The tech recommendation problem nobody talks about
Why the people advising you on software might be the worst ones to ask.
Most solo and small-firm lawyers know they need better technology. The hard part isn’t motivation — it’s figuring out what to actually use.
So you ask around. You hire a consultant. You talk to the IT person someone recommended. And you get advice that sounds reasonable.
But here’s the thing nobody warns you about: the people giving you tech recommendations often have a financial reason to recommend what they recommend. And they may not even realize it.
The Upton Sinclair problem
There’s an old quote from Upton Sinclair: “It is difficult to get a man to understand something when his salary depends upon his not understanding it.”
This is everywhere in legal tech. A consultant who makes money setting up a certain practice management system isn’t going to tell you there’s something better. They might not even believe there’s something better — because their livelihood is built around that one platform. It’s not malice. It’s human nature.
The “nobody gets fired for buying Microsoft” problem
Inside larger organizations, IT departments default to familiar enterprise tools — not because they’re the best fit, but because they’re safe. If something goes wrong with Microsoft, nobody blames the IT person.
Never mind that most security problems come from users, not software. The recommendation was really about protecting the recommender.
Solo and small-firm lawyers run into a version of this, too. The tech person you’re paying doesn’t have your practice in mind. They have their own business model in mind.
The better way to get honest answers
The most reliable tech recommendations come from people who have nothing to sell you — other lawyers who’ve tried the tools themselves and will tell you what worked, what didn’t, and what they wish they’d known sooner.
That’s what happens inside a community like the Inner Circle. Lawyers share real experiences:
“I switched from X to Y and here’s what happened.”
“I tried this tool everyone’s raving about. It wasn’t worth it.”
“Here’s the setup that actually saved me time.”
No one’s getting a commission. No one’s protecting a consulting relationship. It’s just lawyers talking to lawyers.
Bottom line
You can’t fix the incentive problem by finding a “better” consultant. The incentive problem is baked in. What you can do is get your recommendations from people who use the tools the same way you do — in a small firm, with real clients, under real pressure.
That’s where the honest answers live.
;-)
Ernie
P.S. Inside the Inner Circle, lawyers share what’s actually working in their practices — no sales pitches, no hidden incentives. Just real experience from people doing the same work you do. → https://innercircle.ernietheattorney.net/