Last modified on November 12th, 2020
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Charting a course to grow into a leadership role in the property management industry takes time and energy. Opportunities are everywhere, however you must be willing to take risks, seek advice, and rely on the help of others.

To better understand what it takes to become a leader in real estate, we reached out to several well-established industry veterans to hear their stories and the lessons learned along the way. Here are some of the key takeaways from our conversations:

Carve Your Own Path

Alexandra Jackiw, CPM, CAPS, C3P, and Chief Operating Officer of Hayes Gibson Property Services, didn’t have a direct path to get to where she is today, instead she had to work hard to set goals and overcome obstacles, “Everyone’s career development path is unique and depends on the goals each has set for themselves. The ladder is not always linear, nor does it have a direct, upward trajectory. Oftentimes there are detours along the way and opportunities to move laterally within an organization to gain valuable experience.”

Jackiw, who has thrived in leading multiple property management firms during her lengthy career, shared that a mentor of hers once told her to find power vacuums and fill them, which she has taken to heart and it has served her well: “I frequently took on the tough assignments no one else wanted to tackle. Those assignments helped me to build valuable skills, gain confidence and prove my worth to the organization. That attitude and willingness to do the hard stuff ultimately opened many doors for me.”

Throughout her career, Jackiw has been active in her local apartment associations and the National Apartment Association (NAA). She was also nominated to NAA’s Executive Committee by her peers and eventually rose to serve as the Chairman of the Board.

Jackiw believes leadership skills can be gained through building personal relationships with successful peers, “Work on soft skills early in your career and master them. Find a role model – someone whose ethics and emotional intelligence you admire and respect so that you can observe the impact of that person’s leadership. Learn the art of communication and practice active listening. Continually build your network and widen your circle to include as many diverse ideas and opinions as you can. Surround yourself with diverse and interesting people who will challenge your thinking.”

An energetic passion for learning can make an enormous difference when growing as a property management professional and organizational leader.

Jackiw, who has played a significant role as a teacher and curriculum organizer for four-year degree universities that teach property management, such as Virginia Tech and Ball State, stressed the importance of being a lifelong learner:

“Take responsibility for your education and absorb as much information as you can about a wide variety of things. Your learning doesn’t just have to be centered on your profession. Be intellectually curious about a broad range of topics. You’ll be surprised how creativity can be sparked by expanding your knowledge.”

Listen and Learn

Cindy Clare, COO of Bell Partners, concurs that learning – and listening – are top priorities when it comes to leadership, “Learning is the biggest piece you can do as a leader. Though I’ve been in the industry over 35 years, I still learn every day. And that doesn’t necessarily mean just learning from the people above you, it means learning from the people next to you and beneath you, from a responsibility standpoint.”

Clare also believes it’s important to make a conscious effort to learn from everyone, not just those who are above you, “I can learn as much from a leasing consultant today as I can from another COO, simply because the leasing consultant brings different experiences and they’re the ‘boots on the ground’ and I no longer am. I don’t need to be an expert, but I need to have an understanding, whether about new technologies or the way we’re leasing apartments.”

Be Willing to Take Risks

Along with continuing to learn and broaden your skill set, Clare says successful leaders also must be willing to take risks, “You need to get out of your comfort zone. This doesn’t mean being reckless and it doesn’t mean you have to jump from company to company. It means that when there are opportunities to try something different, take them, even if they feel a bit uncomfortable, try it. You can always go back to what you’ve done, but if you don’t try new things, you’re not going to expand your repertoire and expand your depth of experience. The more you know, and the more you try new things, the more you find what you are really good at, and you can make the most impact.”

Give Your Team a Voice

Clare, who also ascended to NAA’s Chairman of the Board, understands that those at the top of an organization should be able to rely on those around them – at all levels – in order to get better. In addition, she recognizes that communication and expectations between a boss and his or her staff members have shifted over the years, “When I came up in the business, there was definitely a hierarchy, and you didn’t cross it; you followed the chain of command. And it’s not that the younger generation doesn’t follow the chain of command, but they see it differently. They see it as more of a partnership than just, ‘This is my boss.’ They feel that they have something to add and that we should listen. And they do have something to add and we should listen.” 

Just Ask

Kate Good, Partner and SVP of Multifamily Development with Hunington Residential, says she is a firm believer that a person who is close to a problem or opportunity has the clearest vision to seek an answer or idea: 

“My advice to younger employees is to speak up and share your great ideas. And when you do so, make sure they are complete, constructive plans.”

When working with her staff, Good says that insisting on an open and educational conversation tends to relieve anxiety and the fear of the unknown that her team might be experiencing,“[Your staff] might be hearing a snippet of information – and as humans, we tend to fill in the blank for what we do not know. Information-based conversations will avoid this natural behavior from occurring, thereby keeping rumors and emotions under control.”

Seek Advice

Dru Armstrong is CEO of Grace Hill, a firm that helps multifamily companies develop and retain their top talent to improve performance and reduce operating risk. She suggests that executives should build a personal board: 

“I always recommend that people recruit mentors and career sponsors, who can advise and even promote them throughout their career. I have found it incredibly valuable to be able to get advice from people who have solved the same challenges I think about. Usually with successful professionals, I have found that they enjoy the opportunity to support those coming up behind them.”

Armstrong also believes  executives should think about ways  they can actively support their team, “Part of becoming a leader is making those around you and that report to you successful.I would start with asking, ‘What are the technology tools required to make them successful? Does your staff know what is required of them and how to do it? Are you telling them when they are being successful?’ We call this establishing the talent performance loop, which is critical to growing and building talent performance over time.”

Becoming a leader in the real estate industry isn’t for the faint of heart, but for those who do rise to the top it can be an incredibly rewarding career. By making the most of these learnings you can begin to chart your own path and develop your leadership skill set.


Looking for even more proven tactics & strategies from real estate executives? Take at look at AppFolio’s guide, “How to Be a More Effective Leader.” 

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