A customer got upset with me, saying I was not being transparent.

★ signal-weak r/smallbusiness · ↑ 174 · 💬 83 · 2025-11-03 · kw: review response template · open on reddit ↗

Tool

none

Issue

Customer perceived optional insurance presented during booking checkout as pressuring/non-transparent despite clear opt-out option, causing customer anxiety and complaint even though business owner followed standard upsell practice with disclosure in confirmation email and verbal explanation.

Cost

unstated

Recommendation

Automate customer communication and remove post-booking insurance offer page to reduce perception of upsell pressure; test alternative booking flow placement for add-ons (disputed—commenter suggests this may harm conversion)

extracted with

anthropic/claude-haiku-4.5 · 2026-05-08

Body

I run a boat rental business and recently partnered with an insurance company to offer optional rental insurance. I made it optional because I did not want to force customers to buy it, even though it costs me a lot to provide the option. I already carry liability insurance, but if a customer damages the boat, they are responsible for those costs. The rental insurance offers several affordable plans to give customers extra peace of mind. After this customer made his reservation, I called him to review the meeting location and details, which are also included in the confirmation email. I like to do this personally to make sure everything is clear and to answer any questions. I also explained that he would receive a second email where he would need to sign the waiver and other documents. After that, the rental insurance page would appear, clearly marked as optional, and he could choose to decline it. He became irritated and said I was not being transparent and that he did not appreciate it. I explained that the insurance is completely optional and that we only offer it because other customers have requested it. It is even mentioned at the beginning of the confirmation email. He told me I had ruined his fun and said he felt obligated to buy insurance. I repeated that he did not have to purchase it, but he said, “Well, now I am worried something might happen during my trip,” and then he hung up. I am honestly confused about how I was not being transparent. If you rent a car or book a flight, they always offer optional insurance. It is the same concept. I just want to make sure my customers feel safe and protected, not pressured.

Top comments (8)

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[score=209] Sentient-Exocomp

Sounds like you may avoid a problem customer.

[score=353] cubswin456

This is just a bad customer - keep doing what you’re doing.

[score=57] theonlybuster

This reaction is exactly why I automate customer communication where possible. Some people go out of their way to look for things as it sounds like this guy did. And while it's not every customer it's enough to discourage me from going the extra mile in this way. The first e-mail went out as a confirmation, the second email went out which included the optional insurance. As long as it's clear what is optional and what's required, let the automated system do its thing. If the customer has a question after receiving the emails, then address it. But until then, I remain hands off. And I get it, you're trying to provide excellent customer service, but today it's typically best to assume the customer knows/understands unless/until they reach out with questions or needing additional information. To be clear, HE'S the problem, not you.

[score=36] muchoqueso26

That problem solved itself.

[score=19] [deleted]

You will never make em all happy. Cancel and move on.

[score=15] Boboshady

This is the customer's problem for the most part, so no harm done...but if you're noticing a lot of people are dropping off at the insurance page, then you might want to think about testing some alternative routes to booking completion. Note, I'm not saying you've done anything wrong at all here, just that you could potentially convert those people who are upsell / add-on averse like what happened here to potentially another successful rental. The problem is, people see that second page and think "why are they trying to sell me insurance now? If I needed it, why isn't it included?" They might even go so far as to start thinking along the lines of "this is how they get you" - and a that would be both ends of that scale - "they sell you insurance you don't need!" AND "they'll screw you for any damage at the other end, and tell you that you should have bought the insurance!!". Obviously neither are true, but people - bloody hell. Instead of making the insurance optional in an additional step, try showing both options on the same page - still making it super clear one is WITH accidental damage insurance, and one WITHOUT. Maybe add some wording that the expectation is they bring their own insurance or take the risk, on their wallet be it. Maybe even try just one price - with insurance included as standard - and having the option to REMOVE it, instead of add it. You just need to be careful about how you can advertise your pricing then, so you don't price yourself out of the market against competitors who don't include insurance. The reason these kinds of approaches can work? You're making them feel more in control - making their own choices, kind of thing. It's not an upsell when the options are all presented the same page, it's an informed choice. Do note however that sometimes, the smallest changes can have the biggest impacts, but good AND bad...so whenever you're testing things like this, be ready to be analysing your numbers as close to realtime as you can - have solid baseline figures recorded so you're not just going off 'feel' (though that is also important), and change or revert these changes if they're showing a negative impact.

[score=13] hestoelena

Sounds like that person has anxiety or a prior bad experience with rentals. I wouldn't take it too seriously unless you start getting similar feedback from other customers.