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Collaboration & Productivity

Buying Software: 8 flawless tips to make the right choice

buying software

Being connected in a global sphere made us more aware of an infinite amount of software that is continually being launched on the market. But with so many options from the same segment, it gets difficult to know which one is going to be the best for someone’s company. That’s why you need to consider some aspects before buying any software that will directly impact your sales, marketing, finances, and others.

The Buying software journey is getting harder and harder. According to Gartner, a typical buying group for a complex B2B solution involves six to 10 decision makers‚ each armed with four or five pieces of information they’ve gathered independently and must deconflict with the group. A survey shows that more than three-quarters of the customers Gartner surveyed described their purchase as very complicated or difficult.

buying complexityAt the same time, a new software implementation has the power to either boost your productivity and results or to discourage your team, depending on the choice you make. Therefore, you need to follow some steps that will make a difference in choosing the right software for your company. Here we have 10 flawless tips to help you with this process, so you can finally find the ideal software you have been looking for.

As hard as it has become to sell in today’s world, it has become that much more difficult to buy. The single biggest challenge of selling today is not selling. It is our customers’ struggle to buy.

-Brent Adamson, Distinguished VP, Advisory, Gartner

1. Understand your needs

The first step of the buying software process is to think about the reasons why there is a need to make the purchase. Sometimes the software will replace an existing one or will be used for a new strategy. The purpose influences directly on how the search will happen, and also many steps of the way.

Talk to your whole team about this decision, always listening to the problems they usually have. Try to come up with better strategies to approach a particular issue the entire team is facing together.

List all the pains points the business is having at the moment, what is lacking for better development of the projects, and exceptional workflow. If you are currently using a software program and want to replace it, pinpoint its pros and cons, so you can know precisely what a substitute needs to have.

You must have this step figured out before moving to the next one. Try to document everything that has been discussed, so you don’t miss anything that matters on the following tips.

2. Define the software requirements

There are countless software products available right now to solve the pain points of your business. And this doesn’t make your decision more difficult because of one simple fact: just a few of them are going to meet your expectations. That’s why buying good software depends on knowing precisely what you are looking for.

We suggest that once you are aware of your problems, now it’s time to create a list containing all the must-have features that can solve these pains points. In other words, features that are essential for your business. Then you can create a second list of features that would be great to have, but you can go without them.

You are going to have two lists, which will guide you through your process of selecting software, and also facilitate your comparisons. The first is the one you should give focus at first, but the second can be a plus depending on the software you are going to find.

There are some other aspects of the software you must consider besides the features:

  • Integration with other software you already use;
  • Number of users it supports, if you can have just one account for the whole team, or separated;
  • How easy it is to use it;
  • If it has case studies proving its efficiency to meet results similar;
  • How much you can spend with the software;

3. Establish a budget

How much are you willing to spend buying new software? It is something you also need to define before beginning your search, mainly because generally, business software can be expensive and may have additional costs that come along with it.

You need to consider that some costs, such as support and maintenance on the following years after the purchase, are really common. It may be necessary to purchase new hardware so the software can work properly, or costs for training your staff, and many other associated costs. All these must be included in your budget plan.

Estimate the costs and how much you plan to earn after implementing the new software. You should be able to get to a budget when you calculate what you have available to spend, and how much ROI you expect to have in the short term.

4. Identify your options

It’s time to start searching for software companies that sell the type of software you need. It is the stage where you need to find a more significant amount of tools possible.

Your list of features will be crucial for gathering all the software options that have what you need. Take your time and search for as many options as you can.  A survey from Showpad shows that:

“On average, B2B buyers will spend up to 20 hours researching before they contact a sales rep”

To help manage your search time, we have four ways of building your list of potential choices to share with you:

Ask your peers

One great way of adding good options to your list is relying on your peers that are part of the same industry as you. Ask your close connections on LinkedIn, for example, or people from the same business community that probably had the same issues you are facing.

Look into reviews in directories 

Directories are usually divided into various categories of software, and there you can find numerous reviews with the pros and cons of each tool.

You can search for the software in your list in Capterra, a directory that divides software into over 700 categories. There you will find complete reviews, containing the reviewer’s job title, industry, number of employees, and time spent using the software. It can be useful to understand the context of how they are using the software.

Another useful directory to look for software is G2. It works similarly to Capterra. In both directories, you can have detailed information about the product made by the reviewers. You can also see if the review source is organic, which makes it possible for you to know the integrity of the information given. The organic reviews are freely given, without any incentive, and this is some valuable information when it comes to evaluating software.

buying software

Search explicitly about your pain point in the web

Try to search not for terms like “accounting software” or “project management software”, but search for your pain points. Think about things such as “Improving workflow management”, or as the example below “shared inbox in Gmail”, if your pain point is to have software inside your email inbox.

buying software

Look for alternatives when you already have a point of reference

If you already know some options, or if you are looking for a substitute for the one you are already using, you can search for alternatives in specific (e.g.,

5. Look for a demo or free trial

When you narrow down your list of software, there will be more time to invest in analyzing each option deeply. And this in-depth analysis can be very efficient when you try each one of the options.

“Write down specific scenarios for things you want to do with the software. Map it out, so when you get into the demo, you can ask the salesperson, ‘Can you walk us through this scenario?’ Evaluate several vendors through this same objective lens. It’s not just about what features they have, but how would those features work in practice for our organization?”

– David Raab (on Martech)

Usually, the software companies offer free trials of 7, 15, and even 30 days. These trials can save you time and money during this stage. Some companies also provide free guided demos through videoconference, which can be immensely clarifying  If it’s not available on their site – which usually is – you can request a demo.

Consider how fast the system is, how many steps you need to take for each action inside it. Check the interface, if it’s easy to find things and know what every button can make.

Write down everything that you like or dislike about each one of your options. And remember that this process must be done together with your team.

6. Think about the implementation

It would be wonderful if a software magically integrates with your team, right? In the real world, you need to set it up according to your needs. There is an onboarding and trial time for the team to learn how to use it. Besides, there are lots of registering to do, and processes to create, and all this takes time. Therefore, all the previous steps should have been already taken to facilitate software implementation and save you time.

When you are searching for software, choose those that are less complex, and meets the expectations of your whole team. The easier it is to deal with it, and to learn how to use it, the better the results will be.

Talking about software to serve as a solution that will impact functional areas of your business, an essential aspect is not the technology. What matters is how your coworkers will handle the change that it will bring.  You can’t measure the software success only by what it does, but what each member of the team can benefit from it to offer better results.

Moreover, if the process of learning the tool takes so much time from the team,  it will make no good for your business. Talk to the company that provides this tool, and ask them for an onboarding, to make the implementation process more thorough.

Remember to ask everyone on the team what they think about the software after the demo or trial, ask them to list their difficulties. The pros and cons that they will bring to you should make a difference in your choice. Keep in mind that buying a software requires attending your coworkers’ needs also, otherwise, you’re wasting valuable money.

7. Consider buying horizontal software

There is horizontal software that can be useful for several different types of industries and replacing multiple niche tools. This kind of software is cost-effective, mainly for those businesses that need to use various devices at the same time since they offer a wide range of features. A few examples are:


Buying software

Drag is a shared inbox inside Gmail and can be used as a Helpdesk, CRM, Task management, or many other workflows.

The fact that Drag works inside Gmail decrease drastically the time to be invested in learning about a new tool. It also centralizes work, by allowing Helpdesk to be managed within the same space as emails and To-Dos.

Here are some other features you can add to your cards in a Kanban board:

  • Delegation of tickets;
  • Progress bar;
  • Due dates with Google Calendar Integration;
  • Checklists;
  • Internal notes;
  • Real-time group chat;
  • Automations;
  • Activity Log is a cloud-based project management software that can benefit businesses across various industry verticals. It helps teams to manage different projects and also facilitates sharing anything among team members.

It offers a collaborative space, where the members can communicate, create a knowledge base, and also share files, images, designs, and other specifications.


pipefyPipefy is a business process management platform that allows users to create their personalized workflows. With Pipefy, you can define work rules and collaborate in real-time with your team. These are some other features that this tool offers:

  • Software development
  • Sales pipeline management
  • Bug tracking
  • Service level agreements and deadline tracking
  • Process integration
  • Visual process management

8. Buying your new software

The final step when buying software is the simplest one, and it consists of just buying the software. But there are some things that you can do that can ensure a better deal for your company

  • Ask about possible discounts that can be available for your business. Some companies offer discounts depending on the number of users or provide better deals for nonprofits.
  • Be aware of all the plans available, and be sure to choose the one who fits your purposes.
  • Ask about discounts for paying annually instead of monthly.
  • Ask about post-purchase services that the software company may offer, such as training for your staff, onboardings, access to software updates.

After making sure that everything is alright and you finally purchase your software, it’s time for the best part to begin: time to work hard and use this software at its best to reach new achievements.

Wrapping up

Buying your new software is a process that can take some time, but when you find the one that helps to boost your business, you will be glad to go through it.

Although the most natural path is to choose a well-known software, it’s good to remember that there are countless software solutions on the market. And many of them have a highly aggregated value with more economical prices than the big software enterprises. So it makes sense to do a thorough search for the software you certainly have never heard about before.

Drag turns Gmail into your Team’s Workspace – One single place to support customers, manage tasks and close deals, from the place teams love: Gmail. We are a Techstars-backed Company, trusted by 30,000 users around the World.

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Samantha Anacleto

Author Samantha Anacleto

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