You’re reading hot dogs and eggs, a blog by Chris Gallo since 2014.

Advice from the Future

This post will take you about 5 minutes to read.

Over the last six months, I slogged through one of the largest projects of my career. Our team built the new Highrise help site, a glorified, 105 article, user manual for our product. We redesigned everything. Rewrote every article. Reorganized every topic and question. Below is the advice I wish I had before we got started.

Dear Chris,

I’m writing this advice from the future. Several support emails and text snippets from where you’re standing now.

It might seem scary, but the next six months will be some of the toughest and most rewarding of your career. There is sure to be frustration and doubt.

Here is some guidance to help you along the way.


Where do I start? If you find yourself asking this question over and over again, stop.

Just start. Anywhere. Cut it all in half.

Don’t try to write a whole section in a day. Break it apart into smaller pieces. Try writing one article today. That’s it.

Before you know it, you’ll build momentum.

Everything is Temporary

In a matter of days, Highrise went from a product that hadn’t been updated in a long time to having its own dedicated development and support team.

The product is changing fast.

A screenshot you take today will look different next week. It’s easy to balk and not start documenting the product.

If you can’t decide whether to start writing documentation because it will all change soon, stop.

Take a breath. And make a decision. It’s not life or death.

If you make the wrong decision, fix it as fast as you can and move on.

Everything is temporary. Accept it and get going.

Embrace Interruption

You work in customer support. The nature of your job breeds interruption.

A customer can email you at any time. You are managing multiple interactions at once. A team member can ask for help whenever.

Don’t fight it. You can’t win.

Make the time. Start to sacrifice and prioritize.

Schedule blocks of time to work on the help site. An hour on Monday. Two hours Friday afternoon.

Don’t abandon your customers, but if replies are slower for a few hours, everyone will survive.

Interruptions happen. Schedule around them and make the time.

It’s worth it.

Ask for help

You cannot do it all alone. Stop waiting to ask for help. You’re not perfect and you don’t have to be.

You’re surrounded by people that can help you. You’re lucky to be part of a team that is wicked smart and talented. They want to help you.

Ask them. Don’t feel guilty.

The help site is the most important resource for your customers. Your team needs to have a say in it, and be able to pitch in. Their perspective is invaluable.

You cannot do it all alone. Don’t try. Ask for help early and often.

If you ask for help, your team will introduce a concept to you. It’s DRY (don’t repeat yourself).

Don’t write the same HTML to create anchor links over and over again. Automate it. Don’t know how to do it?

Ask for help. Michael can knock this out for you in minutes and he wants to help you.

Don’t write the same article twice. Yes, all the content you’re writing is interrelated. You still don’t have to repeat yourself.

You will write over 100 different articles. You can edit all of them on your own or check to make sure you’re not repeating yourself. But that’s tough.

Ask for help. Wren knows her stuff. She can whip the content into shape and make sure you’re not repeating yourself. Wren can find gaps in the content and write new articles to help customers even more.

If you find yourself doing the same things over and over again, stop. Ask for help and see if you can eliminate some steps.

Play the Long Game

This project is not going to give you immediate results. Let go of expectations and the thirst for immediate satisfaction. It won’t happen.

Anything worth doing takes time.

You will write for hours and feel like nothing has changed. You will believe you’re done with the project several times, only to remember something else. You’re going to put all the videos in the wrong format and have to fix them.

This is where the real work happens. There are no shortcuts.

You cannot estimate how long this project is going to take. Accept it will be done when it’s done. Don’t be afraid to launch, but realize it’s an investment.

An investment that needs to be made long before you see any sign that is paying off.

Keep Going

You’re going to feel relief when the help site launches. Good. Celebrate it and congratulate your team.

But remember you’re not done.

You’ll never be done. The help site you built isn’t a filing cabinet that you’re opening for your customers. Don’t make them rummage around.

Make tweaks and pay attention to what your customers are looking for. Do everything you can to make it easy for people to find what they need.

Don’t stop there either.

You need to create more videos. Take new screenshots. Write new articles.

The help site is not a book that has been published. It’s a living, breathing resource that needs to be watered every single day.

The help site is your best friend. Treat it that way. Take care of it and keep making it better.

One more thing

Share your experience with others. There are people going through the same thing as you that need to hear this. Pay it forward.

All the best,

Chris (from the future)

The new help site launched July 6. It was built by the Highrise team using a combination of Jekyll collections, Swiftype, and elbow grease. Notice a typo, have a thought about the help site, or other questions?

Let me know. I’d love to hear it. I’m @cjgallo on Twitter.

PS - special thanks to @natekontny and the Support Driven community for help editing this post.

TL;DR - check out the gif recap :)