A colleague of mine shared an interesting story about a friend of his who would be retiring soon. The friend wanted some advice about financial advisors. “He told me he has worked with a terrific guy for years and done very well investing,” my colleague explained. “But now he wants someone who specializes in retirement. I assured him his advisor could help with retirement needs, but he said he didn’t think so.”

According to my colleague, the client said: “For years, we have talked pretty much only about investing and the markets. Once in a while he will start a conversation about estate planning or Medicare, but he doesn’t really follow through. And he’s met my wife only once.”


If you think this scenario is unlikely, it’s not according to the clients. In surveys, advisory clients indeed say the No. 1 thing they want to hear about from their advisors is retirement income. Two-thirds of them want to hear about issues of longevity planning and health. And many complain that their advisor has not included their spouse in any meaningful planning conversations.

When I talk to advisors (virtually these days) I perceive big disconnects in the retirement planning dialogue they’re having with clients. Some of these gaps have been common for years—and it happens because clients aren’t asking and advisors aren’t offering. Part of the problem is that there’s a lack of regular engagement between the parties and it’s likely that the clients are spreading their assets around, not connecting with a specific advisor. Remember that these clients will eventually consolidate and you want to be on the receiving end.

I’ve seen this movie before. For human fossils like me there lingers a clear memory of the struggle to retain clients that was frustrated by market volatility in the 1980s, particularly in 1987, and the defections taking place from brokerage firms to bank trust departments and investment managers. Since there were very few RIAs in place at the time, brokerage firm advisors were often characterized at the time as “stockbrokers.” That led to the rise of managed accounts. “Real” advisors, the competitors would say, don’t charge commissions and will tell you the performance of your accounts. Why won’t your stockbroker do that?

Fast-forward to 2021, when the baby boomers’ median age hits 65. Many very basic questions about their fears and aspirations have been left unanswered by too many advisors. As the queries about stock performance and investment processes stumped the stockbrokers of the 1980s, these new questions can stump advisors today. It might get clients thinking, and the thought process might end in pink slips for advisors.

Here are some of the questions they’ll be asking:

How much do I need?
They may not be sure about how much income they can draw from their investments, and they fear running out of money in retirement.

How will I pay for my healthcare?
They are not sure about how much they should pay, whether they should buy insurance (or where to get it), what they need to do if they are hospitalized or what is covered. They are afraid because they don’t know how or how much to pay for healthcare as they age.

How do I decide about Social Security and Medicare?
They are not sure about how they make the right choices for benefits, or whether they should work with an advisor or consultant to decide. They are afraid of making a mistake with their elections, and that there’s no going back if they do.

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