The Underwriting of People

Why Discernment in Hiring Determines the Future of Real Estate Organizations

Ethical Leadership Theme: Discernment

Hiring Through the Lens of the 50th Law

Commercial real estate trains us to underwrite risk.

We analyze market fundamentals.

We test assumptions.

We stress models.

We interrogate comparables.

We would never invest millions of dollars in an asset based on surface signals alone.

Yet many leaders routinely make human capital decisions—the decisions that ultimately determine whether the asset performs—with far less discipline.

This paradox is at the heart of Patrick Weeks’ research.

Weeks argues that organizations often rigorously underwrite real estate but fail to underwrite talent with the same care. Instead, leaders rely on flawed proxies—pedigree, familiarity, or the subtle comfort of hiring people who resemble themselves.

The result is predictable: impressive résumés, disappointing outcomes.

Over decades in the commercial real estate business, I have come to a similar conclusion.

Most leadership failures are not failures of intelligence.

They are failures of discernment.

And nowhere is discernment tested more severely than in hiring.

The Résumé Illusion

Résumés tell tidy stories about messy careers.

They summarize experience, credentials, and accomplishments in a format that feels authoritative. In reality, they are often little more than signals of opportunity and context.

They do not measure character.

They do not measure judgment.

They do not measure how someone behaves when certainty disappears.

The deeper one goes in leadership, the clearer this becomes.

Many of the leaders featured on the Icons of DC Area Real Estate podcast make exactly this point.

Sean Caldwell of Mill Creek Residential put it bluntly:

“The least important is technical skills… no one’s ever been fired for not being able to do an Excel spreadsheet.”

Technical capability can be taught. Character cannot.

Shekar Narasimhan of Beekman Advisors goes even further:

“First of all, character. If I cannot be convinced that you have good character and ethics, and I don’t want to do business with you, that’s a gating issue.”

The best leaders understand that hiring decisions are not about filling a role. They are about placing judgment inside the organization.

Hiring Through the 50th Law

In The 50th Law, Greene argues that effective leaders operate without illusions. They confront reality directly—even when it contradicts comforting assumptions.

Fearlessness, in Greene’s formulation, does not mean aggression. It means clarity about what could go wrong.

Hiring demands precisely this mindset.

The average leader asks:

Is this candidate impressive?

The disciplined leader asks:

Where will this person struggle when the playbook fails?

Patrick Weeks emphasizes that organizations too often substitute familiarity for discernment—what he calls the “like-me bias.”

Leaders unconsciously hire people who resemble themselves: similar schools, similar backgrounds, similar instincts.

The problem is that similarity rarely produces strength. It produces blind spots at scale.

What the Icons Actually Look For

When I ask experienced leaders how they evaluate talent, their answers rarely mention credentials.

They talk about judgment, character, and agency.

Ron Gart of Seyfarth frames it simply:

“I need someone with good judgment. I need someone with common sense. They could be smart as hell, but if they don’t have common sense, there’s a synapse.”

John Ziegenhein of Chevy Chase Land Company emphasizes patience in the hiring process:

“I think a lot of people I work with get frustrated because I do take my time… the easy part is assessing someone’s capabilities. The hard part is the personality assessment… once you’ve got a great culture, it only takes one toxic person to destroy it.”

Ziegenhein boils the evaluation down to three deceptively simple questions:

Do they get it?

Do they want it?

Do they have the capacity?

These questions reveal something that résumés cannot.

Proactive Personality

Weeks’ research highlights a trait that consistently predicts performance: proactive personality.

In simple terms, it is the ability to take initiative without waiting for permission.

Several Icons screen explicitly for this trait.

Vicki Davis of Urban Atlantic looks for what she calls extreme ownership:

“You treat the business as though it is your own.”

She also asks candidates a deceptively simple question:

“What’s your five-year plan?”

Her observation is telling.

Many ambitious candidates have none.

At the same time, leaders like Toby Millman of Transwestern design their organizations for self-directed professionals:

“I’m a manager where I let folks do their own thing… I want people who are self-starters who can go off and do their own thing.”

The pattern is clear.

Organizations that rely on initiative must hire people who possess it naturally.

Curiosity and Critical Thinking

Technical skills may open the door, but intellectual curiosity determines how far someone travels.

Tom Burton of ABR Capital Partners believes this is one of the most overlooked signals in hiring:

“Just be curious. Just have a sense of curiosity. I think it’s so valuable.”

Curiosity is what allows professionals to see around corners—to question assumptions and discover opportunities that others miss.

Similarly, Louis Dubin of Red Brick emphasizes independent thinking:

“Critical thinking… we look for people who are not going to default to the industry norm… you challenge everything.”

This kind of thinking is rarely comfortable. It is, however, essential for organizations operating in complex markets.

Discernment and Career Stages

The importance of discernment evolves across a career.

Early in a career, professionals are primarily evaluated on execution. But as responsibility increases, the axis shifts.

Eventually, leaders are judged less by what they personally produce and more by who they choose to empower.

This progression is at the center of the Coe Enterprises coaching curriculum, which organizes career development around stages of influence.

Early careers require direction and structured planning.

Mid-career professionals must learn to translate capability into leverage.

Senior leaders must develop decision principles that guide people and capital under uncertainty.

At the highest levels, leadership becomes stewardship.

Hiring sits at the center of each stage.

Because every hire redistributes opportunity, responsibility, and risk.

The Quiet Cost of Getting It Wrong

Bad hires rarely fail dramatically.

They erode.

They create friction in meetings.

They slow decisions.

They distort culture.

The organization gradually absorbs the cost.

By the time the damage becomes visible, the original decision is often too far in the past to examine clearly.

Discernment prevents that slow leak.

It requires leaders to pause long enough to ask the harder questions.

One Question for the Month

Patrick Weeks’ research and the experiences of many Icons of DC Area Real Estate converge on the same insight:

Hiring is not an HR function.

It is a leadership decision.

Which leads to a question worth sitting with this month:

Where in your organization are hiring decisions being made on signals instead of discernment?

Because in the long run, organizations do not become what their strategies promise.

They become what their hiring decisions allow.

Career growth isn’t linear.

Influence changes the work.

Each stage requires different judgment.