What Clients Really Want: 5 Questions Advisors Should Ask More Often

Financial advisors often face a common dilemma: How often should we proactively reach out In a profession built on trust, conversations are your most powerful tool. But not all conversations are created equal.

Many advisors stick to the usual script: portfolio performance, retirement projections, risk tolerance. These are important—but they only scratch the surface of what clients actually care about.

If your goal is to deepen relationships, increase retention, and create more meaningful planning opportunities, it may be time to ask different questions.

Here are five high-impact questions top advisors ask—and why they matter.

1. “What’s changed in your life since we last talked?”

This may seem obvious, but it’s surprisingly underused. Life moves fast. Health issues, job shifts, family dynamics—all of these can impact financial plans, sometimes without the client realizing it.

Why it matters:
Uncovering change opens doors for deeper planning conversations: insurance, estate updates, cash flow adjustments, or shifting priorities.

2. “What’s something you’ve been putting off financially?”

Every client has a financial to-do list they haven’t tackled. This question helps surface pain points that haven’t made it into prior reviews—often because clients are embarrassed or unsure where to start.

Why it matters:
This is where you can add value quickly. Helping a client take action on something they’ve delayed creates trust, momentum, and goodwill.

3. “How do you define a successful relationship with your advisor?”

Instead of assuming, ask. Some clients value proactive communication. Others want technical expertise. Some just want peace of mind.

Why it matters:
The answer may surprise you—and it gives you a client-specific framework for success. Plus, asking the question alone reinforces your commitment to earning their trust.

4. “What would you do differently if you felt totally confident about your financial future?”

This question shifts the conversation from planning as a chore to planning as empowerment. It also connects money to values, goals, and lifestyle—not just numbers.

Why it matters:
This is where true financial planning lives. The answer often reveals priorities that aren’t reflected in their current plan—and positions you as more than just a portfolio manager.

5. “Who else in your life might benefit from this kind of conversation?”

Done well, this is more than a referral ask—it’s a value-driven prompt. Framing it in the context of helpfulness (not marketing) keeps it aligned with your role as a trusted resource.

Why it matters:
When clients see you as someone who brings clarity and peace of mind, they’re more likely to refer others—especially family members navigating financial transitions.

Make These Part of Your Process

You don’t need to overhaul your meeting agenda to ask better questions. Start small:

• Use one of these questions to open or close every review meeting.
• Train your team to listen for “question cues” during everyday interactions.
• Build time into your process to reflect on what you learn—and how it should inform your advice.

Great advisors don’t just solve problems—they ask the right questions at the right time.