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What Should you Ask Before Buying an AI Tool or Changing Your Fees?

Scott Samborn August 3, 2026 7 min read

TL;DR

Two mistakes show up constantly in professional services right now, and they’re related. Firms buy AI tools that never really enter daily use, and firms keep billing the old way even after AI changes how fast the work gets done. Fixing either one starts before the purchase order or the rate card, not after.

What should you ask before buying an AI tool?

The most common failure pattern in accounting and legal AI adoption isn’t a bad tool. It’s a tool that clears procurement and then almost no one opens more than an hour a month. Before signing anything, run the tool through five questions:

What should you ask before changing your fee structure?

Financial pressure to adopt AI is rising fast, but pricing hasn’t kept pace. Almost four in ten law firm professionals feel pressure to move faster on AI, yet nearly two-thirds say their firm’s pricing structure is unchanged. Meanwhile, clients are explicit about what they want instead: pricing models that reflect AI-driven efficiency through greater cost certainty and transparency.

Three questions worth answering before you touch your rate card:

What’s the bottom line?

Before you buy: does it remove work or add a step, is it grounded and secure, and would it survive two weeks in real use. Before you bill differently: are you charging for outcomes or hours, is every AI-related cost disclosed, and can you defend the number in one sentence.

Bottom line: the firms losing money on AI aren’t the ones moving slowly. They’re the ones that bought first and thought about workflow and pricing after.

Sources: Thomson Reuters Institute, “2026 Future of Professionals Report”, Vaquill AI, “What Lawyers Really Think of Legal AI in 2026”

Aspen Management Group works with boutique advisory firms to clarify key workflows, improve efficiency, layer in AI where it adds value, and build governance and training around that change

Aspen Management Group
Scott Samborn
Founder, Aspen Management Group

Scott spent 20 years running a managed IT services practice serving professional services firms across the DC Metro area, and has worked in technology for 35 years. AMG helps boutique professional services firms get practical value out of AI.

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