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Ashlee Adelman: “Big or small, treat all transactions the same”

Big or small, treat all transactions the same. Luxury is a level of service, not a price point. The client that discloses very little for a quick investment property purchase could need to sell their luxury home to relocate. Make sure your attitude and work reflect the importance of each and every deal. As a part […]

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Big or small, treat all transactions the same. Luxury is a level of service, not a price point. The client that discloses very little for a quick investment property purchase could need to sell their luxury home to relocate. Make sure your attitude and work reflect the importance of each and every deal.


As a part of my series about strong women leaders of the Real Estate industry, I had the pleasure of interviewing Ashlee Adelman.

Ashlee is a third generation REALTOR® with 13 years of experience within Chicago neighborhoods and communities. She currently lives in the Gold Coast where she fell in love with the architecture and being walking distance to Chicago’s Lakefront Trail, where you can find her most mornings. Ashlee’s love for connecting with people makes the buying and selling experience a lifelong friendship. She has grown to see her family’s real estate business, started by her grandmother 52 years ago, evolve and prosper based on an “integrity first” attitude with generations of referrals. She applies the same principles to her business in Chicago which has proven to be successful time and time again. Real Estate is in Ashlee’s blood which is proven in the results she achieves for her clients. Ashlee is currently a broker with Jameson Sotheby’s International Realty.


Thank you so much for doing this with us! Can you tell us the “backstory” about what brought you to the Real Estate industry?

Family and legacy are the moral of my story. I grew up around my family’s real estate business and saw every day the life you can create and the impact you can have on a community with that career. I’ve lived in Chicago for 15 years and built a network through other passions I hold like teaching yoga but always knew I would find my way back to my real estate roots. I absolutely attribute my drive in carrying on our family firm’s legacy to the inspiration garnered from working there from age 14 through the end of business school.

Can you share with our readers the most interesting or amusing story that occured to you in your career so far? Can you share the lesson or take away you took out of that story?

I had a colleague with really difficult clients. She spoke often about them, the issues she perceived they caused and her concern about a deal even falling through on a property. I was chatting with student following a yoga class I teach every Sunday and real estate came up. A woman who is a regular at this class shared with me that she and her family were so close to buying their dream home…these were my colleague’s clients! After realizing that I worked with their agent, they asked me to partner with her and the deal got done. The reality is that we all want to work with people we like and trust. They knew me, trusted me enough to take my class so when they found out I also did real estate, they wanted to work with me. It turns out they weren’t “difficult” clients, there was just a difference in personality causing friction.

The lesson is always, always be kind to people. Whether you are in a small town like where my family’s firm originated or a big city like Chicago, you will always run into people you know or need to work with again. There is no reason not to create a personal environment based on kindness. You never know when it can contribute to closing a deal and, besides that, it’s how I want to live my life.

Are you working on any exciting new projects now? How do you think that will help people?

I am working on producing and creating a digital product that will educate people on how to prepare to buy a home, how to buy a home, and how to build generational wealth through real estate. Whether a younger buyer is starting their real estate journey, or someone has several homes to their credit, it’s essential to determine what an individual’s values and goals are surrounding real estate. Is it to create wealth? That is highly attainable and leads to wealth that can pass to future generations. Is it to get into an up-and-coming neighborhood or specific type of property and make a profit by flipping it? Is it stop wasting money on rent and build equity in a home you’ll be in for 20 years? These are all things we don’t learn in school. Even coming from a family who faced these issues with clients every day, no one ever sat me down and explained how something like a real estate transaction has much more meaning and financial influence than simply moving into a house. This new product will review the how-tos, including real estate goal setting, break it down, and provide transparency that inspires confidence and, ultimately, success. I’ve also partnered with a new firm and the coaching has been everything I’ve been seeking to build on what I learned early at my family’s brokerage.

What do you think makes your company stand out? Can you share a story?

When I was building my company, Live Well with Ashlee, I realized that to truly support my clients, I needed to deeply understand human behavior. Sure, anyone can run a process and tell you what houses are on the market, but I wanted to deliver best in class service and get clients into homes that perfectly fit their lives. Over a decade of travelling, talking, connecting, asking questions, I learned a lot about how important the tiny details are to the thread of life, to the security a home provides. Emotional support is key when making big life changes and that is essentially what real estate is- big life changes that are designed and intended to get people closer to living the lives they have imagined. But there are a lot of moving parts with transition and you need someone who can hold space with you and your immediate family. Factors like loss, marriage, divorce, birth, or special needs are often at play and families may not be on the same page about important details of a deal.

I had clients whose condo was on the market for longer than any of us had hoped. We were all frustrated and trying to do what we could to move it…and pressure was added when they found their dream home in a new area that would allow for their growing family’s needs. There are several moving parts when timing a contingent sale and a move was urgent for these sellers; there was also a lot of attachment to their first home, so emotions were high. When all was said and done, a condo sold and a home purchased, they gave me the feedback that they couldn’t imagine going through this with anyone else. Homes are usually our largest asset and there are always deadlines and inconveniences. You add in emotions and although a closing is always the result of a sale, getting there is not always easy. I really think that it’s the space I was able to hold for this family, their schedules, their small children, their in-laws and pets in addition to the real estate expertise that got us all to a successful place at the end of the transaction.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I have a photo of my grandmother Joyce Ginter that I always keep close by for when I need help connecting to my most authentic, purpose-driven self because that is who she was. Joyce was the matriarch of our family- a registered nurse who earned her Master of Theology and, ultimately, started a real estate company after moving the family from Kentucky to northwest Indiana. Steel mill jobs were booming in the area and she knew there was a huge opportunity to help these workers who needed homes. A mother of 5, Joyce was known as a Real Estate Pioneer in the area for how she would knock on doors throughout the area to meet people and introduce them to the idea they could own a home. She was quite fearless, looking out for her neighbors, paving the way for other women entrepreneurs. A lot of what exists in that area is because my grandmother started it and learning from her and the high bar she set was an honor.

Ok. Thank you for all that. Let’s now jump to the main core of our interview. The Real Estate industry, like the Veterinarian, Nursing and Public Relations fields, is a women dominated industry. Yet despite this, less than 20 percent of senior positions in Real Estate companies are held by women. In your opinion or experience, what do you think is the cause of this imbalance?

This is where leadership and managers within brokerages are key. Women with high emotional intelligence succeed in selling and senior positions are managing positions- they step in to lend a hand or provide guidance with a transaction. This is a different skill set, and I have found it is few and far between that you work with your managing broker. I think a better question is what do women want within this industry? If a senior position is salaried and involves more time in an office, it may not appeal to someone who wants to be out in the field with essentially no earning cap- the more she sells, the more she makes. My bigger concern is when these senior positions impede an agent’s ability to sell or create more hoops to jump through.

Female or male, I believe one needs to be as dedicated to their position helping their people as they would be if they were in the building phases of their sales career working on commission only. Senior positions are usually salaried and successful leaders don’t lose sight of the earning potential in commission role and how that impacts their people.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

It baffles me is how much more typical it is for a large scale, new construction development to go to a male broker. It’s this antiquated assumption that men know construction and can deal with contractors more effectively or, worse, that something big and loud and messy is too overwhelming for a woman. As someone who has built homes, overseen project management of construction and still been offered far more pretty, staged, ready to sell properties, I think this is a big area of opportunity in our industry.

Can you share 3 things that most excite you about the Real Estate industry?

The endless possibilities of personal, professional and financial growth, the ability to help people in sensitive housing transitions and the exciting day-to-day interactions with the folks I get to meet along the way. These are also the reasons as to why I entered the business. The alluring architecture, land, design and finish features of properties are a bonus!

I’m so happy to now be working with Jameson Sotheby- they invest so much into marketing and their people that it’s clear they feel the same way about the industry as I do.

Can you share 3 things that most concern you about the industry? If you had the ability to implement 3 ways to reform or improve the industry, what would you suggest?

1. The lack of education that is provided to buyers and sellers before they enter a deal due to urgency. It’s imperative to meet with clients early for a smooth experience to eliminate stress and trauma. Things are going to coming at clients from all angles during a process but it’s possible to mitigate the stress with thorough communication and planning. If you aren’t comfortable meeting with your broker early, you’re likely not going to be comfortable with them when it’s necessary so I advise to always work with someone you know, like and trust. A good broker can be helpful to a family for life when they are conducting a relationship-based, not simply transactional, business.

2. Selling real estate is not a side hustle or a career that can be successful just because you know a lot of people. It always concerns me when I see agents unaware that success in this industry is a long-game investment. Growing a network, becoming familiar with the ins and outs of processes both academically and with real life experience, navigating the complexities of the relational and emotional aspects of buying and selling, operating objectively with your client’s best interests at heart…these are all essential elements of being in the real estate industry. If someone cannot commit to that, their clients are the ones who suffer.

3. This industry is notorious for ego. There’s a lot of self-promotion that goes into home promotion and hitting a balance between ego and letting people know who you are so they will choose to work with you and empathy is really important.

What advice would you give to other leaders to help their team to thrive?

Instead of rising to your goals, fall to your systems and the wins will come. It’s the day-to-day consistencies that push businesses forward, achieve success and keep people happy.

Ok, here is the main question of our interview. You are a “Real Estate Insider”. If you had to advise someone about 5 non intuitive things one should know to succeed in the Real Estate industry, what would you say? Can you please give a story or an example for each?

1. Work with a brand and people that are committed to supporting your unique needs and goals as you’re building your business. I didn’t feel like I had this until I started with Jameson Sotheby’s International Realty. Their coaching and mentorship combined with a brand that’s proven to successfully evolve in marketing, tech and systems has been a game changer for my career. And we’re just getting started. The history of the Sotheby’s brand is rock solid, and the international network of referrals and support is unsurmountable. I’ve already seen an obvious influx in overall response since my transition. I’ve had such a warm welcome- introductions to successors, closing deals with brokers all over the country with relocations from Chicago to new spaces in new cities. I’ve been able to connect some of my best clients and friends to new brokers and seen that handled with such care by the Jameson Sotheby’s family. When given recommendations from my Managing Broker Jim Miller, there’s a confidence and assurance behind the next call. A lot of real estate is about matchmaking and it’s important to align with people that have been where you are going.

2. Big or small, treat all transactions the same. Luxury is a level of service, not a price point. The client that discloses very little for a quick investment property purchase could need to sell their luxury home to relocate. Make sure your attitude and work reflect the importance of each and every deal.

3. Have a real estate hobby on the side. The old adage about the cobbler’s children going without shoes is often true with real estate agents. An agent might have a career boasting a huge number of sales but never run the process for themselves. Take your own real estate advice and apply it to your own life- this will allow you to advocate more strongly and have a clearer perspective for your clients. I grew up in a family of landlords, good landlords. I bought my first investment property in my 20’s and that taught me how to be a landlord. I’m always looking for good investment opportunities so I can grow my portfolio to create generational wealth for the children in my family.

4. There is no such thing as a part time broker, go all in. Do the work, make the commitment- that is the only way you will see the success. I’ve heard the same story over and over again: friends decide to work with a broker because they are family or a family friend that is licensed but no longer actively practices. The end up not being as helpful as they could be when the client needs it the most, because they are no longer an expert in their craft. I just hosted an Open House where a woman came in without her broker looking to purchase a $3.5M home. She had a laundry list of questions about the neighborhood, the area, schools, etc. because she wasn’t from the area. Her broker is her mother and also not from the area. She needed my help but wasn’t in a position to hire me. That put her at a disadvantage when purchasing. To be effective and represent a client’s best interest, a broker must an expert and actively working to confidently carry a client through their transaction.

5. Let your business reflect you. Just because one broker is doing something one way doesn’t mean you have to! Authenticity is what will set you apart and attract the type of properties and people you want to be working with. Real estate breeds real estate so we always want to be talking about our business. It’s easier to talk about it with your barista, gym pals, lunch friends and friends of places you frequent in your day-to-day that make you, you. This grass roots approach is something I learned from now very large companies that themselves started small and I have found it to be very successful in my own business.

Because of your position, you are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

We’re in the business of, essentially, creating neighbors so I think it all comes back to kindness. Be kind to your neighbor, inspire them to be kind to their neighbor and let’s see that ripple across our growing communities.

How can our readers follow you online?

@livewellwithashlee on Instagram and Facebook!

Thank you for your time, and your excellent insights!

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