{"id":84181,"date":"2026-10-05T18:35:23","date_gmt":"2026-10-05T07:35:23","guid":{"rendered":"https:\/\/riskinfo.com.au\/news\/?p=84181"},"modified":"2026-10-05T18:37:42","modified_gmt":"2026-10-05T07:37:42","slug":"the-five-best-and-worst-discovery-questions","status":"publish","type":"post","link":"https:\/\/riskinfo.com.au\/news\/2026\/10\/05\/the-five-best-and-worst-discovery-questions\/","title":{"rendered":"The Five Best (and Worst) Discovery Questions"},"content":{"rendered":"
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Riskinfo thanks Certainty Advice Group<\/a> Founder and MD, Jim Stackpool, for the opportunity to re-publish a recent post Jim has shared in which he draws on his many years of experience to reflect on the five best and the five worst discovery questions an adviser can ask…<\/i><\/h2>\n<\/div>\n<\/div>\n

<\/p>\n

I was recently reviewing the recording of a discovery meeting. A new client of mine was conducting the discovery with a couple in their fifties.<\/p>\n

Twenty minutes in, the adviser asked one of my favourite discovery questions: “Who, if anyone, is stopping you from achieving some of these significant plans?”<\/p>\n

Silence.<\/p>\n

Still silence.<\/p>\n

Then the wife said, “Honestly? We don\u2019t agree about this. I reckon we are our biggest problem for our financial hopes.<\/p>\n

We just can\u2019t seem to control our finances, control the credit card spending or get on top of things”.<\/p>\n

No response from the husband.<\/p>\n

But then the adviser broke the silence with one of the worst discovery questions. This one feels like missing the kick from right in front of the goals:<\/p>\n

\u201cSo, who makes the financial decisions in your family?\u201d<\/p>\n

The husband answered saying he handled the finances and the wife went silent for the remainder of the meeting.<\/p>\n

Oh my gosh.<\/p>\n

For 22 years, I’ve used recordings to coach advisory teams to run more valuable client meetings.<\/p>\n

I\u2019ve heard great questions. I\u2019ve heard shockers. And I\u2019ve heard what happens or doesn\u2019t happen next.<\/p>\n

Here’s what I know about great discovery meetings:<\/p>\n

A great question with the wrong follow-up does more harm than not asking the great question at all.<\/p>\n

Great questions …make it safe for clients to open up<\/p><\/blockquote>\n

Great questions, done properly, make it safe for clients to open up, take a risk and share what makes advice relationships enduring.<\/p>\n

When done as a team, it also creates valuable relationships – not just with the adviser, but their team.<\/p>\n

If advisers don\u2019t manage the key moments in these conversations, clients are far less likely to take a similar risk again during the meeting.<\/p>\n

So, what are the best and worst discovery questions?<\/p>\n

Five Worst<\/strong><\/p>\n

Here\u2019s what I reckon are the five worst discovery questions:<\/p>\n

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  1. Any question starting with “why”<\/strong><\/li>\n<\/ol>\n

    It hints of judgement.<\/p>\n

    The client could stop exploring and start feeling they have to justify.<\/p>\n

    Their reasons matter enormously. The word itself gets in the way.<\/p>\n

      \n
    1. “How much will you need in retirement?”<\/strong><\/li>\n<\/ol>\n

      This abdicates one of an adviser’s essential responsibilities to the client.<\/p>\n

      Clients rarely have any idea of the right answer and, what’s more, it will definitely change.<\/p>\n

        \n
      1. “Does that make sense?”<\/strong><\/li>\n<\/ol>\n

        At best, it invites a polite yes.<\/p>\n

        But it usually ends the conversation even when the topic doesn\u2019t make sense to the clients.<\/p>\n

          \n
        1. “What is important to you about maintaining your lifestyle?”<\/strong><\/li>\n<\/ol>\n

          The most dangerous of the five because it is a motherhood question and creates circular conversations on what I call baseline value. That’s the value clients themselves are achieving without any help from the adviser.<\/p>\n

            \n
          1. “Who makes the financial decisions in your family?”<\/strong><\/li>\n<\/ol>\n

            It assumes one decision maker, and it can silence, sideline and worse, offend the partner sitting right beside them.<\/p>\n

            Five Best<\/strong><\/p>\n

            Here are the five best discovery questions, in no particular order:<\/p>\n

              \n
            1. “Apart from money, what is stopping you from achieving your financial objectives?”<\/strong><\/li>\n<\/ol>\n

              It identifies and names the complexities clients rarely volunteer.<\/p>\n

                \n
              1. “Who, if anyone, is stopping you from achieving what is significant to you?”<\/strong><\/li>\n<\/ol>\n

                Might sound similar to the fifth worst question but it leads to much more valuable outcomes.<\/p>\n

                Once asked, always stay with the answer. Do not move on too quickly.<\/p>\n

                  \n
                1. “On a scale of 1 to 10, with 10 being most significant, how significant is it to you to achieve the financial objective we\u2019ve just discussed?”<\/strong><\/li>\n<\/ol>\n

                  Here clients are sharing how significant something is.<\/p>\n

                  Crucial to acknowledge their rating and very carefully listen for any response or non-verbal body language from silent partners listening to their partner.<\/p>\n

                    \n
                  1. “How involved do you need to be in the detailed workings of your financial life?”<\/strong><\/li>\n<\/ol>\n

                    Quietly the most commercial question here.<\/p>\n

                    The answer helps shape your service, the frequency of meetings, and what contact is of value to them.<\/p>\n

                    It can also significantly influence your fees.<\/p>\n

                      \n
                    1. “If we were meeting three years from now, what has to happen for you to be happy about the progress you’ve made?”<\/strong><\/li>\n<\/ol>\n

                      Not mine.<\/p>\n

                      This is Dan Sullivan’s R-Factor Question from his Strategic Coach program<\/a>, which I attended 25 years ago.<\/p>\n

                      Ask yourself this question right now.<\/p>\n

                      It\u2019s hard to find a better one, isn\u2019t it?<\/p>\n

                      Value<\/strong><\/p>\n

                      The questions are the easy part.<\/p>\n

                      Your best questions sit inside a greater discovery and engagement framework. They are delivered with skills in positioning, controlling, listening, teamwork, and, of course, knowing \u2018how\u2019 to probe.<\/p>\n

                      They work best in the right order, asked by a skilled team. Otherwise, they are just a script.<\/p>\n

                      Few things suck the trust out of a discovery conversation better than someone following a script.<\/p>\n

                      If you think your clients are different and only want to talk about money, my years of listening to discovery conversations suggest clients talk about money only because it is all they’ve ever been asked about.<\/p>\n

                      So here is my question:<\/p>\n

                      What would you have asked that couple next?<\/p>\n

                      (If you want to know what I would have asked, click here<\/a> to reply with one word: NEXT.<\/em>)<\/p>\n

                      \n

                      \"\"During 30 years of consulting, training and facilitating growth strategies with entrepreneurial financial advisory and accounting firms, Jim Stackpool has built a significant profile in the financial advice profession.<\/p>\n

                      He built Certainty Advice Group<\/span><\/span>\u2019s development curriculum, written numerous white papers on the evolution of financial advice, and created the largest business performance database and benchmarking system for Australian financial advisory practices.<\/p>\n

                      Stackpool has published four books, judged numerous advisory practice of the year awards, and chaired the development committee for the Securities Institute Practice Management Curriculum.<\/p>\n<\/div>\nBack to Adviser Focus Main Page…\u00a0<\/a>\n\n","protected":false},"excerpt":{"rendered":"

                      Riskinfo thanks Certainty Advice Group Founder and MD, Jim Stackpool, for the opportunity to re-publish a recent post Jim has shared in which he draws on his many years of experience to reflect on the five best and the five worst discovery questions an adviser can ask…<\/p>\n","protected":false},"author":3,"featured_media":84184,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[6868,7734,3,4474],"tags":[],"class_list":["post-84181","post","type-post","status-publish","format-standard","has-post-thumbnail","category-adviserfocus","category-featured","category-general","category-practice-management"],"_links":{"self":[{"href":"https:\/\/riskinfo.com.au\/news\/wp-json\/wp\/v2\/posts\/84181","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/riskinfo.com.au\/news\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/riskinfo.com.au\/news\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/riskinfo.com.au\/news\/wp-json\/wp\/v2\/users\/3"}],"replies":[{"embeddable":true,"href":"https:\/\/riskinfo.com.au\/news\/wp-json\/wp\/v2\/comments?post=84181"}],"version-history":[{"count":4,"href":"https:\/\/riskinfo.com.au\/news\/wp-json\/wp\/v2\/posts\/84181\/revisions"}],"predecessor-version":[{"id":84187,"href":"https:\/\/riskinfo.com.au\/news\/wp-json\/wp\/v2\/posts\/84181\/revisions\/84187"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/riskinfo.com.au\/news\/wp-json\/wp\/v2\/media\/84184"}],"wp:attachment":[{"href":"https:\/\/riskinfo.com.au\/news\/wp-json\/wp\/v2\/media?parent=84181"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/riskinfo.com.au\/news\/wp-json\/wp\/v2\/categories?post=84181"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/riskinfo.com.au\/news\/wp-json\/wp\/v2\/tags?post=84181"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}