Why I Press Until It Hurts

Why I Press Until It Hurts

A few years ago, I was a fan of the Netflix series “Suits”. In one of the early episodes, the protagonist Harvey Specter was mentoring his young protégé on how to move a case forward. “Keep pressing until it hurts. Then you’ll know where to look”, he said as he sent off his understudy to get more information.

This is absolutely true for wealth advisors if they want to help clients deal with their most important concerns.

I’m not talking about table-stakes discussions such as determining the clients’ tolerance for risk or what their retirement income goal is. That shouldn’t be difficult, and it shouldn’t require a heavy, uncomfortable conversation to clarify.

I’m talking about the things that people don’t even realize are a problem. It’s often something that needs to be uncovered. It’s what my good friend Kevin Low calls “provocative” conversations.

I’ll give you an example. I was having lunch with someone the other day, talking about all the usual things that get people caught up. “How have you been? How’s the family?”. The person casually offered this about the couple’s adult children. “Our kids still rely on us a lot. They haven’t really grown up”.

That’s a courageous statement I would say. By that I mean, that must not be easy to admit. The individual clearly trusted me and was willing to be vulnerable. So I probed a bit.

“Oh, how do you mean?”. The response was “Well, they’re good kids, but they just don’t seem to be as independent as they should be for their age”. A few examples and more detail were given.

Now, it’s important to understand that this couple is in their 70’s and have built a meaningful amount of wealth. So I sat back and folded my arms and I said this. “I’m going to ask you something that might make you uncomfortable, but I think it’s important. If your kids can’t do what they need to do for themselves, how are they going to help you as you age? At some point, you’ll need people close to you to guide you through changes in your life, with your health and your care. How will they do with that?
And what about the wealth you’ve built? How will they manage that and assume the responsibility that comes with it?”

You’ll know you’re onto something if you watch the person’s body language and it looks unsettled. They fidget. The rub their eyes and take a deep breath. You’ve pressed and you’ve found where it hurts. Well, one spot anyways. Who knows? There could be more.

As an advisor, opening up that conversation within a family and finding solutions is incredibly powerful. It might be the most important thing a trusted advisor could do for clients because it touches at the level of their values. It’s goes beyond numbers and calculations and addresses things that can’t be quantified but are of more importance than things that can be.

Not all issues related to values and family dynamics are hard to uncover. Some are out in the open and the clients know they need to be addressed. The child who needs financial assistance but who is in an unstable marriage. The one adult child who is not responsible with money. The family cottage that is important to and affordable for some siblings and not others. There is something of that nature in almost all our lives.

It’s the issues that need to be revealed that require an advisor skilled at recognizing them and capable of steering the uncomfortable conversation.

I’m reminded of a couple whose single, adult son lived with them and who clashed with the father. The father told me that his wife kept the peace around the house. He knew that everything would be ok, thanks to her, while he was alive. “What if she dies before you and it’s just you and your son?” I asked.

Silent pause.


Ah, I found where it hurts.

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