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The Painful Experience of Breaking up with Customers

Breaking up with customers sucks. It’s like any relationship. You’ve both poured everything you can into making it work, but despite all your best efforts something just doesn’t fit together anymore.

Maybe it’s you, or maybe it’s them. Maybe it’s a bit of both. A toxic situation that’s damaging those involved, and those in their periphery. Negativity is a contagion. It spreads fast, without warning and without restraint.

Sometimes the best thing for everyone is to recognise your own failures and part ways in as amicable a way as possible.

In a customer-centric, bootstrapped startup like HelpDocs, relationships between customers and the company can feel more personal than in established corporations. This is intensified further when you’re part of such a small team.

HelpDocs is us, we are HelpDocs. We make up the culture. We make the tough decisions and decide on the future of the company.

In the short time I’ve been with HelpDocs, I’ve come to feel like I’m part of something important. That what we’re doing matters, and the brand is an important part of my life.

The relationships we cultivate as a company and a service become our relationships—albeit as an extension of our work life.

I think it’s that personal approach that makes us different, though. We are emotionally invested in the success of the company. We measure success by happiness, and judge our work on what feels right. It’s fair to say emotion is tied up in the company.

My point is, in such a small team within a customer-centric, bootstrapped startup, it’s hard not to take things a little personally.

Jake touched on this in this talk for Missinglettr’s Uppercase conference. If you missed it, you should check it out!

It’s an alien concept for me. 👽

I’ve never heard of any company breaking up with customers—for want of a better term. Least of all a startup—where growth is purported to be everything.

For better or worse, it flies in the face of everything I’ve learned throughout a career selling and marketing in various forms. In any other job, my goal has been to convert and retain at all costs. No matter what. At HelpDocs, not so much!

Because we care too much about our customers to keep them in a toxic relationship.

Counterintuitive as it might sound, breaking up with customers is the hardest part of being customer-centric. And it can happen for myriad reasons. Perhaps a customer wants features outside our scope or roadmap, or want more from us than we can easily give as such a small team. There’s only so much we can give before we have to reassess the relationship.

Of course, we do what we can to avoid a break up—Doesn’t everyone?

But sometimes, the hardest thing to do is the right thing to do. Sometimes you need to own your shortfalls, and find a resolution that offers the best experience possible. Sometimes that means breaking up.

This has been on my mind in a big way, because a few weeks ago I experienced my first break up as part of the HelpDocs team.

Dealing with the inevitable

I’d been having a good week. I’d published a post, and was probably planning another one, working on one of our videos or doing something equally productive—because I’m a model employee don’tcha know! 😉

A few support tickets had come through earlier in the day which Jake had been dealing with. And he’d jumped into Slack to get our opinion as a team.

We tend to share responsibilities for support enquiries and it’s not unheard of for one of us—me—to jump into Slack for some advice. But this wasn’t the usual advice-seeking.

In this instance, Jake had taken the ticket and was now on the short end of the customers’ temper—no, that’s not a typo, there were multiple tickets from different users in the same company, about the same issue, within a short space of time.

The short summary is the customers had technical issues with the HelpDocs and wanted to suggest ways for us to improve their user experience.

The longer, more accurate description is the customers were using HelpDocs in ways it was not designed to be used, and causing experience altering bugs as a result. And it wasn’t the first time.

They’d contacted us for a fix, which would usually be fine even in cases of user error like this was. We hate confrontation, so it’s often easier to hack a couple of lines of code than spend hours in a stubborn caps-lock filled stand-off.

This time, though, the customer had opened their ticket with a message designed to berate the platform and belittle those building it. And it wasn’t out of character for them—Jake had a run in with them a few months before.

Jake had responded amicably, not rising to their aggression and instead focusing on the issues they raised. As the conversation continued, it became apparent that it was user error, which was then highlighted to them in amicable terms.

They refused to accept their actions as the root cause, though. Instead, offering their own version of how HelpDocs should work—in their opinion—and demanding we build that version of the service.

It’s easy to see why this caused frustration from both sides. Tempers began to flare 😡 and the break up seemed inevitable.

In hindsight, looking over the conversation logs it’s clear there was never going to be a good outcome.

The customer was no stranger to our support queue. There was often part of our user experience causing them some issue or another. More often, this would prompt a workaround from the engineer team, despite the majority of causes being user error—as I said, we don’t like confrontation.

For any other customer, on any other day would have likely resulted in a fix. But the repeated aggression across many months had mounted. As a team, we dreaded seeing the company name pop up in our tickets.

Our failing was not noticing our misalignment from the multiple previous tickets the company raised. Moreover, we hadn’t set firm boundaries and expectations for their use of the platform.

It’s unfortunate for the cumulative negative influence to build up as much as it did, and as a team we had to reach a decision.

Why we reached our firing decision

Like any relationship, it was a hard decision to come to, and one that took much discussion as a team.

We considered a bunch of different things. Going back and forth as to whether we were reading too much into it, or if it was a communication barrier.

It wasn’t. Jake shared our conversation and ticket history over the past year, and we spotted a pattern of aggressive communication from most of their team. It was consistent, and wasn’t restricted to any one person from their company.

We kept landing on culture, and the customer’s fit with our service.

As a brand and a team, we try to cultivate a culture of positivity—as wanky as that might sound. We measure the success of the company on happiness, both internally as a team, and externally for our customers.

We agreed, the consistently aggressive and negative messages were destructive to that culture. Later in the day, it would also seep into my personal life as I would recount my day with my wife. The negativity was spreading, seeping out from the confines of our work lives, into our personal ones.

It was clear we had to consider whether the cost of keeping the customer happy outweighed the cost of keeping the team happy.

We spoke on Slack for a while longer. We went back and forth trying to figure out the best way to break up with the customer.

We couldn’t just cut ties immediately. We weren’t about to throw their clothes onto the front lawn, or set fire to their property in a fit of anger, like a scene from a bad rom-com. 🔥

Although the issue stemmed from user error, we knew there were failings on both sides. On our part, we needed to get better at educating our customers. We also needed to do better at setting expectations, and recognising when customers aren’t having the best experience.

So, we offered a gradual off-boarding process. We decided to refund the previous month’s charge, and offered the customer 2 months of free hosting while they find a new host for their documentation.

We offered full backups of their knowledge base, and offered assistance in their migration, while keeping communication channels open for anything regarding finding a new platform.

It was a hard, visceral, extraordinary experience for me personally. We have customer churn, like everyone. But being part of a break-up with a customer was intense.

The negativity of it lasted a few days, but as a team, it feels like we did the right thing by us, and by our other customers. It was the only responsible choice.

It became clear we weren’t a good fit—both from a product and culture perspective—and in the end, you can’t force the relationship to work. Sometimes you just have to let go. 💔

The Painful Experience of Breaking up with Customers
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