Inside Two High-Performing Planning Teams: A Live Peer Conversation

Key takeaways

• Vanilla’s AI-powered estate document review turned an hours-long process into seconds, letting both firms extend consultative estate planning support to every client tier instead of reserving it for their largest accounts.
• True North Advisors’ wealth planning team evaluates five core areas for every client: an estate plan, a tax return, a net worth statement, life and annuity products, and property and casualty insurance, regardless of account size.
• Cain Watters & Associates built an estate planning department from scratch and now supports thousands of clients nationwide, using AI to speed up document review, standardize training, and turn drafts around in a few weeks instead of months.
• Both firms said AI is shortening how long it takes new associates to become effective at reading trust and estate documents, compressing a learning curve that used to take years into roughly a week of guided practice.
• Client-facing estate flowcharts generated from clients’ own documents have become a key deliverable, with advisors estimating that around 90% of clients are surprised by what their existing plan actually says happens at each spouse’s death.

Two firms, one planning gap, different starting points (1:53–5:05)

True North Advisors and Cain Watters & Associates arrived at the same problem, estate planning is dense, document-heavy work that doesn’t scale easily, from different starting points.

True North Advisors is a roughly 70-employee Dallas firm managing $5.6 billion in assets, serving ultra-high-net-worth clients. Jamie Scott, CFP®, director of wealth planning, leads a three-person team that functions as a consultative arm for the firm’s advisors: sitting in on client and prospect meetings, building client deliverables, and vetting new technology.

“Our core purpose is to be a consultative arm for our advisory team,” Scott said.

Cain Watters & Associates, based in Frisco, Texas, takes a different shape. The roughly 300-person firm specializes in CPA and wealth management services for dental practitioners, serving clients across the country. Micah Adams, CFP®, an advanced planning wealth advisor, was brought on about a year ago specifically to close an estate planning gap.

“There was no estate planning department, and I kind of built it from scratch,” Adams said. He now serves as a team of one, working as a strategic advisor who helps clients think through their estate planning needs before an attorney ever drafts a document.

The five fundamentals every planning team should check (5:05–8:05)

Scott said her team holds every client, regardless of size, to the same five-point review: an estate plan review, a tax return review, a net worth statement, a review of life and annuity products, and a review of property and casualty insurance. “Those are the five fundamentals that our team says, no matter client size, these need to be looked at for every single client,” she said.

What changed is how fast that review happens. Before adopting Vanilla, Scott’s team spent significant time in Excel and PowerPoint building estate flowcharts by hand and reading through documents line by line. Now, running a full set of estate documents through the platform takes about sixty seconds and produces a summary of who holds each fiduciary role.

That speed changes what a client meeting looks like. “Being able to run all the estate documents through in sixty seconds and having just a summary of who sits in key fiduciary roles can enable us to walk into a client meeting and have a more detailed conversation, be more sticky with the clients,” Scott said.

Instead of asking a client to send documents and waiting weeks for answers, her team can walk in already knowing who’s named in each role and whether that still matches the client’s intent. “It’s taking the nuances out of having to do things in Excel and PowerPoint and giving us the time and attention we can spend with clients back,” she said.

Making advanced planning accessible at every client tier (8:09–13:56)

Cain Watters serves clients across a wide range of account sizes, including a monthly-fee program for clients without significant assets under management alongside traditional AUM clients. Adams said the firm’s goal was to close that gap. “We really wanted to create something that we can provide the same service across the board, and no client feels that there is a lack of quality,” he said.

Faster document review is what made that possible. Adams said the shift cut down the hours he used to spend reading estate documents line by line and let him extend the same attention he once gave a handful of large clients to roughly a hundred. “It’s really cut down the cost of digging through documents and really making me be able to expand my reach from a few clients to a hundred clients, to really make sure everyone’s getting the same quality of service,” he said.

Training new associates faster

Both advisors pointed to associate training as an underrated benefit. Traditionally, training someone to read an estate document from end to end takes years of hands-on repetition. Scott said her team now uses AI as a starting point, then trains associates to focus on the handful of details that actually matter.

“Now we can kind of accelerate that training and make them more impactful from day one,” she said. “Now you can do a hundred [documents] in your first week because you can run them through AI, and then we’re training them on key elements that might come up in different documents.”

Both advisors pushed back on the idea that this shortcuts real learning. Adams argued that estate planning is inherently a relationship-driven conversation, one that clients don’t want to have with an algorithm, and that faster document review frees associates to spend more time in those conversations rather than replacing them.

Turning dense documents into conversations clients understand (14:04–19:37)

Beyond speed, both advisors said technology has changed the depth of what they can show clients. Adams builds presentations and flowcharts directly from a client’s own documents to illustrate what happens at each stage: during their lifetime, at the first spouse’s death, and at the second.

“I’m going to say that ninety percent of the time, clients are surprised by what actually happens at the passing of both of them,” he said. Seeing it mapped out, he said, “creates a conversation where we’re able to change and update it and better reflect what their actual intentions are.”

Scott described a similar shift in scope. Her firm used to reserve full estate reviews for its highest-net-worth clients because of the time involved. “That changed from, used to, we would do the estate reviews for ultra-high-net-worth clients or our top end of our client spectrum. Now we can do it for everyone,” she said.

Her team also uses an AI-driven tax modeling tool to review Form 1040s across its full client base rather than a top tier, and a separate tool that consolidates property and casualty documents so the team can flag renewal dates in a single snapshot.

Preparing the next generation for what they’ll inherit (19:37–24:15)

Both advisors connected faster, cheaper document production to a longer-term goal: reaching clients’ children before a wealth transfer happens, not after. Adams built an internal portal so advisors across Cain Watters’ roughly 50 planners can request an estate planning project and track its status without back-and-forth calls or messages. He also uses templated, state-specific documents to get ancillary documents in front of clients’ kids, particularly ones heading off to college or moving to a new state.

That accessibility created a new line of business at Cain Watters. Clients who previously skipped estate documents because they didn’t feel they had enough assets to justify an attorney’s fee can now get a will, basic trust, or ancillary documents at a lower cost. “Now we’ve created a whole revenue stream to where clients are now paying for documents on Vanilla, and their quality documents,” Adams said, calling it a source of appreciation from clients and incremental revenue for the firm.

Scott’s team frames the same shift around family conversations. Having a visual, numbers-free flowchart to walk through with a client’s adult children, she said, helps capture a generation of wealth that firms risk losing if they wait too long to engage it.

Why these teams picked Vanilla, and how they pair it with other tools (24:15–34:50)

Asked why they chose Vanilla over competing platforms, both advisors pointed to compliance as the deciding factor. “They don’t use their AI to learn from our documents, so that was really important, obviously, with the SEC,” Scott said, adding that her firm evaluated Vanilla against competitors roughly a year before adopting it and found its modeling and pricing structure to be a better fit. That same design lets her team run unrelated documents, like prenuptial or postnuptial agreements, through the platform without raising data concerns.

Both firms also use Vanilla alongside eMoney rather than in place of it. Scott described drawing net worth statements from eMoney but turning to Vanilla for anything that needs to tie to how assets actually flow at death, including exemption amounts already used and portability elections.

Higher-fee clients get a full Vanilla-generated report with a detailed balance sheet, waterfalls, and projected estate values; simpler balance sheet requests still come out of eMoney. Adams added that adopting Vanilla pushed his firm to standardize how its planners title accounts in eMoney in the first place, so that everything transfers cleanly and looks consistent across every planner and client.

Q&A highlights

Is AI going to replace financial advisors and estate planning associates?

No, according to both advisors. Adams argued that estate planning is deeply personal work, the kind of conversation clients want to have with a person rather than an automated tool, and that AI is instead freeing associates to spend more time in those conversations. Scott agreed, noting that AI is helping new associates get up to speed faster without cutting them out of the learning process.

How should advisory firms evaluate estate planning technology before adopting it?

Scott said her team looked at Vanilla alongside several competitors before choosing it, prioritizing compliance (specifically, that the platform doesn’t train its AI on client documents), the depth of its modeling, and a pricing structure that fit a firm with a larger planning and consulting team.

How do firms charge for estate planning services layered on top of AUM or planning fees?

Adams said Cain Watters created a separate engagement agreement and tiered fee structure specifically for estate planning work, charged in addition to any AUM or planning fees a client already pays, with pricing that scales from basic document support up to full strategic coordination with a client’s attorney.

Can younger or lower-asset clients get affordable estate documents?

Yes. Adams said many younger clients skipped estate planning because they felt they didn’t have enough assets to justify an attorney’s fee. Lower-cost, templated documents now let Cain Watters offer wills, basic trusts, and ancillary documents to those clients, including young adults turning 18, at an accessible price point.

About the speakers

Jamie Scott, CFP®
Jamie Scott is director of wealth planning at True North Advisors, where she leads the planning team that serves as a consultative resource for the firm’s advisors. Scott holds a master’s degree in personal financial planning and a bachelor’s degree from Texas Tech University, and she specializes in estate, retirement, tax, and insurance planning.

Micah Adams, CFP®, CAP®, AEP®
Micah Adams is an advanced planning wealth advisor at Cain Watters & Associates, a Frisco, Texas-based CPA and wealth management firm serving dental practitioners nationwide. Adams holds a bachelor’s degree in personal financial planning from Texas Tech University and also serves on the board of Dallas Hope Charities.

The information provided here does not constitute legal, financial, or tax advice. It is provided for general informational purposes only. This information may not be updated or reflect changes in law. Please consult with an estate attorney, financial advisor, or tax professional who can advise as to your particular situation.