What I Learned on Both Sides of the Table

By Jessica Parker, founder of JP Advisory.

Family office technology projects succeed or fail for many reasons. Implementation, training, and ongoing support all play a role. However, one of the most overlooked factors is what happens before any of that begins: the preparation and decisions made in the lead-up to signing. That is the focus of this piece.

I have had the interesting opportunity to see family office investment reporting technology projects from both sides. First, within a Single Family Office, leading technology selection and implementation, where I made my share of mistakes. Then on the vendor side as a solutions consultant, where I worked with family offices globally and saw these same patterns repeat across many projects.

The standard best practice advice on technology implementation is well documented and easy to find. What I want to share here are the things that often get overlooked in the initial phases of the project: the lessons I wish someone had shared with me, and the patterns I saw derail projects from both sides of the table.

Consider this the advice I would give you over a coffee, to help side-step some of the hard lessons. The good news is that when family offices get these foundations right, projects tend to run smoothly.

When deals did not proceed, a common reason I saw was not a competitor winning. It was "deal lost, no decision." Family offices would spend months evaluating platforms, sitting through hours of demos and vendor discussions, holding internal meetings. And then nothing. They would decide not to move forward at all.

Most of the time this happened because the internal work had not been done first. The family office had not yet clarified what they were looking for.

I know this because I was that prospect. My vendor assessment took twelve months before I selected a solution. Every time I learned something new about one vendor I would circle back to the others asking "can you do this too?" even when it was not a must-have. I was chasing shiny features instead of solving a defined problem.

Before you talk to vendors, it is worth getting clear on what problem you are actually solving. Document your must-haves and your nice-to-haves. Understand where investment reporting fits in your existing tech stack and what integrations you will need.

If you are evaluating multiple vendors, a Request for Proposal or evaluation template can help. It keeps your requirements front of mind and makes it easier to compare responses objectively. After several demos, it can be hard to remember which platform does what well.

Something worth keeping in mind: software does not fix your governance, it only exposes it. If you do not have an investment policy statement in place, or your processes need refinement, the technology will surface that quickly. Cleaning house first will save you substantial time during selection and implementation.

One team usually drives the need for a new investment reporting platform, but the platform rarely serves just one group. Thinking through ownership and involvement early prevents delays and helps you realize the full potential of the platform.

I saw this play out in two ways.

The first was about who owns the system long term. In one family office, the investment team selected and implemented the platform, then handed it to the accounting team to maintain. The accounting team had no say in the selection, no opportunity to input into requirements, and needed six months to get up to speed before business as usual could resume. Had they been involved from the start, the onboarding would have been smoother, particularly given they had access to the data required for implementation.

The second was when key people were left out of the conversation. In another family office, the person who had the data and knowledge to do the onboarding was only told about the platform after the contract was signed. They were expected to fit implementation into their day job with no additional support. The result was frustration, which impacted buy-in across the family office.

It is worth thinking about this more broadly than solving a problem for one group. Who are the actual users? Internal staff, family members, or both? Each has different needs and you will get better requirements by involving them early, not just to avoid surprises but because they will surface things you may not have considered.

The person implementing needs access to the data, the authority to make decisions, and the time. If that is not available internally, it is worth bringing in help from the start rather than partway through when things go off course. You are investing a significant amount in the technology, so it makes sense to invest in the resources to get it right.

I watched one family office use a technology project to engage Gen 2 in the business, giving them ownership of platform selection. It was a thoughtful way to build capability and involvement. The challenge came during implementation: a summer intern was tasked with onboarding the system. She was capable and keen, but did not have access to the data or relationships with the long-term staff who did. Without that foundation, the project stalled. It is the kind of situation that can happen to any office trying to balance development opportunities with operational realities.

It also helps to be realistic about what "go live" actually means. We always think it will take less time and fewer resources than it does, so double your estimate. Consider whether you want to run the old and new systems in parallel and for how long. Factor in your team's other commitments like year-end, compliance deadlines, deal flow, and other major projects.

I worked with one family who were determined to replicate a 20-page report in their new platform. Onboarding stalled because the team felt they could not move forward without recreating it exactly. Eventually someone from the family office team asked the principals what they actually looked at each month, hoping to prioritize which elements to tackle first. The answer surprised everyone: about two pages. What started as a blocker turned into a valuable conversation about what the family actually wanted to see and how often.

Platforms have great flexibility and customization, however not the infinite flexibility of Excel. If you go in expecting to replicate everything exactly, you may be disappointed. But remember why you are moving off Excel in the first place: formulas that break, the manual errors, the version control headaches, the key person risk, the hours spent stitching data together, the reporting bottlenecks, and more.

A new system is an opportunity to simplify, refine, and improve your investment data, rather than just finding a faster way to do what you have always done.

The same applies to historical data. Migrating years of transactions is costly, time consuming, and often frustrating when calculations do not match due to different methodologies. Ask yourself what you actually need: private equity positions require full history, but for other investments, consolidated performance figures may be sufficient. You can always add more detail later once you are comfortable with the system.

Data security, cyber security, data ownership. These questions can be pushed to the very end of the discussion, however they deserve more airtime.

Every vendor has a glossy one pager about their "military grade" security, but that is not due diligence. The questions that matter are the ones that do not always get asked:

These are just some of the questions worth asking. I have seen family offices move through this section quickly, only to discover later that what they assumed was covered had not been explicitly agreed.

Unless you have a dedicated IT function, it is hard to know what to ask, let alone how to evaluate the answers. If that sounds familiar, it is worth getting external help. There are firms that specialize in IT and cyber security for family offices who can help you ask the right questions and make sure the key requirements are clearly documented in the contract.

Technology evolves fast and the platform you buy today will look different in two years. It is important to understand where the vendor is headed and what is on their roadmap. Are they investing in areas that benefit family offices like yours, or are they focused on a different client segment?

Vendors have a role to play here too. The best ones will help you scope properly, set realistic expectations, and flag risks early. A good vendor wants the project to succeed as much as you do.

If they are promising to build something specific for you as a condition of signing, get the commitment in writing, and preferably in the contract.

No system will be perfect for the exact and unique needs of every family office. That is not a reason to stay stuck in Excel spreadsheets and manual work forever, but it helps to keep your must-haves front of mind.

Get clear on the problem, do the internal work, bring the right people along, and resource it properly. The relationship with your vendor matters as much as the features on the demo.

I learned lessons the hard way by making the mistakes myself and then watching others make them too. While these lessons come from investment reporting projects, the principles apply to family office technology implementation generally.

If you are about to embark on one, I hope these reflections help you ask better questions, involve the right people earlier, and set yourself up for a smoother path. The investment in getting it right at the start pays off many times over.

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Jessica Parker is the founder of JP Advisory, where she works with family offices as their expert generalist, providing senior expertise and hands-on capacity to move critical work forward. She has seen family offices from three angles: as Group Financial Controller and Finance Lead for a single family office managing a complex global asset base, as an advisor in PwC's Family Office team, and as a solutions architect with a family office reporting platform helping family offices globally design and implement wealth platforms.