Modernizing the financial backbone of a law firm is rarely held up by the technology. It's held up by the questions that come before the commitment and more specifically, the ones partners and finance leaders raise about trust, cost, and whether a new platform earns its place in an organization that scrutinizes every investment without a direct line to revenue.

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Those questions surfaced firsthand when we hosted Adam Knapp, Managing Director of Strategic Finance at Goodwin, alongside TwinSix CEO Justin Merritt. The audience of finance leaders from firms weighing the same decisions asked what they most needed to know: how long before anyone trusts the numbers, what transformation actually costs beyond the license, when a platform becomes a strategic asset, and whether AI is production-ready or just a pitch.

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Here are four of those questions, with Adam and Justin's answers edited for length and clarity.

"How long did it take for people to trust the numbers and the process in Pigment?"

"Trust is earned very incrementally. It certainly doesn't happen all at once. People trust what they can understand and explain. If they can trace outputs back to source and assumptions, that's critical."

His more useful point was about timing. Year one, people were still climbing the learning curve of a new tool and a new process. In Goodwin's case, a changing organization on top of both. "With that change comes some volatility and uncertainty." Real trust showed up in year two, once the platform had been through enough planning cycles for repeated use to validate it, and once the team started building customized use cases for groups beyond finance — client development, event planning, PMO transformation projects. "That really helped people understand what the potential is here."

Justin also added a caution worth mentioning: the calculations are easy to trace, but sometimes tracing them surfaces something uncomfortable.

"Sometimes you put a tool like Pigment in and you find you've been calculating things incorrectly for a very long time. Being prepared for that is good because it doesn't mean things are wrong, it just means you're evolving and getting more accurate."

"What's the true cost of transformation, beyond software licenses and implementation fees?"

Adam had a lot of thoughts on this one, and none of them were about the license.

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"The software cost is really only part of the investment. It's the most visible part. The larger investment is the organizational focus; the time from stakeholders, organizing the data, designing the processes and the dashboards. Software is frankly the easier part to tackle. The organizational alignment is where you're going uphill."

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On pricing itself, he offered this analogy: "Software pricing feels a little like showing up to McDonald's and finding out the six-piece nugget has disappeared. You can order a four-piece off the dollar menu, but the next option is the twenty-piece also known as your enterprise tier. There's not a lot in between."

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But he honed in on the number nobody puts on the invoice: "The cost of not doing anything is likely greater in the long run, in terms of missed opportunities. These are investments, after all."

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Justin picked up the same thread from the delivery side by mentioning that the cost is invisible precisely because someone is absorbing it.

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"People are hammering, working late nights and weekends to get things done, and the recipients of those things usually don't know or appreciate what goes into it. That hidden cost — the cost of doing nothing — is the piece that gets missed when you're thinking about the total cost of transformation, because it's often an offset you're not even considering."

"At what point does a platform like Pigment become a strategic asset, rather than just a financial application you use day to day?"

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Adam has a good self-diagnostic for anyone mid-implementation.

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"The shift happens when people stop asking whether the system can support a process, and start asking what else the platform can do. That's the inflection point where an organization moves from project-based thinking to platform thinking. At that point, the platform has become part of the firm's operating infrastructure and not just a one-off solution."

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Justin reframed it as a change in direction of pull.

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"It shifts from a push activity of ‘hey, we're rolling this new tool out’, to a pull, where the organization is thinking, I've identified this problem, could Pigment help me here? That's a great lens for when the transition has actually occurred."

"Is AI truly production-ready, or is it sometimes overhyped by vendors?"

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"It depends on what we're talking about. There's definitely a lot of marketing hype out there across the board. But the biggest thing I see is that it's less about the capability set and more about whether companies actually know their objective. Is it a reduction in effort? Faster cycle times? Enabling business users to self-serve answers? Those objectives carry different answers and lead you to different paths for how to get there."

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Justin’s warning for the buyers was: 

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"A lot of organizations are approaching it with a shotgun approach - throw a whole bunch of stuff at it without a lot of thought being put into the objective of why you're trying AI, and what you want to get out of it. That, to me, is the only way to answer the question: for the use case you actually want, is that capability ready?"

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Trust comes from traceability, not accuracy claims. Cost lives in focus and time, not licenses and AI pays off when you can name the objective before you buy the tool.

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If today's conversation resonated, read the full Goodwin case study here or watch the on-demand webinar with Goodwin here. If you're running into similar questions at your own firm, we'd love to hear from you. Book time with us here.

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