Business Owner Nag: How to chose software tools
Define what you need and what you want before you compare options.
Oh hello, does your business exist partly on the Internet? Chances are good that that means you’ve hired some software tools to help with the Internet-y-ness of it all. Maybe you pay for them, maybe you don’t, but either way: after a while, it’s a good idea to revisit your software tools. These software tools might be something you install directly on your computer or they might be something you access in your web browser.
Here are some signs it’s time to revisit your choice of tool:
You’re mad about how much it costs when it renews
You dread performing tasks in the software
It’s been three or more years since you last evaluated your choice.
For tool selection, or re-evaluation, here’s my quick and dirty process.
Make a short, lettered list of what the tool must do and what is nice to have. (Example coming up after this, don’t you worry.)
Round up some common tools that do the thing by searching “best [tool] small business.” Then ask real people with businesses similar to yours what they use. Narrow it down to 3-5 options.
Visit the documentation for each tool and make some brief notes using your lettered criteria. Maybe watch a couple ‘how to’ videos, ideally made by third parties. If you’re re-evaluating, remember that migrating software platforms is usually a bummer, so moving for price reasons alone is unlikely to be worth it once you factor in your time. Plan for this whole process to take 1-3 hours; it need not be done in one sitting.
Assess your lettered criteria summaries for each tool. Either the leader will be blindingly obvious (usually it is!) or there will be a tie. In the case of a tie, I recommend you pick the option you find more aesthetically pleasing. You might as well have nice things if the choices are otherwise about equal.
Here’s a real life example from me.
Tool: email marketing/email newsletter tool
Current: Kit (FKA ConvertKit), $290/yr for up to 1,000 subscribers with automations. Takes 0.6% of paid subscriptions/product sales on top of Stripe fees (2.9% + $0.30 for non recurring, additional fee for recurring.) A $19.00 sale netted to $18.04.
Reasons to re-evaluate: wrestling with Kit’s templates fills me with dread. I can’t opt out of the emails telling me how to improve my subscriber engagement, which drives me crazy, because my paid newsletter offering is reminders where the subject line is doing 90% of the work. The email NOT being opened is the email working as intended! The process of scheduling an email to go to a limited set of subscribers also works very poorly on a grayscale screen with type sizes/zoom turned up.
Tool selection criteria:
A: low-vision friendly. I don’t want a fancy WYSIWYG visual editor, I want to send text-based emails.
B: Can segment list and have subscribers self-manage what segments they belong to. I send four kinds of different emails, would like to only have one newsletter where all those things are happening.
C: Great documentation - I want to be able to answer my own questions.
D: Someone I trust is happy using it and can explain why.
E: Paid subscription options; pay-what-you-want subscriptions would be nice to have
F: (optional) automations and sequences so I can re-send my evergreen content easily.
Tool candidates:
Kit, ButtonDown, MailChimp, Substack
Kit
Product position: email marketing.
A: No.
B: Yes, but in practice the implementation is horrible.
C: 6/10.
D: Yes, several.
E: Yes (no).
F: Yes and yes.
Buttondown
Product position: bulk email tool.
A: This is basically their manifesto.
B: Yes.
C: 9/10, a few inconsistencies.
D: Yes.
E: Yes (and yes).
F: feasible, but definitely a little built-for-those-with-prior-automation-experience. Which I have, so it’ll be fine.
Price: same as ConvertKit for similar features, except they don’t add on to your Stripe fees for paid subscribers. (And if you have better than standard Stripe volume pricing already for your business, it applies to your Buttondown sales.) Bonus: they explicitly prioritize accessibility fixes to the platform.
MailChimp
Product position: email marketing.
A: failed so hard here I didn’t evaluate it further.
Substack
Product position: newsletter/content management platform.
A: Better than Kit, still not great.
B: only paid/unpaid for segments.
C: ehhhhh.
D: mostly I got “it’s better than MailChimp, it’s nice that it has an ecosystem people are already spending time in” but not people who were explicitly… happy.
E: Yes (no).
F: No.
Pricing: no fees upfront, substack takes 10% on top of Stripe’s fees. Based on my current number of paid vs unpaid subscribers, this would save me some money.
At this point, I think it will not shock you to learn that I spent about 20 hours after re-evaluating migrating from Kit to Buttondown. I’ve actually gasp enjoyed preparing this email for you in Buttondown, and if you want to mess around with custom domains, they’re the only service I’ve ever heard of who will help you get your DNS records sorted. A+ support, 10/10 would recommend if DESIGN is not a primary concern for your emails.
While this example is specifically about software selection, this method of making a lettered list of criteria and then evaluating a series of options against that criteria works well for all kinds of medium-sized decisions. I’ve also used it for choosing home contractors and deciding what to do to celebrate a milestone birthday. Let me know how it works for you!