In late 2020 I tried Superhuman, which is marketed as software, but more like a business book about productivity with software on top. It did not work for me. I missed emails from potential clients. I didn't want to respond to email the way that worked best in the Superhuman system, which prioritized immediacy over well-considered reading and responses. Switching to Superhuman made my life more stressful, and I believe that software should reduce cognitive load and lessen anxiety.

I returned to Gmail, a system I've been using since college, where I've trained all my tabs and filters to do my bidding. Plenty of people use and enjoy Superhuman. Just not me!

Whether you're looking for a solution to your crowded inbox, seeking a new notes app, or identifying enterprise content operations solutions for an entire company, these rules should help you choose wisely and find more long-term satisfaction with your software investment.

Don't break what already works

Software companies have a stake in making you think that your operations are out of date, that your technology is not up-to-par. In reality, many tools apply a layer of engineering to processes that humans have already figured out just fine.

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Choosing software rule #1: If the tool/software/system you are currently using works for you, your team, and your business, you do not need to switch.

As much as I hate emailed Word docs and PDF attachments, if they work for your team and everything else is running smoothly, then I don't recommend that you switch. So much in our tech-assisted worlds breaks and challenges us (hello, parents and teachers still struggling with remote learning) that I don't recommend adding new complexities to systems that are working just fine. As we've learned since the social media and streaming explosion of the 2010s, just because technology is new doesn't automatically make it better or necessary for your business to thrive.

But if you're hearing from your team or clients that they'd like to try something new, or if you're curious about different ways of working, or if you're concerned about security, then by all means: try new software!

To avoid getting stuck with an overpriced tool that your team hates, however, I recommend following this process:

Choose software that is determined by your needs

What do you need the software to do? I recommend writing down the basic functions you require from your software. If you're used to using Microsoft Office or Adobe Creative Suite, which cram a bazillion features into every product, you'll probably be surprised to learn how bare bones some software startups can be.

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Choosing software rule #2: Make a list of your needs and your nice-to-haves, considering jobs to be done, working styles and budget.

For example, if you're looking for new writing software, you may want to define whether you want a program that supports input in Markdown or one that has Focus mode.

If you're looking for new content operations tools, you may want to consider sharing and collaborative editing capabilities. How does the software support tracked changes and real-time collaboration? Roles? Notifications?

Having a defined list of how you need a tool to work will keep you focused throughout the purchase process. It's like one of those house selection shows: you probably shouldn't buy the house with the swimming pool in the backyard if there aren't enough bathrooms for your family to share comfortably. Focus on the needs, then the nice-to-haves.

Software is only working if it helps you do your job.

I started The Content Technologist to focus on software because I had been on so many teams and worked with so many clients whose IT or executive teams had chosen software for content operations, without ever checking the opinions of the people who used the software daily.

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Choosing software rule #3: Check in with your collaborators.

Inclusive business practices incorporate the opinions and experiences of your team members. It's highly likely that your teammates have different expectations of software than you. They're also the ones dealing with errors or slowness or frustrations in their tool stack. In the remote work world, software is the workplace.

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