How to really feel empathy with your customers using ChatGPT

“Great salespeople help customers make progress in their lives, on their terms" - Bob Moesta

Normally, in the selling world—which I have always been a part of in one way or another in my career —we are always thinking of ways to sell more of whatever we sell.

If it’s real estate, it’s the right to sell, lease, or buy a property on someone’s behalf.

But in real estate, we are a product looking for a problem (someone needs somewhere to live or somewhere to move).

Nigel Dalton, a social scientist at Thoughtworks and well-known to the real estate industry, recommended I read a book by Bob Moesta called Demand-Side Sales 101.

So, I took his advice and read the book, and it changed much of what I thought about sales and marketing.

Supply-side vs Demand side

Moesta says the ‘default’ sales perspective – focuses on the product or service and its features and benefits.

This is the ‘Supply-Side’ - often the approach of more inexperienced salespeople.

A standard real estate listing presentation is highly likely to be' Supply–Side' if it centres on the features and benefits of listing with you (whether it’s PM or sales).

On the other hand, the ‘demand-side’ perspective tries to understand how people buy things and then helps you design your product – and your sales and marketing strategy – by looking at the situation through their eyes and meeting their needs - aka ‘solving the struggle’.

I won’t recount my whole article here, but if you’re interested in learning more about how Mark and I made some personal real estate decisions, the article is here.

The bottom line is that you need to be able to see things the way your customers see them.

Today’s prompt of the day

It turns out that if you’re having a hard time doing this, ChatGPT can help you here, too.

If you can figure out someone’s pain points and solve them (or at least empathise with them), the experience can be completely different for everyone involved.

Here is a generic fill-in-the-blank prompt:

Compose a 500-word heartfelt diary entry from the viewpoint of [your perfect customer] who is grappling with [challenges]. This individual experiences [feelings] and aspires to achieve [desired results].

And now here is one completed for an all too common ‘real estate’ situation:

Compose a 500-word heartfelt diary entry from the viewpoint of a homeseller who is grappling with a divorce, who is struggling to find somewhere he can afford that the kids will love coming to visit Dad. This seller is experiencing a fair bit of anxiety with all the arguments and uncertainty at home, and realistically wants to achieve a comfortable pad - even though its not the big house - so the kids who are 8 and 10 would like to come to visit.

The response from ChatGPT is a little bit sad for a Tuesday night, but it’s also a reality check.


Dear Diary,

Today has been a whirlwind of emotions. The heavy weight of my divorce and the battle to find a new home that I can afford and that my kids will love has been overwhelming. I never imagined I'd be in this position, but here I am, a father of two amazing children, grappling with the reality of a broken marriage and the uncertainty of where we'll all call home. Anxiety is a constant companion these days, and the arguments between me and my soon-to-be ex are taking their toll.

As I searched for houses today, I couldn't help but think of how much simpler life was before all this. I miss the days when we were a family, and I wish I could turn back time to when my kids' laughter filled every corner of our home. But life has a way of moving forward, and I need to adapt to the changes and focus on what's truly important – my kids, Jack and Emily. I want them to have a happy and stable environment, even if it means moving to a smaller place.

I've been scouring the real estate listings, trying to find something that suits our needs without breaking the bank. It's been disheartening to see how expensive housing has become, and I worry about how this will impact our ability to find a comfortable home. I can't help but feel a sense of defeat as I look at the listings, knowing that the big house is now just a dream. However, I have to remind myself that a house doesn't make a home – it's the love and memories we create that truly matter.

I've been visiting different neighbourhoods, trying to find a place that will be perfect for my kids. They deserve a safe and nurturing environment, where they can thrive and be happy. I want them to look forward to visiting their dad and feel excited about coming over. I've been considering apartments, townhouses, and small houses, keeping an open mind and hoping that something will catch my eye.

While the process has been emotionally draining, I've also had moments of hope. Yesterday, I visited a cosy townhouse that seemed promising. The living room had a fireplace, perfect for snuggling up with Jack and Emily on chilly nights. The small backyard had enough space for a swing set and a garden, where we could grow our own vegetables and flowers. I could almost picture our weekends together – grilling on the patio, playing board games, and creating new memories.

But the real estate market is competitive, and I can't help but worry that someone else will snatch up that townhouse before I can secure it. I wish I could find a way to alleviate my anxiety, but the uncertainty of the future continues to haunt me. I know I have to be strong for my kids, and I must put on a brave face despite the turmoil within.

In the end, I will do everything in my power to provide a loving and welcoming home for my children. I might not be able to give them the big house, but I will ensure that they always have a place where they can feel safe, happy, and loved. I hope that in time, the pain of the divorce will fade, and our family can find healing and happiness in our new reality.

Until then, I'll keep searching, holding onto the hope that our perfect home is just around the corner.

With a heavy heart, A hopeful father.

Can we all agree that what this customer needs most probably isn’t a branded bottle of wine?

What he might need more…

  • A referral to someone you know who is perhaps upgrading their furniture and has some comfy things to sell.

  • Someone who has a barbeque for sale second-hand.

  • A guide to growing vegies at home.

  • A referral to the local security company.

  • A guide to the kid’s parks and bike tracks in the area, locations of family-friendly cafes and restaurants.

  • Expert leadership through the transaction when uncertainty creeps in - and patience through the tough days.

And, of course, ChatGPT can’t know all that about one person, but what this gives you is a little insight into the types of questions you could ask your customers to find out what’s really going on for them. (Do you have a barbeque, are you a gardener, what sort of food do the kids like, what sports do they play… etc etc)

If you can do that, then you might start to help them solve their struggle.

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