Posted by Ryan Hardy on Tuesday, September 30th, 2025 6:46pm.
When it comes time to sell your Chicago home or condo, choosing the right real estate agent is one of the most important steps you can take. A skilled real estate agent doesn’t just place your property on the market — they help you prepare it, price it correctly, and position it within the market to attract serious buyers. When interviewing realtors, the best way to ensure you’re making the right choice is to ask the right questions before you list. By doing so, you’ll gain insight into how an agent works and how they can help you achieve the strongest possible outcome.
This is called a knockout question. It cuts to the chase and there's nowhere to hide. If the answer is a low number, do yourself a favor and move on.
The barrier to entry to become a realtor is very low—just a few hours of online classes. According to Google Gemini, there are 1.5 million realtors in the United States, and the majority of them sell less than one home per year. For most, it's not even a full-time job. Eighty-five percent do it as a second job—there's nothing wrong with that; we like hustle, but is that who you want selling your home? It's up to you, but I'll take a full-time professional who's done it many times and has a proven track record of success.
Pricing is one of the most critical factors in a successful sale. Ask your agent how they determine the right listing price and what data they use to support their recommendation. Do they rely on recent comparable sales, current buyer demand, or a blend of both? The answer will give you a sense of their market knowledge and strategy. A well-reasoned pricing plan helps avoid costly mistakes — whether overpricing that leads to a stale listing or underpricing that leaves money on the table. Realistic pricing is strategic pricing.
Not every improvement pays off equally, which is why it’s essential to ask your agent where to focus. Should you paint, stage, or make small repairs? Or do we just need to declutter? A good agent will know which updates resonate most with buyers in your neighborhood and which won’t justify the cost. Good guidance ensures your home makes a strong first impression without unnecessary spending.
In today’s market, exposure matters. Ask your agent about their marketing plan — both online and offline. Do they use professional photography, virtual tours, and targeted digital advertising? Will they hold open houses or rely more on private showings? Their approach should be comprehensive and tailored to your home’s strengths. Understanding how they plan to showcase your property helps you gauge how effectively they’ll connect with potential buyers.
Every neighborhood has its own dynamics, and buyers often respond differently depending on location. Ask your agent about their track record in your area. Have they sold homes similar to yours in size, style, or price point? Their local experience can make a significant difference, from setting the right price to highlighting the lifestyle features that matter most to buyers.
Selling a home is a team effort, and communication is key. Ask your agent how often you can expect updates and what methods they use — phone, email, text, or in-person meetings. Having clear expectations upfront helps you stay informed and reduces stress during the selling process.
In my opinion the best way to start the conversation is with a phone call, 312-523-6383
Preparing to list your home for sale requires more than just decluttering and staging; it means partnering with the right agent and asking the right questions. From pricing strategy to marketing plans and communication style, these conversations set the foundation for a smooth and successful sale.