The Help Center That Everyone Hated

It’s time that I tell the story of the first help center that I ever built.

This introspective tale is one full of mistakes and hard lessons (it’s also incredibly embarrassing).  In sharing this moment, it is my hope that I will be able to prevent at least one person from making the same mistakes that I have.

Once Upon A Time…

The year was 2010, and I was working on my first startup – WorkZero. I had been going strong for three years (the most recent of which was my first full-time year) and was putting in an average of 100 hours a week as the sole technical co-founder. My days would usually start around 6/8AM and end somewhere between midnight and 3 AM. I spent the majority of my time hammering through code, but at the beginning and end of each day, I would deal with my e-mail.

Whenever I got around to it, my inbox would invariably be filled with e-mails from prospective customers, existing customers, and my non-technical co-founders. Almost every day, these e-mails would deal with the same questions.  Sometimes they were previous questions just with a different phrasing.  Other times, they were old topics re-opened as a result of new misunderstandings. This happened again and again and again. I got so frustrated with the problem that I created my first help center.

I thought that would put an end to it. But, even with the new help center, the e-mails didn’t stop.

And, for me, the frustrations started bubbling to the surface. In my mind, WorkZero was a simple concept; I didn’t understand why people couldn’t get it. Why did I have to answer the same questions time and again? I put it down in print as plain as day! What was wrong with them? Why did they hate my help center and feel the need to waste my time by peppering me with questions?! If you asked any of my partners about it now, they would probably say that this was about the time I started to become pretty damn insufferable (if I hadn’t already been).

I ended up walking away from WorkZero two years later; I was tired and needed a change of pace. In the three years since then, I’ve learned a lot of valuable lessons. I’ve also had a lot of great conversations with fantastic people. All of this has resulted in me having the ability to look back and say the following about my “much despised” help center:

1. I Was The Main Problem

The list of my transgressions was many and varied. Chief among these was that my overall attitude was horrible (definitely a topic for another post), my communication skills were almost non-existent, and my empathy for the people asking these questions of me was disgracefully absent.

As a result of living, breathing, and bleeding for a product, the people who build, create, and champion the product will always know more about it than anyone else. The net result is that, no matter what, customers and users (even super-users) will always be at a knowledge disadvantage. I knew these concepts from my time in the consulting trenches, yet somehow I failed to put them together and arrive at the inescapable conclusion that as a co-founder, one of my most important duties was to answer questions and share my knowledge. I was oblivious to the idea that the product was simple to me because I was the one that built it from the ground up. Instead of valuing the opportunity to have the dialogue with people and help them along their user journey, I reacted with scorn, frustration, and disregard.

Someone, please connect me with the Department of Shaking My Head In Disbelief.

2. My Help Center Was Built For All The Wrong Reasons

One of the main reasons that I started working on the help center in the first place is because I wanted to be left alone. I was trying to stop the dialogue that people wanted to have with me. Go ahead and give that another read – I’m not going anywhere.

After building enough help centers, I’ve realized that best ones are a storehouse of conversations. This core aspect makes them excellent tools for extending, supplementing, and/or improving the overall quality of communication and experience for your audience. In the absolute simplest terms I can think of: a help center is a tool to create a better more focused dialogue; not a means to stop the conversation. By being completely oblivious to that fact, I was already starting from a faulty premise.

My help center never really had a chance.

3. I Didn’t Use The Same Language As My Audience

Even if I had started my help center for the right reasons and didn’t have an attitude problem, there was still one more fundamental flaw with how I built my help center – my initial collection of content.

Since a great help center is a storehouse of conversations and communications, this means that the best content for them comes from discussions that have already been conducted.  E-mails, trouble tickets, and sales conversations are all great places to find content.  As long as you retain the original phrasing from the discussions, you will discover that people are ready, willing, and able to connect with your content.

Unfortunately, I didn’t do this.  I had all of the e-mails, trouble tickets, and notes from sales calls.  I could have easily added these items verbatim and left things alone.  However, instead of doing that, I attempted to “optimize” the content and make it match along the broadest parameters possible.  Instead of being an optimization, this had the net effect of completely transforming my audience’s words into my own.

Given my “stellar” communication skills at the time, it’s a wonder that anyone at all managed to connect with my content.

4. I Didn’t Seek Out Feedback

I don’t remember how long it took me to build the entire help center.  I built it from scratch with a dynamic backend, added some simple search functionality, and then had to take the time to write all of the content.  I know it was no less than two weeks and no more than a month. As a co-founder of a nascent business, this is a ridiculous amount of time to spend on something that won’t contribute to sales.

What’s even more ridiculous is that I had no way of knowing whether or not people found my help center content to be helpful in any way. There were no options for voting, no recording of searches. I honestly never even bothered looking at the Google Analytics statistics for the help center pages to see if people were ever visiting them.

Without measuring the quality of a help center, how can you ever hope to improve it and make it more effective? If you don’t look at any statistics, how can you know whether or not you’re even doing a good job guiding people there? And without some sort of feedback mechanism, how can you even know what people think of the content that you’ve written?

The answer is that you can’t. The only thing you truly end up with is frustration.


It’s easy for me to look back on this period in my life and shake my head.  WorkZero didn’t end up eating the world; it didn’t even really make a dent in the universe.  Instead, it made a dent in me.  These lessons that I had to learn the hard way will always be with me.

And hopefully, after reading this, they will always be with you as well.