Speak Truth to Power: Fearless Assertiveness in Commercial Real Estate

Welcome back to Iconic Journey in CRE’s Ethical Leadership series.

A confident professional addresses her colleagues, effectively articulating her perspectives during a pivotal meeting.

If you’re trying to build influence in commercial real estate, let’s be honest—competence alone won’t get you there. It’s necessary, but it’s not enough. To stand out, you also need fearless assertiveness: the confidence to speak up, the clarity to challenge what’s not working, and the integrity to do both in a way that builds trust rather than erodes it.

This isn’t just theory. It’s a theme we hear over and over again on the Icons of DC Area Real Estate podcast—through the stories, the advice, and the lessons shared by industry leaders who have walked the walk.

Integrity Is the Ground You Stand On

In real estate, where the stakes are high and the networks run deep, reputation moves faster than any transaction. As Gary Rappaport plainly put it:

“Reputation is more important than anything else in this business.”

And they’re right. If people don’t trust you, they won’t do business with you. Full stop.

That’s why fearless assertiveness starts with integrity. It’s not about being loud. It’s about being honest. Transparent. Clear about your intentions—even when it’s uncomfortable.

Ron Gart reminds us that being a professional means bringing “expertise and the ability to provide input at senior levels.”But that ability to contribute only matters if people trust the person behind the insight.

The most respected leaders act with consistency, fairness, and ethics. That’s what gives their voice weight.

Speak Up—But Do the Work First

Assertiveness means more than confidence. It means contribution. And contribution means effort—often above and beyond your job description.

One consistent message from our guests is to take initiative and offer real value.

As John Green put it: “Be proactive about your opinion.” Your insights matter, but they won’t if you keep them to yourself.

Whether it’s staying late to rethink a pitch or digging deeper into a problem before offering a solution, thought leadership is earned—not assigned.

Sean Caldwell said it well:

“Be curious… ask better questions.”

And Herman Bulls added:

“Get feedback on the quality of your thinking.”

Smart questions signal that you're thinking strategically. Good listening makes you better at identifying solutions. And yes—when it’s your turn to speak, your words will land with more impact because they’re grounded in understanding, not just opinion.

Gwen Wright’s advice to her younger self?

“Say less and listen more.”That’s not about being passive. It’s about being intentional.

Act. Even When It’s Not Perfect.

If there’s one through-line from every icon we’ve interviewed, it’s this: You can’t wait for perfect conditions. You move anyway.

James Barlia put it clearly:

“Just start doing things… start testing hypotheses.” “Perfection doesn’t really exist.”

Jessie Barter’s closing thought was even simpler:

“Start now. Just do the thing.”

Action creates momentum. And yes—failure is part of the equation. But as Bob Buchanan reminds us:

“Get in the ring. Don’t be afraid to get in the ring. And once you’re in the ring… get back in the ring.”

That’s resilience. That’s leadership.

Bill Collins emphasized the importance of learning to fail well, while Cameron Pratt encouraged his younger self to “dream big” and “just go for it.”

Hilary Goldfarb shared her father’s advice:

“Hard work gets noticed… and beats luck, coincidence, and favors.”

There’s no shortcut to being taken seriously. It takes time. It takes persistence. But if you show up with the right mindset, consistent effort, and the courage to speak truth with integrity, people will listen—and they’ll remember.

To influence power, you first have to earn respect. That comes from doing the work, standing by your values, and speaking with purpose.

It’s not always easy. But that’s what makes it worth doing.