Pete the Planner: Invite your financial adviser to criticize your thinking

The YouTube algorithm has me in a weird place these days. I’m not sure how or why it’s stopped serving me Indian head-massage videos and bourbon-hunting videos in lieu of expert-car-selling videos. But it has.

Therefore, over the last week, I’ve watched no less than an hour of a “master” car salesman deploy a combination of verbal gymnastics and unexpected handshakes to win curbside negotiations. I leave each viewing more confused than the last. Alas, I keep clicking play.

Thank goodness I was shaken back into healthy business communication the other day when I was interviewing candidates for a few job openings at my company. While I’ve interviewed hundreds of people over the years, this past week I noticed a trend of many candidates asking the same beautiful question—a question so good that it gave me hope that we’re not all out here trying to trick one another.

“What gives you any pause about hiring me for this position?”

It’s brilliant. Not only does it convey the desire to communicate with candor, but it then allows the person to address whatever concerns I might have had.

As I sat and reflected on my week, it occurred to me how these two seemingly unrelated anecdotes do a really good job of framing the importance of healthy communication with a financial adviser.

You’re not as naturally aligned as you think with your financial adviser. Sure, if they make you money, they’re often compensated for it. But I don’t think that’s the alignment you’re seeking. In fact, I think you should be looking for them to tell you what you don’t want to hear. I think you need to ask them a modified version of the interviewee question.

“What gives you pause about my ability to accomplish this financial plan?”

Allow me to peel back the onion a bit more. A vast majority of financial professionals plug your numbers into some sort of software, and that software spits out a financial plan. The ridiculous assumption is that you follow the plan. It’s one of the strangest, unchallenged assumptions in all of the process. Combine this peculiarity with an adviser’s desire to not lose you as a client, and you can begin to see how the communication dynamic doesn’t naturally support candor and transparency.

Don’t misconstrue my point. I’m not suggesting your adviser is operating with malfeasance. Instead, I’m suggesting that, if you give them express permission to observe and speak frankly, you will benefit exponentially. Too often, you assume the variables of your financial plans are left to fate. Inflation needs to stay at X. Your rate of return must stay above Y. Despite the fact that I’ve been in the financial industry for over two decades, I’m still shocked by the amount of strategic finger-crossing people employ, as opposed to cooperative ownership.

Are you ready for the nuance?

When you ask your adviser, “What could go wrong?,” you shouldn’t limit your inquiry to exploring various types of bad luck. Of course, a market crash could hurt you. The real answer might be, “You’re taking too much risk, in order to make your plan work.” Read that sentence again. If your assumptions and decisions are the problem, then you have to depend on what you call luck. Giving your adviser permission to criticize your assumptions and decisions is vital to accomplishing your goals.

Don’t expect anything earth-shattering the first time you broach this idea with your adviser. It’s not the typical cadence of the financial planning industry. If the initial question doesn’t jar anything loose, try, “What gives you pause about the assumptions I’ve made or the risks I’ve accepted?” And if that doesn’t work, try, “Are you seeing any patterns of behavior or decision-making that, if left unchallenged, could compromise our plan?” Keep pressing them to be critical until they offer something. Once that seal is broken, candor can take hold. Again, this isn’t natural for most financial advisers. But you need it to be, so you’ve got to force it.

“It’s wildly important to me to receive constructive criticism, as it relates to my role in my financial plan. Can you please take some time to consider where I can improve?”

You have to give your adviser permission to serve you more transparently. And if all else fails, just send them this column.•

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Dunn is CEO of Your Money Line powered by Pete the Planner, an employee-benefit organization focused on solving employees’ financial challenges. Email your financial questions to askpete@petetheplanner.com.