My Failures as a Rent Roll Owner

I’ve been in leadership positions since I was 21.

In fact, I was promoted to the role of Senior Property Manager at 21, because I was the most experienced property manager on the team. I was a confident property manager, and I had directors in the business who believed in me and supported me to step up into this leadership position.

Now, 21 years old is young. In hindsight, I wasn’t ready for that level of leadership. I thought I was, but I didn’t know what was involved in leading a team. Sure, I knew how to be a great property manager, but I did not know how to be a leader.

A couple of years later, I bought my first business and I’ve been in business ever since. This means I’ve been in leadership positions since I was 21. You might assume that I’m a natural born leader. But I’m not. In fact, there have been moments where I’ve been a terrible leader. So in this article, I want to be honest with you. I want to share some vulnerabilities with you and talk about my failures. In this article I’ll share two times I’ve failed and one time I had success as a leader, and what I’ve learned from these experiences.

I hope that, in my honesty, you’ll see that leadership is a learned skill. Something that requires effort, attention and practice. That even if you’re not a “natural born leader” it’s a skill you can develop. That in leadership, as in life, sometimes you’ll fail.

Failure # 1

After spending five years in property management, I purchased a retail business when I was 23 years old. A beauty salon, to be exact. One of the most important aspects of running a beauty salon is personal presentation. My team knew our personal presentation standards, and that this was a requirement in their roles. For many years, my team presented themselves well, and then one day a particular member of my team decided to stop ironing her uniform, stop brushing her hair and stop wearing makeup. Now, I didn’t require makeup wearing as a condition of employment (it’s great to show your natural and unique beauty in a beauty salon), but I did have a personal presentation policy. This team member was not adhering to our presentation policy, and it was stressing me out.

Do you know what I did about it? Nothing. I silently stewed about it, turned myself inside out, received questions from my clients about it, and I did nothing at all. Actually, I did worse than that. I became passive aggressive. I avoided this team member, distanced myself, and eventually she quit.

What I learned from failure # 1

Here’s the thing. This team member had been amazing for years. She probably had a reasonable explanation for the change in her professional presentation. She probably had “stuff going on” that I didn’t know about. But because of my terrible leadership, she didn’t get to explain what was going on, she wasn’t supported by her boss (that’s me), and I lost a great employee.

My immaturity and lack of leadership lead to her leaving. She was (otherwise) and excellent staff member but my unwillingness to confront and address a problem led to me losing a great person and probably causing her a lot of pain in the process. To this day, I’m embarrassed about the way I handled the situation.

I still struggle to have difficult conversations with my team. It’s my least favourite part of being leader. But I’ll never make the same mistake again. I’ve learned to take a deep breath and have the difficult conversation, to be candid and compassionate with my team. It’s the only way I can lead my team forward.

Failure # 2

When I finally took the plunge and started my own rent roll, I was a total control freak. This meant that when I first I hired staff to help me out, I didn’t train them sufficiently. Truth is, I was afraid. I was afraid that I would train up excellent property managers, and they’d leave, and take my clients with them.

Turns out, if you don’t train your team effectively, they can’t do their job well. If they can’t do their job well, you just end up being a super-stressed leader still doing all the work. It took me about 12 months of working with my first employee to discover that my job, as the leader, is to train my team and trust my team.

What I learned from failure # 2

I was so excited to hire my first team member, about 12 months after starting my rent roll. I couldn’t wait to get help with the day-to-day management of my portfolio of properties. However, I discovered that, because I wasn’t willing to “let go” and trust my new team, it didn’t save me any time at all!

Honestly, I wasted 12 months in my business, paying my employees to do work that I wasn’t willing to let them do. Eventually, I realised that I’d never be able to grow my rent roll any further if I didn’t let go. So, over a period of 3 months, I created systems, processes and training to empower my employees to do their job.

Turns out, empowering your employees to do their job makes the world of difference! When I let go of control and trusted my team to do their job, they did!

The Single Success

For all my failures as a leader, I know I’ve done one thing right. Interestingly, I made this decision by accident, in an act of desperation. But it turned out to be one of my biggest successes as a leader.

Many years ago, I experienced a personal crisis. I was forced to take a significant amount of time away from my business, and I had to trust my team to take care of my clients for me. Not only did I have to trust them to take care of my clients, I had to trust them to resolve complex situations at times that I was not able to be contacted.

So, I gave my team a “get it fixed” budget. This made a world of difference to my team, my business, and my own state of mind. I gave my team permission to spend up to $100 to fix any problem that popped up. If a client was unhappy with our service, my team could offer a refund of our fee, send a bunch of flowers, buy a gift card or do anything to help fix the problem, up to $100, without even speaking to me about it.

What I’ve learned from The Single Success

You know what happened? My team handled every single problem that popped up while I was away, my clients were happy, and my business grew. In fact, my team didn’t even spend the $100 “get it fixed” budget once! But you know what else happened? My team stepped up. When I returned to my business, after being away for about 4 weeks, the business was thriving, the team was united, and my clients were happy. That simple act of empowering my team, while navigating a personal crisis, was one of the best leadership decisions I’ve ever made. And it’s one I’ve used as part of my leadership strategy ever since.

Leadership isn’t always a natural born talent. For me, it’s been one of the biggest challenges of business ownership. But it’s been in my moments of failure, as a leader, that I’ve learned the most.


If you’re thinking of starting your own rent roll this year, make sure you download my Rent Roll Start Up Checklist.






A version of this article first appeared on Elite Agent.

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