Chad’s Blog
Pragmatic Technologies for Life and Business Success®
How often are your clients using AI to question your advice? When they do, how do you respond? Do you reject it, fight it, take offense, or encourage it? My recommendation is to encourage it. Then give their conclusions the same serious examination you want AI to give your own. Let me tell you why.
A client preparing for retirement recently told me she had used ChatGPT to help evaluate which of our services she would still need. I used ChatGPT to help think through my response, too. I recommended reducing the work supporting her publishing while keeping basic website maintenance and hosting.
Having AI on both sides raises the expectation that our work together will produce a better decision. That expectation has to be earned. Client and advisor can both use AI to build more persuasive arguments for positions they have not fully examined.
In the Evergreen.ai Financial Decisions Study 2026, 63.8% of respondents with financial advisors said they had asked AI about money in the past year, compared with 38.5% of those without advisors. The analyzed sample included 1,981 respondents and overrepresented wealthier households. Its sponsor offers AI financial advice. The figures describe that financial sample
In Your AI Agrees With You. That Is the Problem., I examined the danger of agreeable AI. The question now extends to the whole advisory relationship. A client can have two advisors and still have no one seriously challenging the decision.
1. One Decision May Be Hiding Another
Reducing a workload and deciding what contribution still matters are separate choices. My client’s publishing arrangement needed reconsidering. Her future contribution deserved its own conversation. I wrote a follow up asking what she might still enjoy contributing on her own terms. That could involve no additional services from us. I do not know whether her AI conversation explored that question, and I do not yet have her answer.
Before accepting a recommendation, ask what else it might decide for the client. Choosing the right level of publishing support and deciding what to contribute in retirement deserve separate consideration.
2. Make Your Disagreement Worth Hearing
When you disagree with a client’s AI recommendation, identify the assumption you question, the consequence you see, or the option it overlooks. Explain why it matters to the client’s goals. If a client proposes cutting a service, show which desired outcome would become harder to achieve and why. Be equally ready to recognize that the service has become unnecessary. Agreement deserves the same care: explain why the recommendation holds up.
Recently, I used AI to analyze my portfolio and brought its recommendations to my financial advisor. He agreed with the assessment. I found myself questioning what I needed him for.
I would have welcomed either a substantiated challenge or a reasoned confirmation. I wanted to understand why he believed the recommendations fit my circumstances and what he had examined. A different perspective could have confirmed AI’s assessment while giving me a better basis for trusting it.
3. Be Willing to Change Your Mind
Enter the conversation with an open mind, ready to challenge the client’s thinking and have your own challenged in return. Make your reasoning clear so the client can examine it. Ask your AI to build the strongest case against your recommendation and consider whether your commercial interests or personal preferences are influencing your advice. If a different recommendation better serves the client, change your mind.
For my retiring client, reducing the work we supported was a valid recommendation even when it could reduce our fees. The advice that best serves the client should prevail, whether it comes from the advisor, the client, or AI.
4. Their Potential Is Not Their Obligation
I want to keep learning and contributing for as long as I have something useful to offer. My vision for the future does not tell me what retirement should mean for someone else. My client may find satisfaction in keeping her existing work available while making no new professional commitments. That could be exactly right for her, and my follow up explicitly acknowledged that.
An advisor can make a persuasive argument while quietly substituting their own ambitions for the client’s wishes. Helping someone examine a choice carries a responsibility to respect the informed choice they make.
5. The Right Advice May Change Your Role
Examining an AI recommendation together may confirm that a client needs less of your involvement. Recommend that reduction when it serves their goals. The same examination may reveal an overlooked need that calls for more of your help or a different contribution. Explain how that involvement would serve the client’s goals.
Doing what is right for the client strengthens their trust in you. Recommending less involvement when it serves their needs demonstrates that their interests come first. That trust gives them greater confidence in continuing to seek your guidance on more complex issues and decisions.
By the end of that conversation, the client should understand the assumptions you examined, why the recommendation fits their goals, and why your involvement should change or stay the same. Agreement can be valuable when the reasoning behind it is clear.
If you and your client both use AI to strengthen your arguments, how will you know the client’s decision has actually improved? Reply and tell me how you would judge that. If you would like to develop better ways of working with AI, explore the AI Insider Lab.
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