The Non-Techie’s Guide to Finding and Choosing Online Software


Get Shift Done: Management

It’s easy to become overwhelmed when trying to find, evaluate and select online software for your business. Why? Because:

  • There are a lot of software solutions available.
  • There’s a lot of distracting noise in the form of how- to articles and advice.
  • Most folks are not familiar with an effective process for business software selection .

It’s for these three reasons that I created this guide. Below, I’ve detailed the six-step process that I use to find, evaluate and select online software.

This process uses your specific business needs as a filter to cut through the noise and distractions so you can focus-in and find the right online software solution time-and-time again.

Each step is designed to be as painless as possible without sacrificing your need to find the best software online to support your business goals.

Step 1: Conduct a Software Needs Assessment

Goal: Create a checklist of what you need the software to do

Deciding what you need the software to do is the cornerstone of my process for finding and choosing online solutions. If you don’t do this step first then the end result, the best software online to fulfill your business needs, is at risk.

If you don’t decide what you need the software to do first, then the entire process is at risk.

To compound this problem, online software comes in many shapes and sizes, making it hard to find the right solution for your individual needs.

Take online time tracking solutions for example:

  • Solution 1 offers just time tracking, plain and simple. You can track your personal time only.
  • Solution 2 offers just time tracking, plain and simple however, you can track everyone’s time (your employees, contractors and clients) in addition to your own.
  • Solution 3 offers time tracking for everyone and invoicing. You can track time and send an e-mail invoice to your clients.
  • Solution 4 offers time tracking for everyone, invoicing and payment. You can track time and send an e-mail invoice to your clients that they can pay online.
  • Solution 5 offers time tracking for everyone, invoicing, payment, and the ability to download data formatted for the most popular business accounting programs. You can track time, send an e-mail invoice to your clients which they can pay online, and then you can download the transactions to update your accounting system.
  • Solution 6 offers time tracking for everyone, invoicing, payment and an API ( You can track time, send an e-mail invoice to your clients which they can pay online at the site, and then the transactions are automatically added to your accounting system.
  • Solution 7 offers time tracking for everyone, invoicing, payment and a full-featured accounting system. You can now have an all-in-one accounting system that tracks time, sends an e-mail invoice to your clients which they can pay online at the site, and all of this is managed and kept up-to-date in the same spot.

The key action here is to sit down with pad and pencil (or whiteboard and markers) and try to capture every feature you’d like the software to have and every function you’d like it to perform. Go nuts, you can always scale it back later, but this is the time to try and find the best solution so shoot for the moon.

It does help however, if you can keep “shoot-for-the-moon” features separated from “must-have” features. You’ll see why in Step 2.

During this process:

  • Keep in mind what you already have in place. For example, if you already have an accounting system that works fine and does not need to be replaced, do not add, “full-featured accounting system” to your list of software criteria.
  • Keep your budget in mind. Most online software providers offer a limited free option and then a few tiers of membership, each increasing in both cost and features. Charges are typically monthly, however many of them allow you to pre-pay for longer periods (typically annually) for a discounted amount. So, figure out what you can (or want to) pay monthly for this particular solution and add it to the list of features.

One more important note on budget: when you look at each solution, make sure that it scales affordably. In other words, if you start using one and it gets too expensive to use down the line because you’re growing and need more storage, transactions or users, that solution is likely not the one for you.

This may sound like a bit of work, but the plus is that once you have your online software needs written down, you have a powerful checklist against which you can evaluate every solution you will consider throughout the next steps. If the solution does not meet one or more of the criteria, off it goes!

Step 2: Identify Possible Online Software Solutions

Goal: Create a short-list of potential online software solutions

Armed with your list of features and functionality, it’s time to hit the Web and find solutions that may fit your business needs.

For me, this is the step I enjoy the most (I’m geeky that way)! I love seeing how people and companies have figured out how to get things done online and this is where you get to explore.

The key action here is to create a short-list of the online software solutions that fit all of your required criteria and (hopefully, but not required) some or all of your “shoot-for- the-moon” criteria.

Resources for Finding Online Software

The best part of step 2 is that a lot of the work has already been done for you. There are many solid resources where lists of online software have been gathered and are kept reasonably up to date (results will vary from site to site).

Below, I have listed some top resources for quickly finding online software solutions. Two tips for using these sites:

  1. Make full use of the search and pre-set category tags that most of these sites offer as they will help you hone in on your targeted solution types.
  2. Depending on how targeted your business needs are (e.g. Simple time tracking vs. a fully-functional accounting system) you may wish to start at a detailed level or at a high level.
  • That said, it often helps to use both detailed and high-level sorting as these are human-created directories and sometimes things are put in weird places (that’s how I often find my best solutions!).
  • So, if a feature should be included in your solution (e.g. billing and payment as part of an accounting system) make sure you take a quick look in each of those subcategories as well.

The resources:

Another place to look is, of course, Google. Try searching for “time-tracking online” and “best time-tracking software” and so on.

  • As you search, vary your search terms with quotes. For example: try putting quotes around “time-tracking” but not online (i.e. search with “time-tracking” online). Each of these can pull up different results and are worth a try.
  • Also, similarly to tip 2 on the previous page, use search terms that are not focused on the main feature (e.g. use “billing and invoicing” as well as “accounting” if those features are part of your criteria list).
  • Lastly, pay attention to the sponsored ads at the top and bottom of your search results. I have found my best targeted results by clicking on those ads. Yes, they’re trying to sell something, but hey, you’re trying to buy something so it all works out!

When you come across an option in the resources listed above, click on the link to view the solution’s site. Once you’re there:

  1. Look for the features that the solution offers. These are usually listed under, “Features”, “Tour” or “Pricing” (the last one is good since it typically gives you an option to view all of the features laid out side-by-side in a comparison matrix — that’s gold and very useful!).
  2. Compare the list of features and functionality created in Step 1 (including cost) with the features that the solution offers. If all of your required criteria and (hopefully, but not required) some or all of your “shoot-for-the-moon” criteria are met, this solution should be added to your short list!
  3. Check the pricing to see if it’s within your budget. Some of the more sophisticated solutions do not include their pricing on their website so feel free to call is you need to.

There are two considerations to keep in mind as you go through step 2:

  1. If you feel that you have enough acceptable solutions on your short-list, feel free to stop at anytime. Heck, if the first one you find looks awesome, go for it! The key here is to be as thorough as you feel you need to be in finding a solution that meets your needs.
  2. If you cannot find anything that matches all (or even most) of your required criteria, two options include:
  • Dialing back some of your required features and functionality.
  • Using two or more solutions to get what you need. With tools like IFTTT, Zapier, and Microsoft Flow, making one or more solutions work together is easier than ever and requires little to no technical know-how.

Step 3: Read the Reviews

Goal: Based on reviews, remove solutions from your short-list

This step focuses on finding and reading reviews of each solution on your short list.

The key action here is to learn about other people’s experiences with each solution, identify issues and, if the issues you discover about a particular solution are beyond your level of comfort , remove that solution from the short-list.

Some red flags to look for:

  • Bad customer service and help systems.
  • Broken functionality.
  • Confusing functionality — poor usability.
  • Frequent or unannounced downtimes.
  • Customer data loss or theft.
  • Vendor company issues such as financing or leadership challenges.

The best source for reviews is our old friend Google. Head over to the search engine and enter: “<solution name>” review (e.g. “Jimdo” review). You want the solution name in quotes to assure you will find reviews for that particular product.

Read through the search results and go a few pages in on those results to assure you discover the most pertinent ones. You can also use the handy Google “Tools” feature to limit your results to the last year so you get only the most recent feedback:

  1. Click here first.
  2. Then click here.

Step 4: Do Some “Social Shopping”

Goal: Based on trusted recommendations, remove solutions from your short-list

This is an optional step yet a very valuable one if you choose to use it during the process of finding and choosing online software.

Social shopping is the act of making a purchase decision using input from your network of family, friends, acquaintances and business connections.

The key action here is to get feedback on each of the remaining solutions on your short-list and, if the feedback for a particular solution is poor, remove that solution from your short-list.

Asking family and friends is pretty straightforward; just pick up the phone, send them an e-mail, reach out on social media, or (gasp!) visit in person and talk.

Some suggestions:

  • Post the options on Facebook and ask for opinions.
  • Tweet the options to your followers or a #hashtag on Twitter and ask for opinions.
  • Ask about the options on LinkedIn either in an update or in a group.

As you can see, there are many possibilities for implementing this step. I urge you to try one or two (or more!) to really tap into the knowledge and experiences of your trusted networks.

Step 5: Take a Test Drive

Goal: Use each of the remaining solutions on your short-list and remove any that do not work for you

Nothing helps you shake out an online software solution better than signing- up and trying it out. This is where the rubber meets the road; where you will say, “Hey this is cool and intuitive” or “This is hard to learn, but powerful” or “This solution stinks!”

The key action here is to use each vendor’s free membership level or trial-period to get a feel for how each of the remaining solutions really work for both you and your business and, if a particular solution does not work, to remove it from the short-list.

You do this step toward the end because hopefully you have narrowed down your short-list to two or three potential solutions which makes for a do-able test drive step. If you have more than three left, try to knock some more solutions off the short-list. It is possible to test drive more than three, but the effort grows with each solution.

Preparing for a Test Drive

Before signing-up for your first test drive, create some “use-cases” or processes that you would like the software to perform. This will assure that you are testing with your “real-world” scenarios and that the software is indeed doing what you want and need it to do.

For example, set up a fake customer and project, enter some times into the time tracker for that project and then bill the fake customer. Make sure you use your e-mail address (or some throw-away ones from Hotmail or Gmail) so you can see what the customer will see as well as what you will manage on your end.

If you want to involve additional people (such as employees who will be performing this process once a solution is selected), form a test drive team with each step in each use case mapped to a person or role. This is a great way to get buy-in for the solution you end up picking from the folks who will be using it once the process for finding and choosing your online software is complete.

Taking a Test Drive

You should run each test drive one-at-time by which I mean sign-up for each solution only when you are ready to start the test drive for that solution (I’ve run out of time before on many a solution’s trial period when I signed-up for all the solutions at one time and then worked my way through one-by-one).

As you test, keep in mind that all test drives should take into account usability: how easy and intuitive is it to get done what you, and everyone else in the system, needs to get done? That said, sometimes usability can be sacrificed for functionality. It’s a balancing game and a judgement only you and your organization can make.

For each solution left on your short-list:

  1. Sign-up for the free tier or trial period. If the vendor does not offer one, or if the free tier does not include the functionality you need to test, contact them and ask for one.
  2. Perform any setup that is required. Is it easy to get up and running? If you needed help, was it easy to find? If you had to contact support because you couldn’t find a solution in the help area, did they respond promptly, cheerfully and most importantly, did they resolve your issues?
  3. Run your use cases through the system and see how they perform. Were you able to run your use-cases all the way through? Even if you experienced some issues, if you can get the use case to work within a reasonable time, that’s a success.
  4. If you had any issues, were they resolved by changing settings or by using a work-around within the solution?
  5. If you must cancel your trial or account before you are charged at the trial-period’s end, cancel it at the end of the test drive.

Wrapping Up the Test Drives

Once all your test drives are complete, sit down (if you had a team, involve them, too) and compare results.

If you have a stand-out winner, great! Otherwise, think or talk it through and try to come to a consensus on the best solution.

Step 6: Trust Your Gut

Goal: Trust the process and yourself

If you followed this process for finding and choosing online software all the way through, you should have arrived at a single solution that will work to fulfill your business needs.

However, if you have two solutions that are neck-and-neck or even one solution that you just don’t feel great about, it’s time to trust your gut.

At the end of the day, you and your company will be living with the online software you select for a long while. Make sure you pick one that not only meets business needs but also fits your culture and feels right.

Good luck with your search!

The GSD Management channel is brought to you by Work Market, the leading labor automation platform. Work Market empowers businesses and skilled professionals to unlock new levels of productivity, engagement and growth across the entire lifecycle of work. Learn more at

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