On Making The Shift From Task First To Trust First

Property Managers…

In past editions of this newsletter, I’ve written about something that’s only becoming clearer:

We are living through a trust crisis.

Social media distorts truth.

AI blurs the line between real and artificial.

Skepticism is at an all-time high.

And in property management, this plays out in a very specific way.

Owners don’t just want high NOI or operational efficiency. What they really crave is certainty.

Why Owners Leave — And It’s Not What You Think

I’ve been thinking a lot about this lately.

Owners rarely leave over one bad maintenance call or a small dip in NOI.

They leave when too many small doubts pile up — when they feel invisible in the moments that matter most.

Here’s what I mean:

• A $6,000 turnover hits, and they’re sitting at the kitchen table asking, “Why didn’t anyone warn me this was coming?”
  
• A tenant issue drags on, and they wonder, “Should I just sell and put this money in the market?”
• The phone rings, and it’s always bad news — and they start flinching every time they see your name pop up.

That’s when they have what I call the Kitchen Table Argument (KTA) — the quiet conversation with their spouse, partner, or advisor where they ask:

“Do I still trust them?”
“Is this worth it anymore?”

These moments don’t show up on dashboards.

But they are the moments that quietly erode your portfolio.

For years, this was just the cost of doing business.

Even great operators — like Vendoroo’s own Dave Normand — have felt the pain of losing early owners, not because of poor performance, but because they couldn’t show up at the moments that mattered most.

The Good News: AI Is About To Change Everything

We’re heading into a world where Agentic AI can handle all task-based processes.

That gives you something property managers have never had enough of before:

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Time.

Time to solve KTAs before they happen.
Time to show up before the storm hits.
Time to shift from firefighting operator to trusted asset advisor.

But here’s the part that’s been staying with me:

To seize that opportunity, you can’t just swap in better tools.

You need to rebuild the whole model.

Because in a world where every PMC has time freed up by AI, your only real differentiator is your people — and how they show up for owners.

How to Build A Relationship-Centric Team In the Age of Agentic AI

#1 Beware of Gravitational Pulls

In Play Bigger, the authors make a striking point:

Companies that solve old problems in new ways capture 76% of their market.

But most fail to capitalize because they cling to the past.

Christopher Lochhead calls this “gravity” — the pull of old habits, old assumptions, old ways of working.

It’s the pull that makes a property manager say: “Well, AI is great… but I’m not ready to let go of control yet.”

Here’s what I’ve noticed:

Once you commit to the future — once you cast a clear vision — you’ll start attracting the right people.

And the ones who can’t come with you? They’ll often opt out on their own.

Take Jason Hull, CEO of DoorGrow.

He embraced the shift toward relationship-first property management — and his culture followed.

The folks who didn’t align with his mission? They left or were let go.
The ones who stayed? They became the backbone of his transformation.

Watch Jason Explain This:

#2 Evangelize. Don’t Convince.

Here’s a hard truth:

You can’t “upskill” someone into changing their values.

Christopher Lochhead doesn’t waste time convincing the unconvinced.
Jason Hull doesn’t either.

Instead, they put the message out boldly and let the right people rally around it.

If you want to build a relationship-first team, hire for alignment on Day 1.
The right people won’t need convincing.

#3 Beware Hiders. Hire Believers.

One of the most powerful lessons Jason shared with me is the difference between:

• Believers → Proactive, mission-driven, eager to own outcomes.
  
• Hiders → Skilled, but disengaged; they hide behind tasks and avoid accountability.

Here’s Jason explaining the concept in detail:

Vendoroo founder Reza Kesh uses a similar lens:

• Group 1 (A-players) → They lead, they elevate, they take pride in results.
  
• Group 2 (B-players) → They wait to be led, need supervision, and quietly pull teams backward.

HERE’S REZA TALKING ABOUT IT IN MORE DETAIL:

Here’s the simple filter:

“Can they own the outcome?”

Do they step up or wait to be told?
Do they offer solutions or just surface problems?
Do they show up when it counts?

In a trust-first business, one weak link can ripple out into lost clients.
The stakes have never been higher.

The Leadership Playbook That Sticks With Me

I recently had a conversation with my dad that reminded me what real leadership looks like.

Years ago, he was brought in to turn around a failing company in Spain.
The challenge?
Lay off a third of the workforce — in a country with some of the strongest unions in Europe.

But here’s what set him apart:

• He cast a clear vision.
  
• He communicated relentlessly.
  
• He held the line on the plan — even when it hurt.
  
• He celebrated progress — both the numbers and the human resilience.
  

And here’s the part that gives me goosebumps:

Seven years after he left, he walked into one of the old stores for breakfast.

The manager recognized him.
The staff comped his meal.
And as he left, the entire team gave him a standing ovation.

Not because he was perfect.
Because he led with clarity, conviction, and care.

That’s the leadership playbook we all need in the Agentic AI era.

Final Thoughts: The Age of Letting Go

AI is going to help you let go of countless tasks.
But the real evolution is letting go of control where you shouldn’t need it — because you’ve built a team you can trust.

The right AI is like a top-tier hire:

It knows what to do, it gets better over time, and it frees you up to focus on what only you can do.

At Vendoroo, we specialize in providing you with the best AI hires for your business.

If you want to see what our AI agents can already handle — let’s talk.

See you soon,

Pablo Gonzalez
Chief Evangelist at Vendoroo

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