For dental practice owners and high-income business owners, a discovery meeting with a wealth advisor is more than an introduction — it’s an opportunity to evaluate whether an advisor can provide proactive guidance across taxes, investments, practice growth, and long-term financial planning.

Many entrepreneurs come to JE Simmons & Co after experiencing the same frustrations:

• Reactive CPAs who only communicate during tax season
• No long-term planning strategy
• Confusing fee structures
• Separate advisors who don’t coordinate together

The right advisor should help you align your personal and business finances into one integrated plan.

Here are the most important wealth advisor discovery meeting questions to ask before choosing a financial partner.

1. Are You a Fiduciary?

One of the most important questions to ask a financial advisor is whether they act as a fiduciary at all times.

Ask:

• Are you legally required to act in my best interest?
• How are you compensated?
• Are there commissions or hidden fees?
• What services are included?

Understanding fee structure and fiduciary duty is essential when evaluating trust and transparency.

2. Do You Work with Business and Practice Owners?

Entrepreneurs face unique financial challenges, including:

• Revenue growth
• Partnership planning
• Cash flow management
• Retirement planning
• Business transitions and succession planning

Ask:

• How many business owners do you work with?
• Have you advised startup or fee-for-service practices?
• How do you coordinate business and personal planning?

At JE Simmons & Co, we specialize in helping practice owners create proactive financial strategies that support both business growth and personal wealth management goals.

3. What Does Your Financial Planning Process Look Like?

A quality financial planning consultation should go beyond investments.

Ask:

• What happens after the discovery meeting?
• How often do we meet?
• What information do you gather?
• How do you track progress?

At JE Simmons & Co, our process includes:

1. Discovery Meeting
2. Financial “full physical” and document review
3. Comprehensive onboarding session
4. Ongoing quarterly reviews and planning

4. How Do You Approach Tax Planning?

Many practice owners seek proactive strategy — not just tax preparation.

Ask:

• Do you provide year-round tax planning?
• How do you help reduce unnecessary taxes?
• What retirement or entity planning strategies do you recommend?
• How do you coordinate investments with tax planning?

The best advisors help clients make strategic decisions before tax consequences happen.

5. What Is Your Investment Philosophy?

Your investment strategy and risk tolerance should align with both your personal goals and your business exposure.

Ask:

• How do you assess risk tolerance?
• How are portfolios customized?
• What role does tax efficiency play?
• How do you help clients during market volatility?

At JE Simmons & Co, our investment philosophy focuses on diversification, tax efficiency, long-term discipline, and risk management.

6. How Do You Help Clients Through Major Life Events?

A wealth advisor should help guide decisions around:

• Business or Practice sales
• Partner buyouts
• Retirement
• Divorce
• Home purchases
• Estate planning

Ask:

• How do you adjust financial plans during major transitions?
• Do you coordinate with CPAs and attorneys?
• How do you help clients prepare for long-term wealth transfer?

Red Flags to Watch For

During an advisor interview checklist review, be cautious if you notice:

• Reactive tax advice
• Product-first conversations
• Confusing pricing
• Little discussion about goals
• No clear planning process
• Limited experience with business owners

The right advisor should feel like a long-term strategic partner — not just an account manager.

Final Thoughts

The best wealth advisors help clients integrate tax planning, investments, retirement strategy, and business planning into one coordinated approach.

At JE Simmons & Co, we work closely with practice owners and entrepreneurs who want proactive guidance, long-term planning, and a clear financial strategy designed around their goals.

Schedule an Introductory Meeting

If you’re looking for a more proactive approach to wealth management, JE Simmons & Co can help you evaluate your current strategy and identify opportunities across tax planning, investments, and long-term financial planning.