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Good questioning and finding the right financial planner for you

I know when a conversation is going well, I hear “Good question!” from the person I am talking to. Good questions (and even better listening) are the best way to get to what really matters.

An excellent financial planner will elicit the real truth, a truth you might be unaware of. Good financial planners do not show off the technical knowledge or show you their certificates. That comes as standard, it is the minimum expected that they are technically competent and well trained.

Few planners ask really good questions really well, even fewer listen clear-minded to the answers. Good questions and listening are the way to new thinking. And new thinking is the way to different outcomes.

It is all about the questions (and listening).

So, what are my favourite questions to ask?

I like to start off with “How are you feeling?” or “What’s on your mind?”.

This usually leads into something like:

“What do you need to feel to make a follow up call/Zoom worthwhile for you?”

“How would you like to be feeling at the end of this meeting?”

“What should we do next to get you closer to that?” / “What needs to happen to get you there?”

The listening really is crucial. We already know we have an inherent wisdom that tells us where the conversation should go, what question should come next. It is very simply a matter of letting that happen.

Questions should not be reeled off. It should be an organic, iterative and collaborative process, not a checkbox exercise.

We know from experience that our best, most meaningful and impactful conversations are those that flow naturally, they are not forced, there is an obvious end and there are silences throughout.

In the back of my head I have a store of further questions which tend to pop out if appropriate:

“What help are you looking for?”, “What goals / outcomes do you want help with?”

“Why haven’t they happened yet?”

“Where do you think you are now, where do you want to end up?”

“What is the one thing you want more than anything?”

“What do you think you want to do about that?”

“Given that this is your situation, what would you like to create?”


“What do you fear happening?” / “What’s your worst nightmare?” / “What does disaster look like to you?” “How could that happen?”

“How do you feel about that?”


“When you go, how would you like things to be left?”

“What do you want to be remembered for?”

“If you could hear what was said about you when you’re no longer here, what’s the best thing you could hear?”


Those all strike me as pretty obvious questions to ask. We are doing little more than spitting in the wind unless we explore them, aren’t we?

And you will notice the absence of a single certain type of question:

“How much money have you got?”

It is not important if you are trying to find out what is important.

I would pay really close attention to the questions you are asked and how well you feel listened to before choosing your financial planner.


future proofing your finances 

Town Close are expert financial planners. Our goal is the same as yours – to help you do the things that are important to you in the time you have remaining.

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