One of the hardest things for financial professionals to do is make retirement planning discussions more personal. I know this because it’s what I get paid to do—teach others how to move from pure financial questions to discussions about emotional matters so that they can deepen their client relationships.

Earlier this year, I spent a full 10 hours training a group of advisors on what I call the “Power 20.” This is a list of 20 questions and answers advisors can use to overcome the difficulties they might have switching gears to a more holistic approach.

To my surprise, the advisors in the session took to the questions like ducks to water. We spent time identifying the goals of each question and building a framework to help clients think more deeply about the non-financial side of retirement. Then we took time to role-play and help the attendees feel more comfortable in these new situations. I was a little surprised at the responses I got to the questions. I expected some pushback or worries from advisors about what would happen if they got too personal with their clients. But the overwhelming response was, “We are doing a disservice if we aren’t using information like this.”

Before I became a financial advisor, I knew very little about money or investing. I grew up a blue-collar kid in Detroit, and my only financial guidance was that money doesn’t grow on trees. Before I became a financial professional, I decided to start trading some hot internet stocks in the late ’90s. The good news is that the $200 I scrapped together almost doubled in two weeks. I decided to lock in my gains and sell the portfolio. However, back then it was only $10 to buy a stock and $15 to sell it. In the end, the trading fees not only ate a portion of my initial investment but basically chewed up most of my profits from the sale. No doubt, I wish someone would have sat down with me and explained the finer details of the investment world.

The same holds true for the non-financial aspects of retirement; both advisors and clients need to be trained or walked down this new path so they not only understand it but also apply it.

So I want to share an abbreviated version of my power questions. Here I offer five of them to help financial professionals wake up to the potential they have to impact a client’s personal life and legacy.

1. Do you think we need to retire the word “retirement”?
Talk about a simple layup question to get the ball rolling. Right now, more than ever, people don’t like the word “retirement.” They assume it means done, old, out to pasture and irrelevant. A set of images no retiree wants to be attached to. Therefore, by simply asking clients’ opinion on such a hot and pressing topic, you will not only get a glimpse into what they don’t like about the image of aging, but also a sense of what their definition of retirement is.

2. How will you know if you are winning in retirement?
This is one of my favorite questions because most people, including advisors, have no idea about how to answer it. Which is the whole point—it gets people thinking in different terms about life after work. We all know how to win at work, golf and volleyball, or maybe even at our health and relationships. But helping a client understand how to win at retirement is better than the magic of compounding interest. Hint: It has very little to do with money.

3. How has Covid served as a precursor for what retirement might look and feel like?
This is a good question for those of you who need training wheels for these types of conversations. It won’t shock the clients into silence or confusion. Unlike the previous question, this one will have most clients offering an immediate answer, though it may not be what you expect. All too often, we have heard the horror stories of being in lockdown and spending 24 hours a day with a spouse, kids or annoying neighbor, and clients will likely readily give you their own experiences.

Some couples and families, of course, have thrived through the pandemic and grown closer. People who once thought they would travel more in retirement may now feel differently about it because of the last couple of years. Either way, their answers will give you extra insight into what makes them tick and gives them happiness.

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