Small Business Software: What To Consider Before You Buy

by Rachel Steininger

minutes |  words

Like Alice, you too can go down the rabbit hole of new software selection.

And, thinking that this is a valid on-the-business activity, many professional service owners do exactly that.

Only to risk endless time, lost billings, and massive frustration on the endeavor.

Or end up with a bad decision you'll regret just months later.

NBD right?

Think again.

Quick Software Solutions Can Happen

With all the software options out there - from off-the-shelf to custom, with or without AI enhancements - it seems like it should be straightforward to find something that fits your needs and your budget.

I mean... why shouldn't you be able to source a system that will handle everything you're already doing PLUS scale with everything you want to do in the years to come?

And do it over your lunch hour?

Sometimes you can find that kind of quick solution... if you need something very specific.

Need a calendar booking tool? Calendly is amazing. Email management? Try Superhuman (my affiliate link gets you a month free). The $40ish dollars I spend between the two systems saves me gobs of time every month. I will use them in retirement someday.

When complexity goes up exponentially

But when something more comprehensive is needed, like trying to coordinate your staff + contractors, get invoices out the door and revenue collected with ease, or see your project or matter level profitability with hour by hour precision, the complexity goes up exponentially.

And so does your likelihood of losing time and sanity to the Wonderland-level marketing pitch that glosses over the implementation work.

It's rare that the less expensive/cookie cutter solutions will serve your truly non-cookie cutter needs without some deliberate work to integrate workflows and best practices.

Yet building something fully custom in a rapidly evolving market isn't often the best choice, or the affordable choice, especially for a sub-$20 million business that is itself evolving.

There's enough which-end-is-up feeling to the selection process alone that you might start wondering... is it even worth going down the path of software upgrades?

It's enough to think "mo' money, mo' problems" and go back to playing small or putting up with or putting out the small fires day-to-day.

But according to one of my clients, they wish they'd done the upgrade earlier.

That's where having outside help makes a big difference.

What to settle before you buy software

To make sure the tool is both used and usable for your bigger business goals, you'll need to

  • detail the scope you want to solve for
  • synthesize and sync the data and integrations involved, and
  • identify and create a plan to onboard the key players, from eager adopters to cynical stakeholders

And that's before you put your credit card in.

Don't Forget The Rollout

And after... you still need to mesh your new technology with your processes and data needs, roll it out, and get everyone on board with training and change management techniques.

And you thought the selection process was a rabbit hole?

Before you play Alice and drop into Wonderland without a plan, reach out. We can help you through the scope, selection, and roll out (or with the remap of a current system)...

Ensuring you realize your short and long term business goals while staying focused on client work and business growth.


about the author
Rachel Steininger

As a Fractional COO and the founder of Upward Acceleration, Rachel builds the operational infrastructure that turns what founders envision into what their business can actually do.

This article was first published as Rachel's COO Insights, a section of the weekly Upward Acceleration newsletter. Written without the use of AI.  

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