Documentation: the silver bullet for your Customer Success team - Glide Consulting
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Documentation: the silver bullet for your Customer Success team

A lot of CS leaders ask “what’s the one thing we can do to be more proactive?”

They want a silver bullet to strengthen their customer relationships, improve communication with sales and seal the deal when renewal time comes around.

You will face the same challenge. Unfortunately, there isn’t just one thing you can do to achieve the massive results your brain thinks you can achieve. Life is a game full of infinite variables, and it’s our job to figure out which ones we have a degree of control over.

The four foundations of Customer Success we’ve proposed are:

  1. onboarding
  2. education
  3. support
  4. leadership

Good onboarding can yield massive improvements in organizational efficiency, but you’re probably at the whim of the product team to deliver features (unless you have a front-end developer who can modify your app on the fly). It’s unlikely you can “fix onboarding” today.

If your company is growing, your Customer Support team is buried. They could try to be more efficient with how they’re batching tickets and improving your auto-responses, but they may never have the chance to be proactive.

Leadership is complicated. There’s no formulaic way to make your team more proactive. There’s no switch you can flick to get everybody on the same page, and ego clashes prevent teams from becoming elite.

So, that leaves you with education. Fortunately, you have complete control over this one! It’s an easy place to start, and you can improve it today in just 15-30 minutes.

Improving your documentation might be the closest thing to the silver bullet you’re looking for.

But let’s face it – improving documentation is absurdly boring. It’s not something people love spending time on. How do you know this is the thing to spend your time on?

If your team says these three things, then you have work to do:

  1. “The customers never read our docs…”
  2. “I’ve sent the same canned response ten times today…”
  3. “If I have to answer that question one more time, I might just lose it…”

As a Director of CS, the support queue falcon-punched my team in the throat every day. We ran into recurring issues we knew better documentation would solve, but we were so anxious to get onto the next problem that we put docs on the back burner. We had a serious case of documentation debt. The 30 articles in our doc backlog hung over my head like a cloud of vultures.

We spent way too much time answering the same questions over and over again. Even worse, there were some features we didn’t even know how to support properly, as we hadn’t gone through the setup and documented the processes ourselves. As such, we had no way of seeing the product through the customer’s eyes, and missed some key UX issues for months as a result. At one point, we “didn’t even have time” to update documentation on old features, let alone the new ones.

Some of our customers felt lost in a vicious cycle of miscommunication and churned. The fatigue my team experienced from answering the same question over and over again was palpable.

Documentation gets put on the back burner more often than not, especially when a CS org spends most of its time reacting to crises.

The quality of your documentation represents the quality of your Customer Success organization.” – Click here to share this quote on LinkedIn

So, how do you know when you have amazing documentation? Your customers will tell you…






Before we dive into ways to improve your documentation today, let’s define what ‘great documentation’ really is.

Great documentation helps your customers achieve a successful outcome without needing your intervention.

Here’s exactly what you can do to move the needle on documentation today:

1. Write for the person who’s using it.

Here’s a simple, three bullet avatar to get you started:

• Write a brief explanation of who they are and what their challenges are:

“Director Dawn has been tasked with rolling out Customer Success at her company. She cares most about finding fast solutions, as she doesn’t have time to strategize or see the bigger picture.”

• What language would this customer use to identify their current problem?

“I’m very new to customer success. I’d like to explore some strategies to get started on implementing a new customer success program for a SaaS company.”

• What are the likely search terms they will use?

  1. “how to build a cs org.”
  2. “cs best practices.”
  3. “cs playbook.”
  4. “cs compensation.”

Now you have an idea of who you’re helping.

2. Pick one workflow/feature you get asked about all the time, then read that doc from your avatar’s perspective.

You do have a document for this workflow/feature, right? If you don’t, skip straight to step 3.

If you do, ask yourself the following questions:

  1. Does this speak to my customer? For example, do you beat a non-technical customer down with technical terms?
  2. Will they be able to find it using their own natural words?
  3. Is it easy to access? At the very least, it would be great to have this link as a canned response in your support ticketing system.

Look at the last emails/tickets you received for this issue and distill them into a single, natural language string. For example, if your customer asks the knowledge-base ‘how do I set up a landing page?’ and the result is ‘how to configure an evergreen webinar funnel’, you have a gap.

3. Thoughtfully write version 2.0 of your doc.

Remember the tweets of people who lavished praise upon companies with great docs?  Check out those companies, and use their help centers for inspiration about how to improve your documentation. You don’t have to reinvent the wheel.

Digital Ocean breaks down highly technical products and features into easy to understand language here.

Like Digital Ocean, FreeBSD explains technology in ‘human’ language. For example,“Can FreeBSD replace my current operating system? For most people, yes. But this question is not quite that cut-and-dried.” That type of honesty is both refreshing and human. Instead of setting false expectations, they set the context and break down their answer in a thoughtful way, the same way you’d write an email to a customer. Read more of this doc here.

Stripe uses a logical breakdown of their products, (Payments | Subscriptions | Connect | Relay) on their homepage to help you take the right path, rather than drown in boring, irrelevant documentation.

Optimizely tells you what you’re going to learn in a few bullet points at the top of their help page. Here’s an example. They explicitly define prerequisites, so you know if the article applies to your particular use-case.

Asana uses natural language to give you the chance to self-select which documentation path you should use, based on which kind of user you are. If you’re a brand-new Asana user, you probably want to know how to use Asana to plan your day. If you love Asana and want to bring your team onboard, you probably want to know how to go about introducing Asana to your team. As an Asana Premium user, you probably want to know how to customize your dashboard.

4. Send your doc to a teammate or manager for review.

You don’t have to bear the burden of writing docs in a vacuum. All it takes is a simple email like this:


You might even grab your manager’s attention because you’re taking the initiative.

5. Rinse and repeat

Don’t try to rewrite your entire documentation stack in one day. Ain’t nobody got time for that, homie. Instead, try and fix just one doc per day. Set a recurring invite in your calendar and you’ll be able to chip away at it regularly, which is how real change happens.


Want some real-life examples of world-class documentation? Watch this teardown I recorded for you:



The #1 excuse we hear from CS organizations about why they can’t get on top of documentation is “we just don’t have the time.” If you aren’t keeping on top of it, who will?

Want more Customer Success Manager insights? Keep reading…

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