10 Questions Every Advisor Should Ask Before Choosing an Estate Planning Solution

By nature, the practice of estate planning has a level of seriousness and substantiality that few other advisor-client conversations will ever reach. When you bring technology into that process, you want to make sure it reflects the importance of the topic at hand. 

Choosing an estate planning software that brings the appropriate credibility and accuracy is no small task, and it’s easy to get lost in the details when comparing solutions. 

To help cut through the noise, we built the Buyer’s Guide to Estate Planning Platforms for Advisory Firms, which walks through the criteria to consider when choosing a solution and provides tips for evaluating your firm’s unique needs. 

Here, we’ll go through the top 10 questions to ask as you evaluate and trial estate planning platforms. Use these as guideposts to weigh pros and cons, determine your specific needs, and choose the most appropriate solution for you and your team.

For a deeper dive, download the complete Buyer’s Guide here. 

The top 10 questions to ask when choosing estate planning software

1. How does the solution help differentiate my firm and showcase my value?

True differentiation doesn’t come from better investment advice—it comes from deeper relationships and holistic planning.

Estate planning technology allows you to offer value that goes far beyond portfolio management. When you integrate estate strategy directly into financial planning, you demonstrate that you’re not just growing wealth—you’re helping clients preserve it across generations.

A platform that combines visual clarity, accuracy, and collaboration reinforces your brand as forward-thinking and comprehensive. It helps answer the question clients often ask (silently): “What am I really paying for?”

2. Does this solution enable me to prospect more effectively?

The best estate planning platforms aren’t just operational tools; they’re conversation starters. Estate planning technology provides a powerful entry point with prospective clients who are often confused or overwhelmed by the process. When you can clearly visualize their estate, explain their options, and identify strategy gaps on the spot, you demonstrate both expertise and empathy.

In short: the right tech helps you show your value before you’re even hired.

By turning a complex topic into something tangible, you build trust faster and make your advisory indispensable from the first meeting.

3. Is it created and used by people with first-hand experience doing what I do every day?

It should be.

The difference between a tool that “gets it” and one that doesn’t comes down to the experience of the people who built it. The best estate planning software is developed by teams with deep backgrounds in estate law, financial advising, and technology—not just software engineers and tech CEOs.

That cross-disciplinary foundation ensures that the platform aligns with how advisors actually work, supports collaboration with attorneys, and respects the boundaries of licensed legal practice. It also means the platform is continuously improved based on real advisor feedback and evolving client needs.

4. Does it use AI to simplify my workflows, save time for me/my team, and identify gaps?

Leading estate planning platforms are using AI to automate manual and time-consuming work like summarizing documents, extracting key data, or identifying missing components in existing estate plans—so you can focus on strategy and client conversations.

Look for solutions where AI enhances accuracy and transparency, not complexity.

For example, AI that can analyze an estate plan, flag inconsistencies, or answer document-related questions can dramatically reduce administrative time while improving client trust and understanding.

5. Does it integrate with my other tools?

Holistic wealth management is easier to deliver when your tools can talk to each other. A great estate planning platform doesn’t operate in isolation, rather it connects seamlessly with your other systems. The best solutions integrate with financial platforms like eMoney, Addepar, Black Diamond, and Orion, updating daily to reflect clients’ full and current asset picture.

These integrations ensure you’re working from a complete, accurate dataset—covering both managed and unmanaged assets—and give you a single pane of glass view for all planning decisions.

6. How can it help me go deeper with my existing clients?

A great estate planning platform opens doors to broader and deeper client engagement.

When you build a comprehensive estate view, you naturally uncover assets and relationships beyond the portion of a client’s portfolio you currently manage. This holistic visibility lets you identify opportunities for new services, strengthen trust, and ensure your value is felt across the client’s full financial life. Plus, estate planning is a natural inroad to conversations about your clients’ families and values—conversations that help spark personal connection. Starting a client call with, “How was Connor’s college graduation ceremony?” is far more meaningful than small talk about sports or the weather.

The best platforms support ongoing updates and collaborative discussions, turning estate planning into a dynamic, continuous conversation instead of a one-time event.

7. How could it help me connect with the next generation?

Estate planning is one of the most powerful bridges between generations for advisors.

The right tech provides organic ways for advisors and clients invite heirs into the conversation early and more seamlesly—helping families visualize legacy decisions and understand their long-term impact. By using visual scenarios and simplified next-gen presentations, you demonstrate continuity, care, and foresight.

Advisors who do this retain family relationships far more effectively: While 80% of heirs typically leave their parents’ advisor, those engaged through estate planning are far more likely to stay.

8. Does it let me easily and accurately model scenarios and “what ifs” for my clients’ plans?

Sophisticated scenario modeling tools that let you explore “what if” questions in real time make the estate planning process feel more collaborative and accessible for your clients. A solid tool should be able to help you model and answer questions like:

• What happens if we create a GRAT or SLAT?
• How would moving to another state affect taxes?
• What if a beneficiary changes or an asset is sold?

Advanced planning modules—like Vanilla Scenarios™—enable side-by-side comparisons with accurate estate tax and cash flow projections, so clients can make confident, informed decisions.

These dynamic visuals turn abstract strategies into stories clients can understand.

9. Does it have enterprise-grade security and compliance protocols?

No matter how large or small your firm is, top-tier security and compliance is a non-negotiable. 

Estate planning data includes some of the most sensitive client information imaginable. The best platforms adhere to SOC 2 Type II standards, use trusted cloud providers like AWS or Azure, and employ robust detection, analysis, and incident response protocols.

Look for vendors that regularly meet enterprise-level compliance requirements and prioritize resilience against cyber threats. A strong security posture not only protects your clients—it protects your reputation.

10. Does the company provide robust support and ongoing training and education?

The right partner doesn’t just sell you the software—it provides ongoing support for your firm’s long-term success. 

Top-tier estate planning tech providers offer dedicated support teams, documentation, and responsive help when you need it. They also invest in ongoing education like webinars, CE-eligible courses, and resources that keep you and your team sharp. 

For example, Vanilla offers free CFP® CE courses through Vanilla Academy, designed to deepen advisors’ estate planning expertise and client communication skills.

When evaluating vendors, ask whether they’re equally committed to your education as they are to their product roadmap.

With Vanilla, the answer to all of these questions is, “Yes, and…” 

Schedule a call today to learn why Vanilla is the most trusted name in estate planning technology and see how it can elevate your firm’s offering. 

To learn more about evaluating estate planning solutions, download the Buyer’s Guide to Estate Planning Platforms for Advisory Firms here.

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.