Apr 25, 2025

How to Use AI as Your Own Personal Strategy Consultant

Leaders leverage consultants to bring in outside perspective and expertise. Great consultants, to steal a phrase from McKinsey, bring an "obligation to dissent", which can be hard for your direct reports to do given power dynamics in most organizations.

But you don't have to pay the high fees that consultants (including me) charge to get dissenting perspectives on your business. Generative AI can help.

Here's how.

1. Provide Context

If you want AI to be helpful, then it needs context. The more the better. If you're not sure what context to provide, tell your AI that you want it to help you solve _____ challenge and what documents and/or data would help it to that job well. Assemble all of the documents and data, upload them to your AI, and write a long-ish prompt explaining your problem. In your prompt, tell the AI that, "you are an expert ______ consultant with deep expertise in __________", filling in those blanks with whatever is the ideal profile of a consultant to solve your problem.

2. Align on the Nuances

Before you immediately jump into solution-ing, ensure that you and the AI both understand the problem to be solved in the right way. After providing context, encourage the AI to ask you follow-up questions. Have it summarize how it would think about approaching the problem. The goal in this step is to ensure that you're focusing on the right problem. Be prepared here for your perpsective to shift as the AI asks you questions.

3. Talk it Out

I love to put generative AI in voice mode and have a live conversation with it for these kind of "advice" conversations. If you're using ChatGPT for this, note that if you start a chat with typing before entering voice mode, it defaults to the older more "walkie talkie" style of voice mode. TBH, I prefer it; the new voice mode can be a bit eager for this kind of a more thoughtful, slower conversation. Work towards identifying a discrete set of unique choices you might make to address your problem.

4. "What's the strongest argument against..."

This is where things get fun. Invite your AI to dissent. Ask it to make the strongest arguments both for and against each of your choices. Ask it, "What would have to be true for this to be the right choice?" Have that robust debate that your team might be hesitant to have given power dynamics.

While consultants aren't con men, at a fundamental level what we sell is confidence. Great consultants help their clients build belief in what they should do next in an increasingly hard-to-predict world.

I think (hope!) it's going to be quite some time before generative AI is able to deliver this confidence in all contexts, but there are countless moments when leaders need some outside perspective and engaging a human consultant simply isn't an option. In those moments, generative AI can help.

Justin Massa
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justin-massa

Owner @ Midwest Quality Consulting

Chicago, IL

Publisher of AI for SMBs Weekly and founder of MQC, helping SMBs innovate with tech. Former SVP at Newlab and partner at IDEO. Board member at Northern Illinois Food Bank and 1848 Ventures.

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