What Questions Should You Be Asking That You’re Not?

Are there any questions I should be asking that I’m not?

In most cases, I say yes. I’ll then go through a couple of them I think they should hear. Asking and then answering my own question. As I do, that often triggers new questions. We work through those, which might raise more questions.

And so on until the client has a good understanding of the idea.

But I’m also sometimes asked to sit in on conversations clients are having with their existing advisors, be it an accountant, lawyer, or financial advisor.

Most of the time, it’s clear I’m there to ask the “dumb” questions – the ones that a professional with decades of experience shouldn’t need to ask, but that someone with little experience of such things wouldn’t think to.

A few months ago, I was asked to sit in on a client’s conversation with a well-known international trust lawyer. He had a lot of knowledge and clearly knew what he was doing.

But he had a bad habit of talking over our client’s head, glossing over topics that were obvious to him but not to the client.

So I sat there and asked the dumb questions. One after another after another until I felt sure our client understood what was being proposed – the pros and cons of the structure they had already agreed to – and whether it truly made sense to proceed.

There’s real value in having someone there who can indeed ask those dumb questions.

In fact, it might just be about the smartest thing you can do.

To be honest, I rarely take on such engagements anymore for the simple reason that I’m only one person and only have so much time. But if you don’t yet have a “dumb questions asker” and need some help, feel free to reach out.