Dickson: Upgrading the Family Office Without Overhauling It — Observations

System upgrades in a single family office rarely fail because the technology doesn’t work. Instead, they fail because the office overlooks the very things that make or break a project—people, process, and governance.

In a recent episode of “Family Office Tech Implementation,” Jon Carroll sat down with Chris Dickson, Senior Manager at RSM’s Family Office Advisory practice, to unpack how families can future-proof their operations through smarter implementation. Dickson, who has over a decade of experience advising ultra-high-net-worth families, doesn’t just implement software—he transforms the way family offices function.

Here are three essential ways to upgrade your family office, based on lessons learned from countless successful (and some painful) system rollouts.

1. Involve Everyone, Not Just the Experts

Too often, family offices assign technology implementation to a single team—usually accounting or investments—without consulting others affected by the change. That creates blind spots and missed requirements that ripple throughout the organization.

“More often than not, it’s a lack of involvement from all of the people that would be impacted by the future technology that’s being put in place,” Dickson emphasized. “It’s important to include not just accounting and tax, but the HR team, the investment team, the legal team, the charitable team.”

Upgrading a general ledger, for example, impacts how data flows to philanthropy reports, payroll, and even legal risk management. The more input you gather at the beginning, the fewer surprises you’ll encounter when the system goes live.

To improve this, establish a cross-functional team early in the selection process. Include a diverse group of voices who understand how the new system could affect day-to-day operations and reporting. Their input ensures the technology aligns with how the office actually works—not just how one team imagines it does.

2. Fix Your Processes Before You Automate Them

Technology doesn’t solve process problems—it magnifies them.

Family offices often lack documented policies and procedures. That leaves teams applying workflows inconsistently, which becomes a liability when implementing new software. Dickson explains that a successful implementation demands two key steps: first, map out how work gets done today, then redesign it for where you want to go.

“If the current process is being deployed with slight nuances in five different ways,” he said, “it doesn’t benefit anybody.” That inconsistency creates headaches during implementation and undermines adoption after go-live.

Instead, treat system upgrades as an opportunity for process optimization. Start by documenting existing workflows—how you pay invoices, approve capital calls, prepare balance sheets—and identify inconsistencies or inefficiencies. Then, redesign those processes based on what your new system can do better. Don’t replicate bad habits in a digital format.

Also, ensure staff understand not only that the process will change, but why it’s changing. Dickson notes that getting buy-in from stakeholders depends on showing them the benefit, whether it’s “effectiveness, efficiency, or control.” When people grasp how the new process helps them, they’re far more likely to adopt it.

3. Govern the Change Like a Business Project

Here’s where many family offices stumble: they assign responsibility for the implementation to someone already overburdened—usually someone in accounting, tax, or operations. These people already have full-time jobs. Piling on a system rollout sets the stage for delays, missed deadlines, and burnout.

Instead, appoint a dedicated project manager or create a lightweight project management office (PMO). This person doesn’t need to be a technologist—they just need to own the calendar, keep people accountable, and drive communication.

“Those people have day jobs,” Dickson said of accounting or operations leads. “So what we see is that it would really be beneficial for many family offices to deploy a project management office… coordinating calendars, setting schedules, providing status updates, and really just supporting communication throughout the process.”

This role acts as the connective tissue between technical teams, stakeholders, and external vendors. It also increases transparency and momentum—a major reason implementations succeed.

Bonus: Measure ROI with Real-World Wins

When families question the value of business process improvement, Dickson offers real-life wins that go beyond vague efficiencies.

Take accounts payable: many offices still rely on paper approvals, email threads, or even text messages to approve payments. That creates bottlenecks and makes it hard to track where invoices stand. By automating AP workflows through a cloud-based system, offices gain transparency, reduce friction, and free up valuable time. Plus, mobile-friendly tools now allow secure approvals from anywhere—yes, even the beach.

Another win? Automating personal net worth reporting. Traditionally, offices compile these manually, sometimes only once or twice a year. That means family members receive outdated insights and controllers spend weeks wrangling data. A smart implementation can pull feeds from banks, brokers, and custodians into a real-time dashboard. The result: family members stay better informed, and staff reclaim time for higher-value work.

Even dashboards matter. Modern systems now offer role-based dashboards tailored to CFOs, family members, or trustees. That reduces the learning curve and makes it easier to get what you need without digging through reports.

Final Word: Don’t Just Install Tech—Transform How You Work

A system upgrade is more than a software project—it’s a strategic investment in your family office’s future, but success depends less on what technology you invest in and more on how you implement it.

As Dickson wisely pointed out, “People aren’t implementing new technology out of a mere desire to implement new systems. They’re implementing new technology to address existing operational deficiencies.”

Use that moment of change to your advantage. Involve your whole team. Fix what’s broken and manage the transition with the same rigor you’d expect from your portfolio. That’s how you upgrade your family office without starting from scratch—and set yourself up for long-term success.

Want to learn more about process optimization, tech selection, or governance best practices for family offices? Reach out to us at Jon Carroll + Family or explore our Family Office Project YouTube Channel.