I need new home insurance. When I last purchased it, I used Square One. The process went like this:

• Type in my home address
• Select the level of coverage I need
• Type in my payment information

That was it. Sadly, I’m not able to use Square in Montreal. So I figured I’d use TD; after all, they’re my bank. Here’s how this process went—and it’s a staggering indictment of incumbents.

• Go to my bank’s website
• Fail to find anything about insurance
• Google “TD home insurance”
• Fill out a simple web form with address, property value. (At this point I’m not logged in or recognized as a bank.)
• After completing the form, I’m given a number to call to confirm things.
• Call the number, and after being on hold for a few minutes, I’m asked if I have graduated from university. I say yes.
• Get transferred to someone else, after being on hold. They ask me where the apartment is. I say Montreal.
• Get transferred to someone else, after being on hold. They start off in French.
• They ask me to prove that I’m a graduate of Dalhousie by telling them “who is the director of home inspection programs at Dalhousie.” I tell them I didn’t graduate with a degree in home inspection.
• I get put on hold for ten minutes. The agent returns and tells me “I asked you that because you were flagged as a caller from Western Canada (I was in Toronto) and we have different deals by region.” She then tells me I should send a copy of my Dal diploma within 30 days, but doesn’t say where to send it or what the resulting rebate will be.
• We’ve now been on the phone for around 50 minutes and I have a conference call to get to. She asks if she can call me back later today. I say I’m pretty busy but she’s welcome to try.
• I get an automatic mail from TD, with a slightly different rate, sent to my inbox shortly after. It, too, contains a number to call.
• At 4:10 PM she calls back. She confirms my identity (even though she called me) and starts asking me questions again, from scratch. I ask her about the email quote I received; she doesn’t know what it is or where it came from.
• She wants to confirm some details about the building. The facts they have about the new apartment are all wrong (they think it was built in 2018; and that it has wood siding—not brick—for example. This despite the fact thatthe person whose lease I’m taking over used them for insurance.)
• She says I have to listen to some disclaimer announcement. It’s automated. I’m put on hold with music for 3 minutes before the AUTOMATIC announcement starts.
• She asks me if I have any items over a thousand dollars. I do (my computer, for starters), so she starts upselling me on things. Then she puts me on hold again to find out whether individual items can be listed that are over a certain amount.
• She comes back suggesting a total of $110K, because my computer is $45,000. She mis-heard me and apparently there are $45,000 computers. I explain that it’s $4,500 taxes in. “Oh,” she says, “I don’t know much about computers.”
• The final quote amount is MUCH higher than the online amount ($35 rather than $23 a month); when I ask why, she says, “well, there is a 12% discount from having done it online but now that you’ve spoken with me, I can’t give you that discount, so I’m going to have to go and find the department and have them add the rebate for you.”
• Some more questions, which I’ve already answered: Do I have a home business; do I rent via AirBnB; etc.
• She starts asking me payment questions. They have no idea who I am payment-wise, because they’re two separate organizations. So the only reason I called TD in the first place—that they already had my information—is moot.
• I’m on hold again listening to music so I can hear another automated message, this time about payment terms. My headphones start to beep because the battery is dying.
• After being on hold with music, and no message, she comes back on saying, “well, if you work from home, we need something different.”
• With no reason to use them (they aren’t affiliated with my bank) and two hours spent on the phone, and being back to square one, I decide I’m going to go find someone else. I can’t imagine what filing a claim would be like.

I feel a bit bad. The sales rep worked in earnest to get me as a customer. She was polite and apologetic. She deserved the sale. But this was atinypolicy ($300 a year.) What’s worse is that I’d been happily paying Square Onesignificantlymore ($40 versus the $23 a month on the TD website) because they were so damned easy to get working.

I kinda wish I could make this into a movie and play it for executives everywhere.

This, right here, is why you’re losing.

No amount of predatory upselling, or bait-and-switch positioning, or even tenacious, well-intentioned employees is a substitute for one thing:

Easy.

That’s it. How do you make it easy? How do you shed the draconian, Byzantine baggage of bygone eras, and make things Just Magically Work? The cost (of the occasional bad policy, of the time spent on the phone) is far outweighed by the ease and adoption.