I was recently speaking to a friend and colleague about the conversations he has with new clients. He is one of a new wave of wealth managers (and other professionals) who are as interested in getting to know the full picture of their client’s lives as they are about investment and planning strategies. He asked for my thoughts on deepening client conversations.

Opening up conversations about money, business, family and legacy with a new client or even a prospect can feel overwhelming and uncomfortable. These topics (particularly family and money) are usually loaded with emotion. I’ve gained expertise in having these conversations through my work as a family therapist/psychoanalyst, consultant to enterprising families and educator of professionals serving these families.

In this blog I’ll share some ideas for deepening conversations at the very beginning of a client relationship (whether your main topic is wealth management, accounting, law or another field of practice) and for opening up discussion in a few specific realms.

As this is a blog designed to be read in a minute (OK, maybe a few at times), these are the introductory basics. Feel free to reach out if you’d like to discuss more deeply.




Most professionals have an approach to these initial conversations. Stick with what you usually do (if that is working) and look for ways to add to that. Most important is to find language that feels like you and is comfortable for how you speak and think about the world. If my suggestions do not feel genuine to you – revise them and make them your own.

“What are you looking for in a wealth manager (CPA, attorney) and what kinds of experiences have you had in the past – both positive and troubling?”

This allows them to speak and you to listen which you should do carefully. It also increases the chances of learning about negative experiences and gives you the chance to describe how you would address the same circumstances in your practice.

“Are there areas of my work you do not completely understand? I welcome all questions and if I ever explain something in a confusing manner – please let me know so I can try to better explain it.”

This shows humility and patience. I often have my clients tell me they do not totally understand elements of the work another professional does for them and are often hesitant to ask for clarification. This is an unstable foundation for a professional relationship. By letting all clients know up front you welcome their questions and you are committed to going over things as often as necessary, you begin to create good will and trust.

“Some of my clients like to stick to the basics (e.g., tax planning, investment strategy, trusts) and I’m completely fine with that. At the same time, when clients get to know me and can be more open about their family and other significant relationships, what is most important to them, and how they want their wealth to make a positive impact and what concerns them, we develop a collaboration that can be quite powerful in meeting their goals in many aspects of life. When I am not the resource for all those areas, I have extensive relationships with colleagues in a wide variety of fields and am happy to connect you.”

This is an “open door” for those folks who are not looking for more than basic, technical services (at least not at this point) but plants a seed. And it lets those looking for a more personal relationship, with hopes and dreams beyond the technical, know that you are open and comfortable.

“What is most challenging for you in selecting a new wealth manager (CPA, attorney…)?”

This is a potentially golden question. It is a trust-builder and relationship-builder if you can empathize with their concerns, let them know they make perfect sense to you and why it does based on experiences you’ve had.




“We have lots of family business clients in our practice. Family often feels tricky enough on its own. Combining family and business can be incredibly rewarding and has challenges. There are several people on our team who have seen a lot in this realm. We are always happy to talk. Keep in mind – if everything is going smoothly now, that is the best time to take steps to manage the interplay of family and business. The messiest situations we have seen could have been handled with much less drama and heartache early on before problems arose.”

This tells the client you have experience with their situation and keys them into the reality that waiting for a crisis is a recipe for disaster. You should also give some general examples of things you often see become problematic. For example, “Many family business clients are very informal which can be a nice business culture. However, often these families do little formal planning for an exit or transition and then get caught with a less than ideal time frame for what they want to accomplish and tremendous pressure of family relationships.”




“How do you hope your success will affect your children’s lives? Do you have any concerns? Years ago professionals and families thought little about this. Today there are experts in parenting, child development and family wealth. We can connect you for a free consult if you want to learn more about the opportunities for your family.”

Hopes and concerns give you two opportunities to glean details you can use to connect to specifics of what you do well. If they tell you they have a child with special needs and you have experience with this, let them know what you have done and be sure to check in and ask if what you are describing sounds relevant. If they tell you it does not, apologize and ask why; clarify if they do not understand or back off, and ask how your ideas are missing the mark and meet them there. If you do not have experience with, in this example, special needs issues, tell them that and let them know you have a network of colleagues and offer to connect them for a free consult with a colleague willing to do that. Generosity of resources in your network helps the client and sends them to a colleague to add value.




“Blended families are so common and what interests me is that these families handle their finances in so many different ways. We want to learn about your relationship and family and figure out together how we can serve what you are trying to achieve.”

This is very open and normalizing for what can be a tough issue. You can create comfort and trust by letting them know you have seen a bunch of clients like them and that you do not pigeon-hole them into a preconceived strategy.

Writing suggested approaches is less than ideal. Tone can be lost in written word or it may simply not be how you speak or think. My hope is that you will take my suggestions here and tailor them. The main idea is that by gently and thoughtfully opening up topics of conversation that professionals do not typically open up, you can set yourself apart and offer new and potential clients a more direct path to what matters most to them.