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4 Step Guide to Choosing the Best Help Desk Software for Your Business

Choosing the right help desk software for your company can be daunting. Every provider has its own page demonstrating how their product is at least three checkmarks better than anyone else’s. They really should come with a warning:

CAUTION: Exposure to checklisteria is known to cause poor decision making and can lead to chronic buyer’s remorse. If you have been exposed to software feature checklists, please consult your doctor immediately.

The help desk you choose is often the first step in setting up customer support at your company, because it will help you deliver the level of customer service you want to provide.

Of course, making an informed choice starts well before you begin comparing feature lists.

To chooose the best help desk software for you, there are some questions you need to answer about your customer, your team, and your company first.

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From your initial search to final purchase and setup, this (unbiased) resource will help make choosing any help desk easier.

Define the service you will provide

When you’re deep into comparison shopping, it’s easy to forget why you’re picking a help desk tool at all. Here are the most important questions to answer up front:

  1. What do your customers expect? Your specific customer base will come to you with their own requirements. Do they prefer email? Are they comfortable using self-service tools? Do they expect an answer within an hour, or a day? Look for clues as to what your customers expect from you and how satisfied they are currently.

  2. What experience do you want to offer your customers? Imagine the ideal interaction from your customer’s perspective. Do they need to use a website to get help, or can they just email in? Can they choose to contact support via multiple channels? Can they answer their own questions easily?

  3. What experience do you want to offer your support team? Peanuts creator Charles Schulz loved his favorite pen so much that he bought the entire stock when it was discontinued. While your support team may never have the same love for help desk software, they will use it constantly and rely on it heavily. As the first line of customer retention, you want to make sure they have the right tool. A clear, usable and attractive tool will save them time and effort that is better spent on your customers.

  4. What can you change about your current customer service? Whether you’re moving from a shared Gmail inbox or you’re switching from one help desk tool to another, this change is an opportunity to rethink your approach.

For example, many small companies use their support inbox for all types of company contacts, which means their one- or two-person support team handles everything from sales contacts to domain renewal notifications and advertising offers.

Years later, the sales team is still receiving forwards from a much larger and busier support inbox! Choosing a new help desk is a great time to think about streaming those into a separate mailbox or automating their distribution with workflows.

Look at your existing customer service activities and consider the following:

  • Is this still the best way to solve this issue?
  • Is this approach essential to our customer experience, or could we get the same result another way?
  • What is our team capable of now that we weren’t capable of the last time we thought about our tools?

Once you sketch out a clear picture of the customer service you want to offer, you have a goal to measure help desk features against. Whatever you choose, it needs to help you deliver the type of service you outline.

Refine your choices

Now it’s time to go one step further and create your list of essential features and “nice to have” features. Ask your customer service team to write down all the customer service tasks they can think of, and sort them into two buckets.

What are your essential help desk features?

Help desk software that has your essential features beats a tool that implements more “nice to haves.”

Essential features: If the help desk does not do X, then we cannot create the customer service experience we want to provide.

Non-essential features: If the help desk does X, we could potentially make use of it to improve the customer experience.

Keep the first list as short as possible. There’s a reason your butcher carries just a few high-quality knives instead of the world’s biggest Swiss Army Knife on her belt.

Features that sound good on a list but are poorly implemented or rarely used inhibit good service by frustrating your support team.

By focusing on your core requirements, you can reduce the amount of work it takes to choose the best fit and give yourself more time for testing your shortlisted help desks.

How to evaluate help desk features:

  • Does this feature need to be built in to the help desk, or could we connect a separate tool that does the job better?
  • Are there legal requirements we need to meet (e.g., data storage and privacy controls)?
  • What value does this feature add to our customers? To our team?
  • Are there technical requirements to meet (e.g., data format and accessibility)?
  • What other products or services do we need to connect this to? Is it possible?

Shortlisting help desks

Now you can exclude from consideration any products that don’t cover all of your required features (either directly or by tight integration). The next step is to create an evaluation team to test your shortlisted help desks.

If you’re just starting out, or at a very small company, the evaluation team may be just you. If you have a larger team, we recommend the following mix:

  • One junior level customer service person
  • A couple of help desk power users
  • A manager or senior leader

Combining their different needs and backgrounds will give you a more effective way to tell if the help desk really will be a good fit for your whole organization. We also recommend you get the whole evaluation team looking at the same tool at the same time, rather than each person reviewing a different option.

Effectively trialing a help desk is tough, because you’re never going to be able to use the tool in exactly the same way you will when you’re handling real customers at your full volume. Here are some of the most important features you’ll want to evaluate. Choose your top few options, the tools you’ll spend significant time investigating.

Customer experience

Use some of your typical customer questions as examples, and complete a support conversation from the customer perspective. What will the customer see? How easy is the process for them? (Help Scout, for example, has no customer-facing portal or ticket numbers, so your customer only receives personal emails.)

Consider the experience you want to create for your customers, and test that against each tool.

Help desk user experience

Your customer service team will be using this tool all day, every day. How easy is it for them to navigate around, how fast does it load, and how quickly can they find answers? The help desk you choose should, as much as possible, be frictionless for your team, allowing them to use all their energy helping customers and not fighting their tools.


Will this solution continue to work as your business grows? Help desk sales and success teams should be able to share with you an idea of their bigger customers’ support volume. You don’t want to pay huge fees for more software than you need, but you also don’t want to have to pick a new help desk 12 months from now.

Related: Scaling Support on a Growing Team


Testing reporting is tricky when you don’t have real data to report. Demonstration accounts can give you a sense of the possibilities. If you’ve thought carefully about which customer service metrics you use and why, talk to the help desk provider about how they can help you get those results with their tool.

Reliability and support

Who supports the support team? When the help desk has an outage, when a feature is confusing, or when a process needs reworking, how will you get help? Not only do you need to know what support channels are available, but also how quickly you’ll be helped and with what level of competency.

Every software product experiences issues, but some companies do much better than others in handling those situations. Submit sample requests to each help desk support team, and see how timely, useful and friendly the responses are. When you can’t help your own customers because of a help desk issue, a responsive, informed support team is hugely valuable. You can also review the twitter feeds and status pages of your top choices to see how responsive and communicative they are when issues arise.

As well as your own trial experience, you can make use of external reviews and opinions to inform your choice. Customer service communities such as Support Driven are full of people who use help desk tools every day, and they are happy to share their experiences.

Take time to prepare

When you’re ready to make a move, sit down with your team and write down all the different areas you might need to change. Here are a few questions to consider:

  • Do you have contact forms that need to be updated?
  • Will your knowledge base be moving to a new tool too?
  • Do you need to recreate (or rethink) workflows and automated filters in the new tool?
  • How will you train your team on the new tool?
  • Are there integrations to move or reconnect?

Moving to a new help desk is a huge investment in your customer service team, your customers, and — ultimately — your company. A long feature list is nice to have, but you should make your choice with a broader framework in mind. Remember, the cost of picking a tool that works for your team (and your customers) is high, so take the time to make an informed decision.


Your help desk tool is only one piece of the customer service experience. Learn how to build out your customer support department.

Mathew Patterson

After running a support team for years, Mat Patterson joined the marketing team at Help Scout, the invisible help desk software. Learn how Help Scout takes the headache out of email support.

4 Step Guide to Choosing the Best Help Desk Software for Your Business


Choosing Tools

Learn how to select the right help desk for your team, how to evaluate the best customer support tools, and resources and how to smoothly switch between customer service tools when the time is right.

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