How to Have Better Customer Service to Win Over Your Users

Andy Cabasso

September 20th


I think a lot of startups think about customer service wrong.

And I want to fix that…

Many startups tend to view customer service as just “support” – answering people’s questions with either email tickets and/or live chat. That’s it.

But, that reductive view misses out on some big opportunities.

For instance, good customer service can help a business stand out from competitors.

Good customer service can help you cultivate evangelist users who spread the word about your product and refer it to their colleagues and friends.

Also, good customer service can help you better retain your existing customers, which is more cost-effective than having to find new customers.

And, it’s not difficult to execute on.

In this article, I’m going to do a few things.

First, I will break down a new way of looking at customer service: a proactive vs. reactive, offense vs. defense approach to customer service – that will help you think of customer service in a new way to help you boost your business.

Next, I will to show you how you can better provide customer service across your business, which will help you better retain your existing customers, and stand out among your competitors to attract new customers.

Customer Service – Offense vs. Defense?

First, let’s talk about this – Where does “offense” and “defense” come into play with customer service?

Typically when people think of customer service, they are thinking of support requests – where users reach out with questions about your product.

At this point, addressing these concerns is being “reactive” – responding to a specific question of a user.

But, in addition to that, customer service can also be “proactive” – anticipating issues that users may have and addressing them before it becomes an issue that they need to reach out to you for help.

This Proactive vs. Reactive approach is what I call the Offense and Defense of customer service.

On the proactive / offense side – you are anticipating your users’ potential issues and addressing them so that a user does not need your assistance.

On the reactive / defense side – one specific user is letting you know that they have a problem and they need your help fixing it.

A support request means that someone was unable to get a solution to their problem, wanted to find the solution, and was willing to reach out to you about it.

For the most part (with some exceptions), I view support requests as a failing on my part. I think, “If I had made something easier to understand, or had better user onboarding, the user would not have needed to reach out to me.”

Here is an additional reason I worry about “reactive” customer service:

There might be plenty of users who do not end up reaching out to you for a fix to their problem. Those people may just end up churning.

Keep in mind: it can cost up to 5x as much to acquire a new customer as to retain an existing one.

This is why it’s better to be proactive than reactive.

By being able to anticipate major user issues and addressing them head-on, you can reduce the number of support requests that you have, and also improve retention by addressing the issues of users who would not otherwise reach out to let you know when they are facing a problem with your business.

Each support request takes resources and time to respond to. I know that, in a perfect world for a lot of SaaS founders, customers would never need to reach out to support – they would all just pay for software and use it, without any issues.

So, that all being said, we still need to figure out how to best provide customer service

There are different aspects to proactive and reactive customer service

The Offense – Proactive Customer Service

Now, let’s talk about proactive customer service.

Proactive customer service entails everything around your customer’s understanding of your product that keeps them from needing to reach out to you for help.

For example:

  • User onboarding
  • Video demos and walkthroughs
  • Drip emails
  • Help docs
  • Blog articles
  • Webinars and demos
  • In-app analytics

For products, it should start with user onboarding.

As soon as a user signs up to try your product, you should be able to walk them through how it works, what to expect, and where to go next.

Without any user onboarding, users will be confused, leave, and never come back. Or, they will hit you up on support to ask a bunch of questions on what to do next.

Beyond that, help docs are super-important.

I know that creating help docs is no fun, but providing responses for frequently asked questions is going to save you from getting the same support questions over and over again.

In addition, one way to help your users better get a deep understanding of your product is to hold regular demo sessions and webinars. In these sessions, you can walk through how to use your product, and allow audience members to ask questions. In my experience, showing how to use your product, tied with real-world examples from users’ use cases, gets them much more invested and moves them along better with your product.

One thing I want to highlight in particular for preventative customer service is in-app analytics.

Do you know how your users are using your product? Do you know what they’re getting stuck on?

Sure, this may sound like a UI / UX problem, but it becomes a customer service problem when they churn or reach out to support because it’s not clear to them what they are supposed to do.

If you have in-app analytics, with a platform like Heap, Mixpanel, or Amplitude, or even Google Analytics to some degree, you can better understand your users, and where they are running into problems.

The Defense – Reactive Customer Service

Reactive customer service is where your customer reaches out to you for help with your product.

This typically takes the form of:

  • Live chat
  • Email ticket support
  • Socials
  • Phone support

Some businesses don’t provide live chat or phone support, or only provide a certain level of service to paid or premium-paying customers.

With each of these channels, the support you are providing is coming when a user is stuck or doesn’t know how to do something within your software.

If it’s a major issue, they can’t move forward at all.

So, being responsive is key.

Whatever channels you choose to have, the number one thing with delivering on them is being quick to respond to inquiries. The faster you respond, the faster you can resolve the user’s issue and the sooner they can keep using your product.

It’s also something that many companies fail on, so being quick to respond to support inquiries can really make you stand out and impress your users.

Speaking of which…

Standing Out with Good Customer Service (or, How to Lose Customers with Poor Customer Service)

If you are an early-stage business, chances are you will probably not be able to compete with all of the incumbents on product alone.

If there are established competitors and brands in your space, it’s hard to stand out as a newer company.

But, one thing more-established brands may not be able to do as well as you is being responsive to your earliest customers and users.

In the early days of any startup in particular, you are in this stage of building your product and developing it, figuring out the direction of where you want the business to go, and by listening to your users and promptly communicating with them, they will feel valued in a way that they wouldn’t from more established players in the space.

In my career, I can think of several times where I have switched using products and services to different competitors because of the quality of support alone.

For one example…

When I was first looking at a particular payment processor, a company with which we would be spending thousands of dollars each month, I had a lot of questions for them. We were going to need to integrate with their API, so we had a lot of development and testing involved.

And every day or so, we would have some questions.

But, their API documentation and help docs were not thorough. So, we had to reach out for support.

The company would reply to us about 24-48 hours later with a simple email reply.

Of course, we would have follow-up questions for them. But, they had no chat support, only email support with a big delay between replies.

This made it difficult for us to make progress on our integration so we could build out our billing platform for our software.

After a few weeks of this terrible support, we made the decision to switch to another platform.

The platform we switched to was much less well-known, so it was riskier, but they had much better support. They gave us a 1:1 onboarding call, had incredibly-responsive live chat and email support. It was like night and day.

So we gave that platform our business. And the product we switched to may not have been as robust as the one we were initially considering, but given how critical support was to our needs and how badly the first company failed us, we were happy we ended up where we did.

This is all to say – good support can win you customers, and bad support can lose it.

And “bad support” doesn’t just mean providing bad answers or poor documentation. Taking a long time to respond, failing to live up to user’s expectations for what is a reasonable amount of time in responding, that’s bad support.

Good support can sometimes seem invisible.

The product works and the user understands everything. Awesome.

Or, the user reaches out to live chat support and gets an immediate response to their query.

But, at the end of the day, your users will have certain emotions tied to their use of your product, whether it’s frustration or excitement, that can be linked to your proactive and reactive customer service, and when colleagues of theirs ask for recommendations, that’s what they will be thinking about when they think of your product.

I will note that providing good customer service is not difficult. The fundamentals are all easy, it just requires your desire to execute on it.

Good customer service is easy, in part, because the bar is not very high.

Many companies that people interact with every day provide terrible customer service.

So, given these low expectations, when you exceed them, you look amazing.

If you think of your average customer service interaction, you might be thinking of:

  • Long wait times
  • Lack of supporting documentation or self-help remedies that address your specific issues
  • Lots of back-and-forth or dealing with different departments
  • Answers that do not actually address your problem

It’s not hard to overcome these common frustrations people have with customer service, so when you do, you look amazing by comparison.

How to Have Good Proactive Customer Service

Here are some quick tips for how to provide great proactive customer service to preemptively address your users’ potential questions.

1. Have thorough help documentation that addresses FAQs and also walks through setup

The more help docs you have, the better.

Help users help themselves to understand your product and every aspect of it.

If there are things that people get tripped up on, create more extensive and detailed help docs.

Customers do read them. In particular, when people reach out to you directly, you may end up referring them to a help doc for a particular issue. This will save you from having to address it over and over again.

2. Walk new users through your product with a user onboarding product tour

A user onboarding tour is helpful so that users can know how to use your product.

Without any sort of product tour or demo, they have to figure out your software themselves. And then they might start by doing things you don’t want them to do. Guide them. Show them what they should look at first and how they should navigate your software.

3. Educate new users about your product through drip emails

When a user signs up for your product, send them a series of educational emails to help them more quickly master your product.

Each email should be dedicated to one specific aspect of your product – like a demo video, case study, walkthrough, or something else – so they can get up and running faster.

4. Have a library of video content showing how to use different aspects of the product

Videos are especially helpful to help customers understand your product. Seeing your product in action can be more effective to make things click for users.

One other benefit is for people who are not native English speakers and don’t want to read through English help docs. As an example, my company’s help docs are all in English. On a few occasions, users who are not native English speakers have asked if there are videos, in particular because videos showing the steps would make it easier to understand how the product can best be used. Make videos so that your customers know what they can expect once they buy the product.

How to Have Good Reactive Customer Service

Good reactive customer service in particular is an opportunity to “wow” your users.

We already discussed the ideas of having live chat and support tickets, but I want to break these down a bit further with some specific tips.

1. Be quick to reply, even if you don’t have an answer

Whether you have live chat or email support, it’s important to respond quickly.

With some inquiries, you may not have an answer right away. There could be a bug that needs fixing, or someone else on the team you need to confer with. That’s fine.

But, even if you do not have an answer that resolves the problem, taking the time to acknowledge that you have received their inquiry and are working on it helps the user feel heard. And, if they are currently in a frustrated mood, may alleviate that. If a user is upset and you don’t have a quick answer or response for them, they may just get more upset over time with the lack of acknowledgement.

2. Be thorough in your responses

I have personally seen on several occasions how being thorough can win new evangelists and paying customers.

I have received support inquiries from users asking for advice, like, “How can my business, which focuses on [X] best use your product?” Now, you might be thinking, “Well, can’t you read our website and figure it out for yourself?”

But, that’s not great customer service.

So, I would take the time to thoroughly write out a response to suggest what I would do if I was that particular user, given their particular business and their industry. And their reply was one of shock, amazement, and appreciation.

And ultimately, they followed all my recommendations, upgraded from their free trial to paying customer, and ended up recommending us to other people. This was all because I took the time to provide some thorough recommendations and give more support than they might have otherwise expected.

Of course, giving thorough, friendly advice to every customer you encounter is simple enough when you’re only dealing with 1 or 2 enquiries per day. But if you’re struggling to find the time to give every customer the attention and care they deserve, this is the first indicator that it’s time to scale up your support offering. Thankfully, experienced customer care agents aren’t in short supply — especially now that hiring internationally is equally as feasible as sourcing local employees — so if you’re having trouble, don’t be afraid to draft in some extra help!

3. “Thank you for reaching out”

Customer service emails can be a wild card. Some might be pleasant. Others might start off irate.

As a rule of thumb, I typically like to start every response with, “Thank you for reaching out.”


In this sentence, I am both acknowledging their message and issue, and also setting a tone for the rest of this conversation.

By thanking them for reaching out, you are acknowledging their issue and making them feel heard.

You are also setting a tone that says, “I want to help you solve this problem.”

If the customer is frustrated, annoyed, or confused, this statement can also help to “lower the temperature” of the conversation and put you onto a path of problem-solving. Sometimes customers want to complain or vent, but that won’t help you solve their problem. So, starting off with this statement can serve to acknowledge their frustration without being combative or defensive.

Then, you can segue into a problem-solving approach to help get their issue resolved.

4. Aim towards a solution, and never get defensive

Emotions can run high with frustrated customers, but taking a defensive tone won’t often help when people are acting out of emotion. In fact, it can make things worse.

So, when addressing customers’ issues, take the time to acknowledge the issue, and then provide solutions. Even if the solutions are not ideal or what the customer will want to hear, offering a solution shows that you are trying to resolve the issue.

5. Keep track of regular support questions to make new help docs, or UX revisions

If someone is reaching out to you, it’s because they can’t figure out how to do it themselves – because something is not obvious to them.

So, the problem is either:

  • a) the solution is not abundantly clear from your product;
  •  b) there is no quick, obvious self-help answer to the problem; or
  • c) the customer is a jabroni – but, start with A and B before jumping to C

Over time, you will notice if many customers have the same issues. Take notes. If these problems are persistent, you might want to beef up your help docs or make adjustments to your product so that people do not keep running into this issue.Consider getting a time tracking system to keep up with how your team treats customer support and cover any gaps.


By having customer service that takes both a proactive and reactive approach can help you better serve and retain your customers, and get them to spread the word about your business. Happy customer will even consider reviewing your product without any incentives. Learn more on how to get more product reviews.


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