How to Work Smarter, Not Harder: A YPN Breakfast Recap

On Wednesday, April 27, 2022, we hosted our monthly YPN breakfast “Work Harder, Not Smarter!” at our home base, Manny’s Deli. We were so excited to get together in person, connect with our peers and devour advice from local industry experts. You can stay up-to-date on upcoming YPN events by following the YPN Facebook page!


Our guest speakers Bill Dwyer, COMPASS, Elena Tamillo, @properties | Christie’s International Real Estate, and Alex Wolking, Keller Williams ONEChicago, shared the tips and tricks they’ve picked up throughout their careers to help with self-management, productivity and essential habits for success.

Set Expectations with Your Clients

Whether you’re just starting in the industry or you’ve been in it for a while, it’s important to remember that a respectful relationship with your clients goes both ways. Part of that respect comes from setting boundaries.

For instance, Alex goes into all of his relationships with his clients with two rules pre-set: be kind and be reasonable. If he finds that his clients aren’t meeting these standards, he’s not afraid to let them know and cut off the relationship if things don’t change. He is also super clear about when he’s taking his time off. He schedules it far in advance, towards the beginning of the year, and sets up automatic notifications for his clients to let them know he’ll be away from the office.

For Elena, she knows the importance of her time as a mother of two. “My days have become infinitely shorter,” she said. Between 5:00 to 7:00 PM, her time is dedicated to her family, and no work is allowed. She lets her clients know this right from the beginning of their working relationship, and more often than not, they are receptive to these boundaries.

Identify & Remove Your Bad Habits

We all do things that don’t serve us in the long run. If you’re ready to streamline systems and become more efficient, it’s time to figure out what those are and take them out of your work life.

For Bill, one of his bad habits is sleeping in and laying in bed. He realized this was a problem when he would find himself playing Angry Birds instead of getting up and taking on the day. Now, he says his routine is to, “Get up, start my day and figure out what I need to do.”

One day, Alex decided to track his time to truly see where it was going. Within the first day of the exercise, he realized that mindlessly scrolling through Instagram was sucking up a shocking amount of time! He came to the agreement with himself that he needed to set down his phone more frequently. Now, he finds himself being mindful of that not just at work, but also at dinner time and when he’s spending time with friends and family.

Know When, and Who, To Hire

Making the choice to bring on a team member is hard but necessary, and deciding who to add to your team may not always be an obvious choice.

“For the first three to four years, I had a lot of momentum,” Alex said. Then, he hit a plateau. Instead of hiring another broker, which may have been the obvious choice, he decided to hire an assistant to help with the administrative duties that were eating up his time. Once his assistant was hired, he quickly doubled his business, signifying, to him, that he had made the right choice.

Elena got into real estate as an assistant, learned the ropes and then got her license, so she’s known the importance of having an assistant all along. Once her business got off the ground with her business partner, they hired an assistant who they now can’t imagine working without.

Top Technology Picks

What game-changing tools does the panel use personally and for their business?

  • Calm: A guided meditation app.
  • ToDoist: An online to-do list.
  • Foxtrot: For quickly and easily sending gifts to clients.
  • Google Workspace: For collaborations and easy sharing within your team.
  • Airtable: An organizational and task management platform.


Chicago REALTORS® · 2022 YPN March Breakfast: Breaking Ground With Developers