What to Expect When Shopping for Support Software
Illustration by Meg Lewis

Every time I need to buy a pair of jeans, I trick myself into thinking it’ll be an easy process. I’m sure I can simply order from the last place I bought them or just check a few stores. Inevitably, the place I ordered from last time changed something about the fit or material, and the in-store options are lacking.

I end up making a bunch of trips, printing out shipping labels like it’s a part-time job, and still have no denim to show for the trouble. If only I remembered the last time and wrote my future self a note; at least I’d know what to expect going in and be able to plan accordingly.

The truth of the matter is any number of purchases tend to go the same way. Take, for example, buying support software. It might seem like a simple task on the surface, but once you start getting into the weeds, it can quickly become overwhelming.

In my experience, the best way to limit frustrations and have a successful search is by properly setting expectations upfront and going in with a plan.

In this article, we show a realistic view of what you can expect when purchasing support software, plus some tips on how to best approach the process to make it as painless as possible.

Answer these 3 questions before you start shopping

Whether you’re starting from scratch or making a change, selecting a new support tool is a big undertaking. Though there are bound to be bumps in the road, a strong initial game plan can help mitigate any number of issues.

There isn’t one approach that's perfect for every team, but answering the three questions below is a beneficial first step for anyone beginning their support software search.

1. What are you looking for in a support tool?

It’s hard to find the right tool if you don’t know what you’re looking for. For teams searching for their first support tool, think about your current needs as well as your projected future needs.

For example, you may only plan on offering email support initially, but you know within the next year you want to add chat support. Since you don’t want to switch tools every few years, it’s good to try to anticipate those future needs.

If you’re switching from a current tool to a new one, it may seem like you’re best served focusing on where your current tool is lacking, but that could be a mistake. Though you do want to address any deficiencies, you also need to list out what’s working well in your current tool. If not, it’s possible you’ll end up just trading one problem for another.

Whether you’re new to support software or switching from one product to another, consider setting up a search committee. Getting multiple perspectives means you’re less likely to miss something.

Pro tip: It's also helpful to have diversity of position, background, and seniority level in your search committee. For example, managers and agents have different perspectives, needs, and wants, and all of them should be considered.

You could even send out a team survey to see what people are interested in for a new tool. Similar to forming a committee, it helps bring in new perspectives and gives a broader view of needs and uses for a support tool.

This is even more important when looking for support software, as it’s common for teams outside support to also use the tool. For example, sales may use the shared inbox or chat features to interact with potential leads, or product and marketing might use metric insights to better understand customers’ wants and needs.

Make sure you consider all the potential uses and stakeholders when starting your initial search, which will mean less work later on.

2. How urgent is your need?

It’s nice to envision a world where you have all the time you need to search through tools, sit in on demos, and gather every detail. However, that’s rarely reality. When you’re starting your search, it’s important to be very honest with yourself about how much time you actually have to find a solution.

However long you think it’s going to take to find a tool, double that timeframe. That may sound extreme, but it’ll help you set expectations for others. And if you finish early, chances are people won’t be upset.

If you know you need a tool quickly, you should have fewer initial tools to review.

You may also consider a “divide and conquer” approach, where each person on your search committee does independent research on a tool using some sort of scorecard to grade each option. Then each can present to the group and you can make a decision on how to move forward.

If you have a little more time, you can have a larger base pool of tools to look at and can schedule more demos. Even in this scenario, it’s probably good to have some sort of scorecard to objectively measure each tool and easily compare them side-by-side.

3. Do you have any constraints?

As mentioned above, you may have a time constraint, but there are others to consider as well. For example, many teams have some level of budget constraint. Though some may have a blank check, it’s hardly the norm.

Another aspect to think about is any constraint you have as it relates to connecting to other tools. For example, if you’re currently using a certain CRM, you probably need a support tool that integrates directly with it. It’s important that any new tool you invest in fits well with your current software stack.

Ask about the integrations the tools you're considering offer — both native and third-party. Also, be sure to get clarity on the support they offer with integrations. Can someone help guide you through the process? Or is it totally up to your team to implement them?

One last thing to consider is any constraint you have around the type of company you want to work with. Though it may not weigh as heavily as some of the other constraints, it’s possible a company could have policies or practices that don’t align with your own values.

Create a shortlist of support tools to consider

After you’ve answered the above questions to get your bearings, you’ll want to put together a shortlist of potential tools to consider.

As with any purchase, a great place to start is reading reviews. Sites like G2 and Capterra are great resources to see how different tools rank. You’re even able to do side-by-side comparisons to further evaluate different product areas that matter to you most.

After reading reviews, consider reaching out to other support professionals in your network to see if they have any additional insights or tool suggestions to offer.

Outside of personal connections, you can also check out different online communities to source some more perspectives. A community like Support Driven can give you access to a large number of support professionals who may be able to further aid you in your search.

You should also consider reading through different tool roundups. Help Scout’s guide to the best customer service software for small businesses is a great example of the kind of post you may want to seek out.

Evaluate the tools on your shortlist

Once you have a shortlist of tools you want to consider, you need to dive deeper to better understand each offering and how well it matches up with your needs. Things like demos with a salesperson and hands-on experience with a product are helpful in fully understanding any software you’re considering.

Talk to salespeople

When purchasing support software, it’s common to interact with a salesperson. Sometimes you can completely self-serve, but when you do interact with sales, you can expect a process like this:

  • Fill out some sort of sales request form.

  • Get qualified by a BDR or SDR (this is more common when purchasing from larger companies).

  • Do an initial demo call with a salesperson.

  • Do a secondary sales call for any deeper information.

The idea of talking to a salesperson is anxiety-inducing for some. It’s easy to assume they’ll be pushy. However, the truth of the matter is most salespeople take a consultative approach; they’re more laid back and less pushy.

That said, at the end of the day, salespeople have quotas to hit, and selling is their job. So will they try to persuade you to buy? Of course. However, you can take precautions on your end to guide the process:

  • DO be upfront with the salesperson. Let them know where you’re at in the process and the role you play. By doing so, you can help guide the conversation from the start and limit time spent on areas you’re not worried about.

  • DON’T give them contact information for any channel (phone, etc.) you don’t want to be contacted on. It helps limit unwanted messages and keeps you in control of the conversation.

Pro tip: Consider creating an email address specifically for scheduling demos and talking with salespeople. That way you have further control and are able to get distance when needed.

  • DO be sure you ask all the questions you need answered. Salespeople know their products very well, so don’t shy away from using them as a resource.

  • DO let them know if you decide a product is no longer in the running. It’s not only the courteous thing to do, it should also stop you from receiving any unwanted messages in the future.

Measure team fit with a trial

Demos and sales calls are great for gathering information, but in order to truly understand how a tool works, you need to actually use it. Many support tools offer the ability to try the product out, and this is something you should do.

Most of the time, there’s a trial period of around one to two weeks. In those cases, you usually have full access to all features of the product. For some, after the trial period, you’re moved down to a free plan with a limited feature set. For others, you’re simply locked out of the account after the trial.

Since it’s a bit more involved, chances are you’ll want to limit the number of trials you pursue. Research shows having too many options starts making us more indecisive and less satisfied with our final choice, so you should keep your number of trials lower — probably around three to four options.

If possible, it’s great to have other team members work out of the trial account, too. Similar to your search committee, having diversity of role and seniority level is also something to aim for when picking testers. Remember, there are nuances of use, and in order to fully understand team fit, each use case should be considered.

You may also consider using the same scorecard from before — or a slightly updated one. It allows some level of objective measurement and also makes it easier to compare tools side by side.

One last thing you can do is actually reach out to the support teams for the final contenders with a few questions. By doing so, you’ll get a better idea of the level of support they offer and what you can expect if you decide to become a customer.

The truth is there’s no perfect way to truly measure team fit outside of having your whole team use a tool for an extended period of time, so it’s important to be as thorough as possible with the resources you have at your disposal.

Decide which tool is right for your team

After all the due diligence, picking the right tool should be a no-brainer, right? Well, it may be a little more complicated than that. People might have differing opinions, or one tool may address a specific need better than another.

Basically, even after doing all the research, things could still be a little murky. Fear not, though: A few more steps should help provide more clarity and help you on your way to picking the right support software for you and your team.

Do a final review

As with most things in life, when you’re right in the middle of something, it can be hard to get perspective. As famed statistician Howard Moskowitz says, “to a worm in horseradish, the world is horseradish.”

By taking a step back to do one final review of all the tools, you’re able to gain that much-needed perspective. If possible, consider taking a weeklong break after your final demo call or trial to ensure you’re able to look at things with fresh eyes.

Once you’re ready, compare each tool based on the scorecard you kept. Reviewing them side by side should offer some additional clarity. Along with scorecards, you should note any other product nuances you noticed during demos or trials that could impact your overall decision.

If there were others involved in the process, this is a good time to meet up and compare notes. It’s very possible you may have a bias toward a certain tool. By engaging with other opinions, you’ll limit the effects of any bias you may have.

Ask for outside help

Sometimes the people who are most able to help you gain perspective are those completely outside the process, who may be able to give insights you would’ve otherwise missed.

When looking for an outside opinion, there are a few things to aim for:

  • Make it a safe environment. When you’re bringing someone in from the outside, they may be hesitant to be too critical. Let them know upfront that nothing they say will be taken personally and that they’re free to share all their thoughts and opinions.

  • Go to a different department. There are many studies showing the benefits of getting diverse perspectives. Remember, what you’re after is someone who’s able to see things you can’t.

  • Listen to their feedback. The only way you get any true value out of this exercise is if you’re willing to really hear the feedback offered. Keep an open mind, and you’ll get the most benefit.

Though you could realistically benefit from an outside opinion anywhere in the process, it’ll probably best serve you at the end when making choices is a little more difficult. You also want to limit how much time you ask of someone as this will almost certainly fall outside their standard scope of work.

Present your findings

Depending on team structure, you may have to present your final choice to a manager or someone else for approval. Articulating why you think one tool works better than another is a great way to narrow the field.

When you were simply thinking about how the tool would benefit you and your team, it’s possible you may have overlooked something. However, presenting to gain approval from an outside party can help you think critically and may actually end up changing your opinion. Even if you don’t have to present for approval, it can be a great exercise if you’re struggling to choose between two or three options.

If you do need approval, consider doing a test pitch to solidify your talking points, get feedback, and maybe even surface some other objections that you weren’t thinking about previously.

Manage your expectations to find the right tool

Buying support software can be a big undertaking, but it shouldn't be something you dread. When you plan ahead and are thoughtful about the process upfront, you’re able to limit some struggles and set expectations for yourself and others.

As famous TV dad Phil Dunphy once said, “The most amazing things that can happen to a human being will happen to you if you just lower your expectations.” So keep an open mind, seek diverse opinions, adjust your expectations accordingly, and you’ll be set.

Oh, and if you know where to find a good pair of jeans, I’m all ears.

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