In the world of financial advising and life insurance sales, success doesn’t come from having a powerful pitch or a slick presentation. It comes from the ability to connect, understand, and build trust—and that begins with asking great questions.

Too often, advisors and agents spend too little time fact-finding, filling in a form with details about someone’s investments and insurance.  Then, without really understanding the specific needs, dreams, desires and fears of their prospect, they unload technical jargon and product features in the hope that something will stick. 

But the most successful professionals understand that the real power lies not in what they say, but in what they ask.

Why Asking Great Questions Matters

At its core, financial advising and life insurance sales are about solving problems. But before you can solve a client’s problem, you have to understand them at their deepest “why” level. That requires more than the surface-level information in some fact-finding form—it demands insight into their values, goals, fears, and life circumstances.

Great questions serve several essential purposes:

• Build Trust: When you ask thoughtful questions and genuinely listen, clients feel heard and understood. This is foundational to building the trust necessary for long-term relationships.

• Uncover Motivation: People don’t buy life insurance or invest in retirement plans without an emotional reason—they want to protect their family, achieve a goal, or avoid a fear. Great questions uncover these deeper motivations.

• Help You Get to “Yes” By Being Able to Personalize the Solution: Asking the right questions allows you to tailor your recommendations to the client’s unique situation. Once you’ve explored their deepest fears and desires, you can tie the benefits of your recommendations back to their specific concerns.

• Reduce Resistance: When clients feel like they’re guiding the conversation and reaching their own conclusions (through your questions), they’re far less likely to push back or feel pressured.

The Art of Asking Great Questions

Asking good questions is a strategic skill. Here are a few principles gleaned from top advisors to guide you:

1. Start Open-Ended

Begin with broad, open-ended questions that invite the client to speak freely.

• “What inspired you to start thinking about life insurance now?”
• “What concerns do you have about your financial future?

These types of questions encourage storytelling, which gives you richer insight into the client’s mindset.

2. Dig Deeper

When a client gives you a surface-level answer, don’t stop there. Follow up with “why,” “how,” or “tell me more.”

• “You mentioned wanting to leave a legacy—what does that look like for you?”
• “You said you’re worried about outliving your money—what specifically concerns you?”

This deepens the conversation and moves it from transactional to transformational.

3. Address Emotions

Financial and life insurance decisions are emotional—even for engineers. Whether it’s the fear of not providing for their family, the anxiety of running out of money in retirement, or the desire to leave a legacy, emotions drive decisions. Acknowledging this can be a powerful tool.

• “How would it feel to know your family is financially secure if something happened to you?”
• “What keeps you up at night when it comes to your finances?”

4. Clarify Priorities

Clients often have competing goals. Help them identify what matters most.

• “If you had to choose between maximizing growth and minimizing risk, which is more important right now?”
• “What’s your top financial priority over the next 5 years?”

This helps both you and the client get clear on where to focus.

Personal Offers Create Clients 

Once you understand your prospects at a deep level, you can make your proposal about their specific needs.  

Instead of “This will give you $500,000 to pay off your mortgage, you can say “This will allow your family to stay in their home.”  Instead of “This will help ensure that you have all the money you need into your nineties,” you can say “This is designed to ensure that you won’t end up broke in your eighties like your uncle did.”

Practice going much deeper in your questions and then tying your solutions to the answers you’ve received. 

I teach a simple “question technology” you can use to easily get deeper.  If you’d like me to share it, e-mail me with the word “QUESTION” and your email address and I’ll send it to you.

In the meantime, keep REACHING…