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Building relationships with customers through support didn't turn out as hoped

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I had an idea when I bought Castro that human support based around actual user experience was an easy differentiator. I’ve rarely gotten useful answers from support from services I use. I thought if I used my own product every day, read every email and answered it thoughtfully, people would appreciate this, and it would build some degree of loyalty and appreciation. This way, customers would feel their subscription dollars were actually going toward something. When emails overwhelmed me, I asked a thoughtful user who emailed frequently and seemed to know as much about the product as I did if he’d help answer the emails, so I paid him to do that. And he did a great job, especially in terms of directly solving user problems.

However, what I found is this whole thing didn’t work as I thought it would. Sure sometimes we were able to wow customers, particularly when we responded right away with an exact fix for them. But the vast majority of our honest, thoughtful answers were deeply unsatisfactory to users, and it often annoyed them more than anything else.

Here are my unscientific categories of support requests/emails we get and why the approach is flawed.

Complaints about subscriptions and pricing

I have already thought about this a great deal. I am not changing anything based on your email. I can of course try to justify why we charge what we do, and I’m happy to explain why an essential app is worth your money, and why software lends itself to subscription so well. But in reality the user is not satisfied with this. I can think of exactly one customer in two years who was surprised that software costs money and we’re actually doing work every day, thus charging a subscription makes sense. 99% of the time, no matter how carefully or kindly it’s explained, the reply will be more negative than the initial email. I tried just offering an additional 30-day trial to anyone who asked, but this didn’t change the sentiment of the emails, and those trials had a substantially lower hit rate than our typical free trials. I could fill several blog posts with thoughts on subscriptions, but suffice it to say, emails about pricing are not helpful in terms of building rapport.

Bugs

These emails are genuinely useful to me, the receiver. I want to know about the bugs people are experiencing on a daily basis. In the best case, I can say we know about this and are actively working on a fix or have already fixed it. Due to the way shipping works in the App Store, it’s common for a bug to be fixed but not distributed yet. Those are great emails to answer and we can satisfy the customer.

But there’s a long tail of bugs that are not like this:

We have heard this before, but we cannot see it or replicate it. The user gets to do work for us and/or get no resolution. Bad experience for them, bad experience for us, mostly a waste of everyone’s time. Very, very occasionally a user will send a detailed report with steps to reproduce or a meaningful factor. Still we need to get these emails to know what people are seeing.

We have never heard this before. User can provide details for us, but if others aren’t experiencing it, it’s unlikely to be prioritized. Still, useful signal for us.

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