There is a frenetic dynamism around artificial intelligence (AI) in the financial sector. In an environment defined and dominated by complexity, compliance, and accountability, AI promises an industry-shifting increase in speed and efficiency. Massive volumes of data can be parsed, raw numbers can be translated into actionable insights, and undiscovered value can be identified in a matter of seconds. But in high-stakes advisory work, speed without structure introduces its own set of risks.

For Certified Exit Planning Advisors and their clients, the conversation must shift from what AI can do to how it should be used. To contribute to this conversation, ELLA, a digital workbench for trusted advisors, examines the risks of unguarded AI, introduces the idea of Sensemaking, and highlights why advisors should still be central to the exit process.

The Risks of Generic AI Tools

There is no question that AI offers exit planning professionals new ways to accelerate analysis, synthesize information, and generate insight. Frontier models, such as Grok and ChatGPT, can also provide context around the broader world of exit planning.

The challenge is that generic AI tools operate on the information provided in the moment. They lack a persistent understanding of the client and a connection to verified fact-finding data. Without a framework grounded in exit planning, generic AI tools are prone to overgeneralization, context-switching errors, and hallucinated conclusions. These issues are particularly prevalent when data is missing or prompts aren’t precise.

Exit Planning Is a High-Stakes Use Case

There are so many low-stakes use cases for generic AI: drafting emails, summarizing meetings, tightening ad copy, creating checklists, proofreading memos, and the list could go on. Unfortunately, exit planning isn’t on it.

At its core, exit planning requires continuity. Accordingly, context is not optional; it is the foundation of sound advice.

Advisors need to synthesize years of financial, legal, and estate documents and understand them through the lens of who the owner is, what they want/need out of the sale, where the business is located, why the owner is selling the business, when they want out, and how they operate.

Exit planning also demands accountability. Advisors are not simply analyzing data. They’re guiding decisions that involve life savings, succession outcomes, and tax exposure. In this setting, even slight inaccuracies can have outsized consequences.

Without context, guardrails, or professional oversight, even small AI-driven assumptions can cascade into serious consequences. In exit planning, these errors rarely remain theoretical; instead, they manifest in actual outcomes.

What’s at Stake When AI Lacks Guardrails

Without guardrails, small AI assumptions can easily become embedded in strategy, and as strategy is translated into action, those actions produce outcomes that may be irreversible. Ultimately, speed becomes risk, and generic-AI assistance increased the potential for:

Perhaps most importantly, though, exit planning is inherently about relationships. Advisors and business owners build trust through informed conversations, not AI-driven insights. AI can support fact-finding and the production of deliverables, but it cannot replace an advisor’s knowledge and experience. Put simply: AI should strengthen judgment, not replace it.

From Prompting to Sensemaking

It’s not a question of whether or not advisors use AI; it’s about how they should use it.

Most generic AI tools are built around prompting. Advisors ask a question, provide some background, and receive a response. The problem is, generic AI lacks the holistic view and contextual knowledge of a client to make a practical (not theoretical) exit strategy.

ELLA’s Sensemaking, on the other hand, takes a fundamentally different approach.

Rather than asking advisors to explain a client’s situation repeatedly, Sensemaking is grounded in the structured fact-finding data already captured within ELLA. It draws from verified information about the business and the owner, preserving context across time, meetings, and deliverables.

This distinction matters. AI engineers have designed prompt-based tools to generate answers. ELLA designed Sensemaking to support understanding. Meaning, when information is incomplete, Sensemaking can help flag gaps instead of guessing with generalizations. When questions require nuance, it can surface patterns, risks, and priorities for the exit team to review without presenting conclusions as facts. This feature enables advisors and the exit team to maintain firm control over decision-making.

Guardrails Aren’t a Limitation

A common concern of AI guardrails is that they’ll restrict capability. In high-stakes advisory work, the opposite is true. Guardrails enhance usability and reliability, protecting what matters most to clients: trust, data integrity, and accountability.

ELLA enforces these protections by redacting certain sensitive information before any model interaction, isolating client workspaces, and preventing client data from being retained or used for training. These controls align the use of AI with the same ethical and professional standards that advisors already follow.

Additionally, by grounding frontier models with verified fact-finding data, Sensemaking prevents the system from inventing context or filling gaps with assumptions. This framework is also known as retrieval-augmented generation (RAG).

RAG combines the strengths of traditional information retrieval systems with the capabilities of generative large language models (LLMs). By combining your data with the entire corpus of exit planning data, deliverables and insights become more accurate, up-to-date, and relevant to your specific needs. When dealing with factual information or data-driven responses, RAG offers several advantages over generic AI tools, including:

• Access to new information

• Factual grounding

• Vector database searches

• Improved relevance, accuracy, and quality

• More effective agents and chatbots

Using a RAG approach to ELLA’s augmented-AI, it removes friction and risk from advisor work by ensuring that:

• Context is persistent and client-specific

• Sensitive information remains protected

• Outputs are grounded in verified fact-finding data

• Missing or ambiguous information is surfaced instead of being inferred

• Hallucinations and irrelevant conclusions are filtered out

• Advisor judgment remains central to interpretation and decision-making

• Insights can be safely reused across meetings, deliverables, and time

In exit planning, insights are only as good as the data, history, and intent behind them. For this reason, it’s critical to have an AI tool that supports all the information gathered during the Discover phase, where advisors deliver a business valuation, determine owner needs, and create a prioritized action plan. Without context, AI can produce answers that sound plausible but fail to accurately reflect the reality of the business or the owner's priorities.

By anchoring AI to structured fact-finding, ELLA ensures that insights remain connected to the whole picture, eliminating the need for members of an exit team to reinput background information. Ultimately, advisors can move faster and spend more time with their clients without sacrificing rigor, helping them focus less on reestablishing context and more on guiding decisions that produce lasting value.

A Better Way to Use AI in Exit Planning

AI is here to stay, and advisors are right to explore how it can support their work. The real question is not whether AI belongs in exit planning, but whether advisors are using it in a way that respects the complexity and responsibility inherent in the process. In high-stakes advisory work, speed alone is not the goal; trust is.

We built ELLA to foster relationships. By grounding AI in structured fact-finding, ELLA allows advisors to provide more value to their clients. When it comes down to it, Sensemaking doesn’t replace an advisor’s judgment or shortcut relationships; it strengthens them. If you would like to learn more about how ELLA Sensemaking tools can help you advise your clients, reach out to us for a free demo of our advisor workbench.