The November 2025 Boomer Technology Circles brought together CPA firm leaders who are shaping how their organizations use technology to drive strategy. Across two days in Kansas City, one theme kept surfacing: firms are tired of duct-taped processes and ready for real, sustainable progress.
And yes, we made sure people were fed. More on that in a moment.
Process and automation: the “finally, let’s fix this” projects
Many firms are moving ahead with long-delayed process improvement efforts. Reducing manual data entry, enabling auto-flow and building onboarding automation through ticketing systems were top of mind.
Everyone asked the same question in different ways: How do we streamline onboarding so clients and staff aren’t stuck in limbo? Better processes usually beat more apps. Several leaders also noted that overloaded IT teams spend more time maintaining environments than supporting operational needs, which is pushing process efficiency higher on the priority list.
AI governance and training: cautious optimism with a side of reality
AI wasn’t framed as magic. It showed up as responsibility.
Governance around copilots and large-language-model tools sparked a lot of discussion, especially around auto-labeling, compliance and oversight. Many leaders admitted they’re still figuring out where to start.
Training came up repeatedly. Firms want guardrails, not guesswork. Teaching people how to use AI is one thing. Teaching them when to use it, how to avoid risk and how to control cost is an entirely different project.
Data hygiene was another pressure point, especially lingering concerns about old or duplicative SharePoint content and oversharing risk. Many firms recognized that governance and cleanup must come before broader AI rollout.
AI maturity varied sharply between the two groups, with the Thursday cohort generally earlier in their journey than the Tuesday group.
Infrastructure and cloud moves: the shift continues
Several firms talked through their cloud migration journey. Many have moved workloads to Azure or similar platforms and reported no regrets. They did point out that cloud environments require different expertise, which is why many leaned on MSP partners.
The big questions in the room focused on scope. What needs to move? What doesn’t? How do we upskill teams? How do we use external partners without losing internal ownership?
Conversations also touched on accountability, resiliency during occasional Azure outages and the importance of real bench strength instead of a single point of failure. Firms want to know who owns what in the environment and how performance stays predictable during busy season.
Practice management and ownership: who actually owns what
A recurring challenge is decision-making. As firms shift responsibilities away from senior partners, they’re rethinking who owns processes and cross-firm initiatives.
Newly merged firms also surfaced the reality that technical alignment is often easier than workflow alignment. Leaving process harmonization for “later” tends to make it later and harder.
Policy, security and compliance: foundational but increasingly visible
Client requests for proof of basic policies are rising. Security, data retention, acceptable use and other foundational documents used to be internal housekeeping. Now clients want to see them.
Security training also came up. Many firms use standard platforms and now have “three strike” policies for non-compliance over a set period.
M&A lessons were shared, too. If you wait to harmonize processes across merged entities, it gets harder, not easier. The tech may match, but the workflows rarely do. Firms also talked about security expectations rising across the board, including stronger MFA or passkeys, 24/7 monitoring and response and clear, auditable compliance documentation. Many expect support with data governance as AI accelerates.
Service strategy and 2026 planning
Leaders looked ahead to 2026. They talked about what employee raise expectations could look like and how client rate strategies may shift. Some firms are trimming lower-value services and rethinking where different engagements fit in the long game.
Audit tools came up as well. Platforms like Caseware and OnPoint are gaining attention, though adoption is still mixed.
Several leaders also highlighted the importance of making policy documentation and security posture easy to find online. Transparency is good for clients and great for reducing late-night email scrambles. Firms also tied next-year planning to decisions around cloud stability, security programs and AI readiness, signaling that these areas are becoming part of core service strategy rather than side projects.
A quick moment outside the conference room
After a full day of discussions, we shifted gears. We partnered with our friends at Suralink to host a dinner at 1587 Prime, Kansas City’s newest (and perhaps most exclusive) steakhouse. Good food tends to produce even better conversations, and this group didn’t disappoint.
Sometimes alignment happens fastest when there’s a ribeye on the table.
Closing thoughts
This Tech Circles session reinforced what many firms already feel: the next two years will reward those who invest in clarity, governance and process discipline. Technology is no longer a side conversation. It’s the steering mechanism.
If you want help thinking through AI readiness, cloud strategy, security posture or the policies clients are now asking for, we’re here. And while we can’t promise steak every time, we can promise straightforward guidance and practical next steps.