Asking better questions

26/05/2026

The journey to financial success is often fraught with anxiety and uncertainty as we struggle to identify the most effective path towards our desired lifestyle. With countless investment options, complex economic conditions, and unique personal financial situations, selecting the best course of action can feel overwhelming.

Investors must also contend with contradictory advice, misinformation, and their own behavioural biases, knowing that today’s decisions can profoundly impact their future financial security and aspirations.

In these moments of confusion, many turn to financial advisers for guidance and clarity. However, from our experience, the key to overcoming such struggles often lies not in new and better answers but in asking different and better questions.

The wrong questions

Unfortunately, investors frequently approach their financial decisions by asking the wrong questions. They do this influenced by the financial media, well-meaning but misinformed friends and family, and generic rules of thumb that fail to account for individual circumstances.

The wrong questions can trigger common behavioural biases (loss aversion, fear of missing out, and mental accounting) that steer investors down dangerous paths.

A few of the questions we frequently see investors asking are:

1.    Where is the stock market heading in the next few months?

2.    How can I maximise my returns in the short term?

3.    Should I invest in the latest hot thing?

4.    Is now the right time to buy or sell a particular investment?

5.    Is now a good time to keep my money in cash?

We understand that being too closely involved and financially invested in one’s situation can make it challenging to view matters objectively. Financial clarity often requires an external perspective, which is one of the underappreciated benefits we provide to our clients.

Focusing on the previous questions tends to result in anxiety and myopic decision-making (acting in the moment), undermining your long-term financial stability.

When investors approach us for help, they expect to receive good answers to their questions (and we certainly have strong opinions on them), but from experience, we understand that what they need is to start asking better questions.

Better questions

From our work with clients, we have found that asking the right questions can quickly guide investors towards a healthier mindset and more positive outcomes.

These questions usually extract the client’s focus from the tactical route they need to take and redirect it to consider the strategic considerations that will allow the practical answers to become fairly obvious.

While the most relevant questions vary depending on the individual scenario, a selection of helpful questions to ask are:

1.    What are my long-term financial goals, and how does this decision impact them?

2.    How will this decision affect my ability to reach or maintain financial independence?

3.    What is the historical performance and volatility of this asset?

4.    Can I hold onto this investment for the long term, even in market downturns, without panicking?

5.    What impact will this investment choice have on my all-encompassing financial strategy?

6.    What upcoming transitions am I likely to go through that impact this decision?

7.    How will this decision affect those who are financially dependent on me?

Compiling a set of high-quality questions can be an invaluable tool for navigating the world of investing, whether you’re doing it alone or with the help of a third party.

Take a step back

In pursuing financial clarity, asking better questions is essential for investors to confidently and effectively navigate the investment landscape.

We are confident that focusing on the right questions leads to a greater understanding of one’s financial situation, increased confidence in decision-making, and improved long-term outcomes.

As you approach your financial decisions, we encourage you to reflect on the right question to ask. Of course, for those who already work with us as clients, we’ll continue adding unique insight into your decisions by playing the role of a thinking partner as you continue on your financial journey.