Leadership Under Fire: Three Lessons From a Tough Month in Property Management

Last month, my business fell apart.

Not really. But there were more than a few days with heavy head-trash. I documented the journey with some LinkedIn posts that were quite popular so in this issue I am telling the ‘Rest of the Story’ for three semi-viral LinkedIn posts over the last few weeks.

Within 30 days, three of my property managers quit. A client publicly accused us of negligence in a scathing 2-star review. And a loyal client of 7+ years fired us with nine devastating words: "I would like to cancel my agreements with you, immediately."

I interrogated myself, hard. I felt bad. I was a bit short-tempered for a few days. But then it kicked in – the same mindset that gets me through the darkest miles of ultramarathons: "This is what we came for."

The hardest moments aren't detours from success – THEY ARE THE PATH. Here are three critical lessons from my month that might help you navigate your own leadership valleys.

Take Full Responsibility, Even When It Burns

I posted that three PM’s quit and that I only have 3 PM positions. What I didn’t mention is that one of the PM’s who left was actually a replacement for a PM who quit two weeks prior. PM 1 quit, PM 2 filled the spot and then quit. Also PM 3 quit. So I still have Diane, our Sr. PM who has been with us for about 6 years.

When all three property managers quit within weeks of each other, it felt like a betrayal. My first instinct? Get really down on myself. Feel like an imposter. Hide the failure.

In fact, Jordan Muela, CEO of Leadsimple and Peter Lohmann were scheduled to visit my business to check out my ‘great’ operation right when this happened. How could I host two professionals I really admire with this seemingly epic failure overshadowing the visit?

Leadership requires looking in the mirror. As a CEO, I'm responsible for creating an environment where great people want to stay. Period. No exceptions, no excuses.

Here's what worked: I leaned into the pain. I got raw and open and vulnerable about it. It was the first thing I shared with Peter and Jordan when they arrived at my office. I posted about it candidly on LinkedIn. I conducted exit interviews to face the pain directly. I talked with my wife, my Director of Operations, with friends…

The result: lots of support and lots of learning. All three PM’s who left had nice things to say about the company and the culture. One of them reached out via text to me after seeing the LinkedIn post to assure me, in fact, that the only reason she left had to do with a personal family issue. One of the comments on my LinkedIn post is from a client who has been with us for 10 years now. He shared about his journey with us so far, expressed continued commitment and offered encouragement.

Wow. That felt really good.

Taking extreme ownership works. Being open and vulnerable works. Reaching out for help and squarely facing reality works. Rich and I figured out a new and better way to interview PM’s and we are super excited about a new hire starting later this month. This is an opportunity to level up our PM talent. I’m so excited about what this will enable us to do.

Beyond the Bottom Line: Why I Turned Down $55,000 to Protect What Matters Most

"You're looking to steal money from ignorant people. Good luck with that…"

This one also stung a bit.

A potential client (let's call him Brad) offered us 26 single-family rentals – approximately $55,000 in annual revenue. We turned him down and he shot back in an email that smart businesses say ‘yes’ and we are clearly looking to rip off stupid people. ouch.

Here’s the rest of the story: When I listened in on the recorded call Brad had with my super awesome Director of Inbound Sales, Spencer Hall, Brad sounded a bit rough. He described himself as ‘old school’ which is ok, but he demanded an in-person meeting with me, which is still ok. But when Spencer started qualifying Brad to determine whether he would be supportive of our processes, I started getting concerned.

“Oh! You’ve never met anyone like me. I guarantee it.” Brad said. “I live in Arizona 5 months out of the year and I handle all my own turns…” Brad was looking to be heavily involved in the management of his properties and he was looking for a discount in fees. Brad sounded very confident and very proud of his portfolio. Nothing wrong with that, but Brad was giving off heavy vibes that he knew exactly how his properties should be managed and whoever worked for him would need to toe the line.

Ten years ago, I would have taken on Brad as a client, discounted my fee and convinced myself I could blow him away with incredible service. My staff would have been stressed and intimidated by Brad and my Director of Operations would have told me (as he should) that I needed to personally service Brad because the team couldn’t handle him.

No thanks. Not now. Brad’s $55,000 in annual property management fees present at least $150k in annual cost. “How so?” you ask. Because I understand the value of my time, the emotional costs of working with Brad and what we would be giving up in business and brand growth upside for saying yes to him. It’s not worth it.

Jennifer Ruelens posted on LinkedIn:

Jennifer understands opportunity cost and I think her price to co-manage is too low.

Don’t make your best clients pay for your worst clients. They deserve better.

The Fragile Foundation: Why Trust in Property Management Requires Constant Reinforcement

"I would like to cancel my agreements with you, effective immediately." After 7 years of service to this client, the email felt like a punch to the gut.

The client was upset about $13,000 in recommended upgrades and repairs completed by my maintenance company, BT Property Services. Though we'd disclosed my ownership and kept pricing competitive, we failed to disclose the relationship often enough and clearly enough to avoid this client feeling like it was not disclosed.

My fault totally.

Here’s the rest of the story: she had just moved out of a house 1 year prior and turned it over to us to manage (her 2nd property under management). We hit her with $13,000 in combined recommended and required work just one year after we onboarded the property when our initial ‘rent-ready’ inspection hadn’t included any of these recommendations.

The story in her head: “Mark is trying to take me for $13k by abusing my trust funneling un-necessary and overpriced work to his home services business now that he has lured me in as a client.” It’s not the truth, but here’s the reality:

People make up stories in their heads about our motives and intentions. Most people are wired to assume the worst about other’s motives and intents unless and until the trust account balance has built up to a high level. And even then trust takes just a few moments to completely destroy.

I messed up here. We need to disclose better and more frequently the great benefit our home services business brings to our clients. We need to call owners before we send over $13k turn reports. We need to build better relationships of trust with our clients so they feel they can call and have a candid conversation when they start making up stories about our behavior in their heads.

This painful lesson reaffirmed something fundamental: in property management, trust isn't just about initial disclosures—it's about transparent communication at every critical stage. When clients invest their properties with us, they're entrusting more than assets; they're sharing their financial future. Each recommendation we make must be delivered with the care this trust deserves. We don't just manage properties—we manage trust.

Stronger Through Breaking

These challenges aren’t just exposing my weaknesses – they are accelerating our transformation. My loyal team has stepped up magnificently to maintain our service while we rebuild.

Someone commented on one of these three LinkedIn posts:

Brandy Landon did a great write-up about “Why I chose property management - and why it chose me”. It’s worth a read.

If we dare to ‘Own the Outcome’ so much in this very difficult business, why not just become a general partner and start syndicating? No unsupportive owners, more money, more control… During this challenging month I asked myself this question, and the question demanded and received a satisfactory answer.

What do you think my answer is? What’s your answer? Why are you doing this? Read Brandy’s answer and then shoot me your answer. I would love to hear your story, truly.