Selling
Most sellers interview two or three agents and choose on instinct: who seemed nicest, who suggested the highest price, who they met first. It is an understandable way to make the decision and a poor way to make it. You are hiring someone to run a six-figure transaction on the largest asset you own, and the interview is the only part of the process where you hold all the leverage.
The good news is that you do not need to know the industry to interview well. You need five questions and the patience to listen to how they are answered. Here they are, along with what a strong answer sounds like in the Midland, Penetanguishene, Tiny, Tay and Wasaga Beach market.
1. How did you arrive at this price, and can you show me the sales behind it?
Any agent can name a number. The number is not the answer. The reasoning is the answer.
A strong response walks you through the specific comparable sales: which homes, what they listed for, what they actually closed at, how long they took, and how the agent adjusted for the differences between those homes and yours. On Georgian Bay those adjustments matter more than almost anywhere, because two homes on the same road can be separated by shoreline type, water depth, exposure, road access in winter, and whether the property is a four-season residence or a seasonal cottage. An agent who prices Tiny waterfront the way they price an in-town Midland bungalow is not pricing at all.
Be especially careful with the highest number in the room. Suggesting an ambitious price costs an agent nothing at the listing appointment and costs you months afterward. Overpriced listings accumulate days on market, that history is visible to every buyer and every agent who looks, and the eventual price reduction often draws lower offers than an accurate price would have attracted in the first two weeks.
2. What exactly is included in your marketing, and who pays for it?
This is where vague answers become invoices. Ask for the marketing plan in writing before you sign anything, and ask three sub-questions: what is included at no cost to you, what is optional, and what gets billed back.
For a Georgian Bay property the list worth confirming is short and specific. Professional photography. Drone or aerial footage, which for any waterfront or acreage property is not a luxury, because a single aerial frame communicates shoreline, lot depth and setting in a way that ten ground-level photos cannot. Video, and whether it is a produced walkthrough or a slideshow of the same stills. Floor plans. Where the listing gets distributed beyond MLS, and whether any paid promotion is running behind it.
If the answer to most of this is that it depends on the property, that is a fair answer, provided the agent then tells you what it means for your property.
3. Can I see the last three listings you marketed?
Not the best three. The last three.
Curated portfolios show what an agent can do at their peak. The most recent three show what they actually do on an ordinary Tuesday, which is the version you are buying. Look at the photography quality, whether there is video, how the copy reads, and how the listing presents on a phone, since that is where nearly every buyer sees it first.
This question also surfaces something more useful than any answer: whether the agent hesitates. An agent whose standard is consistent has nothing to manage here.
4. Who will I actually be dealing with?
Agents work in different structures, and none of them is inherently wrong. Solo agents, partnerships, and teams with assistants and coordinators all sell homes successfully. What matters is that you know before you sign, not after.
Ask specifically who handles your showings, who calls you with feedback and how often, who is physically in the room when offers are negotiated, and who to reach on a Sunday when something goes wrong. Negotiation is the point in the transaction where the difference between people is measured in real money, and you want to know whose judgement is being applied to yours.
5. What are your numbers, and will you walk me through them?
Ask how many homes they closed in the last twelve months. Ask their average list-to-sale ratio. Ask how long their listings typically take to sell, and how many did not sell at all.
That last one gets skipped most often and tells you the most. Expired listings are a normal part of any real career, and an agent who can talk about one candidly, explaining what happened and what they would do differently, is showing you exactly the judgement you are hiring.
Ask for these numbers face to face rather than looking for them on a website. Production figures without context are close to meaningless: a high transaction count can come from volume at a lower price point, and a strong list-to-sale ratio can come from pricing conservatively. In a listing appointment you can ask the second question, which is the one that matters. Any agent worth hiring will put the numbers in front of you and answer it.
What the five questions are really testing
Read together, these questions test one thing: whether the agent has a system or a personality. Both feel good at a kitchen table. Only one of them still works in week seven when the showings have slowed and a decision has to be made about price.
The agent who can show you the comparable sales, hand you a written marketing plan, pull up their last three listings without flinching, name exactly who does what, and talk plainly about the listing that did not sell, is telling you they have done this deliberately rather than hopefully.
Interviewing agents in Midland or on Georgian Bay?
Jonathan Wallace is a full-time REALTOR® with Faris Team Real Estate, Brokerage, working across Midland, Penetanguishene, Tiny, Tay and Wasaga Beach. Bring these five questions to the appointment, and bring them to every other agent you meet.
To start, get a valuation on your home or see how the selling process works. If you would rather just talk it through first, that is usually the better place to begin.
Jonathan Wallace, Salesperson, Faris Team Real Estate, Brokerage. 705-433-2525. Rated 4.97 on RateMyAgent. 2025 Midland Readers' Choice, Best Realtor.