Beyond the List: COO’s Thoughts on Getting from “To-Do” to “Done” in Estate and Trust Administration
Most of us don’t have a productivity problem. We have a completion problem.
We capture tasks. We make lists. We feel organized for a minute. And then the work sits there. It stalls. It lingers. It becomes a slow-moving backlog that makes you wonder if you’re missing something obvious.
I learned that lesson the hard way, not from a book, but from my own family.
The 3.5-year “simple” estate
I went back to Montreal for one summer during college and met up with my cousin. Our grandmother had passed away when I was a freshman. By that point, we were three and a half years into administering her estate.
And this wasn’t complex. No property. A small investment account. Three beneficiaries who got along. The kind of scenario people call a “simple estate,” as if that should guarantee a quick and painless process.
But three and a half years is three and a half years.
So we asked the uncomfortable question out loud: is this normal? And if it’s not, are we doing something wrong?
My cousin had years of experience on the planning side of estates and trusts, the wills, the structures, the “before” work. I was a human factors major. What I kept noticing wasn’t just complexity. It was friction. Confusion, waiting, handoffs, and systems that didn’t seem built for finishing.
We got curious and started talking to people: families going through it, professionals working in it, and leaders inside financial institutions. What surprised us most was how quickly doors opened. There was an emotional tie to this work. People wanted to talk about it because they’d felt the pain personally, even if they experienced it professionally.
Then we started asking a simple follow-up: what technology do you use to manage all of this?
That’s when we got the “eyes glazed over” look.
We heard things like: “We use fax machines for task management. We copy pages and put them on someone’s desk each morning.” Or: “If we need a form updated, someone comes to the office with a USB stick.”
This was 2018. Not 1998.
And that’s when the light bulb went off: in this industry, “to-do” often wasn’t a tool for progress. It was a static artifact, paper lists, PDFs, fragmented systems, that made work feel documented without actually moving it forward.
The mindset shift: from list-making to finishing
Here’s what I’ve learned since then: “to-do” is cheap. Anyone can write a list.
“Done” costs more. Done requires:
- clarity (what’s the next action?)
- sequence (what happens first, and what depends on what?)
- ownership (who’s accountable?)
- proof (how do we show progress to others?)
- a system that still works when people are busy, stressed, or new
That’s true in estate administration, and it’s true in my own day-to-day work.
I’ll be honest: I’m not perfect at task management. Startup life is constant context switching. Things slip if you let them. That’s exactly why I rely on structure and tools, not because I’m trying to be a productivity guru, but because work still needs to move when I’m tired, distracted, in meetings, or juggling too many threads.
I don’t build systems because I’m disciplined. I build systems because I’m human.
The Anatomy of “Done”
If “to-do” is intent, “done” is a flow. In estate and trust administration, the flow breaks down in three predictable places:
- Intake: getting information and documents into the file
- Execution: turning requirements into clear tasks and timelines
- Output: producing accounting and reporting that proves progress
1) Clear the entryway (Intake)
You can’t get to done if you’re stuck at the start.
One of the most painful parts of administration is data input. Every month you get statements from institutions and accounts. Too often, the process is printing documents and manually keying transactions line by line.
That kind of work doesn’t move a file forward. It drains people before the real work even starts.
My personal rule is simple: capture fast, decide later. The professional equivalent is the same: reduce friction at intake so files don’t die at the beginning. This is also where AI and automation can help in the least glamorous but most meaningful way: quietly removing hours, or days, of manual grind so teams can actually progress.
2) Guide execution (Task management that moves)
A to-do list is only useful if it tells you what to do next.
What we kept seeing, especially in trust companies and larger teams, was fragmentation. Tasks living in email, paper, notes, and “ask someone who knows.” New team members join and don’t know what “good” looks like, or what order things happen in. People work hard, but the file doesn’t move.
Done requires more than a list. It requires guided execution:
- clear statuses (incomplete, in progress, complete)
- prompted steps (especially when the work is unfamiliar)
- consistency across the team (so training doesn’t depend on tribal knowledge)
When there’s no system, the loudest task wins. The important task waits. And waiting is where estates go to die.
3) Make output easy enough to share (Accounting and reporting)
The final step of done is proving it to other humans.
In this industry, professionals are often expected to produce detailed reporting, sometimes 20-page reports that can take an entire week to assemble. Not because the work wasn’t done, but because pulling the evidence together is its own project.
That’s a problem, because “done” isn’t just completing tasks. Done is:
- the beneficiary understanding what’s happening
- the executor feeling supported
- the professional being able to show progress without losing days to assembling documents
When reporting is painful, updates get delayed. When updates get delayed, trust erodes. If you want a human-centered experience, done has to include communication, not just completion.
Why this matters: it’s humans, not just checklists
The most important reminder from all of this is simple: estate and trust work is deeply human.
We’re helping people settle an estate or administer a trust for someone they loved. People are grieving, stressed, busy, and often confused. Professionals are carrying a heavy load. The system should support them, not fight them.
There’s a massive intergenerational wealth transfer coming. You’ll see different numbers depending on the source, but it’s often cited around $60T over the next few decades. The planning side has seen a lot of innovation. The administration side has been under-served.
Not because professionals don’t care.
Because “to-do” has been allowed to masquerade as progress.
The takeaway
If you’re surrounded by lists but still feel stuck, the fix usually isn’t “try harder.”
It’s redesigning the path to completion:
- reduce intake friction
- guide execution with clarity
- make output easy enough to share early and often
And that’s also the lens we use when we build. We think about “done” as three connected pillars across estate and trust work: getting information in cleanly (intake), keeping the work moving with guided steps (execution), and generating outputs you can trust and share (reporting). Not as bells and whistles, but as the practical basics that help professionals stay organized, move faster, and support families with more confidence.
Because at the end of the day, the goal isn’t a better to-do list. It’s fewer open loops, less lingering work, and more forward motion, for the humans on both sides of the process.
