?

Still Confused? Yeah, Me Too

There’s no universal dress code anymore.

Overdressing is still safe. Nobody’s ever lost a deal for looking too sharp.

But in a relationship driven business, authenticity matters, and how you dress can absolutely impact how confident, relaxed, and relatable you feel in a meeting.

If putting on a suit makes you feel like you’re at a funeral, that’s going to show.

And if your competitor walks into the same room in a sharp but casual outfit that fits their vibe, and the client connects with that? You might lose a deal, not because of your pitch, but because you came off stiff or unrelatable to their brand and culture.

Know Your Audience, Know Yourself

My advice to everyone, especially younger brokers: define your ideal client.

• Is it tech startups and ecommerce brands?

• Is it legacy family offices and institutional landlords?

• Is it mom and pop owners looking to sell the business and keep the real estate?

Your style should match their world, but not to the point of faking, but aligned in your own way.

Here’s a quick story:

I was about a year into the business after jumping in straight out of college. We had just landed a statewide tenant rep assignment with a regional restaurant group. They’d been acquired by private equity. The team was flying in on a private jet. I figured, "Big money. Time to suit up."

We pulled up to the FBO in full suits and ties.

Out walks the team... in Tommy Bahama shirts and shorts. One of the original founders shook our hands and said:

That moment changed how I thought about if dressing like I worked at a big bank really mattered as much as it may have in the past.

Authenticity Is Your Superpower

In an industry obsessed with credibility, authenticity is your edge.

• Authenticity builds trust

• Trust builds rapport

• Rapport gets you deals

Clients want to work with someone they actually like. Someone who feels like a real person, not a mannequin with coffee breath.

Let’s be clear…this doesn’t mean show up in sweatpants, or blast trap music from your iPhone during a tour. (Unless that’s actually your brand. Then...carry on.)

It’s not about rebellion. It’s about alignment.

Dress sharp. Speak clearly. Be professional. But don’t erase yourself in the process.

If you’re funny, be funny.
If you nerd out on the in-depth history of every building in your market, lean into it.
If you rock vintage watches and hate fleece vests, own it.

The clients who get you will remember you, especially if you know your sh*t.

Merch Store Update!

I was hoping to have the site launched this week, but I’m still waiting for the final sample of the finished hoodie. I debated just going ahead and launching, but I fundamentally refuse to sell something that I haven’t already put my hands on the verify the quality any of my followers should expect when spending their hard-earned commissions on it. I’m hoping to have the sample in the next few days and will most likely go live next week if so.

Here’s a link to the landing page if you want to drop your email there, but don’t feel obligated to as I’m planning to send out an update email through the newsletter the moment it launches.

That’s all for now! I appreciate everyone who’s been part of this community across all the different social media platforms. My goal with this newsletter is to dive deeper into various aspects of the CRE industry, with a focus on the brokerage side. I aim to bring the same levity and reality to these insights as I’ve done with the memes.

If you have any input, feedback, or questions, feel free to reach out. The DMs, emails, and real-life connections have been some of the coolest experiences along this journey.

-CapRateCraig